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The diorganotin(IV) complexes (5-20) were synthesized in the present research from 4-fluorophenoxyacetic hydrazide and salicylaldehyde derivatives-based hydrazone ligands (1-4) to get an effective biological agent to combat microbial and oxidant deformities. Numerous spectral techniques such as ( 1 H, 13 C, 119 Sn) NMR, UV-Vis, IR, and mass spectrometry were executed to illuminate the composition of complexes. These techniques ascertained tridentate chelation of hydrazone ligands with tin metal through enolic, phenolic oxygens and imine nitrogen, revealing pentacoordinated geometry of the complexes. The single crystal XRD of complex (5) confirmed distorted trigonal bipyramidal geometry. The TGA studies showed thermal stability up to 180 °C of the complexes, whereas the low conductance observed pointed to the non-electrolytic nature of the compounds. Furthermore, serial dilution assay was implemented to uncover the microbial inhibition efficacy (against six strains) of the compounds using ciprofloxacin and fluconazole. Among the synthesized compounds, (1, 8) exhibited comparable MIC value to standard. The compound (8) was reported as four times more potent than the fluconazole against C. albicans. Using DPPH assay, the antioxidant efficiency was examined which advocates enhanced efficacy of complexes than the ligands. The potency of complex (8) against C. albicans makes it a point of interest for molecular docking investigation, so, complex (8) and its ligand (1) were studied against protein of C. albicans (5TZ1), revealing the more efficacy of complex (binding energy-11.6 kcal/mol) than ligand. Further, the compounds were analysed for ADME prediction which concluded the efficacy of compounds as orally efficient pharmaceuticals., (© 2024. The Author(s), under exclusive licence to Springer Nature B.V.)

Bacterial diseases caused by superbugs are expected to be the main cause of death worldwide within a decade as a consequence of the resistance they are acquiring to the antibiotics currently in use, therefore, the field of new antibacterial treatments is currently being thoroughly studied. The present work focuses on the synthesis, functionalization, characterization and antibacterial behaviour of different systems based on three different silica-based nanostructured materials (MSN, mesoporous silica nanoparticles, SBA-15 Santa Barbara amorphous-15 and FSP fibrous slica nanoparticles) which serve as scaffolds for the support of different platforms to target and treat bacterial diseases and biofilm formation. Thus, (3-carboxypropyl)triphenylphosphonium bromide (PPh 3 + ) and a cytotoxic organotin(IV) fragment (Sn) have been incorporated in the silica-based materials to study their potential activity in different antibacterial applications. After a complete characterization of the synthesized systems, which confirmed the incorporation of both the targeting and the therapeutic fragments within the nanostructured materials, the antibacterial study of the materials demonstrated bactericidal capacity against Escherichia coli and perturbation of the bacteria metabolism via oxidative stress through an enhanced ROS (reactive oxygen species) production. In addition, biofilm inhibition and eradication tests of bacterial strains were carried out, showing that the activity of the materials in both biofilm inhibition and eradication is dependent on the concentration of the material. Furthemore, the material MSN-AP(1:1)-PPh 3 + -Sn containing the targeting triphenylphosphonium and a "SnPh 3 " fragment is capable of inhibiting and eradicating up to 50% of the formation of biofilms, which is outstanding for metallodrug-functionalized silica-based systems compared with other materials based on metal nanoparticles supported on silica. Finally, a hemolysis study was carried out with the nanostructured systems proving to be non-toxic, making them adequate for their subsequent use in preclinical trials through in vivo models.

Three distinctive end group-containing organotin (IV) carboxylates complexes (YDCOOSn, CLCOOSn and BZCOOSn) were designed and synthesized. Together with theoretical calculations, a thorough examination was carried out to investigate the photophysical properties of these compounds. The cytotoxicity of the synthesized compounds was tested using normal cell line GES-1 and was assessed against four cancer cell lines (A549, Hela, H1299 and HepG2). The outcomes of the experiments demonstrated that these complexes had superior selectivity than cisplatin towards cancerous cells, particularly in the A549 cell line. BZCOOSn was selected as a candidate compound for additional research because it exhibited the lowest IC 50 value and the most impressive inducing effect on cell death and G2/M phase arrest. Increased caspase-3 and -9 enzyme activity, a decline in mitochondrial membrane potential (MMP), characteristic nuclear apoptotic morphology, and an accumulation of intracellular reactive oxygen species (ROS) were seen in A549 exposed to BZCOOSn. These findings demonstrated that BZCOOSn exhibited strong cytotoxicity by triggering cell death in A549 via the mitochondrial route. Furthermore, using the scratch wound healing assay, it was discovered that BZCOOSn reduced the migration of A549 cancerous cells. These data all pointed to BZCOOSn as a possible candidate for more research and development as a chemotherapeutic drug., Competing Interests: Declaration of competing interest We certify that none of the work disclosed in this publication may have been influenced by any known conflicting financial interests or personal relationships., (Copyright © 2024 Elsevier Inc. All rights reserved.)

Organotin(IV) and iridium(III) complexes have shown good application potential in the field of anticancer; however, the aggregation-caused quenching (ACQ) effect induced by high concentration or dose has limited the research on their targeting and anticancer mechanism. Then, a series of aggregation-induced emission (AIE)-activated butyltin(IV)-iridium(III) imidazole-phenanthroline complexes were prepared in this study. Complexes exhibited significant fluorescence improvement in the aggregated state because of the restricted intramolecular rotation (RIR), accompanied by an absolute fluorescence quantum yield of up to 29.2% (IrSn9). Complexes demonstrated potential in vitro antiproliferative and antimigration activity against A549 cells, following a lysosomal-mitochondrial apoptotic pathway. Nude mouse models further confirmed that complexes had favorable in vivo antitumor and antimigration activity in comparison to cisplatin. Therefore, butyltin(IV)-iridium(III) imidazole-phenanthroline complexes possess the potential as potential substitutes for platinum-based drugs.

Nine new organotin (IV) derivatives from L-amino acids (l-lysine, L-ornithine, L-glutamic acid, and L-aspartic acid) were synthesized by one-pot ultrasound-assisted methodology. All compounds were characterized by ATR-FTIR (Attenuated Total Reflectance-Fourier Transform Infrared), LRMS (Low-Resolution Mass Spectrometry), and solution NMR ( 1 H, 13 C, 119 Sn Nuclear Magnetic Resonance) spectroscopies. Complexes Bu 2 Sn(Lys) (1), Ph 2 Sn(Lys) (2), Bu 2 Sn(Orn) (3), and Ph 2 Sn (Glu-OMe) (6a) were crystallized, and the structures were established by single-crystal X-ray diffraction analysis. Diffraction results evidenced that complexes 1 to 3 were five-coordinated mononuclear species while the phenyl substituted derivative Ph 2 Sn (Glu-OMe) (6a) forms a polymeric network via Sn-O-Sn bridging whereby the tin atom is six-coordinated. In turn, 119 Sn NMR results revealed that all tin complexes exist as mononuclear penta-coordinated species in solution. The tin derivatives were screened for ADME (Adsorption, Distribution, Metabolism, and Excretion) properties via the freely available tools SWISS ADME, and the results were analyzed hereafter. The antiproliferative activity of the complexes was tested against three human cancer cell lines: colorectal adenocarcinoma HT-29, breast adenocarcinoma MDA-MB-231, and chondrosarcoma SW-1353 using a non-tumoral cell line of human osteoblast as control, demonstrating selective inhibitory activities against cancer cells. Hence, these compounds could be a promising alternative to classical chemotherapy agents., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2023. Published by Elsevier Inc.)

