105 results on '"Magne O. Sydnes"'
Search Results
2. Investigation of the enantioselectivity of acetylcholinesterase and butyrylcholinesterase upon inhibition by tacrine-iminosugar heterodimers
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I. Caroline Vaaland, Óscar López, Adrián Puerta, Miguel X. Fernandes, José M. Padrón, José G. Fernández-Bolaños, Magne O. Sydnes, and Emil Lindbäck
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Cholinesterases ,inhibitors ,enantiomers ,modelling ,Alzheimer’s disease ,Therapeutics. Pharmacology ,RM1-950 - Abstract
The copper-catalysed azide-alkyne cycloaddition was applied to prepare three enantiomeric pairs of heterodimers containing a tacrine residue and a 1,4-dideoxy-1,4-imino-D-arabinitol (DAB) or 1,4-dideoxy-1,4-imino-L-arabinitol (LAB) moiety held together via linkers of variable lengths containing a 1,2,3-triazole ring and 3, 4, or 7 CH2 groups. The heterodimers were tested as inhibitors of butyrylcholinesterase (BuChE) and acetylcholinesterase (AChE). The enantiomeric heterodimers with the longest linkers exhibited the highest inhibition potencies for AChE (IC50 = 9.7 nM and 11 nM) and BuChE (IC50 = 8.1 nM and 9.1 nM). AChE exhibited the highest enantioselectivity (ca. 4-fold). The enantiomeric pairs of the heterodimers were found to be inactive (GI50 > 100 µM), or to have weak antiproliferative properties (GI50 = 84–97 µM) against a panel of human cancer cells.
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- 2023
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3. A hybrid of 1-deoxynojirimycin and benzotriazole induces preferential inhibition of butyrylcholinesterase (BuChE) over acetylcholinesterase (AChE)
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Tereza Cristina Santos Evangelista, Óscar López, Adrián Puerta, Miguel X. Fernandes, Sabrina Baptista Ferreira, José M. Padrón, José G. Fernández-Bolaños, Magne O. Sydnes, and Emil Lindbäck
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Iminosugars ,Inhibitors ,Cholinesterases ,Alzheimer’s disease ,Therapeutics. Pharmacology ,RM1-950 - Abstract
The synthesis of four heterodimers in which the copper(I)-catalysed azide-alkyne cycloaddition was employed to connect a 1-deoxynojirimycin moiety with a benzotriazole scaffold is reported. The heterodimers were investigated as inhibitors against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). The heterodimers displayed preferential inhibition (> 9) of BuChE over AChE in the micromolar concentration range (IC50 = 7–50 µM). For the most potent inhibitor of BuChE, Cornish-Bowden plots were used, which demonstrated that it behaves as a mixed inhibitor. Modelling studies of the same inhibitor demonstrated that the benzotriazole and 1-deoxynojirimycin moiety is accommodated in the peripheral anionic site and catalytic anionic site, respectively, of AChE. The binding mode to BuChE was different as the benzotriazole moiety is accommodated in the catalytic anionic site.
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- 2022
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4. The burden of emerging contaminants upon an Atlantic Ocean marine protected reserve adjacent to Camps Bay, Cape Town, South Africa
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Cecilia Y. Ojemaye, Daniela M. Pampanin, Magne O. Sydnes, Lesley Green, and Leslie Petrik
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Pharmaceuticals ,Industrial chemicals ,Perfluorinated compounds ,Marine organisms ,Bioaccumulation ,Risk assessment ,Science (General) ,Q1-390 ,Social sciences (General) ,H1-99 - Abstract
The presence and levels of fifteen chemicals of emerging concerns, including five perfluorinated compounds (PFCs), two industrial chemicals, seven pharmaceuticals and one personal care product, were evaluated in biota, seawater and sediments obtained from near-shore coastal zone in Camps Bay, Cape Town, South Africa. Eight compounds were found in seawater, and between nine to twelve compounds were quantified in marine invertebrates, sediment and seaweed. Diclofenac was the prevalent pharmaceutical with a maximum concentration of 2.86 ng/L in seawater, ≥110.9 ng/g dry weight (dw) in sediments and ≥67.47 ng/g dw in marine biotas. Among PFCs, perfluoroheptanoic acid was predominant in seawater (0.21–0.46 ng/L). Accumulation of perfluorodecanoic acid (764 ng/g dw) as well as perfluorononanoic acid and perfluorooctanoic acid (504.52 and 597.04 ng/g dw, respectively) was highest in samples of seaweed. The environmental risk assessment carried out in this study showed that although individual pollutants pose a low acute and chronic risk, yet individual compounds each had a high bioaccumulation factor in diverse marine species, and their combination as a complex mixture in marine organisms might have adverse effects upon aquatic organisms. Data revealed that this Atlantic Ocean marine protected environment is affected by the presence of numerous and diverse emerging contaminants that could only have originated from sewage discharges. The complex mixture of persistent chemicals found bioaccumulating in marine organisms could bode ill for the propagation and survival of marine protected species, since many of these compounds are known toxicants.
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- 2022
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5. Development of tacrine clusters as positively cooperative systems for the inhibition of acetylcholinesterase
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Tereza Cristina Santos Evangelista, Óscar López, Sabrina Baptista Ferreira, José G. Fernández-Bolaños, Magne O. Sydnes, and Emil Lindbäck
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acetylcholinesterase ,cuaac ,multivalent interactions ,multivalent inhibition potency ,tacrine ,Therapeutics. Pharmacology ,RM1-950 - Abstract
The synthesis of four tetra-tacrine clusters where the tacrine binding units are attached to a central scaffold via linkers of variable lengths is described. The multivalent inhibition potencies for the tacrine clusters were investigated for the inhibition of acetylcholinesterase. Two of the tacrine clusters displayed a small but significant multivalent inhibition potency in which the binding affinity of each of the tacrine binding units increased up to 3.2 times when they are connected to the central scaffold.
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- 2021
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6. 1,4-Dideoxy-1,4-imino‑d‑arabinitol (DAB) Analogues Possessing a Hydrazide Imide Moiety as Potent and Selective α‑Mannosidase Inhibitors
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Marianne B. Haarr, Óscar Lopéz, Ljupcho Pejov, José G. Fernández-Bolaños, Emil Lindbäck, and Magne O. Sydnes
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Chemistry ,QD1-999 - Published
- 2020
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7. Synthesis of an Alleged Byproduct Precursor in Iodixanol Preparation
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Marianne Bore Haarr, Emil Lindbäck, Torfinn Håland, and Magne O. Sydnes
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Chemistry ,QD1-999 - Published
- 2018
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8. Synthesis and Evaluation of the Tetracyclic Ring-System of Isocryptolepine and Regioisomers for Antimalarial, Antiproliferative and Antimicrobial Activities
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Katja S. Håheim, Emil Lindbäck, Kah Ni Tan, Marte Albrigtsen, Ida T. Urdal Helgeland, Clémence Lauga, Théodora Matringe, Emily K. Kennedy, Jeanette H. Andersen, Vicky M. Avery, and Magne O. Sydnes
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indoloquinoline ,antiplasmodial activity ,antiproliferative activity ,antimicrobial activity ,biofilm inhibition ,Organic chemistry ,QD241-441 - Abstract
A series of novel quinoline-based tetracyclic ring-systems were synthesized and evaluated in vitro for their antiplasmodial, antiproliferative and antimicrobial activities. The novel hydroiodide salts 10 and 21 showed the most promising antiplasmodial inhibition, with compound 10 displaying higher selectivity than the employed standards. The antiproliferative assay revealed novel pyridophenanthridine 4b to be significantly more active against human prostate cancer (IC50 = 24 nM) than Puromycin (IC50 = 270 nM) and Doxorubicin (IC50 = 830 nM), which are used for clinical treatment. Pyridocarbazoles 9 was also moderately effective against all the employed cancer cell lines and moreover showed excellent biofilm inhibition (9a: MBIC = 100 µM; 9b: MBIC = 100 µM).
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- 2021
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9. A Concise Synthesis of Isocryptolepine by C–C Cross-Coupling Followed by a Tandem C–H Activation and C–N Bond Formation
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Ida T. Urdal Helgeland and Magne O. Sydnes
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c–h activation ,c–n bond formation ,isocryptolepine ,one-pot reaction ,suzuki–miyaura cross-coupling ,Chemistry ,QD1-999 - Abstract
Abstract Isocryptolepine (1), a potent antimalarial natural product, was prepared in three steps from 3-bromoquinoline and 2-aminophenylboronic acid hydrochloride. The key transformations were a Suzuki–Miyaura cross-coupling reaction followed by a palladium-initiated intramolecular C–H activation/C–N bond formation between an unprotected amine and an aromatic C–H group. The two key reactions can also be performed in one pot.
