31 results on '"Daniel Szulczyk"'
Search Results
2. Menthol- and thymol-based ciprofloxacin derivatives against Mycobacterium tuberculosis: in vitro activity, lipophilicity, and computational studies
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Daniel Szulczyk, Mateusz Woziński, Michał Koliński, Sebastian Kmiecik, Agnieszka Głogowska, Ewa Augustynowicz-Kopeć, Michał A. Dobrowolski, Piotr Roszkowski, Marta Struga, and Krzesimir Ciura
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Medicine ,Science - Abstract
Abstract In this work, we investigated the antitubercular properties of Ciprofloxacin derivatives conjugated with menthol and thymol moieties. For the sixteen derivatives, we established minimal inhibitory concentrations (MIC) using isolates of Mycobacterium tuberculosis that were resistant or susceptible to other antibiotics. For the most potent compound 1‐cyclopropyl‐6‐fluoro‐7‐{4‐[6‐((1R,2S,5R)‐2‐isopropyl‐5‐methylcyclohexyloxy)‐6‐oxohexyl]piperazin‐1‐yl}‐4‐oxo‐1,4‐dihydroquinoline‐3‐carboxylic acid (6), we determined fractional inhibitory concentration index (FICI) values to confirm antibacterial susceptibility and synergistic effects with other reference drugs. In addition, chromatographic studies of all the derivatives demonstrated a significant three to four-fold increase in lipophilicity and affinity to phospholipids compared to Ciprofloxacin. Finally, we conducted structure-based studies of the investigated compounds using molecular docking and taking into account protein target mutations associated with fluoroquinolone resistance. In summary, our findings indicate that the investigated compounds possess tuberculostatic properties, with some showing similar or even better activity against resistant strains compared to reference drugs. Increased lipophilicity and affinity to phospholipids of the new derivatives can offer several advantages for new drug candidates, beyond just improved cell membrane penetration. However, further studies are needed to fully understand their safety, efficacy, and mechanism of action.
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- 2023
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3. Advancements in Personalized CAR-T Therapy: Comprehensive Overview of Biomarkers and Therapeutic Targets in Hematological Malignancies
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Wioletta Olejarz, Karol Sadowski, Daniel Szulczyk, and Grzegorz Basak
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CAR-T ,EVs ,immunotherapy ,biomarkers ,hematological malignancies ,checkpoint inhibitors ,Biology (General) ,QH301-705.5 ,Chemistry ,QD1-999 - Abstract
Chimeric antigen receptor T-cell (CAR-T) therapy is a novel anticancer therapy using autologous or allogeneic T-cells. To date, six CAR-T therapies for specific B-cell acute lymphoblastic leukemia (B-ALL), non-Hodgkin lymphomas (NHL), and multiple myeloma (MM) have been approved by the Food and Drug Administration (FDA). Significant barriers to the effectiveness of CAR-T therapy include cytokine release syndrome (CRS), neurotoxicity in the case of Allogeneic Stem Cell Transplantation (Allo-SCT) graft-versus-host-disease (GVHD), antigen escape, modest antitumor activity, restricted trafficking, limited persistence, the immunosuppressive microenvironment, and senescence and exhaustion of CAR-Ts. Furthermore, cancer drug resistance remains a major problem in clinical practice. CAR-T therapy, in combination with checkpoint blockades and bispecific T-cell engagers (BiTEs) or other drugs, appears to be an appealing anticancer strategy. Many of these agents have shown impressive results, combining efficacy with tolerability. Biomarkers like extracellular vesicles (EVs), cell-free DNA (cfDNA), circulating tumor (ctDNA) and miRNAs may play an important role in toxicity, relapse assessment, and efficacy prediction, and can be implicated in clinical applications of CAR-T therapy and in establishing safe and efficacious personalized medicine. However, further research is required to fully comprehend the particular side effects of immunomodulation, to ascertain the best order and combination of this medication with conventional chemotherapy and targeted therapies, and to find reliable predictive biomarkers.
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- 2024
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4. Design and Synthesis of Menthol and Thymol Derived Ciprofloxacin: Influence of Structural Modifications on the Antibacterial Activity and Anticancer Properties
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Tomasz Szostek, Daniel Szulczyk, Jolanta Szymańska-Majchrzak, Michał Koliński, Sebastian Kmiecik, Dagmara Otto-Ślusarczyk, Aleksandra Zawodnik, Eliza Rajkowska, Kinga Chaniewicz, Marta Struga, and Piotr Roszkowski
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antimicrobial ,Ciprofloxacin ,antibiotic ,thymol ,menthol ,Biology (General) ,QH301-705.5 ,Chemistry ,QD1-999 - Abstract
Sixteen new Ciprofloxacin derivatives were designed and successfully synthesized. In an in silico experiment, lipophilicity was established for obtained compounds. All compounds were screened for antimicrobial activity using standard and clinical strains. As for Gram-positive hospital microorganisms, all tested derivatives were active. Measured MICs were in the range 1–16 µg/mL, confirming high antimicrobial potency. Derivative 12 demonstrated activity against all standard Gram-positive Staphylococci, within the range of 0.8–1.6 µg/mL and was confirmed as the leading structure with MICs 1 µg/mL for S. pasteuri KR 4358 and S. aureus T 5591 (clinical strains). All compounds were screened for their in vitro cytotoxic properties via the MTT method. Three of the examined compounds (3, 11 and 16) showed good activity against cancer cells, and in parallel were found not to be cytotoxic toward normal cells. Doxorubicin SI ranged 0.14–1.11 while the mentioned three ranged 1.9–3.4. Selected Ciprofloxacin derivatives were docked into the crystal structure of topoisomerase II (DNA gyrase) in complex with DNA (PDB ID: 5BTC). In summary, leading structures were established (3, 11, 12 and 16). We have observed poor results in preformed studies for disubstituted derivatives, suggesting that 3-oxo-4-carboxylic acid core is the active DNA-gyrase binding site, and when structural changes were made in this fragment, there was an observed decrease in antibacterial potency.