Many diorganotin complexes with various alkyl groups exhibit excellent in vitro anticancer activity. However, most diorganotin is the same alkyl group, and the asymmetric alkyl R group has been rarely reported. Hence, in this paper, twenty butylphenyl mixed dialkyltin arylformylhydrazone complexes have been synthesized by microwave "one-pot" reaction with arylformylhydrazine, substituted α-keto acid or its sodium salt and butylphenyltin dichloride. The crystal structures of nine complexes were determined, indicating that the complexes C1, C2, C11, C12, and C16 ∼ C19 possessed a central symmetric structure of a dinuclear Sn 2 O 2 tetrahedral ring; while the complex C9 is a trinuclear tin-oxygen cluster with a 6-membered ring encased in a 12-membered macrocyclic structure. The inhibiting activity of complexes was tested against the human cell lines NCI-H460, MCF-7, HepG2, Huh-7 and HL-7702. Complex C2 demonstrated the optimal inhibitory effect on HepG2 cells, with an IC 50 value of 0.82 ± 0.03 μM. Cellular biology experiments revealed that complex C2 could induce apoptosis and G2/M phase cell cycle arrest in HepG2 and Huh-7 cells. The complex also caused the collapse of the mitochondrial membrane potential and increased intracellular reactive oxygen species in HepG2 and Huh-7 cells. Western blot analysis further clarified that complex C2 could induce cell apoptosis through the mitochondrial pathway along with the release of reactive oxygen species., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier Inc. All rights reserved.)

Three newly synthesized triphenyltin(IV) compounds, Ph3SnL1 (L1- = 3-(4-methyl-2-oxoquinolin-1(2 H )-yl)propanoato), Ph3SnL2 (L2- = 2-(4-methyl-2-oxoquinolin-1(2 H )-yl)ethanoato), and Ph3SnL3 (L3- = 2-(4-hydroxy-2-oxoquinolin-1(2 H )-yl)ethanoato), were characterized by elemental microanalysis, FT-IR spectroscopy and multinuclear ( 1 H, 13 C and 119 Sn) NMR spectroscopy. A single X-ray diffraction study indicates that compounds Ph3SnL1 and Ph3SnL2 exhibit a 1D zig-zag chain polymeric structure, which in the case of Ph3SnL2 is additionally stabilized by π-interactions. In addition, the synthesized compounds were further examined using density functional theory and natural bond orbital analysis. The compounds have been evaluated for their in vitro anticancer activity against three human cell lines: MCF-7 (breast adenocarcinoma), A375 (melanoma), HCT116 (colorectal carcinoma), and three murine cell lines: 4T1 (breast carcinoma), B16 (melanoma), CT26 (colon carcinoma) using MTT and CV assays. The IC 50 values fall in the nanomolar range, indicating that these compounds possess better anticancer activity than cisplatin. The study of the effect of the newly developed drug Ph 3 SnL1 showed its plasticity in achieving an antitumor effect in vitro , which depends on the specificity of the phenotype and the redox status of the malignant cell line and ranges from the initiation of apoptotic cell death to the induction of differentiation to a more mature cell form. In the syngeneic model of murine melanoma, Ph3SnL1 showed the potential to reduce the tumor volume similar to cisplatin, but in a well-tolerated form and with low systemic toxicity, representing a significant advantage over the conventional drug.

Organotins have been widely used in various industrial applications. This study investigated the structure-activity relationship as inhibitors of human, pig, and rat gonadal 3β-hydroxysteroid dehydrogenases (3β-HSD). Human KGN cell, pig, and rat testis microsomes were utilized to assess the inhibitory effects of 18 organotins on the conversion of pregnenolone to progesterone. Among them, diphenyltin, triethyltin, and triphenyltin exhibited significant inhibitory activity against human 3β-HSD2 with IC 50 values of 114.79, 106.98, and 5.40 μM, respectively. For pig 3β-HSD, dipropyltin, diphenyltin, triethyltin, tributyltin, and triphenyltin demonstrated inhibitory effects with IC 50 values of 172.00, 100.19, 87.00, 5.75, and 1.65 μM, respectively. Similarly, for rat 3β-HSD1, dipropyltin, diphenyltin, triethyltin, tributyltin, and triphenyltin displayed inhibitory activity with IC 50 values of 81.35, 43.56, 55.55, 4.09, and 0.035 μM, respectively. They were mixed inhibitors of pig and rat 3β-HSD, while triphenyltin was identified as a competitive inhibitor of human 3β-HSD2. The mechanism underlying the inhibition of organotins on 3β-HSD was explored, revealing that they may disrupt the enzyme activity by binding to cysteine residues in the catalytic sites. This proposition was supported by the observation that the addition of dithiothreitol reversed the inhibition caused by all organotins except for triethyltin, which was partially reversed. In conclusion, this study provides valuable insights into the structure-activity relationship of organotins as inhibitors of human, pig, and rat gonadal 3β-HSD. The mechanistic investigation suggests that these compounds likely exert their inhibitory effects through binding to cysteine residues in the catalytic sites., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2023. Published by Elsevier Inc.)

A series of novel dibutyltin complexes based on salen-like ligands (S01-S03) were synthesized and characterized using ultraviolet-visible spectra，infrared spectra, 1 H, 13 C, and 119 Sn nuclear magnetic resonance, high-resolution mass spectrometry, X-ray crystallography, and thermogravimetric analysis. Complex S03 had excellent anticancer activity in vitro (IC 50  = 1.5 ± 0.2 μM in CAL-27 cell lines), which highly activated ROS expression levels and induced apoptosis and cell cycle arrest at the G2/M phase. Interestingly, complex S03 induced cancer cell death through multiple mechanisms (mitochondrial pathway, ER-stress pathway, and DNA damage pathway). This study reveals new mechanisms of organotin complexes and provides new insights into the development of organotin metal complexes as anticancer drugs in the future, and compounds with multiple anticancer mechanisms may be a new strategy for delaying or overcoming drug resistance to chemotherapy and target therapy., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2023. Published by Elsevier Inc.)

Background: Organotin(IV) complexes of dithiocarbamate are vital in medicinal chemistry, exhibiting potential in targeting cancer cells due to their unique properties that enhance targeted delivery. This study aimed to synthesize and characterize organotin(IV) N -ethyl- N -benzyldithiocarbamate complexes (ONBDCs) and evaluate their cytotoxicity against A549 cells, which are commonly used as a model for human lung cancer research., Methods: The two ONBDC derivatives - ONBDC 1 (dimethyltin(IV) N -ethyl- N -benzyldithiocarbamate) and ONBDC 2 (triphenyltin(IV) N -ethyl- N -benzyldithiocarbamate) - were synthesized via the reaction of tin(IV) chloride with N-ethylbenzylamine in the presence of carbon disulfide. A range of analytical techniques, including elemental analysis, IR spectroscopy, NMR spectroscopy, UV-Vis spectrometry, TGA/DTA analysis, and X-ray crystallography, was conducted to characterize these compounds comprehensively. The cytotoxic effects of ONBDCs against A549 cells were evaluated using MTT assay., Results: Both compounds were synthesized and characterized successfully via elemental and spectroscopies analysis. MTT assay revealed that ONBDC 2 demonstrated remarkable cytotoxicity towards A549 cells, with an IC 50 value of 0.52 μM. Additionally, ONBDC 2 displayed significantly higher cytotoxic activity against the A549 cell line when compared to the commercially available chemotherapeutic agent cisplatin (IC 50 : 32 μM)., Conclusion: Thus, it was shown that ONBDC 2 could have important anticancer properties and should be further explored as a top contender for creating improved and specialized cancer treatments., (Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.net.)

In the last few years, tin(IV) complexes have emerged as very attractive candidates in the field of molecular imaging due to their unique photophysical properties. Despite the few reviews published to date covering the chemistry of organotin and tin complexes and their cytotoxic potential, there are no reviews devoted to their live cell imaging properties. Therefore, this feature article summarizes the discussion of the fundamental photophysical properties of fluorescent tin metal complexes focusing on their recent advances in "biomedical molecular imaging". A debate on the design of tin complexes as cellular imaging agents relating to their chemical, electronic and photophysical properties is enclosed. This paper also discusses the imaging applications of tin complexes in cells, tissues, and organisms via confocal and multiphoton imaging for sensing mechanisms in cellular media, bioimaging, and therapeutic labeling. In addition, it explores and explains the current challenges and prospects associated with these tin complexes as emerging luminescent cellular agents for potential clinical use.

