Triorganotin compounds - ligands for “rexinoid” inducible transcription factors: Biological effects

Brtko, Július; Dvořák, Zdeněk

doi:10.1016/j.toxlet.2015.02.009

Cited by 41 publications

(41 citation statements)

References 104 publications

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“…Organotin compounds are typical environmental contaminants and suspected endocrine disrupting substances (Brtko and Dvorak 2015). Humans are exposed to tributyltin (TBT), previously used as an antifouling paint in ships, mainly through fi sh con-sumption.…”

Section: Organotins Derivates -Rxr Ligandsand Reproductionmentioning

confidence: 99%

“…A remarkable breakthrough in the fi eld came out with the recent fi ndings that triorganotin compounds are agonists of RXR subtypes of NRs (Figure 1), not sharing any structural characteristics with any endogenous ligands of NRs. It has been shown that RXRα with its NR cysteine residue (C432) of helix H11 at the entrance to the ligand binding pocket was found to covalently interact with trialkyltin or triaryltin (Grun 2014;Brtko and Dvorak 2015). Aft er crossing the cell membrane, triorganotins could bind to NRs, which reside in the cytoplasm (e.g.…”

Section: Organotins Derivates -Rxr Ligandsand Reproductionmentioning

confidence: 99%

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The role of retinoic acid receptors and their cognate ligands in reproduction in a context of triorganotin based endocrine disrupting chemicals

Macejova¹,

Toporová²,

Brtko³

2016

Endocrine Regulations

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Retinoic acid (RA), an active form of vitamin A, regulates the embryonic development, male and female reproduction and induces important effects on the cell development, proliferation, and differentiation. These effects are mediated by the retinoid (RAR) and rexinoid nuclear receptors (RXR), which are considered to be a ligand-activated, DNA-binding, trans-acting, and transcription-modulating proteins, involved in a general molecular mechanism responsible for the transcriptional responses in target genes. Organotin compounds are typical environmental contaminants and suspected endocrine disrupting substances. They may affect processes of reproductive system in mammals, predominantly via nuclear receptor signaling pathways. Triorganotins, such as tributyltin chloride (TBTCl) and triphenyltin chloride (TPTCl), are capable to bind to RXR molecules, and thus represent potent agonists of RXR subtypes of nuclear receptors not sharing any structural characteristics with endogenous ligands of nuclear receptors. Th is article summarizes selected effects of biologically active retinoids and rexinoids on both male and female reproduction and also deals with the effects of organotin compounds evoking endocrine disrupting actions in reproduction.

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Section: Organotins Derivates -Rxr Ligandsand Reproductionmentioning

confidence: 99%

Section: Organotins Derivates -Rxr Ligandsand Reproductionmentioning

confidence: 99%

The role of retinoic acid receptors and their cognate ligands in reproduction in a context of triorganotin based endocrine disrupting chemicals

Macejova¹,

Toporová²,

Brtko³

2016

Endocrine Regulations

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“…The di‐organic derivatives affect the cellular metabolism, and tri‐organic tin compounds promote the exchange of hydroxyl ions through the mitochondrial membrane . Moreover, triorganotins can act as nuclear retinoid X receptors (RXR) agonists . Complexes with 2‐mercapto‐nicotinic acid, or 2‐thiobarbituric acid were found to inhibit enzymatic peroxidation of linoleic acid by the lipoxygenase, moreover, the correlation between enzyme inhibitions by organotins and their anti‐tumor activity was revealed.…”

Section: Introductionmentioning

confidence: 99%

“…[11] Moreover, triorganotins can act as nuclear retinoid X receptors (RXR) agonists. [12] Complexes with 2-mercapto-nicotinic acid, [13,14] or 2-thiobarbituric acid [15] were found to inhibit enzymatic peroxidation of linoleic acid by the lipoxygenase, moreover, the correlation between enzyme inhibitions by organotins and their anti-tumor activity was revealed.…”

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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“…Tin-based drugs represent an excellent alternative to platinum ones as antitumor agents, having the considerable advantage to display a lower toxicity. Triorganotins have demonstrated potential antiproliferative activity in vitro [7] against human tumor cell lines, which has been related to their ability to bind to proteins [8,9]. Special attention is given to organotin(IV) carboxylates with significant cytotoxic properties against different cancer cell lines [10,11].…”

Section: Introductionmentioning

confidence: 99%

A novel compound of triphenyltin(IV) with N-tert-butoxycarbonyl-l-ornithine causes cancer cell death by inducing a p53-dependent activation of the mitochondrial pathway of apoptosis

Girasolo

Tesoriere

Casella

et al. 2017

Inorganica Chimica Acta

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Triorganotin compounds - ligands for “rexinoid” inducible transcription factors: Biological effects

Cited by 41 publications

References 104 publications

The role of retinoic acid receptors and their cognate ligands in reproduction in a context of triorganotin based endocrine disrupting chemicals

The role of retinoic acid receptors and their cognate ligands in reproduction in a context of triorganotin based endocrine disrupting chemicals

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

A novel compound of triphenyltin(IV) with N-tert-butoxycarbonyl-l-ornithine causes cancer cell death by inducing a p53-dependent activation of the mitochondrial pathway of apoptosis

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