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- 2022
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5. Novel Tetrazole-Based Antimicrobial Agents Targeting Clinical Bacteria Strains: Exploring the Inhibition of Staphylococcus aureus DNA Topoisomerase IV and Gyrase
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Piotr Roszkowski, Jolanta Szymańska-Majchrzak, Michał Koliński, Sebastian Kmiecik, Małgorzata Wrzosek, Marta Struga, and Daniel Szulczyk
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antimicrobial ,antibacterial ,tetrazole ,gyrase ,topoisomerase ,Biology (General) ,QH301-705.5 ,Chemistry ,QD1-999 - Abstract
Eleven novel imide-tetrazoles were synthesized. In the initial stage of research, in silico structure-based pharmacological prediction was conducted. All compounds were screened for antimicrobial activity using standard and clinical strains. Within the studied group, compounds 1–3 were recognized as leading structures with the most promising results in antimicrobial studies. Minimal inhibitory concentration values for compounds 1, 2, 3 were within the range of 0.8–3.2 μg/mL for standard and clinical Gram-positive and Gram-negative bacterial strains, showing in some cases higher activity than the reference Ciprofloxacin. Additionally, all three inhibited the growth of all clinical Staphylococci panels: Staphylococcus aureus (T5592; T5591) and Staphylococcus epidermidis (5253; 4243) with MIC values of 0.8 μg/mL. Selected compounds were examined in topoisomerase IV decatenation assay and DNA gyrase supercoiling assay, followed by suitable molecular docking studies to explore the possible binding modes. In summary, the presented transition from substrate imide-thioureas to imide-tetrazole derivatives resulted in significant increase of antimicrobial properties. The compounds 1–3 proposed here provide a promising basis for further exploration towards novel antimicrobial drug candidates.
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- 2021
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6. Synthetic Transition from Thiourea-Based Compounds to Tetrazole Derivatives: Structure and Biological Evaluation of Synthesized New N-(Furan-2-ylmethyl)-1H-tetrazol-5-amine Derivatives
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Daniel Szulczyk, Anna Bielenica, Piotr Roszkowski, Michał A. Dobrowolski, Wioletta Olejarz, Sebastian Kmiecik, Małgorzata Podsiad, and Marta Struga
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antimicrobial ,antibacterial ,tetrazole ,cytotoxicity ,crystal structure ,Organic chemistry ,QD241-441 - Abstract
Twelve novel derivatives of N-(furan-2-ylmethyl)-1H-tetrazol-5-amine were synthesized. For obtained compound 8, its corresponding substrate single crystals were isolated and X-ray diffraction experiments were completed. In the initial stage of research, in silico structure-based pharmacological prediction was conducted. All compounds were screened for their antibacterial and antimycobacterial activities using standard and clinical strains. The cytotoxic activity was evaluated against a panel of human cancer cell lines, in contrast to normal (HaCaT) cell lines, by using the MTT method. All examined derivatives were found to be noncytotoxic against normal cell lines. Within the studied group, compound 6 showed the most promising results in antimicrobial studies. It inhibited four hospital S. epidermidis rods’ growth, when applied at the amount of 4 µg/mL. However, the most susceptible to the presence of compound 6 was S. epidermidis T 5501 851/19 clinical strain, for which the MIC value was only 2 µg/mL. Finally, a pharmacophore model was established based on lead compounds from this and our previous work.
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- 2021
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7. Cytotoxicity Evaluation of Novel bis(2-aminoethyl)amine Derivatives
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Daniel Szulczyk, Anna Bielenica, Piotr Roszkowski, Michał A. Dobrowolski, Wioletta Olejarz, Mariola Napiórkowska, and Marta Struga
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bis(2-aminoethyl)amine ,thiourea ,tetrazole ,cytotoxicity ,crystal structure ,Organic chemistry ,QD241-441 - Abstract
Seven novel derivatives of bis(2-aminoethyl)amine were synthesized. For compounds 1 and 7 single crystals were isolated and X-ray diffraction experiments were done. Lipophilicity and drug likeness were calculated in the initial stage of research. All compounds were screened for their in vitro cytotoxic activity against a panel of human cancer cell lines, which is contrary to normal (HaCaT) cell lines, by using the MTT method. Studies were followed by lactate dehydrogenase assay, apoptotic activity, and interleukin-6 assay. Within the studied group, compound 6 showed the most promising results in all biological studies. The strongest influence in A549 cells was denoted for derivative 4, which inhibited interleukin release almost tenfold, as compared to the control.
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- 2020
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8. Synthesis and Biological Evaluation of Novel Indole-Derived Thioureas
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Giuseppina Sanna, Silvia Madeddu, Gabriele Giliberti, Sandra Piras, Marta Struga, Małgorzata Wrzosek, Grażyna Kubiak-Tomaszewska, Anna E. Koziol, Oleksandra Savchenko, Tadeusz Lis, Joanna Stefanska, Piotr Tomaszewski, Michał Skrzycki, and Daniel Szulczyk
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antibacterial activity ,anti-HIV activity ,antiviral activity ,thiourea derivatives of indole ,topoisomerase ,Organic chemistry ,QD241-441 - Abstract
A series of 2-(1H-indol-3-yl)ethylthiourea derivatives were prepared by condensation of 2-(1H-indol-3-yl)ethanamine with appropriate aryl/alkylisothiocyanates in anhydrous media. The structures of the newly synthesized compounds were confirmed by spectroscopic analysis and the molecular structures of 8 and 28 were confirmed by X-ray crystallography. All obtained compounds were tested for antimicrobial activity against Gram-positive cocci, Gram-negative rods and for antifungal activity. Microbiological evaluation was carried out over 20 standard strains and 30 hospital strains. Compound 6 showed significant inhibition against Gram-positive cocci and had inhibitory effect on the S. aureus topoisomerase IV decatenation activity and S. aureus DNA gyrase supercoiling activity. Compounds were tested for cytotoxicity and antiviral activity against a large panel of DNA and RNA viruses, including HIV-1 and other several important human pathogens. Interestingly, derivative 8 showed potent activity against HIV-1 wild type and variants bearing clinically relevant mutations. Newly synthesized tryptamine derivatives showed also a wide spectrum activity, proving to be active against positive- and negative-sense RNA viruses.