Organotin (IV) dithiocarbamate has recently received attention as a therapeutic agent among organotin (IV) compounds. The individual properties of the organotin (IV) and dithiocarbamate moieties in the hybrid complex form a synergy of action that stimulates increased biological activity. Organotin (IV) components have been shown to play a crucial role in cytotoxicity. The biological effects of organotin compounds are believed to be influenced by the number of Sn-C bonds and the number and nature of alkyl or aryl substituents within the organotin structure. Ligands target and react with molecules while preventing unwanted changes in the biomolecules. Organotin (IV) dithiocarbamate compounds have also been shown to have a broad range of cellular, biochemical, and molecular effects, with their toxicity largely determined by their structure. Continuing the investigation of the cytotoxicity of organotin (IV) dithiocarbamates, this mini-review delves into the appropriate method for synthesis and discusses the elemental and spectroscopic analyses and potential cytotoxic effects of these compounds from articles published since 2010.

A number of novel di- and triorganotin(IV) complexes 1 - 5 (Ph 2 SnL 1 , Ph 2 SnL 2 , Et 2 SnL 2 , Ph 3 SnL 3 , Ph 3 SnL 4 ) with mono- or dianionic forms of thio-Schiff bases containing antioxidant sterically hindered phenol or catechol fragments were synthesized. Compounds 1 - 5 were characterized by 1 H, 13 C NMR, IR spectroscopy, and elemental analysis. The molecular structures of complexes 1 and 2 in the crystal state were established by single-crystal X-ray analysis. The antioxidant activity of new complexes as radical scavengers was estimated in DPPH and ABTS assays. It was found that compounds 4 and 5 with free phenol or catechol fragments are more active in these tests than complexes 1 - 3 with tridentate O,N,S-coordinated ligands. The effect of compounds 1 - 5 on the promoted oxidative damage of the DNA by 2,2'-azobis(2-amidinopropane) dihydrochloride and in the process of rat liver (Wistar) homogenate lipid peroxidation in vitro was determined. Complexes 4 and 5 were characterized by more pronounced antioxidant activity in the reaction of lipid peroxidation in vitro than compounds 1 - 3 . The antiproliferative activity of compounds 1 - 5 was investigated against MCF-7, HTC-116, and A-549 cell lines by an MTT test. The values of IC 50 are significantly affected by the presence of free antioxidant fragments and the coordination site for binding.

A series of novel organotin(IV) complexes on the base of 2-(N-3',5'-di- tert -butyl-4'-hydroxyphenyl)-iminomethylphenol ( L ) of formulae Me 2 SnBr 2 (L) 2 ( 1 ), Bu 2 SnCl 2 (L) 2 ( 2 ), Ph 2 SnCl 2 (L) ( 3 ), Ph 2 SnCl 2 (L) 2 ( 4 ) Ph 3 SnBr(L) 2 ( 5 ) were synthesized and characterized by 1 H, 13 C, 119 Sn NMR, IR, ESI-MS and elemental analysis. The crystal structures of initial L and complex 2 were determined by XRD method. It was found that L crystallizes in the orthorhombic syngony. The distorted octahedron geometry around Sn center is observed in the structure of complex 2 . Intra- and inter-molecular hydrogen bonds were found in both structures. The antioxidant activity of new complexes as reducing agents, radical scavengers and lipoxygenase inhibitors was estimated spectrophotometrically in CUPRAC and DPPH tests (compounds 1 and 5 were found to be the most active in both methods), and in the process of enzymatic oxidation in vitro of linoleic acid under the action of lipoxygenase LOX 1-B (EC 50 > 33.3 μM for complex 2 ). Furthermore, compounds 1-5 have been investigated for their antiproliferative activity in vitro towards HCT-116, MCF-7 and A-549 and non-malignant WI-38 human cell lines. Complexes 2 and 5 demonstrated the highest activity. The plausible mechanisms of the antiproliferative activity of compounds, including the influence on the polymerization of Tb+MAP, are discussed. Some of the synthesized compounds have also actively induced apoptosis and blocked proliferation in the cell cycle G2/M phase.

Background: Cancer cases have escalated by approximately 12% since 1900 and the incidence rate has increased faster for females than males. The discovery of cisplatin in 1965 paved the way for metal-based compounds as cancer therapeutics. Unfortunately, cisplatin and other platinum-based medicines cause severe side effects. Therefore, non-platinum metal complexes have been developed as alternate cancer drugs. Among non-platinum metal complexes, organotins are the most effective candidates in oncology due to their wide range of anticancer activities with relatively minimal toxicities towards healthy cells, better excretion from the body, and fewer side effects than platinum drugs., Methods: Using DOI searching, advances made by organotin(IV) complexes coordinated with Sn-O, Sn-N and Sn-S as chemotherapeutic agents since 2018 are summarized in this article. Their chemical structure and in vitro antiproliferative activity in terms of IC 50 /EC 50 /LD 50 are cumulated., Results: As reflected in this perspective, organotin(IV) complexes are found to induce high cell death via apoptosis, and also several complexes demonstrated anticancer activity even higher than standard drugs., Conclusion: Undoubtedly, the organotin(IV) complexes could bring hope to morbidity and mortality of human beings caused by fast-spreading cancer worldwide and can play an important role in drug discovery., (Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.net.)

A novel polydentate chelating antioxidant ligand and series of organotin complexes on its base were synthesized and characterized by NMR 1 H, 13 C, 119 Sn, IR spectroscopy, X-ray, and elemental analysis. Their antioxidant activity was evaluated in DPPH and NBT-tests, and as lipoxygenase inhibitory activity. It was shown that ligand alone is a radical scavenger, while introducing tin in the structure of the compound significantly decreases its activity. For the ligand alone the ability to strongly suppress the formation of advanced glycation end products (AGEs) was shown, which may be associated with the established antiradical activity. All synthesized compounds appeared to be moderate lipoxygenase inhibitors. The stability of compounds to hydrolysis under different pH was estimated. The ligand undergoes decomposition after about an hour, while organotin complexes on its base demonstrate vast stability, showing signs of decomposition only after 5 h of experimentation. Cytotoxicity of compounds was studied by standard MTT-test, which showed unorthodox results: the ligand itself demonstrated noticeable cytotoxicity while the introduction of organotin moiety either did not affect the toxicity levels or reduced them instead of increasing. Organotin complexes possess luminescence both as powders and DMSO solutions, its quantum yields reaching 67% in DMSO. The combination of luminescence with unique cytotoxic properties allows us to propose the synthesized compounds as perspective theranostic agents.

Three di-organotin(IV) complexes have been synthesized by the reaction of Schiff base di-acylhydrazone ligands bis(5-chlorosalicylaldehyde) adipoylhydrazone and R 2 SnCl 2 [R = Me (1), Ph (2), n-Bu (3)]. Structures of all complexes were characterized by 1 H, 13 C, 119 Sn NMR, elemental analysis, IR and mass spectrometry. Experimental results showed that the symmetric diacylhydrazone ligands coordinate the tin atom in a hexadentate form, where the tin atom shows a penta-coordination, in a distorted triangular bipyramid geometry. Using MTT method, in vitro cytotoxicity of three complexes was determined against three cancer cell lines (A549, HeLa, HepG-2). Studies reveal that complex 3 showed the strongest cytotoxic activity among the three complexes, which may be correlated with the generation of intracellular reactive oxygen species. Uptake of complex 3 into cells and promotion of reactive oxygen species were visualized by confocal fluorescence imaging., Competing Interests: Declaration of Competing Interest We declare that we have no financial and personal relationships with other people or organizations that can inappropriately influence our work, there is no professional or other personal interest of any nature or kind in any product, service and/or company that could be construed as influencing the position presented in, or the review of, the manuscript entitled., (Copyright © 2022. Published by Elsevier Inc.)

