Organotin Derivatives Research Articles

Experimental and computational investigations of new organotin(IV) complexes derived from hydrazone ligands: Synthesis, structural analysis and biological assessment

In this article, we have presented the synthesis, structural analysis, and biological assessments of twelve new diorganotin(IV) complexes (derived from heterocyclic hydrazone ligands through condensation reaction between 9-formyl-8-hydroxyjulolidine and aromatic hydrazide derivatives) to discover potent biological agents. The synthesized compounds have been thoroughly characterized using numerous spectroscopic and physicochemical methods, including (1H, 13C and 119Sn) NMR, FT-IR, mass spectrometry, powder XRD and SEM. These scrutinizes indicate that complexes exhibited a pentacoordinated geometry, coordinating through azomethine nitrogen atom, enolic oxygen atom, phenolic oxygen atom and carbon atoms of alkyl/aryl groups of organotin derivatives. DFT (Density functional theory) studies were conducted at the B3LYP/LanL2DZ/6-311G level of hypothesis to investigate the quantum chemical aspects of specified compounds. These properties were facilitated through analyses of charge distribution and molecular orbitals. The antioxidant effectiveness of the prepared compounds was examined employing the DPPH assay and the results revealed that complex 7 exhibited strong antioxidant potential, having an IC50 value of 2.3 µM. Moreover, the prepared compounds were assessed for their effectiveness against four bacterial (B. cereus, B. subtilis, P. aeruginosa, E. coli) as well as two fungal strains (C. albicans and A. niger) using serial dilution approach. Complexes 7, 11, 14 and 15 having MIC values ranging from 0.0051-0.0048 µmol/mL have highest antimicrobial potency equivalent to reference drugs, Fluconazole (MIC = 0.0051 µmol/mL) and Ciprofloxacin (MIC = 0.0048 µmol/mL).

Comparison of Different Organometallics Towards Electrophilic Aromatic 211At-Astatinations of Highly Reactive Tetrazines.

Organometallics can be used as precursors for electrophilic 211At-statinations. In this report, we compared the potential of aryl trimethylsilanes, -germanes, or -stannanes to be used as precursors to 211At-label highly reactive tetrazines. Tetrazines can be used for pretargeted radioligand therapies or be applied as synthons to radiolabel rapidly and orthogonally a broad set of precursors such as peptides, mAbs or nanomedicines. All precursors could successfully be synthesized and radiolabeled. The reactivity of organogermanium reagents ranged between those of respective organotin and organosilicon precursors. Moreover, organogermanium reagents proved promising for accessing more complex and polar tetrazine scaffolds. In contrast to organotin derivatives, the use of protecting groups could be avoided for organogermanium and -silicon precursors. The developed 211At-labeled tetrazines could be labeled in radiochemical conversions of 60-90%. Organogermanium and -silicon precursors were clearly advantaged as additional deprotection steps could avoided. Reported labeling procedures allow astatinations of highly reactive tetrazines to be used for pretargeted approaches or to applied as highly reactive synthons to label the next-generation of 211At-labeled radiopharmaceuticals.

Antiproliferative Activity of an Organometallic Sn(IV) Coordination Compound Based on 1-Methylbenzotriazole against Human Cancer Cell Lines

A motivating class of compounds with interest in the research field of biological active metallopharmaceuticals for cancer treatment is based on organometallic complexes of Sn(IV), exhibiting advantages such as improved cellular uptake and body excretion, lower toxicity, and fewer side effects compared to platinum-based drugs. In this study, the mononuclear organotin coordination complex [(CH3)2SnCl2(mebta)2] was synthesized and characterized using vibrational spectroscopy (IR, Raman), 1H NMR, 13C{1H} NMR, and X-ray crystallography. Its antiproliferative properties were thoroughly assessed across an aggressive triple-negative human breast cancer cell line. Notably, comparative studies with precursor materials verified that the observed biological activity is intrinsic to the complex itself. This study highlights the compound’s ability to induce cell fate by disrupting essential cellular functions, such as proliferation. By exploring the antiproliferative effects of organotin(IV) derivatives, we introduce a novel class of Sn complexes with 1-methylbenzotriazole (mebta), demonstrating significant potential as promising antitumor agents in the field of organotin compounds.