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- 2017
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10. Editorial Note to 'Identification of an albumin-like protein in plasma of Atlantic cod (Gadus morhua) and its biomarker potential for PAH contamination' [Heliyon 3 (8) (August 2017) e00367]
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Karianne Skogland Enerstvedt, Magne O. Sydnes, and Daniela M. Pampanin
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Science (General) ,Q1-390 ,Social sciences (General) ,H1-99 - Published
- 2019
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11. Synthesis of the Hexahydropyrrolo-[3,2-c]-quinoline Core Structure and Strategies for Further Elaboration to Martinelline, Martinellic Acid, Incargranine B, and Seneciobipyrrolidine
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Marianne B. Haarr and Magne O. Sydnes
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natural product synthesis ,hexahydropyrrolo-[3,2-c]-quinoline ,scaffold ,martinelline ,martinellic acid ,incargranine B ,Organic chemistry ,QD241-441 - Abstract
Natural products are rich sources of interesting scaffolds possessing a plethora of biological activity. With the isolation of the martinella alkaloids in 1995, namely martinelline and martinellic acid, the pyrrolo[3,2-c]quinoline scaffold was discovered. Since then, this scaffold has been found in two additional natural products, viz. incargranine B and seneciobipyrrolidine. These natural products have attracted attention from synthetic chemists both due to the interesting scaffold they contain, but also due to the biological activity they possess. This review highlights the synthetic efforts made for the preparation of these alkaloids and formation of analogues with interesting biological activity.
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- 2021
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12. Identification of an albumin-like protein in plasma of Atlantic cod (Gadus morhua) and its biomarker potential for PAH contamination
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Karianne Skogland Enerstvedt, Magne O. Sydnes, and Daniela M. Pampanin
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Bioinformatics ,Toxicology ,Environmental science ,Biological sciences ,Science (General) ,Q1-390 ,Social sciences (General) ,H1-99 - Abstract
Increased research efforts are currently focusing on Atlantic cod (Gadus morhua) and its significance for monitoring the contaminant situation in marine environments. Polycyclic aromatic hydrocarbons (PAHs) are well known toxic and carcinogenic compounds, thus continuous monitoring is required to ensure ecosystem sustainability and human food safety. A sensitive biomarker of PAH exposure in humans is the detection of PAH metabolites bound to albumin in blood. The potential of a similar PAH-albumin biomarker in Atlantic cod was therefore investigated by a desktop bioinformatic study followed by liquid chromatography mass spectrometry/mass spectrometry analysis of plasma from 16 fish. For the first time, an albumin-like protein in plasma of Atlantic cod is described, and the biomarker potential based on PAH-albumin adduct detection is discussed. Due to the detected low abundance of the albumin-like protein, it was found unlikely to be applicable as a new biomarker tool for evaluation of PAH exposure.
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- 2017
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13. The Use of Palladium on Magnetic Support as Catalyst for Suzuki–Miyaura Cross-Coupling Reactions
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Magne O. Sydnes
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palladium ,magnetic support ,Suzuki–Miyaura cross-coupling ,catalyst recycling ,Chemical technology ,TP1-1185 ,Chemistry ,QD1-999 - Abstract
The development of new solid supports for palladium has received a lot of interest lately. These catalysts have been tested in a range of cross-coupling reactions, such as Suzuki–Miyaura, Mizoroki-Heck, and Sonogashira cross-coupling reactions, with good outcomes. Attaching the catalyst to a solid support simplifies the operations required in order to isolate and recycle the catalyst after a reaction has completed. Palladium on solid supports made of magnetic materials is particularly interesting since such catalysts can be removed very simply by utilizing an external magnet, which withholds the catalyst in the reaction vessel. This review will showcase some of the latest magnetic solid supports for palladium and highlight these catalysts’ performance in Suzuki–Miyaura cross-coupling reactions.
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- 2017
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14. Investigation of the enantioselectivity of acetylcholinesterase and butyrylcholinesterase upon inhibition by tacrine-iminosugar heterodimers
- Author
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I. Caroline Vaaland, Óscar López, Adrián Puerta, Miguel X. Fernandes, José M. Padrón, José G. Fernández-Bolaños, Magne O. Sydnes, and Emil Lindbäck
- Subjects
Pharmacology ,Butyrylcholinesterase ,Alkynes ,Drug Discovery ,Acetylcholinesterase ,Tacrine ,Humans ,General Medicine - Abstract
The copper-catalysed azide-alkyne cycloaddition was applied to prepare three enantiomeric pairs of heterodimers containing a tacrine residue and a 1,4-dideoxy-1,4-imino-D-arabinitol (DAB) or 1,4-dideoxy-1,4-imino-L-arabinitol (LAB) moiety held together via linkers of variable lengths containing a 1,2,3-triazole ring and 3, 4, or 7 CH2 groups. The heterodimers were tested as inhibitors of butyrylcholinesterase (BuChE) and acetylcholinesterase (AChE). The enantiomeric heterodimers with the longest linkers exhibited the highest inhibition potencies for AChE (IC50 = 9.7 nM and 11 nM) and BuChE (IC50 = 8.1 nM and 9.1 nM). AChE exhibited the highest enantioselectivity (ca. 4-fold). The enantiomeric pairs of the heterodimers were found to be inactive (GI50 > 100 µM), or to have weak antiproliferative properties (GI50 = 84–97 µM) against a panel of human cancer cells.
- Published
- 2022
15. Study of the long-finned pilot whale (Globicephala melas) bile content - An indicator of ocean health
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Daniela M. Pampanin, William Bossum Arnli, Jason T. Magnuson, Giovanna Monticelli, Maria Dam, Svein-Ole Mikalsen, and Magne O. Sydnes
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Matematikk og Naturvitenskap: 400::Zoologiske og botaniske fag: 480 [VDP] ,Aquatic Science ,Oceanography ,Pollution - Abstract
Globicephala melas has been harvested in the Faroe Islands for centuries. Given the distances travelled by this species, tissue/body fluid samples represent unique matrices to be considered as an integration of environmental condition and pollution status of their prey. For the first time, bile samples were analysed for presence of polycyclic aromatic hydrocarbon (PAH) metabolites and protein content. Concentrations of 2- and 3-ring PAH metabolites ranged from 11 to 25 μg mL−1 pyrene fluorescence equivalents. In total, 658 proteins were identified and 61,5 % were common amongst all individuals. Identified proteins were integrated into in silico software and determined that the top predicted disease and functions were neurological diseases, inflammation, and immunological disorders. The metabolism of reactive oxygen species (ROS) was predicted to be dysregulated, which can have consequences to both the protection against ROS produced during dives and contaminant exposures. The obtained data is valuable for understanding metabolism and physiology of G. melas.
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- 2023
16. Petrogenic Polycyclic Aromatic Hydrocarbons in the Aquatic Environment: Analysis, Synthesis, Toxicity and Environmental Impact
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Daniela M. Pampanin, Magne O. Sydnes and Daniela M. Pampanin, Magne O. Sydnes
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- 2017
17. Functionalized d- and l-Arabino-Pyrrolidines as Potent and Selective Glycosidase Inhibitors
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Magne O. Sydnes, Emil Lindbäck, Marianne B. Haarr, Óscar Lopéz, and Jóse G. Fernández-Bolaños
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Organic Chemistry ,Catalysis - Abstract
The efficient synthesis of enantiomeric pairs of iminosugars including 1,4-dideoxy-1,4-imino-d-arabinitol (DAB) and 1,4-dideoxy-1,4-imino-l-arabinitol (LAB) analogues with an amidine, hydrazide, hydrazide imide, or amide oxime moiety is described. The preparation of DAB and LAB analogues commenced from l-xylose and d-xylose, respectively. The obtained iminosugars are tested against a panel of glycosidases with pharmaceutical relevance, revealing enhanced activity for the DAB analogues in comparison with the LAB analogues. In particular, the d-arabino-configured amidine behaved as a potent (submicromolar range) and selective inhibitor of α-mannosidase.
