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Chemical Compound Review

Fentin     triphenyltin

Synonyms: TRIPHENYLTIN, Triphenyl tin, AC1NSAPP, SureCN124009, AC1Q1GRG, ...
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Disease relevance of triphenyltin


High impact information on triphenyltin


Chemical compound and disease context of triphenyltin


Biological context of triphenyltin

  • Stable beta-phosphatoxy nitroalkanes, readily assembled by the Henry reaction and subsequent phosphorylation, serve as good precursors to alkene radical cations on treatment with triphenyltin or tributyl hydride and AIBN in benzene at reflux [16].
  • Inhibition of exocytosis by triphenyltin can be counteracted by a number of sulfhydryl compounds [17].
  • Tissue distributions of organotin compounds [tributyltin (TBT), triphenyltin (TPhT), and their metabolites] were different for butyltins and phenyltins; a remarkably high accumulation of TBT was observed in the ctenidium, osphradium, and heart, whereas high concentrations of TPhT were detected in the ovary and digestive gland [18].
  • Reduction of allyl 2-iodobenzyl malonates with triphenyltin hydrides generates aryl radicals that partition between 6-exo cyclization, 7-endo cyclization, and 1,5-hydrogen atom transfer [19].
  • Triphenyltin (0.1 mM) reduced the muscle membrane potential, the amplitude of the muscle action potential and the muscle membrane input resistance [14].