ANTIMICROBIAL EFFECT OF SOME ORGANOTIN (IV) DERIVATIVED OF PROPAN-1, 3-DIOIC ACID

Three organotin (IV) derivatives of propan-1,3-dioic acid; potassium dibutyltin(IV)propan-1;3-dioate (1), potassium diphenltin(IV)propan-1;3-dioate (2), and potassium triphenltin(IV)propan-1,3-dioate (3) were synthesized mechanochemically. KOH was ground with propan-1,3-dioic acid to give the ligand L: potassium propan-1,3-dioate, followed by complexation of the ligand, L with Bu2SnO, Ph2SnO and Ph3SnOH separately. Characterization of the ligand and complexes was done using magnetic susceptibility and Scanning Electron Microscopy (SEM). Ligand and complexes were screened for antimicrobial activity against five strains of gram-positive bacteria: Methicillin Resist Staph aureus, Vancomycin Resist enterococci, Staphylococcus aureus, Streptococcus pyogenes and Bacillus cereus and five fungi strains: Aspergillus fumigatus, Aspergillus flavus, Aspergillus nigre, Fusarium oxysporum and Fusarium proliferatum. Ciproflxacin and Ketoconazole were used as controlled drugs. Magnetic susceptibility data revealed complexes (1), (2) and (3) to be paramagnetic with values 0.144 µeff, 0.149 µeff and 0.151 µeff, respectively. SEM revealed that complex (3) pores were better filled by metals than complex (1) during complexation of parent organotin (IV) compound with the ligand, L. Antimicrobial result showed that the complexes synthesized in general exhibited significant activity (20-27 mm) against the microbes at the minimum inhibition concentrations (MIC) in the range 2.5 - 5 µg/mL (gram-positive bacteria) and 5 µg/mL (fungi) and minimum bactericidal/fungicidal concentrations (MBC/MFC) of 5 - 20 µg/mL/10 - 20 µg/mL. The complexes and ligand showed better antimicrobial effect against test microbes at than the control drugs. These complexes hold promise as antibacterial and antifungal agents that may be used as metal-base drugs/formulations.

Synthetic route for O,S‐coordinated organotin (IV) aldehydes: Spectroscopic, computational, XRD, and antibacterial studies

Numerous synthetic routes have been established for the synthesis of organotin (IV) derivatives of carboxylates, thiocarbamates, thiols, alcohols, amines, Schiff bases, etc. However, no synthetic path has been still developed for the synthesis of organotin (IV) aldehydes. We have synthesized four O,S‐coordinated organotin (IV) aldehydes (1–4) of the general formulas LSn(S)(Cl)R2 (where R2 = Me2, n‐Bu2, Ph2 for 1–3, respectively) and LSn(S)Ph3 (4) by reaction of 4‐(dimethylamino)benzaldehyde (L) with KOH, CS2, and R2SnCl2/Ph3SnCl in methanol. The synthesized products were characterized by microanalysis (CHN), FT‐IR analysis, UV–visible spectroscopy, NMR spectroscopy (1H and 13C), thermogravimetric analysis (TGA), computational studies, and single‐crystal XRD. Elemental analysis data were agreed well with the molecular composition of the products. FT‐IR spectroscopy has shown a significant lowering of C=O vibrational frequency after ligand–metal coordination. The electronic spectroscopy of complexes 1–4 demonstrated the π–π* (342–343 nm) and n–π* (279–296 nm) transitions, with the band gap values of 3.15–3.38 eV. 1H NMR spectra displayed distinct signals for the ligand skeleton and organotin (IV) moieties. 13C NMR spectroscopy exhibited an upfield shift of carbonyl oxygen after ligand–metal coordination. The thermogravimetric analysis revealed the thermal stabilities of complexes up to a temperature of 190 to 320°C. Single‐crystal XRD analysis of product 4 has shown a distorted trigonal bipyramidal geometry around Sn (IV), in which the three phenyl groups were positioned equatorially while the carbonyl oxygen (from the aldehyde) and the sulfur atom occupied the apical positions. Employing the 6‐31G(d,p) basis set and the CAM‐B3LYP functional, time‐dependent density functional theory (TD‐DFT) computations were performed for the calculation of absorbance maxima, oscillator strength (f), and matching molecular designations. MEP maps and HOMO–LUMO energy gaps were predicated on the CAM‐B3LYP/6‐31+g(d,p) level of theory and were used to resolve GRD, including chemical potential (μ), global hardness (η), global softness (S), electronegativity (χ), electrophilicity (ω), ionization potential (IP), and electron affinity (EA). The phenyltin (IV) derivatives (3 and 4) have shown a fantastic biofilm inhibition of Escherichia coli, which was even higher as compared with that of the reference drug ciprofloxacin. The bioactivity of 2 against Bacillus subtilis was equivalent to that of the ciprofloxacin. The products 2 and 3 have shown very little (less than 10%) toxic hemolytic effects demonstrating their possible safe use for the human beings.