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- 2022
18. On Our Way to Fulfilling the Twelve Principles of Green Chemistry
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Magne O. Sydnes
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Geography, Planning and Development ,General Earth and Planetary Sciences ,Water Science and Technology - Published
- 2021
19. Evaluation of photodegradable chitin synthetase inhibitors for the treatment of salmon lice (Lepeophtheirus salmonis)
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Magne O. Sydnes, Vebjørn Eikemo, Per Gunnar Espedal, Leiv K. Sydnes, and Frank Nilsen
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Aquatic Science - Published
- 2023
20. Development of tacrine clusters as positively cooperative systems for the inhibition of acetylcholinesterase
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José G. Fernández-Bolaños, Magne O. Sydnes, Sabrina Baptista Ferreira, Óscar López, Emil Lindbäck, Tereza Cristina Santos Evangelista, Universidad de Sevilla. Departamento de Electrónica y Electromagnetismo, Universidad de Sevilla. FQM134: Química Fina de Carbohidratos, Junta de Andalucía, Universidad de Stavanger. Noruega, Ministerio de Ciencia e Innovación (MICIN). España, and European Commission (EC). Fondo Europeo de Desarrollo Regional (FEDER)
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Stereochemistry ,multivalent inhibition potency ,tacrine ,RM1-950 ,chemistry.chemical_compound ,Structure-Activity Relationship ,Drug Development ,Drug Discovery ,medicine ,multivalent interactions ,Potency ,Animals ,Matematikk og Naturvitenskap: 400::Kjemi: 440 [VDP] ,Pharmacology ,Dose-Response Relationship, Drug ,Molecular Structure ,Brief Report ,General Medicine ,acetylcholinesterase ,Acetylcholinesterase ,chemistry ,Tacrine ,Electrophorus ,Cholinesterase Inhibitors ,Therapeutics. Pharmacology ,CuAAC ,medicine.drug ,cuaac - Abstract
The synthesis of four tetra-tacrine clusters where the tacrine binding units are attached to a central scaffold via linkers of variable lengths is described. The multivalent inhibition potencies for the tacrine clusters were investigated for the inhibition of acetylcholinesterase. Two of the tacrine clusters displayed a small but significant multivalent inhibition potency in which the binding affinity of each of the tacrine binding units increased up to 3.2 times when they are connected to the central scaffold. Junta de Andalucía. FQM134 Ministerio de Ciencia e Innovación de España (MICINN) y fondos FEDER de la Unión Europea. CTQ2016-78703-P
- Published
- 2021
21. Photodegradable antimicrobial agents − synthesis, photodegradation, and biological evaluation
- Author
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Vebjørn Eikemo, Magne O. Sydnes, and Leiv K. Sydnes
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biology ,Chemistry ,General Chemical Engineering ,General Chemistry ,biology.organism_classification ,Antimicrobial ,Combinatorial chemistry ,chemistry.chemical_compound ,Ethanolamine ,resistente bakterier ,Moiety ,kjemi ,Photodegradation ,Bacteria ,Matematikk og Naturvitenskap: 400::Kjemi: 440 [VDP] ,Biological evaluation - Abstract
Multi-drug resistant (MDR) bacteria are already a significant health-care problem and are making the combat of infections quite challenging. Here we report the synthesis of several new compounds containing an ethanolamine moiety, of which two exhibit promising antimicrobial activity (at the 6 μM level). All the compounds are degraded when exposed to light and form inactive products. publishedVersion
- Published
- 2021
22. Bioaccumulation potential of the tricyclic antidepressant amitriptyline in a marine Polychaete, Nereis virens
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Jason T. Magnuson, Zoe Longenecker-Wright, Ivo Havranek, Giovanna Monticelli, Hans Kristian Brekken, Roland Kallenborn, Daniel Schlenk, Magne O. Sydnes, and Daniela M. Pampanin
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Geologic Sediments ,Environmental Engineering ,Amitriptyline ,Polychaeta ,Antidepressive Agents, Tricyclic ,Pollution ,Bioaccumulation ,Teknologi: 500 [VDP] ,Pharmaceutical Preparations ,Environmental Chemistry ,Animals ,Waste Management and Disposal ,Water Pollutants, Chemical ,Environmental Monitoring - Abstract
The continual discharge of pharmaceuticals from wastewater treatment plants (WWTPs) into the marine environment, even at concentrations as low as ng/L, can exceed levels that induce sublethal effects to aquatic organisms. Amitriptyline, a tricyclic antidepressant, is the most prescribed antidepressant in Norway, though the presence, potential for transport, and uptake by aquatic biota have not been assessed. To better understand the release and bioaccumulative capacity of amitriptyline, laboratory exposure studies were carried out with field-collected sediments. Influent and effluent composite samples from the WWTP of Stavanger (the 4th largest city in Norway) were taken, and sediment samples were collected in three sites in the proximity of this WWTP discharge at sea (WWTP discharge (IVAR), Boknafjord, and Kvitsøy (reference)). Polychaetes (Nereis virens) were exposed to field-collected sediments, as well as to Kvitsøy sediment spiked with 3 and 30 μg/g amitriptyline for 28 days. The WWTP influent and effluent samples had concentrations of amitriptyline of 4.93 ± 1.40 and 6.24 ± 1.39 ng/L, respectively. Sediment samples collected from IVAR, Boknafjord, and Kvitsøy had concentrations of 6.5 ± 3.9, 15.6 ± 12.7, and 12.7 ± 8.0 ng/g, respectively. Concentrations of amitriptyline were below the limit of detection in polychaetes exposed to sediment collected from Kvitsøy and IVAR, and 5.2 ± 2.8 ng/g in those exposed to Boknafjord sediment. Sediment spiked with 3 and 30 μg/g amitriptyline had measured values of 423.83 ± 33.1 and 763.2 ± 180.5 ng/g, respectively. Concentrations in worms exposed to the amended sediments were 9.5 ± 0.2 and 56.6 ± 2.2 ng/g, respectively. This is the first known study to detect measurable concentrations of amitriptyline in WWTP discharge in Norway and accumulation in polychaetes treated with field-collected sediments, suggesting that amitriptyline has the potential for trophic transfer in marine systems.
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- 2022
23. Photodegradable Antimicrobial Agents: Synthesis and Mechanism of Degradation
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Vebjørn Eikemo, Bjarte Holmelid, Leiv K. Sydnes, and Magne O. Sydnes
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Structure-Activity Relationship ,Antifungal Agents ,Anti-Infective Agents ,Ethanolamines ,Organic Chemistry ,Matematikk og Naturvitenskap: 400 [VDP] ,Anti-Bacterial Agents - Abstract
As a strategy to inactivate antimicrobial agents after use, we designed a range of ethanolamine derivatives where four of them possessed interesting activity. The ethanolamine moiety facilitates photodecomposition, which in a potential drug will take place after use. Herein, the synthetic preparation of these compounds and the mechanism of photoinactivation are described. publishedVersion
- Published
- 2022
24. Green Bio-Based Solvents in C-C Cross-Coupling Reactions
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Magne O. Sydnes
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010405 organic chemistry ,Chemistry ,Computational chemistry ,Geography, Planning and Development ,General Earth and Planetary Sciences ,Bio based ,010402 general chemistry ,01 natural sciences ,Coupling reaction ,0104 chemical sciences ,Water Science and Technology - Abstract
Solvent accounts for majority of the waste derived from synthetic transformations. This implies that by making changes to the solvent used by either switching to greener options, reducing the volume of solvent used, or even better avoiding the use of solvent totally will have a positive impact on the environment. Herein, the focus will be on the use of bio-based-green-solvents in C-C crosscoupling reactions highlighting the recent developments in this field of research. Emphasis in this review will be placed on developments obtained for Mizoroki-Heck, Hiyama, Stille, and Suzuki- Miyaura cross-couplings. For these cross-coupling reactions, good reaction conditions utilizing green solvents are now available.
- Published
- 2019
25. Substituted Two- to Five-Ring Polycyclic Aromatic Compounds Are Potent Agonists of Atlantic Cod (
- Author
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Roger, Lille-Langøy, Kåre Bredeli, Jørgensen, Anders, Goksøyr, Daniela M, Pampanin, Magne O, Sydnes, and Odd André, Karlsen
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Polychlorinated Dibenzodioxins ,alkylated PAH ,Gadus morhua ,Receptors, Aryl Hydrocarbon ,reporter gene assay ,Animals ,Polycyclic Compounds ,Polycyclic Aromatic Hydrocarbons ,chrysenol ,Article ,methylchrysene ,PAH metabolites - Abstract
Polycyclic aromatic hydrocarbons (PAHs) are among the most toxic and bioavailable components found in petroleum and represent a high risk to aquatic organisms. The aryl hydrocarbon receptor (Ahr) is a ligand-activated transcription factor that mediates the toxicity of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) and other planar aromatic hydrocarbons, including certain PAHs. Ahr acts as a xenosensor and modulates the transcription of biotransformation genes in vertebrates, such as cytochrome P450 1A (cyp1a). Atlantic cod (Gadus morhua) possesses two Ahr proteins, Ahr1a and Ahr2a, which diverge in their primary structure, tissue-specific expression, ligand affinities, and transactivation profiles. Here, a luciferase reporter gene assay was used to assess the sensitivity of the Atlantic cod Ahrs to 31 polycyclic aromatic compounds (PACs), including two- to five-ring native PAHs, a sulfur-containing heterocyclic PAC, as well as several methylated, methoxylated, and hydroxylated congeners. Notably, most parent compounds, including naphthalene, phenanthrene, and partly, chrysene, did not act as agonists for the Ahrs, while hydroxylated and/or alkylated versions of these PAHs were potent agonists. Importantly, the greater potencies of substituted PAH derivatives and their ubiquitous occurrence in nature emphasize that more knowledge on the toxicity of these environmentally and toxicologically relevant compounds is imperative., Substituted PAH congeners act as strong aryl hydrocarbon receptor agonists, emphasizing the need to consider these compounds in environmental monitoring and risk assessment of aquatic environments.
