Novel triorganotin complexes based on phosphonic acid ligands: Syntheses, structures and in vitro cytostatic activity

An, Bo-Hang; Zhang, Rufen; Du, Xiu‐Mei; Li, Qianli; Cheng, Shuang; Huang, Han-Ching; Ma, Chunlin

doi:10.1016/j.jinorgbio.2020.111022

Cited by 6 publications

(1 citation statement)

References 48 publications

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“…The shorter tin-oxygen bond is associated with a longer C-O bond and vice versa. The Sn–O bond distances are more close to the sum of the covalent radii of tin and oxygen (2.13 Å), but are considerably less than the van der Waals radii (3.69 Å), indicating a strong Sn–O bonding interactions ( Barsan et al, 2008 ; Shujah et al, 2014 ; An et al, 2020 ). The Sn-O bonded distances are comparable to the other trimethyltin (IV) carboxylate derivatives previously reported ( Iqbal et al, 2013 ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization, Biological Activity and Molecular Docking Studies of Novel Organotin(IV) Carboxylates

et al. 2022

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Four new carboxylates complexes with general formula R2SnL2 and R3SnL, where R = n-butyl (1, 3), methyl (2, 4) and L = 4-Chlorophenoxyacetate, were synthesized in significant yields. FT-IR analysis revealed a chelating (1 and 2) and a bridging bidentate (3 and 4) coordination modes for the carboxylate ligand in solid state which was further confirmed by the single crystal X-ray analysis of complex 4. The NMR data (1H, 13C and 119Sn) revealed a higher coordination number around the tin center in R2SnL2 (1 and 2) compared to R3SnL (3 and 4). A close matching was observed between the experimental and calculated structures (obtained at B3LYP/6-31G* + LANL2DZ basis set). Quantum chemical analysis indicates that the carboxylate moiety has the major contribution in the formation of filled and unfilled orbitals as well as in ligand to ligand intramolecular charge transfer during the electronic transitions. The cytotoxicity data of the screened compounds evaluated against lung cancer cell line (A549) and normal lung fibroblast cell line (MRC-5) revealed that 1, 3 and 4 have shown dose dependent cytotoxic effects while HL and 2 have shown steady and low cytotoxic activities. The antibacterial activity of complexes 1–4 is higher than that of HL. Molecular docking study showed an intercalation binding mode for complex 3 with DNA (docking score = −3.6005) involving four polar interactions. Complex 3 docking with tubulin (PDB ID 1SA0) with colchicine as a target protein resulted in three polar interactions (docking score −5.2957). Further, the docking analysis of the HL and 1–4 has shown an adequate interactions with the coronavirus SARS-CoV-2 spike protein, nucleocapsid protein and human angiotensin converting enzyme (ACE2).

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Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization, Biological Activity and Molecular Docking Studies of Novel Organotin(IV) Carboxylates

et al. 2022

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Syntheses, structures, and the in vitro anticancer mechanism of triorganotin (IV) complexes based on 4,4′‐stilbenedicarboxylic acid

et al. 2023

Applied Organom Chemis

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Five triorganotin (IV) complexes, [(Ph3Sn)2L] (1) [(Me3Sn)2L]n (2), [(n‐Bu3Sn)2L]n (3), [(n‐Bu 3Sn)2L(4,4′‐bpy)]n (4), [(n‐Bu3Sn)2L(bpe)]n (5) [H2L = 4,4′‐stilbenedicarboxylic acid, 4,4′‐bpy = 4,4′‐bipyridine, bpe = 4,4′‐vinylenedipyridine], were successfully prepared and structurally characterized by FT‐IR, elemental analysis, NMR spectroscopy, PXRD, and X‐ray crystallography. Complex 1 is a monomer containing two tin atoms, and 1D infinite chains can be formed between the monomers through CH···π interactions. Complexes 2 and 3 represent 2D network structures containing tetranuclear 38‐membered rings. Meanwhile, complexes 4 and 5 are 1D chain‐like structures and form the 2D network and 3D stereo structure via CH···O intermolecular interactions, respectively. The anticancer activities of the complexes were investigated against different cancer cells (A549, HeLa, and HepG‐2). Complexes 1 and 3–5 showed superior anticancer activity. Meanwhile, the anticancer mechanism of complex 1 was studied with the results that complex 1 can promote the production of excessive reactive oxygen species, induce mitochondrial membrane permeability depolarization, and release proapoptotic factors from mitochondria into the cytosol, followed by caspase‐3 activation, nuclei damage, and apoptosis. Excitingly, complex 1 also has good antimetastatic ability toward HepG‐2 cancer cells.

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Organotin benzohydroxamate derivatives (OTBH) target colchicine-binding site exerting potent antitumor activity both in vitro and vivo revealed by quantitative proteomic analysis

Song

Liu

Yuan

et al. 2023

European Journal of Pharmaceutical Sciences

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Novel triorganotin complexes based on phosphonic acid ligands: Syntheses, structures and in vitro cytostatic activity

Cited by 6 publications

References 48 publications

Synthesis, Characterization, Biological Activity and Molecular Docking Studies of Novel Organotin(IV) Carboxylates

Synthesis, Characterization, Biological Activity and Molecular Docking Studies of Novel Organotin(IV) Carboxylates

Syntheses, structures, and the in vitro anticancer mechanism of triorganotin (IV) complexes based on 4,4′‐stilbenedicarboxylic acid

Organotin benzohydroxamate derivatives (OTBH) target colchicine-binding site exerting potent antitumor activity both in vitro and vivo revealed by quantitative proteomic analysis

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