Theoretical studies for the detailed electronic structure of organotin(IV) derivatives of 4-fluoroanthranilic acid, X-ray structure of n-dibutyltin bis(4-fluoroanthranilate)

The present study describes the detailed DFT-based electronic structure calculations without any symmetry constraints being performed on di- and triorganotin derivatives of 4-fluoroanthranilic acid (AFA), viz. Me2SnL2 (1), n-Bu2SnL2 (2), Me3SnL (3), and Ph3SnL (4) (where L= monoanion of AFA). The structural and atomic charge analysis have confirmed the previously reported our experimental results, i.e. bicapped tetrahedral and distorted tetrahedral geometry for di- and triorganotin derivatives, respectively, and all the complexes 1–4 contain a positively charged central tin atom surrounded by a negatively charged system. The single crystal X-ray structure of complex 2 (n-Bu2SnL2) also suggests that AFA acts as a monoanion and bidentate ligand resulting a bicapped tetrahedral environment around tin. Various population analysis such as Mulliken (MPA), Hirshfeld (HPA), and natural population analysis (NPA) have been employed to calculate the charges at all the atoms. A finite difference approximation method has been used to explain the charge distribution within the studied complexes 1–4 based on the conceptual global and local reactivity DFT-based descriptions, frontier molecular-orbital analysis (FMOA), and molecular electrostatic potential maps (MEP). Further, the conceptual DFT-based global reactivity descriptors and frontier molecular orbital analysis show that the interactions between CT-DNA and complexes 1–4 may be groove binding or electrostatic. The integral equation formalism-polarizable continuum model (IEF-PCM) has been employed to calculate the UV–visible spectra of 1–4 in the solvent field, whereas the same in the gas phase has been obtained with the help of time-dependent DFT (TD-DFT) at the same level of theory. The intramolecular charge distribution in 1–4 has been investigated with the help of natural bond orbital (NBO) analysis. The topological and energetic parameters at the selected bond critical points in the coordination sphere of complexes 1–4 have been calculated using atoms-in-molecules (AIM) theory. The analysis of different kinds of non-covalent interactions (NCI) in complexes 1–4 has also been investigated.

In vitro anticancer, antioxidant, antimicrobial, antileishmanial, enzymes inhibition and in vivo anti-inflammatory activities of organotin(IV) derivatives of 4-bromophenoxyacetic acid

Organotin(IV) derivatives {(n-C4H9)3SnL (1), (CH3)3SnL (2), (n-C4H9)2SnL2 (3) and (CH3)2SnL2 (4)} of 4-bromophenoxyacetic acid (HL) were synthesized and characterized by elemental, FT-IR, NMR and single crystal XRD diffraction analyses. The carboxylate ligand showed bridging/chelating bidentate coordination. The complexes 1 and 2 have adopted polymeric chain structures consisting tin atoms in distorted trigonal bipyramidal geometry. Complex 3 has shown highest DPPH radical scavenging (IC50 = 33.46 µg/mL) and antileishmanial activity (IC50 = 27.06 µg/mL). Complex 3 was also the most efficient agent in acetylcholinesterase (IC50 = 5.12 µg/mL), butyrylcholinesterase (IC50 = 13.79 µg/mL) and Monoamine oxidase (IC50 = 8.50 µg/mL) inhibition assays. Complex 4 (IC50 = 18.73 µg/mL) was the most potent ABTS radical scavenger. Complex 1 with IC50 values of 27.50 and 71.32 µg/mL was the most efficient α-glucosidase and dipeptidyl peptidase-4 enzyme inhibitor, respectively. While complex 2 was found the most potent Cyclooxygenase-2 (7.81 µg/mL) and 5-Lioxygenase (6.69 µg/mL) inhibitor. MTT assay revealed highest inhibitory potency of complexes 4 (IC50 = 8.035 ± 0.05 μg/ml), and 1 (IC50 = 10.16±0.17 μg/ml) towards the brain cancer cell line. The in vivo study performed on mice have shown potent anti-inflammatory effects of 1 and 2 comparable to the standard, indomethacin.