- Published
- 2021
26. Synthesis and Evaluation of the Tetracyclic Ring-System of Isocryptolepine and Regioiso-Mers for Antimalarial, Antiproliferative and Antimicrobial Activities
- Author
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Clémence Lauga, Kah Ni Tan, Magne O. Sydnes, Emily K Kennedy, Ida T. Urdal Helgeland, Vicky M. Avery, Marte Albrigtsen, Katja S. Håheim, Jeanette Hammer Andersen, Théodora Matringe, and Emil Lindbäck
- Subjects
antiproliferative activity ,VDP::Mathematics and natural science: 400::Chemistry: 440::Pharmaceutical chemistry: 448 ,Plasmodium falciparum ,Pharmaceutical Science ,Organic chemistry ,Antineoplastic Agents ,antiplasmodial activity ,010402 general chemistry ,Ring (chemistry) ,01 natural sciences ,Article ,Analytical Chemistry ,Indole Alkaloids ,chemistry.chemical_compound ,Antimalarials ,Structure-Activity Relationship ,QD241-441 ,Anti-Infective Agents ,Cell Line, Tumor ,biofilm inhibition ,Drug Discovery ,medicine ,Humans ,Doxorubicin ,kjemi ,Physical and Theoretical Chemistry ,IC50 ,Cell Proliferation ,Matematikk og Naturvitenskap: 400::Kjemi: 440 [VDP] ,antimicrobial activity ,010405 organic chemistry ,Quinoline ,indoloquinoline ,Antimicrobial ,VDP::Matematikk og Naturvitenskap: 400::Kjemi: 440::Legemiddelkjemi: 448 ,Combinatorial chemistry ,In vitro ,0104 chemical sciences ,chemistry ,Chemistry (miscellaneous) ,Puromycin ,Quinolines ,Molecular Medicine ,Selectivity ,medicine.drug - Abstract
A series of novel quinoline-based tetracyclic ring-systems were synthesized and evaluated in vitro for their antiplasmodial, antiproliferative and antimicrobial activities. The novel hydroiodide salts 10 and 21 showed the most promising antiplasmodial inhibition, with compound 10 displaying higher selectivity than the employed standards. The antiproliferative assay revealed novel pyridophenanthridine 4b to be significantly more active against human prostate cancer (IC50 = 24 nM) than Puromycin (IC50 = 270 nM) and Doxorubicin (IC50 = 830 nM), which are used for clinical treatment. Pyridocarbazoles 9 was also moderately effective against all the employed cancer cell lines and moreover showed excellent biofilm inhibition (9a: MBIC = 100 µM, 9b: MBIC = 100 µM).
- Published
- 2021
- Full Text
- View/download PDF
27. Bicyclic 1-Azafagomine Derivatives: Synthesis and Glycosidase Inhibitory Testing
- Author
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Sabrina Baptista Ferreira, Emil Lindbäck, Óscar López, Tereza Cristina Santos Evangelista, Magne O. Sydnes, and José G. Fernández-Bolaños
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chemistry.chemical_classification ,Bicyclic molecule ,010405 organic chemistry ,Stereochemistry ,Hydrogen bond ,Organic Chemistry ,Glycosidic bond ,010402 general chemistry ,Inhibitory postsynaptic potential ,01 natural sciences ,Acceptor ,Catalysis ,0104 chemical sciences ,Residue (chemistry) ,chemistry ,Glycoside hydrolase - Abstract
The synthesis of a series of 1-azafagomine derivatives that are tethered with five- and six-membered 1,2-annulated ring systems is described. These compounds were used in order to explore whether a hydrogen-bond acceptor group on the carbon atom corresponding to the glycosidic oxygen is able to interact with the catalytic acidic residue of β-glucosidase. The hydrogen-bond acceptor group was installed at various positions on the annulated ring system making it possible to study the effect of altering the position of this group.
- Published
- 2019
28. Mapping the reactivity of the quinoline ring-system – Synthesis of the tetracyclic ring-system of isocryptolepine and regioisomers
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Katja S. Håheim, Ida T. Urdal Helgeland, Magne O. Sydnes, and Emil Lindbäck
- Subjects
010405 organic chemistry ,Chemistry ,Hydrochloride ,Organic Chemistry ,Quinoline ,chemistry.chemical_element ,Isocryptolepine ,010402 general chemistry ,Ring (chemistry) ,01 natural sciences ,Biochemistry ,Medicinal chemistry ,0104 chemical sciences ,Catalysis ,chemistry.chemical_compound ,Drug Discovery ,Structural isomer ,Reactivity (chemistry) ,Palladium - Abstract
Bromoquinolines (2-bromoquinoline – 8-bromoquinoline and 5-bromo-3-methoxyquinoline) and 2-aminophenylboronic acid hydrochloride were subjected to Suzuki-Miyaura cross-coupling conditions resulting in formation of the desired biaryl systems in good yields. The resulting biaryls were then subjected to palladium catalyzed C H activation/C N bond formation utilizing PdCl2(dppf). The reactions revealed large differences in reactivity depending on the attachment point for the 2-aminophenyl group on the quinoline. The variation in the reactivity was rationalized based on the electron distribution around the quinoline ring-system.
- Published
- 2019
29. Tacrine-sugar mimetic conjugates as enhanced cholinesterase inhibitors
- Author
-
Sabrina Baptista Ferreira, Emil Lindbäck, Quelli Larissa Oliveira de Santana, Petra Imhof, Magne O. Sydnes, Óscar López, José G. Fernández-Bolaños, and Tereza Cristina Santos Evangelista
- Subjects
Stereochemistry ,Iminosugar ,Molecular Dynamics Simulation ,Biochemistry ,chemistry.chemical_compound ,Structure-Activity Relationship ,medicine ,Structure–activity relationship ,Animals ,Horses ,Physical and Theoretical Chemistry ,Binding site ,Cholinesterase ,Enzyme Assays ,biology ,Molecular Structure ,Organic Chemistry ,Tryptophan ,Acetylcholinesterase ,Imino Sugars ,Molecular Docking Simulation ,Kinetics ,chemistry ,Tacrine ,Butyrylcholinesterase ,Electrophorus ,biology.protein ,Thermodynamics ,Cholinesterase Inhibitors ,Linker ,medicine.drug ,Protein Binding - Abstract
We have used the Cu(i)-catalyzed azide-alkyne Huisgen cycloaddition reaction to obtain two families of bivalent heterodimers where tacrine is connected to an azasugar or iminosugar, respectively, via linkers of variable length. The heterodimers were investigated as cholinesterase inhibitors and it was found that their activity increased with the length of the linker. Two of the heterodimers were significantly stronger acetylcholinesterase inhibitors than the monomeric tacrine. Molecular modelling indicated that the longer heterodimers fitted better into the active gorge of acetylcholinesterase than the shorter counterparts and the former provided more efficient simultaneous interaction with the tryptophan residues in the catalytic anionic binding site (CAS) and the peripheral anionic binding site (PAS).