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- 2018
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9. Synthesis and Biological Activities of Ethyl 2-(2-pyridylacetate) Derivatives Containing Thiourea, 1,2,4-triazole, Thiadiazole and Oxadiazole Moieties
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Daniel Szulczyk, Piotr Tomaszewski, Michał Jóźwiak, Anna E. Kozioł, Tadeusz Lis, David Collu, Filippo Iuliano, and Marta Struga
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1,2,4-triazole ,1,3,4-thiadiazole ,1,3,4-oxadiazole ,thiourea ,X-ray crystal structure analysis ,biological activity ,Organic chemistry ,QD241-441 - Abstract
Thirty six novel heterocyclic derivatives of ethyl 2-(2-pyridylacetate) were efficiently synthesized. The new compounds involve the linkage of a 2-pyridyl ring with thiosemicarbazide (compounds 1–7), 1,2,4-triazole (compounds 1a–7a), 1,3,4-thiadiazole (compounds 1b–7b), and 1,3,4-oxadiazole (compounds 1f–7f) moieties. The last group of compounds 1e–7e involves the connection of a 2-pyridyl ring with 1,2,4-triazole and thiourea. 1H-NMR, 13C-NMR and MS methods were used to confirm the structures of the obtained derivatives. The molecular structures of 3, 3b, 7a and 7f were further confirmed by X-ray crystallography. All obtained compounds were tested in vitro against a number of microorganisms, including Gram-positive cocci, Gram-negative rods and Candida albicans. In addition, the obtained compounds were tested for cytotoxicity and antiviral activity against HIV-1.
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- 2017
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10. 4-Hydroxy-1-methyl-7-(propan-2-yl)-4-azatricyclo [5.2.2.02,6]undec-8-ene-3,5-dione
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Daniel Szulczyk and Marta Struga
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4-oxatricyclo[5.2.2.02,6]undec-8-ene ,4-azatricyclo[5.2.2.02,6]undec-8-ene ,maleimides ,Inorganic chemistry ,QD146-197 - Abstract
1-Methyl-7-(propan-2-yl)-4-oxatricyclo[5.2.2.02,6]undec-8-ene-3,5-dione (1) as starting material and hydroxylamine were used for the preparation of the title compound 4-hydroxy-1-methyl-7-(propan-2-yl)-4-azatricyclo[5.2.2.02,6]undec-8-ene-3,5-dione (2). This product was characterized by 1H-NMR, 13C-NMR, MS and elemental analysis.
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- 2012
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11. 6-Bromo-2-methylsulfanyl-1,3-benzothiazole
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Michał A. Dobrowolski, Marta Struga, and Daniel Szulczyk
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Crystallography ,QD901-999 - Abstract
The title molecule, C8H6BrNS2, is almost planar with a dihedral angle of 0.9 (1)° between the benzene and thiazole rings. The values of the geometry-based index of aromaticity (HOMA) and the nucleus-independent chemical shift (NICS) for the two cyclic fragments of the title molecule are 0.95 and −9.61, respectively, for the benzene ring, and 0.69 and −7.71, respectively, for the thiazole ring. They show that the benzene ring exhibits substantially higher cyclic π-electron delocalization than the thiazole ring. Comparison with other similar benzothiazole fragments reveals a similar trend.
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- 2011
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12. 4-(3-Fluorophenyl)-1-(propan-2-ylidene)thiosemicarbazone
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Barbara Miroslaw, Daniel Szulczyk, Anna E. Koziol, and Marta Struga
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Crystallography ,QD901-999 - Abstract
The title compound, C10H12FN3S, crystallizes in the same space group (P21/c) as two polymorphic forms of 4-phenyl-1-(propan-2-ylidene)thiosemicarbazone [Jian et al. (2005). Acta Cryst. E61, o653–o654; Venkatraman et al. (2005). Acta Cryst. E61, o3914–o3916]. The arrangement of molecules relative to the twofold screw axes is similar to that in the crystal structure of the lower density polymorph. In the solid state, the molecular conformation is stabilized by an intramolecular N—H...N hydrogen bond. The molecules form centrosymmetric R22(8) dimers in the crystal through pairs of N—H...S hydrogen bonds.
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- 2011
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13. Complexes of 1,5-Disubstituted Tetrazole Derivatives with Cu(Ii) Ions: The Molecular Structure Determination by Xas Spectroscopy with the Cytotoxic and Microbiological Activity Evaluation
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Diana Kalinowska, Marcin Tadeusz Klepka, Daniel Szulczyk, Magdalena Mielczarek-Puta, and Marta Struga
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- 2022
14. Synthetic Transition from Thiourea-Based Compounds to Tetrazole Derivatives: Structure and Biological Evaluation of Synthesized New
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Daniel, Szulczyk, Anna, Bielenica, Piotr, Roszkowski, Michał A, Dobrowolski, Wioletta, Olejarz, Sebastian, Kmiecik, Małgorzata, Podsiad, and Marta, Struga
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tetrazole ,antibacterial ,crystal structure ,Staphylococcus epidermidis ,Thiourea ,Tetrazoles ,antimicrobial ,cytotoxicity ,Article ,Anti-Bacterial Agents - Abstract
Twelve novel derivatives of N-(furan-2-ylmethyl)-1H-tetrazol-5-amine were synthesized. For obtained compound 8, its corresponding substrate single crystals were isolated and X-ray diffraction experiments were completed. In the initial stage of research, in silico structure-based pharmacological prediction was conducted. All compounds were screened for their antibacterial and antimycobacterial activities using standard and clinical strains. The cytotoxic activity was evaluated against a panel of human cancer cell lines, in contrast to normal (HaCaT) cell lines, by using the MTT method. All examined derivatives were found to be noncytotoxic against normal cell lines. Within the studied group, compound 6 showed the most promising results in antimicrobial studies. It inhibited four hospital S. epidermidis rods’ growth, when applied at the amount of 4 µg/mL. However, the most susceptible to the presence of compound 6 was S. epidermidis T 5501 851/19 clinical strain, for which the MIC value was only 2 µg/mL. Finally, a pharmacophore model was established based on lead compounds from this and our previous work.