Anatomical context of triphenyltin


Associations of triphenyltin with other chemical compounds


Gene context of triphenyltin


Analytical, diagnostic and therapeutic context of triphenyltin


  1. Triphenyltin fluoride (TPTF) as a diabetogenic agent. TPTF induces diabetic lipemia by inhibiting insulin secretion from morphologically intact rabbit B-cell. Manabe, S., Wada, O. Diabetes (1981) [Pubmed]
  2. Triphenyltin as a potential human endocrine disruptor. Golub, M., Doherty, J. Journal of toxicology and environmental health. Part B, Critical reviews. (2004) [Pubmed]
  3. Organotin Decomposition by Pyochelin, Secreted by Pseudomonas aeruginosa Even in an Iron-Sufficient Environment. Sun, G.X., Zhou, W.Q., Zhong, J.J. Appl. Environ. Microbiol. (2006) [Pubmed]
  4. Acute triphenyltin intoxication: a case report. Wu, R.M., Chang, Y.C., Chiu, H.C. J. Neurol. Neurosurg. Psychiatr. (1990) [Pubmed]
  5. The effect of F0 inhibitors on the Vibrio alginolyticus membrane ATPase. Capozza, G., Dmitriev OYu, n.u.l.l., Krasnoselskaya, I.A., Papa, S., Skulachev, V.P. FEBS Lett. (1991) [Pubmed]
  6. Triorganotins inhibit the mitochondrial inner membrane anion channel. Powers, M.F., Beavis, A.D. J. Biol. Chem. (1991) [Pubmed]
  7. NF-kappaB activation by triphenyltin triggers apoptosis in HL-60 cells. Marinovich, M., Viviani, B., Corsini, E., Ghilardi, F., Galli, C.L. Exp. Cell Res. (1996) [Pubmed]
  8. Environmental obesogens: organotins and endocrine disruption via nuclear receptor signaling. Grün, F., Blumberg, B. Endocrinology (2006) [Pubmed]
  9. Impaired cytosolic Ca2+ response to glucose and gastric inhibitory polypeptide in pancreatic beta-cells from triphenyltin-induced diabetic hamster. Miura, Y., Kato, M., Ogino, K., Matsui, H. Endocrinology (1997) [Pubmed]
  10. Studies on the nature of the high-affinity trialkyltin binding site of rat liver mitochondria. Dawson, A.P., Farrow, B.G., Selwyn, M.J. Biochem. J. (1982) [Pubmed]
  11. Mechanism of augmentation of organotin decomposition by ferripyochelin: formation of hydroxyl radical and organotin-pyochelin-iron ternary complex. Sun, G.X., Zhong, J.J. Appl. Environ. Microbiol. (2006) [Pubmed]
  12. Toxicity of triorganotin compounds: comparative in vivo studies with a series of trialkyltin compounds and triphenyltin chloride in male rats. Snoeij, N.J., van Iersel, A.A., Penninks, A.H., Seinen, W. Toxicol. Appl. Pharmacol. (1985) [Pubmed]
  13. Enhancement of androgen-dependent transcription and cell proliferation by tributyltin and triphenyltin in human prostate cancer cells. Yamabe, Y., Hoshino, A., Imura, N., Suzuki, T., Himeno, S. Toxicol. Appl. Pharmacol. (2000) [Pubmed]
  14. Studies on the contracture inducing action of triphenyltin in the mouse diaphragm. Liu, S.H., Shiau, S.Y. Eur. J. Pharmacol. (1994) [Pubmed]
  15. In vitro metabolism of tributyltin and triphenyltin by human cytochrome P-450 isoforms. Ohhira, S., Enomoto, M., Matsui, H. Toxicology (2006) [Pubmed]
  16. Generation and reaction of alkene radical cations under nonoxidizing conditions: synthesis of the pyrrolizidine nucleus. Crich, D., Ranganathan, K., Huang, X. Org. Lett. (2001) [Pubmed]
  17. Toxicity of organotin compounds for polymorphonuclear leukocytes: the effect on phagocytosis and exocytosis. Elferink, J.G., Deierkauf, M., Van Steveninck, J. Biochem. Pharmacol. (1986) [Pubmed]
  18. Impact of tributyltin and triphenyltin on ivory shell (Babylonia japonica) populations. Horiguchi, T., Kojima, M., Hamada, F., Kajikawa, A., Shiraishi, H., Morita, M., Shimizu, M. Environ. Health Perspect. (2006) [Pubmed]
  19. Quantitating the effect of an ortho substituent on cyclization and intramolecular hydrogen-transfer reactions of aryl radicals. Curran, D.P., Fairweather, N. J. Org. Chem. (2003) [Pubmed]
  20. Triphenyltin as inductor of mitochondrial membrane permeability transition. Zazueta, C., Reyes-Vivas, H., Bravo, C., Pichardo, J., Corona, N., Chávez, E. J. Bioenerg. Biomembr. (1994) [Pubmed]
  21. Triphenyltin as an inhibitor of membrane-bound pyrophosphatase of Rhodospirillum rubrum. Celis, H., Escobedo, S., Romero, I. Arch. Biochem. Biophys. (1998) [Pubmed]
  22. Studies on the mechanism of action of triphenyltin on proton conduction by the H+-ATPase of mitochondria. Papa, S., Guerrieri, F., de Gomez Puyou, M.T., Barranco, J., Gomez Puyou, A. Eur. J. Biochem. (1982) [Pubmed]
  23. Triphenyltin impairs a protein kinase A (PKA)-dependent increase of cytosolic Na(+) and Ca(2+) and PKA-independent increase of cytosolic Ca(2+) associated with insulin secretion in hamster pancreatic beta-cells. Miura, Y., Matsui, H. Toxicol. Appl. Pharmacol. (2006) [Pubmed]
  24. Tributyltin or triphenyltin inhibits aromatase activity in the human granulosa-like tumor cell line KGN. Saitoh, M., Yanase, T., Morinaga, H., Tanabe, M., Mu, Y.M., Nishi, Y., Nomura, M., Okabe, T., Goto, K., Takayanagi, R., Nawata, H. Biochem. Biophys. Res. Commun. (2001) [Pubmed]
  25. Genotoxic effects of triphenyltin acetate and triphenyltin hydroxide on mammalian cells in vitro and in vivo. Chao, J.S., Wei, L.Y., Huang, M.C., Liang, S.C., Chen, H.H. Mutat. Res. (1999) [Pubmed]
  26. Light-induced membrane-potential increase, ATP synthesis, and proton uptake in Halobacterium halobium, R1mR catalyzed by halorhodopsin: Effects of N,N'-dicyclohexylcarbodiimide, triphenyltin chloride, and 3,5-di-tert-butyl-4-hydroxybenzylidenemalononitrile (SF6847). Mukohata, Y., Kaji, Y. Arch. Biochem. Biophys. (1981) [Pubmed]
  27. Effects of triphenyltin on cytosolic Na(+) and Ca(2+) response to glucose and acetylcholine in pancreatic beta-cells from hamster. Miura, Y., Matsui, H. Toxicol. Appl. Pharmacol. (2001) [Pubmed]
  28. Simultaneous modeling of multiple end points in life-cycle toxicity tests. Jager, T., Crommentuijn, T., van Gestel, C.A., Kooijman, S.A. Environ. Sci. Technol. (2004) [Pubmed]
  29. Molecular targets of organotin compounds in endocrine disruption: do organotin compounds function as aromatase inhibitors in mammals? Nakanishi, T., Nishikawa, J., Tanaka, K. Environmental sciences : an international journal of environmental physiology and toxicology. (2006) [Pubmed]
  30. Dithioerythritol (DTE) prevents inhibitory effects of triphenyltin (TPT) on the key enzymes of the human sex steroid hormone metabolism. Lo, S., Alléra, A., Albers, P., Heimbrecht, J., Jantzen, E., Klingmüller, D., Steckelbroeck, S. J. Steroid Biochem. Mol. Biol. (2003) [Pubmed]
  31. Determination of triorganotin species in water samples by liquid chromatography-electrospray-mass spectrometry. González-Toledo, E., Compañó, R., Prat, M.D., Granados, M. Journal of chromatography. A. (2002) [Pubmed]
  32. Influence of sediment quality on the responses of benthic invertebrates after treatment with the fungicide triphenyltin acetate. de Haas, E.M., Roessink, I., Verbree, B., Koelmans, A.A., Kraak, M.H., Admiraal, W. Environ. Toxicol. Chem. (2005) [Pubmed]
  33. Effects of pretreatment with cytochrome P-450 inducers, especially phenobarbital on triphenyltin metabolism and toxicity in hamsters. Ohhira, S., Matsui, H., Watanabe, K. Toxicology (1999) [Pubmed]
  34. Metabolism of tributyltin and triphenyltin by rat, hamster and human hepatic microsomes. Ohhira, S., Watanabe, M., Matsui, H. Arch. Toxicol. (2003) [Pubmed]
  35. Acute toxicity of triphenyltin hydroxide to three cladoceran species. Kline, E.R., Jarvinen, A.W., Knuth, M.L. Environ. Pollut. (1989) [Pubmed]
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