- Published
- 2021
30. Substituted Two- To Five-Ring Polycyclic Aromatic Compounds Are Potent Agonists of Atlantic Cod (Gadus morhua) Aryl Hydrocarbon Receptors Ahr1a and Ahr2a
- Author
-
Kåre B. Jørgensen, Daniela M. Pampanin, Roger Lille-Langøy, Magne O. Sydnes, Anders Goksøyr, and Odd André Karlsen
- Subjects
chemistry.chemical_classification ,Chrysene ,biology ,Stereochemistry ,Landbruks- og Fiskerifag: 900 [VDP] ,Aryl ,General Chemistry ,Phenanthrene ,biology.organism_classification ,Aryl hydrocarbon receptor ,chemistry.chemical_compound ,Hydrocarbon ,chemistry ,Biotransformation ,biology.protein ,Environmental Chemistry ,Gadus ,Matematikk og Naturvitenskap: 400::Kjemi: 440 [VDP] ,Naphthalene - Abstract
Polycyclic aromatic hydrocarbons (PAHs) are among the most toxic and bioavailable components found in petroleum and represent a high risk to aquatic organisms. The aryl hydrocarbon receptor (Ahr) is a ligand-activated transcription factor that mediates the toxicity of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) and other planar aromatic hydrocarbons, including certain PAHs. Ahr acts as a xenosensor and modulates the transcription of biotransformation genes in vertebrates, such as cytochrome P450 1A (cyp1a). Atlantic cod (Gadus morhua) possesses two Ahr proteins, Ahr1a and Ahr2a, which diverge in their primary structure, tissue-specific expression, ligand affinities, and transactivation profiles. Here, a luciferase reporter gene assay was used to assess the sensitivity of the Atlantic cod Ahrs to 31 polycyclic aromatic compounds (PACs), including two- to five-ring native PAHs, a sulfur-containing heterocyclic PAC, as well as several methylated, methoxylated, and hydroxylated congeners. Notably, most parent compounds, including naphthalene, phenanthrene, and partly, chrysene, did not act as agonists for the Ahrs, while hydroxylated and/or alkylated versions of these PAHs were potent agonists. Importantly, the greater potencies of substituted PAH derivatives and their ubiquitous occurrence in nature emphasize that more knowledge on the toxicity of these environmentally and toxicologically relevant compounds is imperative. publishedVersion
- Published
- 2021
31. Synthesis of the Hexahydropyrrolo-[3,2-c]-quinoline Core Structure and Strategies for Further Elaboration to Martinelline, Martinellic Acid, Incargranine B, and Seneciobipyrrolidine
- Author
-
Marianne Bore Haarr and Magne O. Sydnes
- Subjects
hexahydropyrrolo-[3,2-c]-quinoline ,Scaffold ,Pyrrolidines ,martinelline ,Pharmaceutical Science ,Chemistry Techniques, Synthetic ,Review ,scaffold ,Analytical Chemistry ,lcsh:QD241-441 ,chemistry.chemical_compound ,Alkaloids ,lcsh:Organic chemistry ,Martinelline ,Drug Discovery ,Pyrroles ,Matematikk og Naturvitenskap: 400 [VDP] ,Physical and Theoretical Chemistry ,Martinellic acid ,Incargranine B ,natural product synthesis ,Biological Products ,incargranine B ,Organic Chemistry ,Quinoline ,Biological activity ,Combinatorial chemistry ,seneciobipyrrolidine ,chemistry ,Chemistry (miscellaneous) ,Bignoniaceae ,Quinolines ,Molecular Medicine ,martinellic acid - Abstract
Natural products are rich sources of interesting scaffolds possessing a plethora of biological activity. With the isolation of the martinella alkaloids in 1995, namely martinelline and martinellic acid, the pyrrolo[3,2-c]quinoline scaffold was discovered. Since then, this scaffold has been found in two additional natural products, viz. incargranine B and seneciobipyrrolidine. These natural products have attracted attention from synthetic chemists both due to the interesting scaffold they contain, but also due to the biological activity they possess. This review highlights the synthetic efforts made for the preparation of these alkaloids and formation of analogues with interesting biological activity.
- Published
- 2020
32. Herbicides in Camps Bay (Cape Town, South Africa), supplemented
- Author
-
Magne O. Sydnes, Daniela M. Pampanin, Leslie F. Petrik, Cecilia Y. Ojemaye, and C. T. Onwordi
- Subjects
Geologic Sediments ,Environmental Engineering ,010504 meteorology & atmospheric sciences ,Drainage basin ,Sewage ,Simazine ,010501 environmental sciences ,01 natural sciences ,chemistry.chemical_compound ,South Africa ,Environmental Chemistry ,Cities ,Waste Management and Disposal ,0105 earth and related environmental sciences ,Hydrology ,geography ,geography.geographical_feature_category ,business.industry ,Herbicides ,Outfall ,Biota ,Pollution ,chemistry ,Bays ,Benthic zone ,Environmental science ,business ,Bay ,Marine outfall ,Water Pollutants, Chemical ,Environmental Monitoring - Abstract
During 2017 the herbicides alachlor, atrazine, butachlor, metolachlor, and simazine were detected in water samples, beach sediments and marine biota collected at Camps Bay, Cape Town, South Africa. During that period, the annual rain catchment record was 77,000 m3, whereas the volume of chemically laden sewage discharged via the marine outfall was 693,500 m3 making the marine sewage outfall by far the most predominant source for these herbicides in the bay. The chemical load in the discharged sewage was not removed by the applied pre-treatment step, which only uses a 3 mm screen to eliminate plastic, paper, rags and other foreign materials. After passing through the Camps Bay pump station, the sewage is released to the bay at the following GPS position 33°56′42.214″ S 18°21′59.257″ E (Colenbrander et al., 2021) and at a discharge depth of 23 m and 1497 m from the beach. In our study the presence in marine biota of atrazine and simazine were taken as being indicative of the chemical signature of the sewage being released through the outfall, since these compounds were detected previously in the sewage prior to discharge. To our knowledge, our studies of the herbicides in diverse benthic organisms found in the near shore environment of Camps Bay are the first of their kind for this Western Cape region.
- Published
- 2020
33. Presence and risk assessment of herbicides in the marine environment of Camps Bay (Cape Town, South Africa)
- Author
-
Cecilia Y. Ojemaye, Daniela M. Pampanin, Leslie F. Petrik, C. T. Onwordi, and Magne O. Sydnes
- Subjects
Geologic Sediments ,Environmental Engineering ,010504 meteorology & atmospheric sciences ,Sewage ,010501 environmental sciences ,01 natural sciences ,Risk Assessment ,South Africa ,Environmental Chemistry ,Animals ,Humans ,Cities ,Waste Management and Disposal ,0105 earth and related environmental sciences ,Shore ,geography ,geography.geographical_feature_category ,biology ,business.industry ,Herbicides ,Sediment ,Biota ,biology.organism_classification ,Pollution ,Mytilus ,United States ,Fishery ,Bays ,Environmental science ,Seawater ,business ,Bay ,Marine outfall ,Water Pollutants, Chemical ,Environmental Monitoring - Abstract
The present study was conducted during a time of drought to assess the concentration of herbicides and their potential for accumulation in marine biota found in the near shore marine environment of an urban setting (Camps Bay, Cape Town, South Africa). The purpose was to establish whether raw sewage containing selected persistent chemicals that are released through a local marine outfall would be sufficiently diluted by the ocean to prevent impact on the near-shore marine environment of the suburb Camps Bay. Samples of seawater, sediment, seaweed, and selected marine organisms present in the near shore environment, such as limpets (Cymbula granatina), mussels (Mytilus galloprovincialis), and sea urchins (Parechinus angulosus), were analysed for five indicator herbicides, namely atrazine, alachlor, simazine, metolachlor, and butachlor, with gas chromatography coupled with a mass spectrometer. The concentration of the compounds detected ranged from below the limit of detection (LOD) to 4.2 ng/L in seawater,LOD to 45.3 ng/g dry weight (dw) in sediments,LOD to 157.8 ng/g dw in marine organisms, and between 12.3 and 87.0 ng/g dw in seaweed. Results of ecological risk assessment for acute and chronic risk, calculated following the US Environmental Protection Agency method, showed a possible threat to the near shore environment from sewage released by the marine outfall, as the herbicide contamination in the biota posed a low to high ecotoxicological risk for marine organisms. The hazard quotients and carcinogenic risk caused by herbicide pollution in Camps Bay seawater were above the acceptable level indicating that these chemicals pose adverse health effects, should an average sized human (70 kg) consume any of the marine species analysed herein on a daily basis (daily consumption of 54 g), over a lifetime period (life expectancy of 70 years). The study also indicated the extensive use of these herbicides for cosmetic and ornamental purposes in gardening, or for weed control in an urban setting, thus, it is apparent that consumers and municipalities need to be educated about their inadvertent use and safe disposal of these compounds. The use of these herbicides to control weeds within the area and discharge of sewage to Camps Bay must be checked through adequate control of the trade, handling of herbicides, and enforcement of appropriate sanctions and development of suitable regulations.