Diorganotin (IV) amino acid complexes as potential anticancer agents. Synthesis, structural characterization, and in vitro assays

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 (1H, 13C, 119Sn Nuclear Magnetic Resonance) spectroscopies. Complexes Bu2Sn(Lys) (1), Ph2Sn(Lys) (2), Bu2Sn(Orn) (3), and Ph2Sn (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 Ph2Sn (Glu-OMe) (6a) forms a polymeric network via Sn–O–Sn bridging whereby the tin atom is six-coordinated. In turn, 119Sn 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.

Synthesis, characterization, and bioactivity test of dibutyltin(IV) dihydroxyibenzoate as disinfectant agent

Abstract In this work, three organotin (IV) derivatives namely dibutyltin(IV) di-2-hydroxybenzoate (DBT2-HBz) (2), dibutyltin(IV) di-3-hydroxybenzoate (DBT3-HBz) (3) and dibutyltin(IV) di-4-hydroxybenzoate (DBT4-HBz)) (4) were synthesized and tested as disinfectant against pathogenic bacteria, Staphylococcus aureus. Compounds 2–4 were prepared by reacting dibutyltin(IV) oxide (DBTO) (1) with 2-hydroxybenzoic acid (2-HHBz), 3-hydroxybenzoic acid (3-HHBz) and 4-hydroxybenzoic acid (4-HHBz). The synthesized compounds were characterized by spectroscopic techniques including UV–Vis, FT-IR, 1H NMR, and 13C NMR, and micro-elemental analyzer. The optical density (OD) of compounds was measured by UV–Vis at 600 nm, which showed good bioactivity against the S. aureus. The data obtained indicated that compound 4 has higher bioactivity than compound 2 and 3, and the positive control using a commercial disinfectant containing 5 % benzalkonium chloride. The optimum bioactivity of compound 4 was observed at a concentration of 5 × 10−4 M with a contact time of 10 min, as shown by the decrease in absorbance from 0.6092 to 0.4005. Compound 2 was optimal at a concentration of 5 × 10−4 M with a contact time of 10 min, and the absorbance decreased from 0.6092 to 0.4416. Compound 3 and positive control showed a smaller decrease in absorbance compared to compound 4 and 2. Overall, the results obtained indicated that the compounds synthesized have promising potential as disinfectant against pathogenic bacteria.

Synthetic, structural, and biological studies of organotin(IV) derivatives of 6-amino-2-(methyleneamino)hexanoic acid

L-lysine monohydrate was treated with formaldehyde to produce 6-amino-2-(methyleneamino)hexanoic acid (LH) whose potassium salt (LK) was further refluxed with R2SnCl2 (R = Me, 1; n-Bu, 2; Ph, 3) or R3SnCl (R = Me, 4; n-Bu, 5; Ph, 6) in methanol to yield the organotin(IV) products (1–6). FTIR spectroscopy displayed chelating coordination of the carboxylate group and a trigonal bipyramidal geometry of tin in the solid-state which was also verified by computational studies.1H NMR spectra displayed signals of ligand skeleton and organotin(IV) moieties. Microanalysis (CHN) data agreed well with the molecular composition of products. Thermogravimetric analysis (TGA) showed highest thermal stability of 5. HOMO and LUMO energy levels are −5.44 to −6.04 and −0.10 to +0.1 eV, respectively. The smallest and highest energy (between HOMO and LUMO) were observed in 1 and 6, respectively. The order of dipole moment is 1 > 4>5 > 3>6 > 2. The significant shielding and de-shielding phenomena observed in 13C NMR spectra of 3 and 6 can be attributed to the existence of delocalized electrons. Antibacterial potential (disc diffusion method) decreased in the order Ciprofloxacin > 1 > 3>6 > 4>2 > 5>LH against Escherichia coli and 1 > 3 = Ciprofloxacin > 4 ≥ 6 > 2>5>LH against Staphylococcus aureus.