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- 2020
15. Cytotoxicity Evaluation of Novel bis(2-aminoethyl)amine Derivatives
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Marta Struga, Piotr Roszkowski, Mariola Napiórkowska, Anna Bielenica, Daniel Szulczyk, Michał A. Dobrowolski, and Wioletta Olejarz
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crystal structure ,Pharmaceutical Science ,Antineoplastic Agents ,Apoptosis ,010402 general chemistry ,01 natural sciences ,Article ,Analytical Chemistry ,lcsh:QD241-441 ,chemistry.chemical_compound ,lcsh:Organic chemistry ,Neoplasms ,Lactate dehydrogenase ,Drug Discovery ,Humans ,Tetrazole ,Physical and Theoretical Chemistry ,Cytotoxicity ,thiourea ,A549 cell ,tetrazole ,L-Lactate Dehydrogenase ,Cytotoxins ,Interleukin-6 ,010405 organic chemistry ,Organic Chemistry ,In vitro ,Neoplasm Proteins ,0104 chemical sciences ,HaCaT ,chemistry ,A549 Cells ,Chemistry (miscellaneous) ,bis(2-aminoethyl)amine ,Lipophilicity ,Molecular Medicine ,cytotoxicity ,Amine gas treating ,Caco-2 Cells ,Drug Screening Assays, Antitumor ,Nuclear chemistry - Abstract
Seven novel derivatives of bis(2-aminoethyl)amine were synthesized. For compounds 1 and 7 single crystals were isolated and X-ray diffraction experiments were done. Lipophilicity and drug likeness were calculated in the initial stage of research. All compounds were screened for their in vitro cytotoxic activity against a panel of human cancer cell lines, which is contrary to normal (HaCaT) cell lines, by using the MTT method. Studies were followed by lactate dehydrogenase assay, apoptotic activity, and interleukin-6 assay. Within the studied group, compound 6 showed the most promising results in all biological studies. The strongest influence in A549 cells was denoted for derivative 4, which inhibited interleukin release almost tenfold, as compared to the control.
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- 2020
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16. G protein-coupled receptor binding and pharmacological evaluation of indole-derived thiourea compounds
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Daniel Szulczyk, Ewa Kędzierska, Marta Struga, Anna Bielenica, Irene Saccone, Oleksandra Savchenko, Magdalena Bujalska-Zadrożny, Agata Pawłowska, Anna Leśniak, Ferdinando Fiorino, Rosa Sparaco, Szulczyk, D., Bielenica, A., Kedzierska, E., Lesniak, A., Pawlowska, A., Bujalska-Zadrozny, M., Saccone, I., Sparaco, R., Fiorino, F., Savchenko, O., and Struga, M.
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Male ,Models, Molecular ,Indoles ,Stereochemistry ,Pharmaceutical Science ,Hyperkinesis ,Crystallography, X-Ray ,Serotonergic ,inverse agonist ,01 natural sciences ,Mice ,Structure-Activity Relationship ,chemistry.chemical_compound ,Dopamine receptor D2 ,Drug Discovery ,dopamine receptor ,Animals ,Inverse agonist ,Receptor ,Indole test ,Analgesics ,Binding Sites ,Dose-Response Relationship, Drug ,Molecular Structure ,Receptors, Dopamine D2 ,010405 organic chemistry ,Aryl ,Anti-Inflammatory Agents, Non-Steroidal ,Thiourea ,0104 chemical sciences ,Amphetamine ,010404 medicinal & biomolecular chemistry ,chemistry ,Dopamine receptor ,Receptors, Serotonin, 5-HT2 ,Receptors, Serotonin, 5-HT1 ,serotonin antagonism ,substituent effect - Abstract
Four 2-(1H-indol-3-yl)ethylthiourea derivatives were prepared by condensation of 2-(1H-indol-3-yl)ethanamine with the corresponding aryl/alkylisothiocyanates in a medium-polarity solvent. Their structures were confirmed by spectral techniques, and the molecular structure of 3 was determined by X-ray crystal analysis. For all derivatives, the binding affinities at the 5-HT2A and 5-HT2C receptors, as well as their functional activities at the 5-HT1A and D2 receptors, were determined. The arylthioureas 1 and 4 were the most active at the 5-HT1A receptor, showing, at the same time, significant selectivity over the studied 5-HT2 and D2 receptor subtypes. The compounds were tested for their pharmacological activities within the central nervous system in relevant mouse models. The involvement of the serotonergic system in the activity of 1 and 4 was indicated. The antinociceptive action of 4 was linked to its anti-inflammatory activity.
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- 2020
17. Design and synthesis of novel 1H-tetrazol-5-amine based potent antimicrobial agents: DNA topoisomerase IV and gyrase affinity evaluation supported by molecular docking studies
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Małgorzata Wrzosek, Marta Struga, Michal Kolinski, Sebastian Kmiecik, Anna Bielenica, Daniel Szulczyk, Michał A. Dobrowolski, Wioletta Olejarz, Michał Jóźwiak, Piotr Roszkowski, and Joanna Stefańska
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DNA Topoisomerase IV ,Models, Molecular ,0301 basic medicine ,Topoisomerase IV ,Stereochemistry ,Tetrazoles ,Microbial Sensitivity Tests ,01 natural sciences ,DNA gyrase ,Cell Line ,03 medical and health sciences ,chemistry.chemical_compound ,Drug Discovery ,Humans ,Topoisomerase II Inhibitors ,Tetrazole ,Triethylamine ,Amination ,Pharmacology ,Bacteria ,biology ,010405 organic chemistry ,Organic Chemistry ,Bacterial Infections ,General Medicine ,Antimicrobial ,Anti-Bacterial Agents ,0104 chemical sciences ,Molecular Docking Simulation ,030104 developmental biology ,Thiourea ,chemistry ,DNA Gyrase ,Drug Design ,biology.protein ,Sodium azide ,Amine gas treating - Abstract
A total of 14 of 1,5-disubstituted tetrazole derivatives were prepared by reacting appropriate thiourea and sodium azide in the presence of mercury (II) chloride and triethylamine. All compounds were evaluated in vitro for their antimicrobial activity. Derivatives 10 and 11 showed the highest inhibition against Gram-positive and Gram-negative strains (standard and hospital strains). The observed minimal inhibitory concentrations values were in the range of 1–208 μM (0.25–64 μg/ml). Inhibitory activity of 1,5-tetrazole derivatives 10 and 11 against gyrase and topoisomerase IV isolated from S. aureus was studied. Evaluation was supported by molecular docking studies for all synthesized derivatives and reference ciprofloxacin. Moreover, selected tetrazoles (2, 3, 5, 6, 8, 9, 10 and 11) were evaluated for their cytotoxicity. All tested compounds are non-cytotoxic against HaCaT and A549 cells (CC50 ≤ 60 μM).