- Published
- 2020
34. Synthesis of trans-dihydronaphthalene-diol and evaluation of their use as standards for PAH metabolite analysis in fish bile by GC-MS
- Author
-
Daniela M. Pampanin, Magne O. Sydnes, and I. Caroline Vaaland
- Subjects
Environmental Engineering ,Health, Toxicology and Mutagenesis ,0208 environmental biotechnology ,02 engineering and technology ,010501 environmental sciences ,Naphthalenes ,Mass spectrometry ,01 natural sciences ,Gas Chromatography-Mass Spectrometry ,chemistry.chemical_compound ,polycyclic compounds ,Environmental Chemistry ,Animals ,Bile ,kjemi ,Phenols ,Polycyclic Aromatic Hydrocarbons ,Matematikk og Naturvitenskap: 400::Kjemi: 440 [VDP] ,0105 earth and related environmental sciences ,Naphthalene ,Chromatography ,Water pollutants ,Public Health, Environmental and Occupational Health ,Fishes ,General Medicine ,General Chemistry ,Pah exposure ,Metabolite analysis ,Pollution ,020801 environmental engineering ,chemistry ,Gadus morhua ,%22">Fish ,Gas chromatography–mass spectrometry ,Water Pollutants, Chemical ,Environmental Monitoring - Abstract
Phenols and trans-1,2-dihydro-1,2-diols are metabolites commonly formed in vivo in fish upon exposure to polycyclic aromatic hydrocarbons (PAHs). These metabolites are excreted via the bile and gas chromatography-mass spectrometry (GC-MS) analysis of bile is becoming more frequently used for evaluating PAH exposure levels in fish. Current protocols focus on the detection and quantification of phenols formed during in vivo oxidation of PAHs, leaving out analyses and quantification of other oxidation products such as trans-1,2-dihydro-1,2-diols, potentially underestimating exposure levels. Herein, four trans-1,2-dihydro-1,2-diols, namely trans-1,2-dihydronaphthalene-1,2-diol, trans-6-methyl-1,2-dihydronaphthalene-1,2-diol, trans-5,7-dimethyl-1,2-dihydronaphthalene-1,2-diol, and trans-4,6,7-trimethyl-1,2-dihydronaphthalene-1,2-diol, were successfully prepared and used as standards in the GC-MS analysis, aiming to further develop this qualitative and quantitative analytical method for the determination of PAH exposures. This study shows that the currently used GC-MS analysis, including sample workup, is not suitable for determining the quantity of the corresponding diols derived from naphthalene and methylated naphthalenes. Alternative approaches are needed to provide a correct estimate of PAH exposure levels. publishedVersion
- Published
- 2020
35. Recent progress in the synthesis of antimalarial indoloquinoline natural products and analogues
- Author
-
Magne O. Sydnes
- Subjects
chemistry.chemical_compound ,Cryptolepine ,chemistry ,Traditional medicine ,medicine ,Business ,Artemisinin ,medicine.disease ,Natural (archaeology) ,Malaria ,medicine.drug - Abstract
Clinically used malaria drugs are suffering from increasing drug resistance and with that, the necessity to develop new antimalarial treatments is of great need. Natural products have traditionally been a good source of compounds for the treatment of malaria with the two most well-known drugs being the natural products quinine and artemisinin. These compounds used either alone or in combination with other drugs have provided a good arsenal for combating malaria. Synthetic analogues of the two natural products have also been used with great success in the past. However, increasing drug resistance has made these drugs and combinations of them inactive in some regions of the world. There is therefore a constant need for finding new molecules that can help fight malaria. Natural products are still a rich source of new lead compounds with antimalarial activity as it has been in the past. Over the years, a variety of different compounds have been isolated possessing interesting activity toward malaria. Many of these molecules have inspired synthetic campaigns firstly targeted at preparing the natural products, and secondly to generate analogues of the natural products with the aim to generate compounds with enhanced biological activity. This chapter will focus on the recent progress in the synthesis of the indoloquinoline natural products isocryptolepin, neocryptolepin, and cryptolepine, all possessing antimalarial activity, and synthetic efforts invested into generating more potent analogues of the parent compounds.
- Published
- 2020
36. 1,4-Dideoxy-1,4-imino-d-arabinitol (DAB) Analogues Possessing a Hydrazide Imide Moiety as Potent and Selective α-Mannosidase Inhibitors
- Author
-
Emil Lindbäck, Marianne Bore Haarr, Ljupcho Pejov, Magne O. Sydnes, José G. Fernández-Bolaños, Óscar López, and Universidad de Sevilla. Departamento de Química orgánica
- Subjects
Mannosidase ,Stereochemistry ,General Chemical Engineering ,General Chemistry ,Hydrazide ,D-arabinitol ,Article ,Chemistry ,chemistry.chemical_compound ,chemistry ,Moiety ,kjemi ,Imide ,QD1-999 ,Matematikk og Naturvitenskap: 400::Kjemi: 440 [VDP] - Abstract
The synthesis of two polyhydroxylated pyrrolidines as 1,4-dideoxy-1,4-imino-d-arabinitol (DAB) analogues bearing a hydrazide moiety is described. The DAB analogues act as selective and potent inhibitors of α-mannosidase in the submicromolar concentration ranges (Ki values ranging from 0.23 to 1.4 μM). España, Dirección General de Investigación (CTQ2016-78703-P) Junta de Andalucía (FQM134)
- Published
- 2020
37. One-Pot Strategies for the Synthesis of Nitrogen-Containing Heteroaromatics
- Author
-
Magne O. Sydnes
- Subjects
chemistry ,Geography, Planning and Development ,General Earth and Planetary Sciences ,Organic chemistry ,chemistry.chemical_element ,Nitrogen ,Water Science and Technology - Published
- 2018
38. Gastrointestinal microbial community changes in Atlantic cod (Gadus morhua) exposed to crude oil
- Author
-
Andrea Bagi, Even Sannes Riiser, Daniela M. Pampanin, Bastiaan Star, Hilde Steine Molland, Thomas H A Haverkamp, and Magne O. Sydnes
- Subjects
0301 basic medicine ,forurensing ,Matematikk og Naturvitenskap: 400::Basale biofag: 470::Generell mikrobiologi: 472 [VDP] ,mikrobiologi ,lcsh:QR1-502 ,010501 environmental sciences ,01 natural sciences ,lcsh:Microbiology ,Biotransformation ,RNA, Ribosomal, 16S ,Gadus ,atlanterhavstorsk ,Food science ,Fish gut microbiome ,Phylogeny ,Deferribacterales ,biology ,Microbiota ,polysykliske aromatiske hydrokarboner ,Fishes ,Biodiversity ,Intestinal microbiome ,Polycyclic aromatic hydrocarbons ,Petroleum ,Gadus morhua ,Indans ,Composition (visual arts) ,Temperature gradient gel electrophoresis ,Environmental Monitoring ,Research Article ,Microbiology (medical) ,DNA, Bacterial ,Microbiology ,oljesøl ,Oil exposure ,03 medical and health sciences ,Animals ,Relative species abundance ,0105 earth and related environmental sciences ,Bacteria ,PAH ,biology.organism_classification ,Gastrointestinal Microbiome ,030104 developmental biology ,Microbial population biology ,polycyclic aromatic hydrocarbons (PAHs) ,Atlantic cod ,oil exposure ,Water Pollutants, Chemical - Abstract
Background The expansion of offshore oil exploration increases the risk of marine species being exposed to oil pollution in currently pristine areas. The adverse effects of oil exposure through toxic properties of polycyclic aromatic hydrocarbons (PAHs) have been well studied in Atlantic cod (Gadus morhua). Nevertheless, the fate of conjugated metabolites in the intestinal tract and their effect on the diversity of intestinal microbial community in fish is less understood. Here, we investigated the intestinal microbial community composition of Atlantic cod after 28 days of exposure to crude oil (concentration range 0.0–0.1 mg/L). Results Analysis of PAH metabolites in bile samples confirmed that uptake and biotransformation of oil compounds occurred as a result of the exposure. Various evidence for altered microbial communities was found in fish exposed to high (0.1 mg/L) and medium (0.05 mg/L) concentrations of oil when compared to fish exposed to low oil concentration (0.01 mg/L) or no oil (control). First, altered banding patterns were observed on denaturing gradient gel electrophoresis for samples pooled from each treatment group. Secondly, based on 16S rRNA sequences, higher levels of oil exposure were associated with a loss of overall diversity of the gut microbial communities. Furthermore, 8 operational taxonomic units (OTUs) were found to have significantly different relative abundances in samples from fishes exposed to high and medium oil concentrations when compared to samples from the control group and low oil concentration. Among these, only one OTU, a Deferribacterales, had increased relative abundance in samples from fish exposed to high oil concentration. Conclusions The results presented herein contribute to a better understanding of the effects of oil contamination on the gut microbial community changes in fish and highlight the importance of further studies into the area. Our findings suggest that increased relative abundance of bacteria belonging to the order Deferribacterales may be indicative of exposure to oil at concentrations higher than 0.05 mg/L. Electronic supplementary material The online version of this article (10.1186/s12866-018-1171-2) contains supplementary material, which is available to authorized users.
- Published
- 2018
39. Total synthesis of anithiactins A-C and thiasporine A
- Author
-
Magne O. Sydnes, Emil Lindbäck, and I. Caroline Vaaland
- Subjects
Anithiactin B ,010405 organic chemistry ,Hydrochloride ,Organic Chemistry ,Total synthesis ,Alkylation ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Medicinal chemistry ,0104 chemical sciences ,Hydrolysis ,chemistry.chemical_compound ,Aminolysis ,chemistry ,Drug Discovery - Abstract
The total syntheses of anithiactins A-C (1–3) and thiasporine A (4) have been achieved in good overall yields. The key reaction in the synthetic sequence was the Suzuki-Miyaura cross-coupling between 2-aminophenylboronic acid hydrochloride and methyl 2-bromothiazole-4-carboxylate forming the common intermediate methyl 2-(2-aminophenyl)thiazole-4-carboxylate (8), which could be further transformed by hydrolysis, alkylation, and aminolysis to give the four title natural products. This work represents the first total synthesis of anithiactin B (2) and C (3).