Over the last century, organotin compounds (OTCs) have sprawled over a vast spectrum of applications ranging from industrial to agricultural fields, interlacing with our surrounding environment and the ecosystem in an inseparable manner. The biocidal nature of OTCs, which has been exploited as the servient antifouling property, proved them to be pernicious eco-toxicants and a threat to the entire living system irrespective of the taxonomic hierarchy. Despite the recalcitrant nature of OTCs against chemical decontamination and photodegradation, nature has shown a providential method of their biodegradation by means of organotin-resistant microbes. Although the details of the microbial organotin biodegradation process remain nebulous, the cytochrome P450 (CYP450) family of enzymes has shown to possess the capability of OTC degradation. In this review, we discuss the deep-rooted toxicity problem of the organotin compounds on the biota and explore the plausible mechanistic plots of their enzymatic degradation, keeping the catalytic cycle of the CYP450 enzyme under the limelight. Leveraging the knowledge of CYP450 catalysis and the known organotin metabolites in nature, we attempt to cast transparency on the catalytic mechanism involved in organotin biodegradation, which remains largely elusive. Although several challenges have to be confronted for implementing the process of enzymatic degradation of OTCs in the real world, a sincere attempt will definitely be worth the ultimate greater good for averting the global toxicity problem related to organotin compounds., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2022 Elsevier B.V. All rights reserved.)

Five fluorescent ONO donor-based organotin(IV) complexes, [Sn IV (L 1-5 )Ph 2 ] ( 1-5 ), were synthesized by the one-pot reaction method and fully characterized spectroscopically including the single-crystal X-ray diffraction studies of 2-4 . Detailed photophysical characterization of all compounds was performed. All the compounds exhibited high luminescent properties with a quantum yield of 17-53%. Additionally, the results of cellular permeability analysis suggest that they are lipophilic and easily absorbed by cells. Confocal microscopy was used to examine the live cell imaging capability of 1-5 , and the results show that the compounds are mostly internalized in mitochondria and exhibit negligible cytotoxicity at imaging concentration. Also, 1-5 exhibited high photostability as compared to the commercial dye and can be used in long-term real-time tracking of cell organelles. Also, it is found that the probes ( 1-5 ) are highly tolerable during the changes in mitochondrial morphology. Thus, this kind of low-toxic organotin-based fluorescent probe can assist in imaging of mitochondria within living cells and tracking changes in their morphology.

Eight new diorganotin(IV) complexes (1a-2d), namely {[X-C 6 H 4 (O)C=N-N=C(Me)COO]R 2 Sn(CH 3 OH)} n (1a, 2a), {[X-C 6 H 4 (O)C=N-N=C(Me)COO]R 2 Sn(CH 3 OH)} 2 (1b, 1c, 1d, 2b), and {[X-C 6 H 4 (O)C=N-N=C(Me)COO]R 2 Sn} 2 (2c, 2d) (X = H-, p-Me-, p-OH-, p-NO 2 -; R = o-Cl-C 6 H 4 CH 2 - or o-Me-C 6 H 4 CH 2 -), have been synthesized by microwave "one-pot" reaction with arylformylhydrazine, pyruvic acid, and the corresponding R 2 SnCl 2 . All the complexes have been characterized by FT-IR (Fourier transform infrared spectroscopy), multinuclear NMR ( 1 H, 13 C, and 119 Sn nuclear magnetic resonance spectroscopies), HRMS (high-resolution mass spectroscopy) and single-crystal X-ray structural analysis. The antiproliferative activity of all complexes was tested against the cancer cell lines NCI-H460, MCF-7 and HepG2. The diorganotin complex 1c has been shown to be more potent antitumor agents against HepG2 than other complexes and cisplatin. Flow cytometry analysis observation demonstrated that complex 1c mediated cell apoptosis of HepG2 cells and arrested cell cycle in the S phase. The single cell gel electrophoreses assay results show that the 1c induce DNA damage. The DNA binding activities of the 1c were studied by UV-visible absorption spectrometry, fluorescence competitive, circular dichroism measurements, and molecular docking, results shown 1c can be well embedded in the groove and cleave DNA., (Copyright © 2021. Published by Elsevier Inc.)

Recently inorganic-based metallodrugs provide an effective mechanism for the drugs on the choice of metal and its properties. Medicinal complex compounds provide an efficient platform for various pharmacological and therapeutic applications. Six new organotin and organosilicon complexes containing sulphur and nitrogen donor atoms were synthesised. These complexes of ( E )-2-((4-methoxybenzylidene)amino)benzenethiol were characterized by elemental analyses, molecular weights, conductance measurements, infrared, electronic, and NMR spectroscopy. The data analysis indicated that the Schiff base contains bidentate nitrogen sulfur (NS) domains and was coordinated to silicon (Si) and tin (Sn) moieties via the imine-N and thiolic-S atoms, resulting in penta- and hexa-coordinated complexes in 1 : 1 and 1 : 2 ratios, respectively. The geometries around the Sn and Si atoms in complexes 1, 3, and 5 were five-coordinated and 2, 4, and 6 were six-coordinated octahedra, respectively. Density functional theory (DFT) was used to determine the optimal structural parameters. The antimicrobial activities of the ligand and its complexes were determined. These data indicate that metal complexes are more effective against bacteria and fungi in comparison to the free ligand. Molecular docking was performed to interpret the interaction of protein and various complexes and it was observed that compound 6 showed the highest binding affinity.

In this study, chlorophenyltin(IV) [(C 6 H 5 )(Cl)Sn(L) 2 ] and diphenyltin(IV) [(C6H5)2Sn(L)2] of N -methyl- N -hydroxyethyldithiocarbamate were prepared and characterized using various spectroscopic methods (FTIR, 1 H, 13 C, and 119 Sn NMR) and elemental analysis. The FTIR and NMR spectral data, used to establish the structure of the compounds, showed the formation of the complexes via coordination to the two sulfur atoms from the dithiocarbamate ligand and the respective phenyltin(IV) derivatives. This coordination mode was further explored by DFT calculations, which showed that the bonding around the Sn center in [(C6H5)2Sn(L)2] was more asymmetric compared to the bonding around [(C 6 H 5 )(Cl)Sn(L) 2 ] . However, the Sn-S bonds in [(C 6 H 5 )(Cl)Sn(L) 2 ] were found to be more covalent than those in [(C6H5)2Sn(L)2] . Furthermore, the charge density of the frontier orbitals showed that the Sn atom in the complexes is relatively electrophilic and the Sn atom in [(C6H5)2Sn(L)2] has a lower atomic dipole moment than that of [(C 6 H 5 )(Cl)Sn(L) 2 ] . The cytotoxicity and anti-inflammatory study revealed that [(C6H5)2Sn(L)2] , with the higher number of phenyl substituents, has a higher potency than [(C 6 H 5 )(Cl)Sn(L) 2 ] . The bio-efficacy study of these complexes as cytotoxic and anti-inflammatory agents showed that the complexes possessed moderate to high activity in comparison to the camptothecin and diclofenac in each case. Nevertheless, the diphenyltin(IV) derivative [(C6H5)2Sn(L)2] was found to possess a better activity than its counterpart due to the number of phenyl rings attached to the Sn center.

Due to a lack of therapeutic options for the pathological condition of leishmaniasis, which is characterized by polymorphic lesions and skin surface infections, Leishmania genus parasites damaged dermis and mucosa. There was a need to synthesize and characterize some new complexes. This study evaluated the biological activities preferably anti-Leishmanial activity of organotin (IV) containing sulphonyl hydrazide derivatives. A series of six new organotin (IV) complexes 1-6 labeled as R2SnL2; R = Methyl (1), Butyl (2), Phenyl (3) and R3SnL; R = Methyl (4), Butyl (5), Phenyl (6) has been synthesized as reflux method derived from N'- (2,4-dinitrophenyl)-4-methylphenylsulfonylhydrazide (L). All compounds were characterized through FT-IR, 1HNMR, 13CNMR, and elemental analysis. Structural analysis confirms the formation of six complexes (1-6). All derivatives have been screened for their pharmacological activities. Interestingly, compound 1 showed promising activity against leishmania promastigotes with low cytotoxicity. All results were further elaborated through docking studies performed on leishmania donovoni synthetase PDB: ID 3QW3 that acts as an essential building block for the viability of Leishmania promastigotes. This research effectively synthesized sulphonyl hydrazide ligand and its six new organotin (IV) derivatives, which were tested for biological properties such as antibacterial, anti-fungal, anti-oxidant, and ideally anti-leishmanial activity and cytotoxicity. Studies have confirmed that these compounds have the potency to be a good candidate against leishmaniasis. Computational studies were carried out to recognize the binding affinities for leishmania donovoni synthetase.Communicated by Ramaswamy H. Sarma.