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- 2018
18. The unexpected product of Diels-Alder reaction between 'indanocyclon' and maleimide
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Marta Struga, Daniel Szulczyk, Piotr Roszkowski, and Michał A. Dobrowolski
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chemistry.chemical_classification ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,010402 general chemistry ,01 natural sciences ,Medicinal chemistry ,0104 chemical sciences ,Analytical Chemistry ,Inorganic Chemistry ,chemistry.chemical_compound ,Heterocyclic compound ,Product (mathematics) ,Diels alder ,Organic chemistry ,Single crystal ,Maleimide ,Spectroscopy ,Diels–Alder reaction - Abstract
A heterocyclic compound commonly known as “indanocyclon” undergoes an unexpected Diels-Alder addition with maleimide. The resulting product has been isolated and characterized in order to get an information about its structure and possible mechanism of the reaction. Extensive comparison of single crystal properties of 3-(2,8-dioxo-1,3-diphenyl-2,8-dihydrocyclopenta[a]inden-8a(1H)-yl)pyrrolidine-2,5-dione and favorable product of the reaction has been also performed.
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- 2017
19. Development of (4-methoxyphenyl)-1H-tetrazol-5-amine regioisomers as a new class of selective antitubercular agents
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Marta Struga, Ewa Augustynowicz-Kopeć, Anna Bielenica, Karolina Stępień, Daniel Szulczyk, Agnieszka Głogowska, Michał A. Dobrowolski, Alicja Chrzanowska, and Piotr Roszkowski
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medicine.drug_class ,Stereochemistry ,Mycobacterium scrofulaceum ,Antitubercular Agents ,Tetrazoles ,Microbial Sensitivity Tests ,Antimycobacterial ,01 natural sciences ,Cell Line ,Mycobacterium ,Mycobacterium tuberculosis ,03 medical and health sciences ,chemistry.chemical_compound ,Structure-Activity Relationship ,Drug Discovery ,medicine ,Humans ,Tetrazole ,Amines ,Ethambutol ,030304 developmental biology ,Pharmacology ,0303 health sciences ,biology ,Cell Death ,Dose-Response Relationship, Drug ,Molecular Structure ,010405 organic chemistry ,Organic Chemistry ,Isoniazid ,General Medicine ,biology.organism_classification ,0104 chemical sciences ,Thiourea ,chemistry ,Amine gas treating ,medicine.drug - Abstract
A series of halogenated (4-methoxyphenyl)-1H-tetrazol-5-amine regioisomers (1a-9a, 1b-9b) were synthesized from their corresponding thiourea analogues (1–9). The synthesis pathway was confirmed by an X-ray crystallographic studies of 1a, 1b and 5a. Title derivatives were tested for their in vitro antitubercular activity against standard, “wild-type” and atypical mycobacteria. The highest therapeutic potential was attributed to isomeric N-(bromophenyl)tetrazoles 8a and 9a. Their growth-inhibitory effect against multidrug-resistant Mycobacterium tuberculosis Spec. 210 was 8-16-fold stronger than that of the first-line tuberculostatics. Other new tetrazole-derived compounds were also more or equally effective towards that pathogen comparing to the established pharmaceuticals. Among non-tuberculous strains, Mycobacterium scrofulaceum was the most susceptible to the presence of the majority of tetrazole derivatives. The synergistic interaction was found between 9a and streptomycin, as well as the additivity of both 8a and 9a in pairs with isoniazid, rifampicin and ethambutol. None of the studied compounds displayed antibacterial or cytotoxic properties against normal and cancer cell lines, which indicated their highly selective antimycobacterial effects.
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- 2019
20. Synthetic Transition from Thiourea-Based Compounds to Tetrazole Derivatives: Structure and Biological Evaluation of Synthesized New N-(Furan-2-ylmethyl)-1H-tetrazol-5-amine Derivatives
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Michał A. Dobrowolski, Sebastian Kmiecik, Daniel Szulczyk, Anna Bielenica, Wioletta Olejarz, Marta Struga, Piotr Roszkowski, and Małgorzata Podsiad
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crystal structure ,medicine.drug_class ,Pharmaceutical Science ,010402 general chemistry ,Antimycobacterial ,01 natural sciences ,Analytical Chemistry ,lcsh:QD241-441 ,chemistry.chemical_compound ,lcsh:Organic chemistry ,Furan ,Drug Discovery ,medicine ,Tetrazole ,Physical and Theoretical Chemistry ,tetrazole ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,Substrate (chemistry) ,Antimicrobial ,0104 chemical sciences ,antibacterial ,HaCaT ,Thiourea ,Chemistry (miscellaneous) ,antimicrobial ,cytotoxicity ,Molecular Medicine ,Pharmacophore ,Nuclear chemistry - Abstract
Twelve novel derivatives of N-(furan-2-ylmethyl)-1H-tetrazol-5-amine were synthesized. For obtained compound 8, its corresponding substrate single crystals were isolated and X-ray diffraction experiments were completed. In the initial stage of research, in silico structure-based pharmacological prediction was conducted. All compounds were screened for their antibacterial and antimycobacterial activities using standard and clinical strains. The cytotoxic activity was evaluated against a panel of human cancer cell lines, in contrast to normal (HaCaT) cell lines, by using the MTT method. All examined derivatives were found to be noncytotoxic against normal cell lines. Within the studied group, compound 6 showed the most promising results in antimicrobial studies. It inhibited four hospital S. epidermidis rods&rsquo, growth, when applied at the amount of 4 µ, g/mL. However, the most susceptible to the presence of compound 6 was S. epidermidis T 5501 851/19 clinical strain, for which the MIC value was only 2 µ, g/mL. Finally, a pharmacophore model was established based on lead compounds from this and our previous work.