- Published
- 2019
40. DNA adducts in marine fish as biological marker of genotoxicity in environmental monitoring: The way forward
- Author
-
Bjørn Einar Grøsvik, Steven Brooks, Jérémie Le Goff, Sonnich Meier, Daniela M. Pampanin, and Magne O. Sydnes
- Subjects
0301 basic medicine ,Analyte ,010501 environmental sciences ,Aquatic Science ,Oceanography ,medicine.disease_cause ,01 natural sciences ,Adduct ,DNA Adducts ,03 medical and health sciences ,chemistry.chemical_compound ,DNA adduct ,Environmental monitoring ,medicine ,Animals ,0105 earth and related environmental sciences ,Chemistry ,Fishes ,General Medicine ,Pollution ,030104 developmental biology ,Biochemistry ,Environmental chemistry ,Carcinogenesis ,Xenobiotic ,Biomarkers ,Water Pollutants, Chemical ,Genotoxicity ,DNA ,Environmental Monitoring ,Mutagens - Abstract
DNA adducts in fish represent a very important genotoxicity endpoint in environmental monitoring, being a pre-mutagenic lesion that plays an essential role in the initiation of carcinogenesis. The analysis of DNA adducts is a challenging task due to the low concentration of the analyte. Methods are available to determine the presence of DNA adducts, although further knowledge is required to fully understand the nature of the adducts and responsible xenobiotics (i.e. position of adduct in DNA, most active xenobiotic and metabolite forms, structural information). At present, 32P-postlabeling is the most used method that has the required sensitivity for DNA adduct analyses in both human health and environmental monitoring. Development of new mass spectrometry based methods for identifying DNA adducts in complex matrixes is now considered as a necessary mission in toxicology in order to gain the necessary information regarding adduct formation and facilitate tracking sources of contamination. Mass spectrometry therefore represents the future of DNA adduct detection, bringing along a series of challenges that the scientific community is facing at present.
- Published
- 2017
41. Photochemically Induced Aryl Azide Rearrangement: Solution NMR Spectroscopic Identification of the Rearrangement Product
- Author
-
Hanna Andersson, Jürgen Gräfenstein, Magne O. Sydnes, Minoru Isobe, and Máté Erdélyi
- Subjects
010405 organic chemistry ,Aryl ,Organic Chemistry ,Photodissociation ,Regioselectivity ,chemistry.chemical_element ,010402 general chemistry ,Photochemistry ,01 natural sciences ,Oxygen ,0104 chemical sciences ,Ketenimine ,chemistry.chemical_compound ,chemistry ,Product (mathematics) ,Azide - Abstract
Photolysis of ethyl 3-azido-4,6-difluorobenzoate at room temperature in the presence of oxygen results in the regioselective formation of ethyl 5,7-difluoro-4-azaspiro[2.4]hepta-1,4,6-triene-1-carboxylate, presumably via the corresponding ketenimine intermediate which undergoes a photochemical four-electron electrocyclization followed by a rearrangement. The photorearrangement product was identified by multinuclear solution NMR spectroscopic techniques supported by DFT calculations.
- Published
- 2017
42. Electrochemical Oxygen Removal from Seawater in Industrial Scale Using Silver Cathode
- Author
-
Tor Hemmingsen, Kai Vuorilehto, Magne O. Sydnes, Utsav Raj Dotel, and Hans Urkedal
- Subjects
General Chemical Engineering ,Inorganic chemistry ,chemistry.chemical_element ,02 engineering and technology ,General Chemistry ,010402 general chemistry ,021001 nanoscience & nanotechnology ,Electrochemistry ,01 natural sciences ,Oxygen ,Industrial and Manufacturing Engineering ,Cathode ,0104 chemical sciences ,Electrochemical cell ,law.invention ,Anode ,Volumetric flow rate ,chemistry ,law ,Seawater ,Limiting oxygen concentration ,0210 nano-technology ,ta215 - Abstract
In this study, electrochemical removal of oxygen from seawater in industrial scale is demonstrated. A test rig with an industrial scale electrochemical cell has been constructed and tested with filtrated oxygen rich seawater. The electrochemical cell was comprised of a silver mesh cathode and an iridium oxide anode with a cation exchange membrane. The effects of flow rate, pressure, and applied voltage on oxygen removal efficiency and resulting current were studied. Also, the differential pressure between the anode and cathode chambers affected the performance of the cell, and an overpressure of 0.20–0.30 bar in the anode chamber was optimal in order to obtain maximum oxygen removal. It was possible to achieve an oxygen concentration lower than 5 ppb in seawater at a flow rate of 5 L min–1. No scaling or biofilm problems were observed during a 200 h test period.
- Published
- 2017
43. Editorial Note to 'Identification of an albumin-like protein in plasma of Atlantic cod (Gadus morhua) and its biomarker potential for PAH contamination' [Heliyon 3 (8) (August 2017) e00367]
- Author
-
Daniela M. Pampanin, Karianne Skogland Enerstvedt, and Magne O. Sydnes
- Subjects
Multidisciplinary ,biology ,Chemistry ,Albumin ,Contamination ,biology.organism_classification ,Article ,Biochemistry ,Biomarker (medicine) ,Gadus ,Identification (biology) ,lcsh:H1-99 ,lcsh:Social sciences (General) ,Atlantic cod ,lcsh:Science (General) ,lcsh:Q1-390 - Published
- 2019
44. Kinase chemodiversity from the Arctic: the breitfussins
- Author
-
Matthias Baumann, Sunil Kumar Pandey, Kine Østnes Hansen, Uwe Koch, Jeanette Hammer Andersen, Jan Eickhoff, Bengt Erik Haug, Johan Isaksson, Espen Hansen, Yngve Guttormsen, Magne O. Sydnes, Bert Klebl, Annette Bayer, Marianne Lorentzen, and Kåre B. Jørgensen
- Subjects
Embryo, Nonmammalian ,Indoles ,kjemisk struktur ,PIM1 ,Antineoplastic Agents ,Triple Negative Breast Neoplasms ,01 natural sciences ,Mice ,03 medical and health sciences ,Adenosine Triphosphate ,Proto-Oncogene Proteins c-pim-1 ,karbon ,Cell Line, Tumor ,Toxicity Tests ,Drug Discovery ,Animals ,Humans ,Protein Kinase Inhibitors ,IC50 ,Zebrafish ,Triple-negative breast cancer ,030304 developmental biology ,ADME ,Biological Products ,0303 health sciences ,Binding Sites ,Molecular Structure ,VDP::Mathematics and natural science: 400::Chemistry: 440 ,Arctic Regions ,Kinase ,Chemistry ,Mathematics and natural science: 400::Chemistry: 440 [VDP] ,Total synthesis ,In vitro ,Hydrocarbons, Brominated ,0104 chemical sciences ,Molecular Docking Simulation ,010404 medicinal & biomolecular chemistry ,Hydrozoa ,Biochemistry ,Cell culture ,VDP::Matematikk og Naturvitenskap: 400::Kjemi: 440 ,peptider ,Molecular Medicine ,Female - Abstract
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Medicinal Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see [insert ACS Articles on Request author-directed link to Published Work, see https://doi.org/10.1021/acs.jmedchem.9b01006. In this work, we demonstrate that the indole-oxazole-pyrrole framework of the breitfussin family of natural products is a promising scaffold for kinase inhibition. Six new halogenated natural products, breitfussin C–H (3 – 8) were isolated and characterized from the Arctic, marine hydrozoan Thuiaria breitfussi. The structures of two of the new natural products were also confirmed by total synthesis. Two of the breitfussins (3 and 4) were found to selectively inhibit the survival of several cancer cell lines, with the lowest IC50 value of 340 nM measured against the drug-resistant triple negative breast cancer cell line MDA-MB-468, while leaving the majority of the tested cell lines not or significantly less affected. When tested against panels of protein kinases, 3 gave IC50 and Kd values as low as 200 and 390 nM against the PIM1 and DRAK1 kinases, respectively. The activity was confirmed to be mediated through ATP competitive binding in the ATP binding pocket of the kinases. Furthermore, evaluation of potential off-target and toxicological effects, as well as relevant in vitro ADME parameters for 3 revealed that the breitfussin scaffold holds promise for the development of selective kinase inhibitors.