Lysozyme is often used as a model protein to study interaction with drug molecules and to understand biological processes which help in illuminating the therapeutic effectiveness of the drug. In the present work, in vitro interaction studies of 1-{(2-hydroxyethyl)amino}-2-amino-1,2-dideoxy-d-glucose triphenyl tin (IV) (GATPT) complex with lysozyme were carried out by employing various biophysical methods such as absorption, fluorescence, and circular dichroism (CD) spectroscopies. The experimental results revealed efficient binding affinity of GATPT with lysozyme with intrinsic binding (K b ) and binding constant (K) values in the order of 10 5 M -1 . The number of binding sites and thermodynamic parameters ΔG, ΔH, and ΔS at four different temperatures were also calculated and the interaction of GATPT with lysozyme was found to be enthalpy and entropy driven. The CD spectra revealed alterations in the population of α-helical content within the secondary structure of lysozyme in presence of GATPT complex. The morphological analysis of the complex with lysozyme and lysozyme-DNA condensates was carried out by employing confocal and SEM studies. Furthermore, the molecular docking studies confirmed the interaction of GATPT within the larger hydrophobic pocket of the lysozyme via several non-covalent interactions.

Fluorescent bioimaging is an excellent tool in cellular biology, and it will be a powerful technique in modern medicine as a noninvasive imaging technology where tumoral and normal cells must be distinguished. One of the differences between normal and cancer cells is the intracellular pH. Therefore, the design and synthesis of pH-responsive fluorescent materials are required. Organotin Schiff bases showed halofluorochromic behavior in solution. Microwave-assisted synthesis showed better reaction times and chemical yields compared with conventional heating. All compounds were fully characterized by spectroscopic and spectrometric techniques. The halofluorochromism study showed that some molecules in acidic media have the maximum luminescence intensity due to protonation. All the fluorescent tin complexes showed cell staining on hepatocyte and MCF-7 cells by confocal microscopy. The theoretical study has enabled us to rationalize the optical properties and the halofluorochromism for compounds 1 and 2 synthesized in this work. Our results showed that the emission decrease, in the acid and basic media for compounds 1 and 2, respectively, is caused by intramolecular charge transfer (ICT) deactivation.

Organotin(IV) compounds are a class of non-platinum metallo-conjugates exhibiting antitumor activity. The effects of different organotin types has been related to several mechanisms, including their ability to modify acetylation protein status and to promote apoptosis. Here, we focus on triorganotin(IV) complexes of butyric acid, a well-known HDAC inhibitor with antitumor properties. The conjugated compounds were synthesized and characterised by FTIR spectroscopy, multi-nuclear ( 1 H, 13 C and 119 Sn) NMR, and mass spectrometry (ESI-MS). In the triorganotin(IV) complexes, an anionic monodentate butyrate ligand was observed, which coordinated the tin atom on a tetra-coordinated, monomeric environment similar to ester. FTIR and NMR findings confirm this structure both in solid state and solution. The antitumor efficacy of the triorganotin(IV) butyrates was tested in colon cancer cells and, among them, tributyltin(IV) butyrate (BT2) was selected as the most efficacious. BT2 induced G2/M cell cycle arrest, ER stress, and apoptotic cell death. These effects were obtained using low concentrations of BT2 up to 1 μM, whereas butyric acid alone was completely inefficacious, and the parent compound TBT was poorly effective at the same treatment conditions. To assess whether butyrate in the coordinated form maintains its epigenetic effects, histone acetylation was evaluated and a dramatic decrease in acetyl-H3 and -H4 histones was found. In contrast, butyrate alone stimulated histone acetylation at a higher concentration (5 mM). BT2 was also capable of preventing histone acetylation induced by SAHA, another potent HDAC inhibitor, thus suggesting that it may activate HDACs. These results support a potential use of BT2, a novel epigenetic modulator, in colon cancer treatment.

Although organotin (OT) use is restricted worldwide, with the development of industry and agriculture, a large amount of OT is still discharged into aquatic environments. These OTs may interact with other pollutants that cause adverse biological effects (through bioaccumulation and/or toxicity), resulting in combined toxicity. Most research on OTs have focused on the exposure of a single analyte. Information on the toxicity of OTs and coexisting pollutants is quite limited, but is developing rapidly. This is the first review paper evaluating the current state of knowledge on the combined effects of OTs with co-pollutants. This paper reviews 1) the degradation of organotin; and 2) the combined toxicity of OTs and emerging pollutants (EP), heavy metals, and organic pollutants. Future research needs are discussed to better understand the risks associated with co-exposure to OT pollutants., (Copyright © 2021 Elsevier Inc. All rights reserved.)

Three fluorescent-labeling methods, including DMSO/DBTD, reductive amination and fluoresceinamine (FA), were applied to label arabinoxylan (AX). The conjugates were named AF, ATF and ACF, respectively. Compared to AX, the water solubility of AF significantly decreased while that of ATF significantly increased (p < 0.05); both showed decreased solubility with increasing degree of substitution (DS). However, AX was not successfully labeled by the FA method due to poor solubility. The structural and conformational properties of the AF and ATF conjugates under different DS were compared. Results showed that fluorochrome (FITC) was successfully grafted onto AX molecule by using the DMSO/DBTD and reductive amination methods. A slight increased Mw was noticed for both AF and ATF. AF existed in a more compact conformation, while the chain conformation of ATF was more elongated at a lower DS (1.15 %) and more compact at a higher DS (1.34 %)., (Copyright © 2021 Elsevier Ltd. All rights reserved.)

Tetramethyltin was decomposed in an ion source and the fragment ions produced were identified using a low-energy mass-selected ion beam machine. Dominant fragment ions were found to be H+, CH2+, and Sn+. Subsequently, fragment ions were mass-selected. The mass spectrum of the selected ions indicated that only a single peak appeared at the mass number of 120 u, being suggestive of the presence of 120Sn+ ions. The ion energy was set at the range of 20-100 eV. The Sn+ ion beam was irradiated to a Si substrate, and a film was then found deposited on the substrate after the ion beam irradiation. An X-ray diffraction measurement showed that the film obtained was metallic Sn. Then, the Sn+ ion beam was irradiated to a quartz crystal microbalance substrate. We found that most of the irradiated Sn+ ions were adhered to the substrate, at the ion energy levels of 25 and 58 eV, producing the Sn film, whereas a 107 eV Sn+ beam caused a significant proportion of Sn atoms in the film to detach from the substrate, probably due to sputtering., Competing Interests: The authors have declared that no competing interests exist.

The synthesis of novel triphenyltin(IV) compounds, Ph 3 SnL n ( n = 1-3), with oxaprozin (3-(4,5-diphenyloxazol-2-yl)propanoic acid), HL1 , and the new propanoic acid derivatives 3-(4,5-bis(4-methoxylphenyl)oxazol-2-yl)propanoic acid, HL2 , and 3-(2,5-dioxo-4,4-diphenylimidazolidin-1-yl)propanoic acid, HL3 , has been performed. The ligands represent commercial drugs or their derivatives and the tin complexes have been characterized by standard analytical methods. The in vitro antiproliferative activity of both ligands and organotin(IV) compounds has been evaluated on the following tumour cell lines: human prostate cancer (PC-3), human colorectal adenocarcinoma (HT-29), breast cancer (MCF-7), and hepatocellular cancer (HepG2), as well as on normal mouse embryonic fibroblast cells (NIH3T3) with the aid of MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-12 diphenyltetrazolium bromide) and CV (crystal violet) assays. Contrary to the inactive ligand precursors, all organotin(IV) carboxylates showed very good activity with IC 50 values ranging from 0.100 to 0.758 µM. According to the CV assay (IC 50 = 0.218 ± 0.025 µM), complex Ph 3 SnL1 demonstrated the highest cytotoxicity against the caspase 3 deficient MCF-7 cell line. Inductively coupled plasma mass spectrometry (ICP-MS) analysis indicated a two-fold lower concentration of tin in MCF-7 cells in comparison to platinum. To investigate the mechanism of action of the compound Ph 3 SnL1 on MCF-7 cells, morphological, autophagy and cell cycle analysis, as well as the activation of caspase and ROS/RNS and NO production, has been performed. Results suggest that Ph 3 SnL1 induces caspase-independent apoptosis in MCF-7 cells.