Combined experimental and theoretical studies of diorganotin(IV) complexes of 1,2,4-triazole based Schiff base: Synthesis, spectroscopic investigation, DFT calculation, antifungal activity

Two novel diorganotin(IV) compounds of Schiff base (HL) with a general formula of R2Sn(L)Cl (where R equals n-Bu(1) or Ph (2)) have been formed and structurally identified. The identification was made through examination of various properties including elemental analysis, FT-IR, multinuclear NMR, 2D-HMQC, ESI-MS, and UV–vis analysis. The proposed structure for these organotin(IV) derivatives is a distorted tetrahedron surrounding tin, with the Schiff base ligand acting as a monoanionic monodentate by coordinating through the Ohydroxyl group. The density functional theory (DFT) calculation was accomplished at the B3LYP/6-31G(d,p)/Def2- SVP(Sn) level. The MEP map was used to recognize the reactive sites on the molecules, and atomic charges were determined at specific atoms. The global reactivity descriptors and the Frontier MO's were calculated using conceptual-DFT to understand the behavior of the structure and reactivity. We compared the experimental and simulated vibrational frequencies and found a strong correlation. A time-dependent DFT method utilizing the IEFPCM model was employed to determine the simulated UV–vis spectrum. Both of the analyzed complexes were tested for their ability to inhibit fungal growth in vitro against selected fungal strains. The significant antifungal effect of complexes could be observed against all strains.

Engineered organotin(IV) and vanadium(V) derivatives with distinct coordination modes and luminescent properties for the efficient detection and quantification of permanganate ions.

The distinction in coordination modes of metal complexes leads to their versatile structural features and unique properties. Here, we report two tetradentate Schiff base ligands (H2L1 and H2L2) bearing N2O2 donor sets, tactically selected to provide distinct coordination modes with different metal ions. The ligands were utilized to synthesize their organotin(IV) (1-4) and vanadium(V) (5) derivatives. The synthesized compounds were characterized using elemental analysis, FT-IR spectroscopy, multi-nuclei NMR (1H, 13C, and 119Sn) spectroscopy, mass spectrometry, and single-crystal X-ray diffraction. The organotin(IV) derivatives (1-4) displayed hepta-coordination around both the Sn centres as they were achieved in their dimeric form. Contrariwise, the vanadium(V) compound (5) was isolated as a mononuclear entity exhibiting penta-coordinated geometry around the vanadium centre. The variation in the coordination modes was evident in their UV-vis and fluorescence spectra. The organotin(IV) compounds (1-4) exhibited a strong emission band centred at 468nm when excited at a wavelength of 360nm whereas the vanadium(V) (5) derivative displayed poor fluorogenic response. Compound 1 was further explored for the fluorogenic chemo-sensing of permanganate ions (MnO4-) amongst various anions by quenching response. A detailed investigation of the recognition of permanganate ions was accomplished by spectrofluorometric, spectroscopic (119Sn NMR), mass spectrometric, and computational studies.

Synthesis, Structural Elucidation, and Therapeutic Screening of Organotin(IV) derivatives of oxo-ethyl carbonodithioate

Exploring the therapeutic potential of organotin-based oxo-ethyl carbonodithioates, a series of organotin(IV) thiocarboamates (1-5) were synthesized with diverse alkyl and phenyl substituents. The chemical- composition, morphology, theoretical properties, and drug-DNA binding capabilities of the synthesized derivatives were performed by applying different characterization techniques like FT-IR, NMR (1H, 13C), AFM, DFT analysis, and UV-Vis spectroscopy respectively. The NMR data indicated six and four coordinated geometries, while the AFM results revealed smart surfaces concerning the grain size and root mean square (RMS) roughness, signifying catalytic and biocidal uses. The drug-DNA binding via intercalative mode of interaction with blue and red shifts was determined by using using UV spectroscopy. The in vitro biocidal capacity of selected complexes was evaluated against typical bacterial, fungal, cytotoxic, and leishmanial strains respectively. As a result of the surface and biocidal characterization, the synthesized complexes may be applied with greater potential in biomedical, pharmaceutical, infectious, catalysis, and cosmetics industries

Synthesis and structures of polynuclear organotin(IV) complexes of a polyaromatic carboxylate ligand and cytotoxic evaluation in tumor cell lines