- Published
- 2019
45. The crystal structure of haemoglobin from Atlantic cod
- Author
-
Daniela M. Pampanin, Ulli Rothweiler, Ronny Helland, Eva katrin Bjørkeng, and Magne O. Sydnes
- Subjects
Fish Proteins ,Models, Molecular ,Protein Conformation ,Biophysics ,Crystal structure ,010501 environmental sciences ,Crystallography, X-Ray ,01 natural sciences ,Biochemistry ,Research Communications ,03 medical and health sciences ,Hemoglobins ,0302 clinical medicine ,Structural Biology ,Genetics ,Animals ,VDP::Medisinske Fag: 700 ,VDP::Landbruks- og Fiskerifag: 900::Fiskerifag: 920 ,0105 earth and related environmental sciences ,VDP::Agriculture and fishery disciplines: 900::Fisheries science: 920 ,biology ,Chemistry ,Oxygen transport ,social sciences ,Condensed Matter Physics ,biology.organism_classification ,haemoglobin ,VDP::Medical disciplines: 700 ,Crystallography ,Polymorphism (materials science) ,Gadus morhua ,030220 oncology & carcinogenesis ,Atlantic cod ,Mathematics and natural science: 400 [VDP] ,population characteristics ,geographic locations - Abstract
The isolation of the dominant isoform of haemoglobin from Atlantic cod caught in southwest Norway is reported and its X-ray crystal structure is presented., The crystal structure of haemoglobin from Atlantic cod has been solved to 2.54 Å resolution. The structure consists of two tetramers in the crystallographic asymmetric unit. The structure of haemoglobin obtained from one individual cod suggests polymorphism in the tetrameric assembly.
- Published
- 2019
46. The Effects of Acidic, Alkaline, and Neutral Anolytes on Electrochemical Seawater Deoxygenation
- Author
-
Tor Hemmingsen, Magne O. Sydnes, Hans Urkedal, and Utsav Raj Dotel
- Subjects
cation exchange membrane ,Scanning electron microscope ,Inorganic chemistry ,chemistry.chemical_element ,02 engineering and technology ,Electrolyte ,electrolytes ,Conductivity ,010402 general chemistry ,Electrochemistry ,01 natural sciences ,Oxygen ,lcsh:Technology ,lcsh:Chemistry ,General Materials Science ,Instrumentation ,Deoxygenation ,lcsh:QH301-705.5 ,seawater ,Fluid Flow and Transfer Processes ,Chemistry ,pH ,lcsh:T ,Process Chemistry and Technology ,General Engineering ,deoxygenation ,electrochemical ,021001 nanoscience & nanotechnology ,lcsh:QC1-999 ,0104 chemical sciences ,Computer Science Applications ,Membrane ,lcsh:Biology (General) ,lcsh:QD1-999 ,lcsh:TA1-2040 ,Seawater ,0210 nano-technology ,lcsh:Engineering (General). Civil engineering (General) ,oxygen ,lcsh:Physics - Abstract
Electrochemical deoxygenation of seawater has advantages over available chemical and physical methods. For seawater deoxygenation, acidic, neutral, or alkaline anolytes can be used. The effects of acidic, alkaline, and neutral buffered and non-buffered anolytes were studied in two compartment deoxygenation cells. The pH, conductivity, H2O2 production, and current were measured throughout the experiments. The optimum applied potentials for oxygen reduction were between 1.9 V&ndash, 2.2 V, giving water as product, reducing the applied potential also resulted in the formation of H2O2. Analysis after the experiments using a scanning electron microscope with electron-dispersive X-ray spectroscopy showed that both the silver mesh and the cation exchange membrane remained stable during the experiments. The use of alkaline anolytes resulted in the maximum oxygen removal with minimal side reactions in the cell.
- Published
- 2018
47. Catalytic Enantioselective Synthesis of the Partially Reduced Tricyclic Pyrrolo[3,2-c]quinoline Core Structure of theMartinellaAlkaloids
- Author
-
Emil Lindbäck and Magne O. Sydnes
- Subjects
010405 organic chemistry ,Stereochemistry ,Alkaloid ,Quinoline ,Enantioselective synthesis ,General Chemistry ,010402 general chemistry ,01 natural sciences ,0104 chemical sciences ,Catalysis ,chemistry.chemical_compound ,Acetoxy group ,chemistry ,Intramolecular force ,Organic chemistry ,Sharpless asymmetric dihydroxylation ,Trifluoromethanesulfonate - Abstract
A catalytic enantioselective synthesis of the hexahydropyrrolo[3,2-c]quinoline core structure found in the Martinella alkaloids, martinelline and martinellic acid, is described. The synthesis is completed without the use of any chiral building blocks or chiral auxiliaries. The key steps in our synthesis constituted a Sp2-Sp3 Suzuki-Miyaura cross-coupling reaction between a triflate and an N-protected β-aminoethyl boron species to provide a 1,2-dihydroquinoline carrying a N-protected β-aminoethyl group in the 3-position, Sharpless asymmetric dihydroxylation of the 1,2-dihydroquinoline derived from the Suzuki-Miyaura cross-coupling reaction, and an acid promoted intramolecular diastereoselective amido cyclisation with the aid of a neighbouring acetoxy group to provide the tricyclic architecture of martinelline and martinellic acid. Our catalytic enantioselective synthesis provided the hexahydropyrrolo[3,2-c]quinoline core structure of the Martinella alkaloids in 75 % ee.
- Published
- 2016
48. The Use of Microwave For One-pot Reductive Amination
- Author
-
Magne O. Sydnes
- Subjects
Chemistry ,Geography, Planning and Development ,General Earth and Planetary Sciences ,Organic chemistry ,Reductive amination ,Amination ,Microwave ,Water Science and Technology - Published
- 2016
49. Investigation of fixed wavelength fluorescence results for biliary metabolites of polycyclic aromatic hydrocarbons formed in Atlantic cod (Gadus morhua)
- Author
-
Karianne Skogland, Kåre B. Jørgensen, Eeva K. Kemppainen, Magne O. Sydnes, and Daniela M. Pampanin
- Subjects
0106 biological sciences ,Environmental Engineering ,Health, Toxicology and Mutagenesis ,Naphthalenes ,010501 environmental sciences ,Conjugated system ,01 natural sciences ,chemistry.chemical_compound ,Animals ,Bile ,Environmental Chemistry ,Gadus ,Polycyclic Aromatic Hydrocarbons ,0105 earth and related environmental sciences ,Naphthalene ,biology ,010604 marine biology & hydrobiology ,Public Health, Environmental and Occupational Health ,General Medicine ,General Chemistry ,Phenanthrenes ,Phenanthrene ,biology.organism_classification ,Pollution ,Fluorescence ,Wavelength ,Spectrometry, Fluorescence ,Gadus morhua ,chemistry ,Environmental chemistry ,Atlantic cod ,Water Pollutants, Chemical ,Environmental Monitoring - Abstract
Fixed wavelength fluorescence (FF) and synchronous fluorescence scanning (SFS) of fish bile are commonly used methods to analyze for exposure to polycyclic aromatic hydrocarbons (PAHs) from petrogenic and pyrogenic sources. A range of conjugated oxidation products from petrogenic PAHs are normally accumulated in the bile. Therefore their detection is important. In the present study, phenanthrene and naphthalene metabolites, formed in vivo in Atlantic cod (Gadus morhua), were used to study the response of these compounds in both FF and SFS analyses. The selected synthetic metabolites were (−)-(1R,2R)-1,2-dihydrophenanthrene-1,2-diol and (−)-(1R,2R)-1,2-dihydronaphthalene-1,2-diol. The study findings showed that the recommended excitation and emission wavelengths for FF analysis do not comprise the maximum emission wavelengths for these metabolites, providing an incorrect estimation of the PAH exposure. A method developed in our laboratory for the synthesis of (−)-(1R,2R)-1,2-dihydrophenanthrene-1,2-diol is also described.
- Published
- 2016
50. Experimental Study of Silver Cathode for Electrochemical Deoxygenation of Seawater for Enhanced Oil Recovery
- Author
-
Magne O. Sydnes, Hans Urkedal, Utsav Raj Dotel, Kai Vuorilehto, and Tor Hemmingsen
- Subjects
Materials science ,020209 energy ,General Chemical Engineering ,Metallurgy ,02 engineering and technology ,General Chemistry ,021001 nanoscience & nanotechnology ,Electrochemistry ,Industrial and Manufacturing Engineering ,Cathode ,Electrochemical cell ,Corrosion ,law.invention ,Galvanic corrosion ,law ,Plating ,0202 electrical engineering, electronic engineering, information engineering ,Seawater ,Enhanced oil recovery ,0210 nano-technology ,ta116 - Abstract
Seawater injection into reservoirs is a common method to enhance oil recovery. In order to avoid corrosion in pipes, the oxygen has to be removed from the seawater. This study focuses on the use of silver cathodes in electrochemical cells for oxygen removal, and the physical parameters that affect the efficiency of this process. Three electrochemical cells have been constructed and tested with packed bed cathodes made up of pure silver particles and silver plated brass spheres. Experimental results showed that silver was a suitable cathode material for oxygen removal. The most important parameter for optimizing cell performance was the depth of the cathode chamber. In addition, the thickness of the silver plating is also an important parameter to adjust since a too-thin layer results in erosion giving rise to galvanic corrosion between brass and silver, which reduces the efficiency of the cell.
- Published
- 2016
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