Organotin(IV) derivatives of cholic acid (CAH) with the formulae R 3 Sn(CA) (R = Ph- (1), n-Bu- (2)) and R 2 Sn(CA) 2 (R = Ph- (3), n-Bu- (4) and Me- (5)) were synthesized. The compounds were characterized in solid state by melting point, FT-IR, 119 Sn Mössbauer, X-ray fluorescence (XRF) spectroscopy and in solution by 1 H NMR, UV-Vis spectral data and by Electrospray Ionisation Mass spectrometry (ESI-MS), High Resolution Mass spectrometry (HRMS), and atomic absorption analysis. The in vitro bioactivity of 1-5 against human breast adenocarcinoma cancer cells MCF-7 (positive to hormone receptors) and MDA-MB-231 (negative to hormone receptors) reveal that triorganotin derivatives 1-2 exhibit significantly stronger activity than the corresponding diorganotin ones. Compound 5 is inactive against both cell lines at the concentrations tested. Triorganotins 1-2 inhibit selectively MCF-7 than MDA-MB-231 cells, suggesting hormone mimetic behavior of them. Organotins 1-4 inhibit both cancerous cell lines, stronger than cisplatin which rise up to 55-fold against MCF-7 and 170-fold against MDA-MB-231. The in vitro toxicity of 1-4 was evaluated on normal human fetal lung fibroblast cells (MRC-5), while their genotoxicity in vitro by micronucleus assay (MN). Moreover, the in vivo toxicity of 1-4 was tested by Artemia salina assay and their in vivo genotoxicity with Allium cepa test. The mechanism of action of 1-4 against MCF-7 was clarified in vitro by the means of cell morphology studies, cell cycle arrest, Acridine Orange/Ethidium Bromide (AO/EB) Staining, mitochondrial membrane permeabilization test and by their binding affinity toward the calf thymus (CT) DNA., (Copyright © 2021 Elsevier Inc. All rights reserved.)

We report the formation and characterization of two diastereomeric thiol-ene addition products of the asthma medication Montelukast within chewing tablets. Widespread tin-based thermal stabilizers dioctyltin bis(2-ethylhexyl thioglycolate) and monooctyltin tris(2-ethylhexyl thioglycolate), used in the manufacturing process of the medication's forming foil, were identified as the source of the thiol reactant, showing that these stabilizers may play a part in the degradation of Montelukast and APIs with functionalities similar to those of Montelukast, which should be considered during development of medication. The isolation and analysis of these impurities was performed by HPLC and UV-vis spectroscopy. HRMS and NMR data were collected to characterize and determine the structures of these compounds.

Tetra-tert-butyl-3-chloro-1-hydroxydistannoxane has been found to selectively cleave with high efficiency primary acetates on complex oligosaccharides containing esterified l-iduronic acid and bearing an anomeric acetate. This tin based catalyst was found much more effective than magnesium methoxide to carry out selective deacetylation., (Copyright © 2020 Elsevier Ltd. All rights reserved.)

Two novel triphenyltin(IV) compounds, [Ph 3 SnL1] (L1 = 2-(5-(4-fluorobenzylidene)-2,4-dioxotetrahydrothiazole-3-yl)propanoate (1)) and [Ph 3 SnL2] (L2 = 2-(5-(5-methyl-2-furfurylidene)-2,4-dioxotetrahydrothiazole-3-yl)propanoate (2)) were synthesized and characterized by FT-IR, ( 1 H and 13 C) NMR spectroscopy, mass spectrometry, and elemental microanalysis. The in vitro anticancer activity of the synthesized organotin(IV) compounds was determined against four tumor cell lines: PC-3 (prostate), HT-29 (colon), MCF-7 (breast), and HepG2 (hepatic) using MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-12 diphenyltetrazolium bromide) and CV (crystal violet) assays. The IC 50 values are found to be in the range from 0.11 to 0.50 μM. Compound 1 exhibits the highest activity toward PC-3 cells (IC 50  = 0.115 ± 0.009 μM; CV assay). The tin and platinum uptake in PC-3 cells showed a threefold lower uptake of tin in comparison to platinum (as cisplatin). Together with its higher activity this indicates a much higher cell inhibition potential of the tin compounds (calculated to ca. 50 to 100 times). Morphological analysis suggested that the compounds induce apoptosis in PC-3 cells, and flow cytometry analysis revealed that 1 and 2 induce autophagy as well as NO (nitric oxide) production., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2020. Published by Elsevier Inc.)

The metalloantibiotic of formula Ph2Sn(CIP)2 (CIPTIN) (HCIP = ciprofloxacin) was synthesized by reacting ciprofloxacin hydrochloride (HCIP·HCl) (an antibiotic in clinical use) with diphenyltin dichloride (Ph2SnCl2DPTD). The complex was characterized in the solid state by melting point, FT-IR, X-ray Powder Diffraction (XRPD) analysis, 119Sn Mössbauer spectroscopy, X-ray Fluorescence (XRF) spectroscopy, and Thermogravimetry/Differential Thermal Analysis (TG-DTA) and in solution by UV-Vis, 1H NMR spectroscopic techniques and Electrospray Ionisation Mass Spectrometry (ESI-MS). The crystal structure of CIPTIN and its processor HCIP was also determined by X-ray crystallography. The antibacterial activity of CIPTIN, HCIP·HCl, HCIP and DPTD was evaluated against the bacterial species Pseudomonas aeruginosa (P. aeruginosa), Escherichia coli (E. coli), Staphylococcus aureus (S. aureus) and Staphylococcus epidermidis (S. epidermidis), by the means of Minimum Inhibitory Concentration (MIC), Minimum Bactericidal Concentration (MBC) and Inhibition Zones (IZs). CIPTIN shows lower MIC values than those of HCIP·HCl (up to 4.2-fold), HCIP (up to 2.7-fold) or DPTD (>135-fold), towards the tested microbes. CIPTIN is classified into bactericidal agents according to MBC/MIC values. The developing IZs are 40.8 ± 1.5, 34.0 ± 0.8, 36.0 ± 1.1 and 42.7 ± 0.8 mm, respectively which classify the microbes P. aeruginosa, E. coli, S. aureus and S. epidermidis to susceptible ones to CIPTIN. These IZs are greater than the corresponding ones of HCIP·HCl by 1.1 to 1.5-fold against both the tested Gram negative and Gram positive bacteria. CIPTIN eradicates the biofilm of P. aeruginosa and S. aureus more efficiently than HCIP·HCl and HCIP. The in vitro toxicity and genotoxicity of CIPTIN were tested against human skin keratinocyte cells (HaCaT) (IC50 = 2.33 μM). CIPTIN exhibits 2 to 9-fold lower MIC values than its IC50 against HaCaT, while its genotoxic effect determined by micronucleus assay is equivalent to the corresponding ones of HCIP·HCl or HCIP.

Prostate cancer (PCa) incidence is surging in United States and other parts of the world. Synthetic and natural compounds have been explored as potential modulators of PI3K/Akt signaling that is known to drive PCa growth. Here, we evaluated the efficacy of a series of triphenyltin (IV) carboxylate derivatives against PCa. From this library, triphenylstannyl 2-(benzylcarbamoyl)benzoate (Ch-319) resulted in reduced viability and induction of cell cycle arrest in PTEN -/- PC3M and PTEN +/- DU145 cells. In parallel, downregulation of PI3K p85/p110 subunits, dephosphorylation of Akt-1 and increase in FOXO3a expression were observed. In silico studies indicated binding interactions of Ch-319 within the ATP binding site of Akt-1 at Met 281 , Phe 442 and Glu 234 residues. Elevated po-pulation of apoptotic cells, activation of Bax and reduced Bcl2 expression indicated apoptosis by Ch-319. Pre-sensitization of PCa cells with Ch-319 augmented the effect of cabazitaxel, a commonly used taxane in patients with castration-resistant PCa. Next, in a prostate-specific PTEN p-/- mice, Ch-319 showed reduced weights of genitourinary apparatus as compared to DMSO treated controls. Histological studies indicated absence of neoplastic foci in Ch-319 treated prostates. Consistently, dephosphorylation of Akt-1, reduced expression of PRAS40 and androgen receptor and increase in FOXO3a were observed in treated group. Notably, no overt organ toxicity was noted in Ch-319 treated animals. Our studies identify Akt/FOXO3a signaling as a target of triphenyltin (IV) carboxylate Ch-319 and provide a molecular basis of its growth inhibitory effect in PCa cells. We propose that Ch-319 has the potential to be developed as an anticancer agent against PCa., Competing Interests: Declaration of Competing Interest Authors declare no conflict of interest., (Published by Elsevier Inc.)