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- 2021
21. Synthesis and Biological Evaluation of Novel Indole-Derived Thioureas
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Grażyna Kubiak-Tomaszewska, Marta Struga, Oleksandra Savchenko, Joanna Stefańska, Silvia Madeddu, Michał Skrzycki, Anna E. Koziol, Tadeusz Lis, Małgorzata Wrzosek, Daniel Szulczyk, Giuseppina Sanna, Gabriele Giliberti, Piotr Tomaszewski, and Sandra Piras
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Tryptamine ,DNA Topoisomerase IV ,Staphylococcus aureus ,Indoles ,Topoisomerase IV ,Pharmaceutical Science ,Microbial Sensitivity Tests ,Crystallography, X-Ray ,01 natural sciences ,DNA gyrase ,Article ,Analytical Chemistry ,lcsh:QD241-441 ,chemistry.chemical_compound ,thiourea derivatives of indole ,lcsh:Organic chemistry ,antibacterial activity ,Drug Discovery ,Humans ,Topoisomerase II Inhibitors ,Physical and Theoretical Chemistry ,topoisomerase ,biology ,Molecular Structure ,010405 organic chemistry ,Topoisomerase ,anti-HIV activity ,Organic Chemistry ,Thiourea ,RNA ,0104 chemical sciences ,Anti-Bacterial Agents ,010404 medicinal & biomolecular chemistry ,chemistry ,Biochemistry ,Chemistry (miscellaneous) ,DNA Gyrase ,biology.protein ,antiviral activity ,Molecular Medicine ,DNA supercoil ,Antibacterial activity ,DNA - Abstract
A series of 2-(1H-indol-3-yl)ethylthiourea derivatives were prepared by condensation of 2-(1H-indol-3-yl)ethanamine with appropriate aryl/alkylisothiocyanates in anhydrous media. The structures of the newly synthesized compounds were confirmed by spectroscopic analysis and the molecular structures of 8 and 28 were confirmed by X-ray crystallography. All obtained compounds were tested for antimicrobial activity against Gram-positive cocci, Gram-negative rods and for antifungal activity. Microbiological evaluation was carried out over 20 standard strains and 30 hospital strains. Compound 6 showed significant inhibition against Gram-positive cocci and had inhibitory effect on the S. aureus topoisomerase IV decatenation activity and S. aureus DNA gyrase supercoiling activity. Compounds were tested for cytotoxicity and antiviral activity against a large panel of DNA and RNA viruses, including HIV-1 and other several important human pathogens. Interestingly, derivative 8 showed potent activity against HIV-1 wild type and variants bearing clinically relevant mutations. Newly synthesized tryptamine derivatives showed also a wide spectrum activity, proving to be active against positive- and negative-sense RNA viruses.
- Published
- 2018
22. 1H-Tetrazol-5-amine and 1,3-thiazolidin-4-one derivatives containing 3-(trifluoromethyl)phenyl scaffold: Synthesis, cytotoxic and anti-HIV studies
- Author
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Anna Bielenica, Wioletta Olejarz, Gabriele Giliberti, Anna E. Koziol, Daniel Szulczyk, Marta Struga, Silvia Madeddu, and Ilona B. Materek
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Anti-HIV Agents ,Tetrazoles ,Antineoplastic Agents ,HIV Infections ,Crystallography, X-Ray ,01 natural sciences ,chemistry.chemical_compound ,Structure-Activity Relationship ,Cell Line, Tumor ,Neoplasms ,Humans ,MTT assay ,Amines ,Cytotoxicity ,Cells, Cultured ,Pharmacology ,Trifluoromethyl ,010405 organic chemistry ,Biological activity ,General Medicine ,Combinatorial chemistry ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,HaCaT ,Thiourea ,chemistry ,Biochemistry ,Cell culture ,Thiazolidines ,Amine gas treating - Abstract
On the basis of recently reported biologically active 3-(trifluoromethyl)phenylthioureas, a series of diaryl derivatives incorporating 1 H -tetrazol-5-yl ( 1a–11a , 1a’–11a’ ) and 1,3-thiazolidin-4-one ( 1b–11b ) scaffolds were synthesized. The synthesis pathway was confirmed by an X-ray crystallographic studies of 3a’ , 6a , 8a , 6b and 8b . The cytotoxicity against MT-4 cells and anti-HIV properties of new derivatives were evaluated. As compared to initial thiourea connections, the cyclisation reduced the cytotoxicity of compounds by 2–15 times. The most promising N-(4-nitrophenyl)-1 H -tetrazol-5-amine 7a was found to be more active than the origin thiourea. Its cytotoxicity was evaluated on A549, HTB-140 and HaCaT cell lines using MTT assay. The compound shows significant influence on cancer, but not on normal cells. Obtained results can provide some constructive data for further designing of novel family of potentially bioactive analogs.
- Published
- 2017
23. Synthesis and Biological Activities of Ethyl 2-(2-pyridylacetate) Derivatives Containing Thiourea, 1,2,4-triazole, Thiadiazole and Oxadiazole Moieties
- Author
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Anna E. Koziol, David Collu, Filippo Iuliano, Piotr Tomaszewski, Michał Jóźwiak, Daniel Szulczyk, Tadeusz Lis, and Marta Struga
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Models, Molecular ,Pharmaceutical Science ,Oxadiazole ,biological activity ,Microbial Sensitivity Tests ,010402 general chemistry ,Ring (chemistry) ,Crystallography, X-Ray ,01 natural sciences ,Article ,Analytical Chemistry ,X-ray crystal structure analysis ,Cell Line ,lcsh:QD241-441 ,chemistry.chemical_compound ,Structure-Activity Relationship ,1,2,4-triazole ,lcsh:Organic chemistry ,Anti-Infective Agents ,Drug Discovery ,Thiadiazoles ,1,3,4-oxadiazole ,Organic chemistry ,Humans ,Physical and Theoretical Chemistry ,Candida albicans ,Cytotoxicity ,Heterocyclic derivatives ,Cells, Cultured ,1,3,4-thiadiazole ,Oxadiazoles ,biology ,Bacteria ,Molecular Structure ,010405 organic chemistry ,Organic Chemistry ,Fungi ,Thiourea ,1,2,4-Triazole ,thiourea ,Triazoles ,biology.organism_classification ,In vitro ,0104 chemical sciences ,chemistry ,Chemistry (miscellaneous) ,HIV-1 ,Molecular Medicine - Abstract
Thirty six novel heterocyclic derivatives of ethyl 2-(2-pyridylacetate) were efficiently synthesized. The new compounds involve the linkage of a 2-pyridyl ring with thiosemicarbazide (compounds 1–7), 1,2,4-triazole (compounds 1a–7a), 1,3,4-thiadiazole (compounds 1b–7b), and 1,3,4-oxadiazole (compounds 1f–7f) moieties. The last group of compounds 1e–7e involves the connection of a 2-pyridyl ring with 1,2,4-triazole and thiourea. 1H-NMR, 13C-NMR and MS methods were used to confirm the structures of the obtained derivatives. The molecular structures of 3, 3b, 7a and 7f were further confirmed by X-ray crystallography. All obtained compounds were tested in vitro against a number of microorganisms, including Gram-positive cocci, Gram-negative rods and Candida albicans. In addition, the obtained compounds were tested for cytotoxicity and antiviral activity against HIV-1.
