Synthesis and antioxidant activity of new organotin compounds containing a 2,6-di-tert-butylphenol moiety

Mukhatova, E. M.; Осипова, В. П.; Kolyada, M. N.; Movchan, N. O.; Shpakovsky, D. B.; Gracheva, Yu. A.; Orlova, S. I.; Милаева, Е. Р.

doi:10.1134/s001250081307001x

Cited by 14 publications

(10 citation statements)

References 13 publications

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“…Compounds 1 and 6 were synthesized as was described previously. 13 New organotin(IV) complexes 2-5 and 7 have been synthesized by interaction of organotin chlorides R n SnCl 4−n (n = 2, 3) with 2,6-di-tert-butyl-4-mercaptophenol (RSH) in methanol solution in the presence of an equivalent amount of KOH as shown in Scheme 1. The diorganotin dichloride 8 was obtained by the remetallation reaction of RHgCl and Sn in o-xylene under reflux.…”

Section: Synthesesmentioning

confidence: 99%

Synthesis, antiradical activity and in vitro cytotoxicity of novel organotin complexes based on 2,6-di-tert-butyl-4-mercaptophenol

et al. 2014

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A series of organotin complexes with Sn-S bonds of formulae Me2Sn(SR)2 (1); Et2Sn(SR)2 (2); (n-Bu)2Sn(SR)2 (3); Ph2Sn(SR)2 (4); R2Sn(SR)2 (5); Me3SnSR (6); Ph3SnSR (7) (R = 3,5-di-tert-butyl-4-hydroxyphenyl) were synthesized and characterized by elemental analysis, (1)H, (13)C NMR, and IR. The crystal structures of compounds 1, 4, 5, and 7 were determined by X-ray diffraction analysis. The tetrahedral geometry around the Sn center in the monocrystals of 1, 4, 5, and 7 was confirmed by X-ray crystallography. The high radical scavenging activity of the complexes was confirmed spectrophotometrically in a DPPH-test. The binding affinity of 1-7 and the starting R2SnCl2 (8) towards tubulin through their interaction with SH groups of proteins was studied. It was found that the hindered organotin complexes could interact with the colchicine site of tubulin, which makes them promising antimitotic drugs. Compounds 1-8 were tested for their in vitro cytotoxicity against human breast (MCF-7) and human cervix (HeLa) adenocarcinoma cells. Complexes 1-8 were also tested against normal human fetal lung fibroblast cells (MRC-5). Complexes 2-4 and 8 exhibit significantly lower cytostatic activity against the normal MRC-5 cell line compared to the tumor cell lines MCF-7 and HeLa used. A high activity against both cell lines 250 nM (MCF-7) and 160 nM (HeLa) was determined for the triphenyltin complex 7 while the introduction of hindered phenol groups decreases the cytotoxicity of the complexes against normal cells.

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Section: Synthesesmentioning

confidence: 99%

Synthesis, antiradical activity and in vitro cytotoxicity of novel organotin complexes based on 2,6-di-tert-butyl-4-mercaptophenol

et al. 2014

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“…Synthesis of complexes 1–7 from 2,6‐di‐ tert ‐butyl‐4‐mercaptophenol ( L 1 S H) has been reported by us . Starting Schiff base 2‐(N‐3 ′ ,5 ′ ‐di‐ tert ‐butyl‐4 ′ ‐hydroxyphenyl)‐iminomethylphenol ( L 2 ) was prepared as described previously .…”

Section: Methodsmentioning

confidence: 99%

“…The chelating ligands bearing 2,6‐di‐ tert ‐butylphenol pendant were proposed for neutralisation of non‐specific toxicity of organotins . We have recently published the synthesis, antioxidant and cytotoxic properties of organotin thiolates Me 2 Sn(L 1 S) 2 ( 1, L 1 = 3,5‐di‐ tert ‐butyl‐4‐hydroxyphenyl); Et 2 Sn(L 1 S) 2 ( 2 ); Bu 2 Sn(L 1 S) 2 ( 3 ); Ph 2 Sn(L 1 S) 2 ( 4 ); (L 1 ) 2 Sn(L 1 S) 2 ( 5 ); Me 3 Sn(L 1 S) ( 6 ) Ph 3 Sn(L 1 S) ( 7 ) on the base of 2,6‐di‐ tert ‐butyl‐4‐mercaptophenol ( L 1 SH ) . In order to establish possible mechanisms of their cytotoxicity the interaction with tubulin as molecular target and molecular docking were explored.…”

Section: Introductionmentioning

confidence: 99%

Antioxidative vs cytotoxic activities of organotin complexes bearing 2,6‐di‐tert‐butylphenol moieties