Carbohydrates, one of the three primary macromolecules of living organisms, play significant roles in various biological processes such as intercellular communication, cell recognition, and immune activity. While the majority of established methods for the installation of carbohydrates through the anomeric carbon rely on nucleophilic displacement, anomeric radicals represent an attractive alternative because of their functional group compatibility and high anomeric selectivities. Herein, we demonstrate that anomeric nucleophiles such as C1 stannanes can be converted into anomeric radicals by merging Cu(I) catalysis with blue light irradiation to achieve highly stereoselective C(sp 3 )-S cross-coupling reactions. Mechanistic studies and DFT calculations revealed that the C-S bond-forming step occurs via the transfer of the anomeric radical directly to a sulfur electrophile bound to Cu(II) species. This pathway complements a radical chain observed for photochemical metal-free conditions where a disulfide initiator can be activated by a Lewis base additive. Both strategies utilize anomeric nucleophiles as efficient radical donors and achieve a switch from an ionic to a radical pathway. Taken together, the stability of glycosyl nucleophiles, a broad substrate scope, and high anomeric selectivities observed for the thermal and photochemical protocols make this novel C-S cross coupling a practical tool for late-stage glycodiversification of bioactive natural products and drug candidates.

Six novel organotin phosphonate complexes, [(Me 3 Sn) 4 (HL 1 ) 4 ] n 1, [(Me 3 Sn) 2 (HL 2 ) 2 ] n 2, [(Me 3 Sn) 2 L 3 (H 2 O)] n 3, [(Ph 3 Sn)(HL 1 )] 6 4, [(Ph 3 Sn) 2 L 2 ] n 5 and [(Ph 3 Sn) 2 L 3 ] 6 6, derived from phosphonic acid ligands [NaHL 1  = 1-C 10 H 7 OPO 2 (OH)Na, H 2 L 2  = 1-C 10 H 7 PO(OH) 2 , H 2 L 3  = 2-C 10 H 7 PO(OH) 2 ], have been synthesized and characterized by elemental analysis, FT-IR, NMR ( 1 H, 13 C, 31 P and 119 Sn) spectroscopy and X-ray crystallography. The structural analysis reveals that complexes 1 and 5 display 1D infinite zig-zag chain structures, and complex 2 shows 1D right-handed helical chain structure, while complex 3 displays 1D left-handed helical chain structure. Complexes 4 and 6 are 24-membered macrocyclic rings interconnected by P, O and Sn atoms. Additionally, the molecules of complexes 1 and 3 are further linked through intermolecular π···π and O-H···O interaction into supramolecular structures, respectively. Furthermore, we preliminarily estimated in vitro cytostatic activity of complexes 1-6 against the human cervix tumor cells (HeLa), human hepatocellular carcinoma cells (HepG-2) and human normal breast cells (HBL-100). Importantly, the anti-proliferative properties and possible pathway of complex 6 are investigated, and the results demonstrate that complex 6 could induce apoptotic cell death via an overload of intracellular reactive oxygen species (ROS) levels and the dysfunctional depolarization of mitochondrial membranes., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2020 Elsevier Inc. All rights reserved.)

In the last few decades, organotin hydrides have proven their potential as building blocks for a great variety of organometallic compounds. In this context, organotin hydrides with sterically shielding aryl substituents have attracted special interest, as these ligands can kinetically stabilize metastable products. The selective synthesis of aryltin halide compounds Ar* 2 SnCl 2 and Ar*SnI 3 featuring the highly sterically encumbered aryl ligand Ar* ( i Pr Ar* = 2,6-(Ph 2 CH) 2 -4- i PrC 6 H 2 ; Me Ar* = 2,6-(Ph 2 CH) 2 -4-MeC 6 H 2 ) is presented. These aryltin halides were converted into corresponding aryltin hydrides Ar* 2 SnH 2 and Ar*SnH 3 , which exhibit a surprisingly high thermal stability and oxygen tolerance.

Visual detection of the methylglyoxal (MGO) level in the brain is critical for understanding its role in the onset and progression of AD. Herein, we disclosed a NIR fluorescent probe, DBTPP, for detecting MGO by utilizing a thiadiazole-fused o-phenylenediamine moiety as a MGO-specific sensing unit. DBTPP exhibits a series of distinct advantages, such as NIR emission, high selectivity and sensitivity, excellent acid-stability, and a huge off-on ratio. The probe could accurately monitor both exogenous and endogenous MGO variations in SH-SY5Y cells. Besides, it was able to image the endogenous MGO in a transgenic AD mouse model successfully, suggesting the great potential of MGO as a biomarker for early AD diagnosis.

Eight organotin(IV) complexes (C1-C8) have been synthesized and characterized by elemental analysis, fourier transform infrared spectroscopy (FT-IR), multinuclear nuclear magnetic resonance ( 1 H, 13 C and 119 Sn NMR), high resolution mass spectroscopy (HRMS) and single crystal X-ray structural analysis. Crystallographic data show that C1 was a tetranuclear 16-membered macrocycle complex, C2-C4 and C7 were centrosymmetric dimer distannoxane and there was a Sn 2 O 2 four-membered ring in the middle of the molecule, respectively, C5 and C6 are monoorganotin complexes due to the dehydroalkylation effect during the reaction, while C8 forms a one-dimensional chain structure. The cytotoxicity of all complexes were tested by 3-(4,5)-dimethylthiahiazo(-z-y1)-3,5-di-phenytetrazoliumromide (MTT) assays against three human tumor cell lines NCI-H460, MCF-7 and HepG2. The dibutyltin complex C2 has been shown to be more potent antitumor agents than other complexes and carboplatin. Cell apoptosis study of C2 with the high activity on HepG2 and MCF-7 cancer cell lines was investigated by flow cytometry, it was shown that the antitumor activity of C2 was related to apoptosis, but it has different cell cycle arrest characteristics from platinum compounds, and the proliferation was inhibited by blocking cells in S phase. The DNA binding activity of the C2 was studied by UV-visible absorption spectrometry, fluorescence competitive, viscosity measurements and gel electrophoresis, results shown C2 can be well embedded in the double helix of DNA and cleave DNA., (Copyright © 2019 Elsevier Inc. All rights reserved.)

The aim of this article is to investigate the potential cytotoxic and antitumor effects of the resonant electromagnetic fields (rEMFs) derived from the 1 H NMR spectrum of the Ph 3 Sn(Mercaptonicotinic)SnPh 3 complex (SnMNA). The ability of the complex's rEMFs to induce leiomyosarcoma (LMS) cell death and to recess tumor (leiomyosarcoma) development in Wistar rats was evaluated. The effects of the simultaneous administration of the SnMNA complex at extremely low concentrations and exposure to its rEMFs was also investigated. The emission of the 1 H NMR spectrum of the complex alone or in a combination with low ineffective doses of the complex decreased LMS cell viability mainly through apoptosis. Moreover, the results from the in vivo experiments showed a significant prolongation of life expectancy in tumor-bearing rats exposed to the rEMFs alongside a deceleration in tumor growth rate. We speculate that the rEMFs of a biologically active substance could exert similar biological effects as the substance itself, mainly when is combined with extremely low ineffective concentrations of the substance., (Copyright © 2019. Published by Elsevier Ltd.)