- Published
- 2017
24. Disubstituted thiourea derivatives and their activity on CNS: Synthesis and biological evaluation
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Bernardetta Busonera, Anna E. Koziol, Gabriele Giliberti, Daniel Szulczyk, Joanna Stefańska, Ewa Kędzierska, Giuseppina Sanna, Sylwia Fidecka, Marta Struga, Barbara Miroslaw, and Paolo La Colla
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Central Nervous System ,Male ,Anti-HIV Agents ,Stereochemistry ,Chemistry Techniques, Synthetic ,Motor Activity ,Mice ,chemistry.chemical_compound ,Anti-Infective Agents ,Cell Line, Tumor ,Drug Discovery ,Animals ,Humans ,Endogenous opioid ,Pharmacology ,Bacteria ,Behavior, Animal ,Chemistry ,Aryl ,Organic Chemistry ,Fungi ,Thiourea ,Biological activity ,General Medicine ,Carbon-13 NMR ,Drug Design ,Isothiocyanate ,Proton NMR ,Antibacterial activity - Abstract
A series of new thiourea derivatives of 1,2,4-triazole have been synthesized. The difference in structures of obtained compounds are directly connected with the kind of isothiocyanate (aryl/alkyl). The 1H NMR, 13C NMR, MS methods were used to confirm structures of obtained thiourea derivatives. The molecular structure of (1, 17) was determined by an X-ray analysis. Two of the new compounds (8 and 14) were tested for their pharmacological activity on animal central nervous system (CNS) in behavioural animal tests. The results presented in this work indicate the possible involvement of the serotonergic system in the activity of 8 and 14. In the case of 14 is also a possible link between its activity and the endogenous opioid system. All obtained compounds were tested for antibacterial activity against Gram-positive cocci, Gram-negative rods and antifungal activity. Compounds (1, 2, 5, 7, 9) showed significant inhibition against Gram-positive cocci. Microbiological evaluation was carried out over 20 standard strains and 30 hospital strains. Selected compounds (1–13) were examined for cytotoxicity, antitumor, and anti-HIV activity.
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- 2012
25. Antimicrobial and anti-biofilm activity of thiourea derivatives incorporating a 2-aminothiazole scaffold
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Marta Struga, Anna Filipowska, Daniel Szulczyk, Stefano Boi, Silvia Madeddu, Anna E. Koziol, Paolo La Colla, Giuseppina Sanna, Ewa Augustynowicz-Kopeć, Wojciech Filipowski, Anna Bielenica, Aleksandra Drzewiecka, Gabriele Giliberti, Agnieszka Napiórkowska, Joanna Stefańska, and Grażyna Nowicka
- Subjects
Microbial Sensitivity Tests ,Coxsackievirus ,Microbiology ,chemistry.chemical_compound ,Anti-Infective Agents ,Cricetinae ,Drug Discovery ,Chlorocebus aethiops ,Animals ,Humans ,Cytotoxicity ,Candida albicans ,Vero Cells ,biology ,Dose-Response Relationship, Drug ,Biofilm ,Thiourea ,General Chemistry ,General Medicine ,biology.organism_classification ,Antimicrobial ,In vitro ,Thiazoles ,chemistry ,Biofilms ,Cattle ,DNA - Abstract
A series of new thiourea derivatives of 1,3-thiazole have been synthesized. All obtained compounds were tested in vitro against a number of microorganisms, including Gram-positive cocci, Gram-negative rods and Candida albicans. Compounds were also tested for their in vitro tuberculostatic activity against the Mycobacterium tuberculosis H37Rv strain, as well as two 'wild' strains isolated from tuberculosis patients. Compounds 3 and 9 showed significant inhibition against Gram-positive cocci (standard strains and hospital strain). The range of MIC values is 2-32 µg/mL. Products 3 and 9 effectively inhibited the biofilm formation of both methicillin-resistant and standard strains of S. epidermidis. The halogen atom, especially at the 3rd position of the phenyl group, is significantly important for this antimicrobial activity. Moreover, all obtained compounds resulted in cytotoxicity and antiviral activity on a large set of DNA and RNA viruses, including Human Immunodeficiency Virus type 1 (HIV-1) and other several important human pathogens. Compound 4 showed activity against HIV-1 and Coxsackievirus type B5. Seven compounds resulted in cytotoxicity against MT-4 cells (CC50
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- 2015
26. Antimicrobial and Anti-biofilm Activity of Thiourea Derivatives Bearing 3-amino-1H-1,2,4-triazole Scaffold
- Author
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Karolina Stępień, Daniel Szulczyk, Anna E. Koziol, Giuseppina Sanna, Anna Bielenica, Joanna Stefańska, Marta Struga, Filippo Iuliano, Michal Jozwiak, Silvia Madeddu, and Barbara Miroslaw
- Subjects
Methicillin-Resistant Staphylococcus aureus ,Stereochemistry ,Triazole ,Microbial Sensitivity Tests ,010402 general chemistry ,01 natural sciences ,chemistry.chemical_compound ,Drug Discovery ,Staphylococcus epidermidis ,Cytotoxicity ,010405 organic chemistry ,Aryl ,Thiourea ,1,2,4-Triazole ,Triazoles ,Antimicrobial ,0104 chemical sciences ,Anti-Bacterial Agents ,Thioamides ,chemistry ,Reagent ,Biofilms ,Isothiocyanate ,Methicillin Resistance ,Nuclear chemistry - Abstract
A set of 21 thiourea derivatives were prepared through reacting 3-amino-1H-1,2,4-triazole with the commercial aliphatic and aromatic isothiocyanates. The aliphatic isothiocyanate was used as reagent leading to substitution on NH atom of 3-aminotriazole ring, whereas the triazole amino group was substituted when isothiocyanate group was bonded to the Csp2 hybridized atom, e.g. an aryl or C=O fragment. All compounds were evaluated in vitro for the antimicrobial activity. The derivatives 1, 2, 4, 8, 9, 10 and 12 showed the highest inhibition against Gram-positive cocci (S. aureus and S. epidermidis). The observed MIC values were in the range of 4-32 μg/mL. Compounds were also tested for their in vitro antimicrobial activity against the hospital methicillin-resistant strains of S. aureus. The observed MIC values varied from 4 to 64 μg/mL. The products 4 and 10 effectively inhibited the formation of biofilms of the methicillin-resistant and standard strains of S. epidermidis. The compound 10 was found to be more promising with IC50 values of 2-6 μg/mL as compared to the control. Moreover, the cytotoxicity against the MT-4 cells of all studied thioureas was evaluated. The compound 18 was significantly cytotoxic (CC50 = 8 μM).