Three polynuclear organotin(IV) derivatives of composition [n-Bu3Sn(HL)]n1, [Ph3Sn(HL)]n2 and [n-Bu2Sn(HL)2]23 were synthesized by reacting 2-((E)-(4-hydroxy-3-((E)-((4-(methoxycarbonyl)phenyl)imino)methyl)phenyl)diazenyl)benzoic acid (H'HL) with (n-Bu3Sn)2O, Ph3SnOH and n-Bu2SnO, respectively. The structures 1–3 were fully characterized by elemental analysis, IR and NMR (1H, 13C, and 119Sn), 119Sn Mössbauer spectroscopy, and additionally, the molecular and crystal structures of 1–3 and its pro-ligand (H'HL) were established by single-crystal X-ray diffraction analysis. The tributyltin(IV) complex 1 is a one-dimensional coordination polymer, in which the azo ligand bridges adjacent Sn(IV) centres solely via the two carboxylate O-atoms. The hydroxy H atom forms an intramolecular O–H···N hydrogen bond with the imine N-atom, as observed in the crystal structure of H'HL. The triphenyltin(IV) complex 2 is also a one-dimensional coordination polymer, but in this case the azo ligand bridges adjacent Sn(IV) centres via its carboxylate group and the deprotonated phenol O-atom. Unlike in 1, the phenol H-atom has migrated to the imine N-atom, to give a zwitterionic form of the azo ligand. The tin centers in 1 and 2 are pentacoordinated and reveal a distorted trans-R3SnO2 trigonal-bipyramidal environment. The dibutyltin(IV) complex 3 crystallizes as discrete centrosymmetric dinuclear entities where the unique Sn(IV) center is heptacoordinated in a distorted pentagonal bipyramid coordination geometry. In vitro cytotoxicity studies of compound 1 were performed and compared with 2 across a panel of human tumor cell lines and the results were compared with the data of six clinically used anticancer drugs.

A Broad Spectrum Antiparasitic Activity of Organotin (IV) Derivatives and Its Untargeted Proteomic Profiling Using Leishmania donovani.

Metals have been used in medicine since ancient times for the treatment of different ailments with various elements such as iron, gold and arsenic. Metal complexes have also been reported to show antibiotic and antiparasitic activity. In this context, we tested the antiparasitic potential of 10 organotin (IV) derivatives from 4-(4-methoxyphenylamino)-4 oxobutanoic acid (MS26) against seven eukaryotic pathogens of medical importance: Leishmania donovani, Trypanosoma cruzi, Trypanosoma brucei, Entamoeba histolytica, Giardia lamblia, Naegleria fowleri and Schistosoma mansoni. Among the compounds with and without antiparasitic activity, compound MS26Et3 stood out with a 50% effective concentration (EC50) of 0.21 and 0.19 µM against promastigotes and intracellular amastigotes of L. donovani, respectively, 0.24 µM against intracellular amastigotes of T. cruzi, 0.09 µM against T. brucei, 1.4 µM against N. fowleri and impaired adult S. mansoni viability at 1.25 µM. In terms of host/pathogen selectivity, MS26Et3 demonstrated relatively mild cytotoxicity toward host cells with a 50% viability concentration of 4.87 µM against B10R cells (mouse monocyte cell line), 2.79 µM against C2C12 cells (mouse myoblast cell line) and 1.24 µM against HEK923 cells (human embryonic kidney cell line). The selectivity index supports this molecule as a therapeutic starting point for a broad spectrum antiparasitic alternative. Proteomic analysis of host cells infected with L. donovani after exposure to MS26Et3 showed a reduced expression of Rab7, which may affect the fusion of the endosome with the lysosome, and, consequently, impairing the differentiation of L. donovani to the amastigote form. Future studies to investigate the molecular target(s) and mechanism of action of MS26Et3 will support its chemical optimization.

O-22 - Organotin derivatives as versatile precursors for the radioiodination and radiofluorination of 1,2,3,4-tetrahydro-7-hydroxyisoquinoline-3-carboxylic acid (TIC(OH)) analogues

O-22 - Organotin derivatives as versatile precursors for the radioiodination and radiofluorination of 1,2,3,4-tetrahydro-7-hydroxyisoquinoline-3-carboxylic acid (TIC(OH)) analogues

Synthesis, characterization, and biological evaluation of eight new organotin(IV) complexes derived from (1R, 2S) ephedrinedithiocarbamate ligand