There is a growing interest in the cancer cell growth inhibitory effects of organotin (IV) compounds and, accordingly, a new series of dimethyl-, di-(n-butyl)-, diphenyl- and chloro-phenyl tin(IV) complexes with a Schiff base core were prepared. Their binding to DNA was assessed by UV thermal denaturation showing no interaction and by UV-vis titration exhibiting moderate interaction by intercalation. Complexes having n-butyl substituents were more potent and cytotoxic against human leukemia, breast and cervical cancer cell lines than other organotin(IV) complexes tested. Unfortunately, some of these compounds showed similar cytotoxicity in a non-cancerous cell line. We may conclude that cytotoxic activity was dependent on the nature (lipophilicity and size, according to the structure-activity relationship studies) and substitution pattern on the different structures. These results may aid in the rational design of metallodrugs, expanding the scope of organotin complexes in formulating new metal based drugs with dibutyl moieties., (Copyright © 2019 Elsevier Masson SAS. All rights reserved.)

The Stille coupling between organostannanes and organohalides is an effective catalytic method for organic synthesis. Despite the ample amount of published results in this area, finding the optimal conditions for this transformation is often not straightforward. It was observed that this reaction could be accelerated with improved efficiency by the addition of a Cu(i) salt and fluoride. This review summarises the application of this simple protocol in the synthesis of natural products, their analogues and other biologically active molecules, from 2004 to 2018.

Poly(vinyl chloride) (PVC), a polymer widely used in common household and industrial materials, undergoes photodegradation upon ultraviolet irradiation, leading to undesirable physicochemical properties and a reduced lifetime. In this study, four telmisartan organotin(IV) compounds were tested as photostabilizers against photodegradation. PVC films (40-µm thickness) containing these compounds (0.5 wt%) were irradiated with ultraviolet light at room temperature for up to 300 h. Changes in various polymeric parameters, including the growth of hydroxyl, carbonyl, and alkene functional groups, weight loss, reduction in molecular weight, and appearance of surface irregularities, were investigated to test the efficiency of the photostabilizers. The changes were more noticeable in the blank PVC film than in the films containing the telmisartan organotin(IV) compounds. These results reflect that these compounds effectively inhibit the photodegradation of PVC, possibly by acting as hydrogen chloride and radical scavengers, peroxide decomposers, and primary photostabilizers. The synthesized organotin(IV) complexes could be used as PVC additives to enhance photostability.

The effect of polystyrene (PS) particles on the toxicity of triphenyltin (TPT) to the marine diatom Skeletonema costatum was investigated. The 0.1-μm PS particles attached to the cell walls of S. costatum but did not cause adverse effects on the growth of the diatom. The adsorption of TPT to PS particles was negligible in seawater systems, but the presence of 0.1-μm PS significantly reduced the bioavailable concentrations of TPT in f/2-Si medium, indicating a potential three-way interaction between TPT, PS particles, and components of f/2-Si medium. The adsorption of TPT to PS of smaller size (i.e., 0.1 μm) was stronger than that of PS of larger size (i.e., 5 μm), which was probably attributed to larger surface areas of smaller PS particles. The presence of PS could reduce the toxicity of TPT. IC 50 values of TPT increased from 0.56 to 0.85 and 0.71 μg/L at the presence of 20 mg/L 0.1-μm PS and 5-μm PS, respectively. The overall results of this study profiled the combined toxic effects of PS and TPT on marine phytoplankton species and highlighted the difference in adsorption of organic pollutants by microplastics in different ambient mediums.

Background/aim: Triple-negative breast cancer (TNBC) constitutes 15-20% of all breast carcinomas, affecting younger women more often and has a worse prognosis than other types of breast cancer, due to the combination of more aggressive clinical behavior and lack of molecular targets for therapy. This study assessed the effects of non-genotoxic concentrations of tributyltin isothiocyanate (TBT-ITC) and triphenyltin isothiocyanate (TPT-ITC) on MDA-MB-231 cells., Materials and Methods: MTT assay, comet assay, kinetic imaging and flow cytometry were used for analysis of MDA-MB-231 cells., Results: The results showed that 100 nM concentration of TBT-ITC and TPT-ITC, that did not affect viability or DNA integrity, slowed-down migration by CD44 down-regulation. Moreover, both compounds demonstrated immunomodulatory properties, attenuating PD-L1 expression in MDA-MB-231 cells., Conclusion: TPT-ITC was more effective in down-regulating CD44 expression and reducing migration than TBT-ITC, while TBT-ITC was more potent in lowering PD-L1 expression in comparison with TPT-ITC., (Copyright© 2019, International Institute of Anticancer Research (Dr. George J. Delinasios), All rights reserved.)

The tin-tin triple bond in the distannyne Ar i Pr4 SnSnAr i Pr4 , Ar i Pr4 = C 6 H 3 -2,6(C 6 H 3 -2,6- i Pr 2 ) 2 , undergoes reversible cleavage in deuterated toluene to afford two :SṅAr i Pr4 radicals in solution as shown by 1 H nuclear magnetic resonance and electron paramagnetic resonance spectroscopy. Variable temperature data afforded an enthalpy of dissociation of Δ H diss = 17.2 ± 1.7 kcal mol -1 via van't Hoff analysis.

In the search for new therapeutic agents we have synthesized 13 new organotin(IV) carboxylate derivatives of (E)-4-((4-methoxy-2-nitrophenyl)amino)-4-oxobut-2-enoic acid. The synthesized complexes were characterized by several spectroscopic techniques. A chelating or bridging bidentate nature of the carboxylate ligand was suggested from the solid state FT-IR results. Solution state multinuclear NMR ( 1 H, 13 C and 119 Sn) results reveal that the geometry around the Sn atom in triorganotin(IV) complexes is trigonal bipyramidal and in diorganotin(IV) complexes is octahedral. The ligand, (E)-4-((4-methoxy-2-nitrophenyl)amino)-4-oxobut-2-enoic acid, complex 1 and complex 2 were also analyzed by single crystal X-ray technique and the results fully supports the spectroscopic data. For 1 and 2 the geometry optimized by the single crystal X-ray analyses is distorted trigonal bipyramidal. The interaction of the studied compounds with SS-DNA was investigated by UV-Vis. Spectroscopy and Molecular docking showing an intercalative mode of binding. The evaluation of the screened compounds for cancer treatment displays even higher than that of the vincristine used as a standard drug. Similarly the performance of the tested compounds as an antileishmanial agent considers them very close in activity to the standard drug, amphotericin B. The antibacterial results show that the most of the compounds have a moderate sensitivity against the studied bacterial pathogens., (Copyright © 2019 Elsevier B.V. All rights reserved.)

Herein appropriateness of nonfunctionalized mesoporous silica nanoparticles SBA-15 and functionalized with (3-chloropropyl)triethoxysilane (→ SBA-15~Cl) and (3-aminopropyl)triethoxysilane (→ SBA-15~NH 2 ) on delivery of physically adsorbed Ph 3 Sn(CH 2 ) 6 OH (Sn6) is evaluated. Fluorescent nanomaterial, bearing isatoic moiety, loaded with Sn6 (→ SBA-15~NF|Sn6) was used for cellular uptake study. The fluorescent nanomaterial is efficiently acquired and distributed into the cytoplasm of the cells even after 2 h of cultivation. According to the attained data, all SBA-15 materials loaded with Sn6 diminished cellular viability in dose dependent manner while carriers alone (SBA-15, SBA-15~Cl, SBA-15~NH 2 ) did not show cytotoxicity against B16 cells. According to the MC 50 values structural modification of SBA-15 did not improve the efficacy of tested drug. While progressive apoptosis was detected upon the treatment with SBA-15|Sn6, exposure of cells to SBA-15~NH 2 |Sn6 revealed extinguished apoptosis in time, accompanied with lower caspase activity. This effect is probably due to triggered autophagic process under the treatment with the SBA-15~NH 2 |Sn6, thus opposed to apoptosis. Presented results suggested that functionalization of SBA-15 was not beneficial for the efficacy of loaded drug, thus, all of them are almost equally efficient considering loaded Sn6 content. Importantly, functionalization of SBA-15 does have an influence on the mode of action and differentiation inducing properties., (Copyright © 2019 Elsevier B.V. All rights reserved.)