- Published
- 2015
27. Vibrational spectroscopy (FT-IR and Laser-Raman) investigation, and computational (M06-2X and B3LYP) analysis on the structure of 4-(3-fluorophenyl)-1-(propan-2-ylidene)-thiosemicarbazone
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Marta Struga, Hatice Doğan, Yusuf Sert, Barbara Miroslaw, Çağrı Çırak, and Daniel Szulczyk
- Subjects
Models, Molecular ,Thiosemicarbazones ,Hydrocarbons, Fluorinated ,Molecular Structure ,Chemistry ,Analytical chemistry ,Infrared spectroscopy ,Spectrum Analysis, Raman ,Potential energy ,Atomic and Molecular Physics, and Optics ,Analytical Chemistry ,Bond length ,Molecular geometry ,Correlation function ,Spectroscopy, Fourier Transform Infrared ,Physics::Atomic and Molecular Clusters ,Density functional theory ,Physics::Chemical Physics ,Instrumentation ,HOMO/LUMO ,Spectroscopy ,Basis set ,Software - Abstract
In this study, the experimental and theoretical vibrational spectral analysis of 4-(3-fluorophenyl)-1-(propan-2-ylidene)-thiosemicarbazone have been carried out. The experimental FT-IR (4000–400 cm−1) and Laser-Raman spectra (4000–100 cm−1) have been recorded for the solid state samples. The theoretical vibrational frequencies and the optimized geometric parameters (bond lengths and angles) have been calculated for gas phase using density functional theory (DFT/B3LYP: Becke, 3-parameter, Lee–Yang–Parr) and M06-2X (the highly parametrized, empirical exchange correlation function) quantum chemical methods with 6-311++G(d,p) basis set. The diversity in molecular geometry of fluorophenyl substituted thiosemicarbazones has been discussed based on the X-ray crystal structure reports and theoretical calculation results from the literature. The assignments of the vibrational frequencies have been done on the basis of potential energy distribution (PED) analysis by using VEDA4 software. A good correlation was found between the computed and experimental geometric and vibrational data. In addition, the highest occupied (HOMO) and lowest unoccupied (LUMO) molecular orbital energy levels and other related molecular energy values of the compound have been determined using the same level of theoretical calculations.
- Published
- 2014
28. 6-Bromo-2-methylsulfanyl-1,3-benzothiazole
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Marta Struga, Daniel Szulczyk, and Michał A. Dobrowolski
- Subjects
Aromaticity ,General Chemistry ,Dihedral angle ,Condensed Matter Physics ,Ring (chemistry) ,Bioinformatics ,Organic Papers ,Medicinal chemistry ,lcsh:Chemistry ,Delocalized electron ,chemistry.chemical_compound ,lcsh:QD1-999 ,chemistry ,Sulfanyl ,General Materials Science ,Benzene - Abstract
The title molecule, C8H6BrNS2, is almost planar with a dihedral angle of 0.9 (1)° between the benzene and thiazole rings. The values of the geometry-based index of aromaticity (HOMA) and the nucleus-independent chemical shift (NICS) for the two cyclic fragments of the title molecule are 0.95 and −9.61, respectively, for the benzene ring, and 0.69 and −7.71, respectively, for the thiazole ring. They show that the benzene ring exhibits substantially higher cyclic π-electron delocalization than the thiazole ring. Comparison with other similar benzothiazole fragments reveals a similar trend.
- Published
- 2011
29. 4-(3-Fluorophenyl)-1-(propan-2-ylidene)thiosemicarbazone
- Author
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Marta Struga, Daniel Szulczyk, Barbara Miroslaw, and Anna E. Koziol
- Subjects
Crystallography ,Hydrogen bond ,Solid-state ,Thio ,General Chemistry ,Crystal structure ,Condensed Matter Physics ,Bioinformatics ,Organic Papers ,Crystal ,chemistry.chemical_compound ,chemistry ,QD901-999 ,General Materials Science ,Semicarbazone - Abstract
The title compound, C10H12FN3S, crystallizes in the same space group (P21/c) as two polymorphic forms of 4-phenyl-1-(propan-2-ylidene)thiosemicarbazone [Jian et al. (2005). Acta Cryst. E61, o653–o654; Venkatraman et al. (2005). Acta Cryst. E61, o3914–o3916]. The arrangement of molecules relative to the twofold screw axes is similar to that in the crystal structure of the lower density polymorph. In the solid state, the molecular conformation is stabilized by an intramolecular N—H...N hydrogen bond. The molecules form centrosymmetric R22(8) dimers in the crystal through pairs of N—H...S hydrogen bonds.
- Published
- 2011
30. Synthesis and structure evaluation of new complex butylarylpiperazin-1-yl derivatives
- Author
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Marta Struga, Anna Bielenica, Mariola Krawiecka, Daniel Szulczyk, Bożena Kuran, Łukasz Dobrzycki, and Michał A. Dobrowolski
- Subjects
Chemistry ,Ligand binding assay ,Pharmacology toxicology ,Organic Chemistry ,Human immunodeficiency virus (HIV) ,medicine.disease_cause ,Combinatorial chemistry ,Arylpiperazines ,Pharmacology, Toxicology and Pharmaceutics(all) ,Diels–Alder reaction ,medicine ,5-HT1A receptor ,General Pharmacology, Toxicology and Pharmaceutics ,Receptor ,Arylpiperazine derivatives ,Original Research ,X-ray crystallography - Abstract
A series of arylpiperazine derivatives of 1,16-diphenyl-19-azahexacyclo-[14.5.1.02,15.03,8.09,14.017,21]docosa-2,3,5,7,8,9,11,13,14-nonaene-18,20,22-trione and 4,10-diphenyl-1H,2H,3H,5H-indeno[1,2-f]isoindole-1,3,5-trione was synthesized. The pharmacological profile of compound 4 at the 5-HT1A receptor was measured by binding assay. The title compounds were tested in cell-based assay against the human immunodeficiency virus type-1. The X-ray crystallographic studies of derivatives 2, 6, 7, 11, 19, and 20 were presented.
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31. Synthesis and preliminary evaluation of antimicrobial activity of selected derivatives of 2-benzofurancarboxylic acid
- Author
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Krawiecka, M., Kuran, B., Daniel Szulczyk, Kossakowski, J., Szymanek, K., and Młynarczyk, G.
Catalog
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