Antonenko

Shpakovsky

Vorobyov

et al. 2018

Applied Organom Chemis

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Two series of organotin(IV) complexes with Sn–S bonds on the base of 2,6‐di‐tert‐butyl‐4‐mercaptophenol (L1SH) of formulae Me2Sn(L1S)2 (1); Et2Sn(L1S)2 (2); Bu2Sn(L1S)2 (3); Ph2Sn(L1S)2 (4); (L1)2Sn(L1S)2 (5); Me3Sn(L1S) (6); Ph3Sn(L1S) (7) (L1 = 3,5‐di‐tert‐butyl‐4‐hydroxyphenyl), together with the new ones [Me3SnCl(L2)] (8), [Me2SnCl2(L2)2] (9) (L2 = 2‐(N‐3′,5′‐di‐tert‐butyl‐4′‐hydroxyphenyl)‐iminomethylphenol) were used to study their antioxidant and cytotoxic activity. Novel complexes 8, 9 of MenSnCl4 − n (n = 3, 2) with Schiff base were synthesized and characterized by 1H, 13C NMR, IR and elemental analysis. The crystal structures of compounds 8 and 9 were determined by X‐ray diffraction analysis. The distorted tetrahedral geometry around the Sn center in the monocrystals of 8 was revealed, the Schiff base is coordinated to the tin(IV) atom by electrostatic interaction and formation of short contact Sn–O 2.805 Å. In the case of complex 9 the distorted octahedron coordination of Sn atom is formed. The antioxidant activity of compounds as radical scavengers and reducing agents was proved spectrophotometrically in tests with stable radical DPPH, reduction of Cu2+ (CUPRAC method) and interaction with superoxide radical‐anion. Moreover, compounds have been screened for in vitro cytotoxicity on eight human cancer cell lines. A high activity against all cell lines with IC50 values 60–160 nM was determined for the triphenyltin complex 7, while the introduction of Schiff base decreased the cytotoxicity of the complexes. The influence on mitochondrial potential and mitochondrial permeability for the compounds 8 and 9 has been studied. It is shown that studied complexes depolarize the mitochondria but don't influence the calcium‐induced mitochondrial permeability transition.

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“…The structures of bis-(3,5-di-tret-butyl-4-hydroxyphenylthiolate) dimethyltin (Ме3) and (3,5-di-tert-bu-tyl-4-hydroxyphenylthiolate) triphenyltin (Ме5) are shown in Figure 1. Synthesis of Me3 and Me5 has been described earlier (Mukhatova et al 2013;Shpakovsky et al 2014).…”

Section: Compounds Under Studymentioning

confidence: 99%

Impact of organotin compounds on the growth of epidermoid Lewis carcinoma

Додохова¹,

Сафроненко²,

Котиева³

et al. 2021

RRP

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Introduction: Search for new compounds with a broad antitumor and antimetastatic potency due to multiple targeting remains important in medicinal chemistry, pharmacology and oncology. We report the efficacy of hybrid organotin agents bis-(3,5-di-tert-butyl-4-hydroxyphenylthiolate) dimethyltin (Ме3) and (3,5-di-tert-butyl-4-hydroxyphenylthiolate) triphenyltin (Ме5). Materials and methods: The compounds were administered to mice bearing the spontaneously metastatic epidermoid Lewis lung carcinoma (LLC). The efficacy of the treatment was evaluated by mean life span, percentage of tumor growth inhibition, number of lung metastases, frequency of metastasis, tumor weight 21 days after tumor cell inoculation, and a degree of lung damage according to the method of D. Tarin and J.E. Price. Results and discussion: For new organotin compounds containing an antioxidant protective fragment of 2,6-di-tert-butylphenol, moderate antitumor and pronounced antimetastatic effects were revealed in the Lewis model of epidermoid lung carcinoma; more active for Me5. Some features of the development of the process of metastasis were recorded with the introduction of various doses of hybrid organotin compounds. Conclusion: Substances Ме3 and Ме5 possess specific activity on the model under investigation, which allows one to suggest these organotins as promising series of antitumor and antimetastatic agents with multiple targeting mode of action.

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Synthesis and antioxidant activity of new organotin compounds containing a 2,6-di-tert-butylphenol moiety

Cited by 14 publications

References 13 publications

Synthesis, antiradical activity and in vitro cytotoxicity of novel organotin complexes based on 2,6-di-tert-butyl-4-mercaptophenol

Synthesis, antiradical activity and in vitro cytotoxicity of novel organotin complexes based on 2,6-di-tert-butyl-4-mercaptophenol

Antioxidative vs cytotoxic activities of organotin complexes bearing 2,6‐di‐tert‐butylphenol moieties

Impact of organotin compounds on the growth of epidermoid Lewis carcinoma

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