Syntheses, structures and anti-tumor activity of four new organotin(iv) carboxylates based on 2-thienylselenoacetic acid

Abstract

With the 2-thienylselenoacetic acid ligand, four new organotin complexes, [Me3Sn(O2CCH2SeC4H3S-o)]n (), [(Ph3Sn)6(O2CCH2SeC4H3S-o)6] (), [(Me2Sn)4(μ3-O)2(O2CCH2SeC4H3S-o)4] (), and [(PhSn)6(μ3-O)6(O2CCH2SeC4H3S-o)6] (), have been synthesized and characterized by X-ray crystallography, elemental analysis, FT-IR and NMR ((1)H, (13)C, and (119)Sn) spectroscopy. The structure analysis indicates that complex adopts a 1D infinite zig-zag chain structure, while complex shows a centrosymmetric hexanuclear 24-membered macrocycle. In contrast, complex and complex display ladder and drum structures, respectively. Examination of the non-covalent intermolecular contacts in complex reveals the existence of the C-HO and C-Hπ interactions, which play an important function in the supramolecular construction. These compounds are rare examples of selenium carboxylic acid-based organotin derivatives. Furthermore, the anti-tumor activity of complexes has also been studied. Importantly, the anti-proliferative properties and possible mechanism of complex are preliminarily investigated. The results demonstrate that complex could induce apoptotic cell death via accumulation of ROS and collapse of the mitochondrial membrane permeabilization (MMP).

o-Vanillin Derived Schiff Bases and Their Organotin(IV) Compounds: Synthesis, Structural Characterisation, In-Silico Studies and Cytotoxicity

“…Theoretically, as the coordination number about tin increases, chemical shifts in 119 Sn NMR move towards lower frequencies [53]. 119 Sn NMR spectra are also very sensitive to the type of donor atom coordinated to the tin and its environment, e.g., alkyl or aryl groups in the case of a C donor and to the bond angles around the tin centre [54]. However, shielding or deshielding of the tin nucleus does not have a significant effect on the chemical shifts [55].…”

Triorganotin(IV) derivatives with semirigid heteroditopic hydroxo‐carboxylato ligands: Synthesis, characterization, and cytotoxic properties

“…As a consequence of the structural differences, similar to macrocycle A in compound 5 , the macrocyclic ring conformation is slightly tiered (Figure S59). Although macrocyclic structures are quite commonly found in organotin complexes, [ 7,82–84 ] so far, there are only few examples for assemblies based on large heteroditopic ligands. [ 5,17,19,21,85 ]…”

“…As a consequence of the structural differences, similar to macrocycle A in compound 5, the macrocyclic ring conformation is slightly tiered ( Figure S59). Although macrocyclic structures are quite commonly found in organotin complexes, [7,[82][83][84] so far, there are only few examples for assemblies based on large heteroditopic ligands. [5,17,19,21,85] With pro-ligand H 0 HL 1 , the trimethyltin and triethyltin moieties explored (i.e., compounds 1 and 2) gave 1D coordination polymers based on carboxylate bridging.…”

“…The coordination chemistry of a wide range of straightforward heterodifunctional chelating ligands containing hard-soft donor sets provides a rigid, unsymmetrical metal coordination environment. Because additional synthetic effort is required, metal coordination polymers and metallo-macrocycles derived from heteroditopic ligands [1][2][3][4][5][6][7][8][9][10][11] are still significantly less explored than analogous systems based on two different ligands, which are frequently organic carboxylates and pyridine or imidazole derivatives. Because heteroditopic ligands can facilitate the generation of heterodimetallic assemblies [12,13] and reduce occurrences related to structural diversification, the development of such ligands is being explored in metal coordination chemistry.…”

Mechanisms of the Cytotoxic Action of Organotin Compounds

“…Различные исследования показывают, что ООС влияют на макромолекулы клетки (ДНК или белки), а также на энергетику клетки и функции митохондрий, взаимодействуют с клеточными мембранами, увеличивают концентрацию Ca 2+ в цитоплазме [3] [38]. Кроме того, ингибирование ферментов, вызванное ООС, также связано с их антипролиферативной активностью.…”