The synthesis of eight new organotin derivatives containing ephedrine-substituted dithiocarbamate ligands [R3Sn(ephedtc)] 2–5. 2: R = Me; 3: R = Bu; 4: R = Cy; 5: R = Ph and [R2Sn(ephdtc)2] 6–9. 6: R = Me; 7: R = Bu; 8: R = t-Bu; 9: R = Ph is reported. The complexes were obtained from sodium ephedrinedithiocarbamate [Na(ephedtc)] 1 and the corresponding tri-organotin(IV) chlorides, R3SnCl 2–5 or di-organotin(IV) dichlorides, R2SnCl26–9. They were characterized by elemental analysis, IR, and NMR spectroscopy (1H, 13C, and 119Sn). The infrared spectra (solid-state) suggest that the Sn(IV) is coordinated to the ligand ephedtc, through the two sulfur atoms in an anisobidentate coordination mode. In solution, the 119Sn NMR indicates the coordination numbers: tetracoordinated for 2–4, pentacoordinate for 5, and hexacoordinated for 6–9. The single-crystal X-ray diffraction analysis of 4 reveals an anisobidentate coordination mode with a trigonal bipyramid distorted geometry around the Sn(IV). All compounds except 2, show inhibition in at least one bacterial strain, and 7 and 9 have the best antibacterial activity, mainly in the clinically isolated strains.

C,O‐Chelated organotin(IV) derivatives as potential anticancer agents: Synthesis, characterization, and cytotoxic activity

AbstractOrganotin(IV) chemistry is nowadays in a continuous expansion due to the biological and medicinal potential found for some of these species. Within this study, the cytotoxic activity of several organotin(IV) compounds was investigated on two lung cancer cell lines (H522 and SK‐MES‐1) and on a normal lung cell line in order to have an overview of the toxicity and the selectivity of these derivatives. Moreover, the synthetic protocols, as well as the structural particularities of the novel organotin(IV) species, are also discussed. Hydrolysis of [2‐{(CH2O)2CR}C6H4]2SnPh2[R = H (1), Me (2)] withp‐toluenesulfonic acid as a proton source afford the expected derivatives [2‐(O═CR)C6H4]2SnPh2[R = H (3), Me (4)]. When hydrochloric acid is used in these reactions, a chlorine‐phenyl exchange took place in addition to the removal of the acetal fragments and the following products [2‐(O═CR)C6H4]2SnPhCl [R = H (5), Me (6)] were isolated. Treatment of5with 2 equiv of 3‐aminomethylpyridine in neat affords the imino(aryl)tin compound 2‐(3′‐PyCH2N═CH)C6H4]2SnPhCl (7). The reaction between6and potassium nicotinate allows the isolation of the organotin(IV) carboxylate [2‐{O═C (CH3)}C6H4]2SnPh[O(O)CC5H4N‐3] (8). Compounds1–8were characterized by multinuclear NMR spectroscopy in solution, mass spectrometry, and IR spectroscopy, and their molecular structures were confirmed by X‐ray diffraction analysis. Compounds1–8were investigated for their antitumoral effects onHomo sapienslung cancer cell lines (H522 and SK‐MES‐1) and on a normal bronchial epithelial cell line, BEAS‐2B.

Organotin (IV) complexes with sulphonyl hydrazide moiety. Design, synthesis, characterization, docking studies, cytotoxic and anti-leishmanial activity

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

Cellular Basis of Organotin(IV) Derivatives as Anticancer Metallodrugs: A Review.

Organotin(IV) compounds have wide applications in industrial and agricultural fields owing to their ability to act as poly(vinyl chloride) stabilizers and catalytic agents as well as their medicinal properties. Moreover, organotin(IV) compounds may have applications as antitumor, anti-inflammatory, antifungal, or antimicrobial agents based on the observation of synergistic effects following the binding of their respective ligands, resulting in the enhancement of their biological activities. In this review, we describe the antiproliferative activities of organotin(IV) compounds in various human cancer cell lines based on different types of ligands. We also discuss the molecular mechanisms through which organotin(IV) compounds induce cell death via apoptosis through the mitochondrial intrinsic pathway. Finally, we present the mechanisms of cell cycle arrest induced by organotin(IV) compounds. Our report provides a basis for studies of the antitumor activities of organotin(IV) compounds and highlights the potential applications of these compounds as anticancer metallodrugs with low toxicity and few side effects.