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Chemical Compound Review

Hexabutylditin     tributyltin

Synonyms: NSC-65520, NSC-92633, NSC-227367, NSC65520, NSC92633, ...
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Disease relevance of tributyltin

  • This study assesses targeting of lung metastases in mice with the radioiodinated thymidine analog 5-[(123)I/(125)I]iodo-2'-deoxyuridine ((123)I-IUdR/(125)I-IUdR), formulated with varying amounts of tributyltin precursor and injected intravenously [1].
  • Only 11.0% (range 7.7-17.6) of the BAL lymphocytes from sarcoidosis patients were annexin V positive after exposure to the apoptotic stimulus tributyltin compared with 55.0% (range 42.0-62.0) of BAL lymphocytes from healthy controls (p<0.001) [2].
  • Red blood cells (RBC) exposed to micromolar concentrations of tributyltin compounds (TBTX) undergo morphological changes and hemolysis [3].
  • Isolation of Escherichia coli mutants which are resistant to an inhibitor of H+-ATPase, tributyltin and also to uncouplers of oxidative phosphorylation [4].
  • Results indicate that FAD and TBT inhibit aromatase activity in o,p -DDT-treated fish but do not prevent feminization, indicating that increased brain aromatase activity is not critical to EDC-induced male-to-female sex inversion [5].

Psychiatry related information on tributyltin


High impact information on tributyltin


Chemical compound and disease context of tributyltin


Biological context of tributyltin


Anatomical context of tributyltin


Associations of tributyltin with other chemical compounds


Gene context of tributyltin


Analytical, diagnostic and therapeutic context of tributyltin


  1. 5-[123I/125I]iodo-2'-deoxyuridine in metastatic lung cancer: radiopharmaceutical formulation affects targeting. Semnani, E.S., Wang, K., Adelstein, S.J., Kassis, A.I. J. Nucl. Med. (2005) [Pubmed]
  2. Apoptosis resistant bronchoalveolar lavage (BAL) fluid lymphocytes in sarcoidosis. Stridh, H., Planck, A., Gigliotti, D., Eklund, A., Grunewald, J. Thorax (2002) [Pubmed]
  3. In vitro activation of lipophilic tributyltins by superoxide produces tributylstannyl superoxo radicals, proposed initiators of lipid peroxidation: an EPR model study. Rivera, J.A., Cummings, S.C., Macys, D.A. Chem. Res. Toxicol. (1992) [Pubmed]
  4. Isolation of Escherichia coli mutants which are resistant to an inhibitor of H+-ATPase, tributyltin and also to uncouplers of oxidative phosphorylation. Ito, M., Ohnishi, Y. FEBS Lett. (1981) [Pubmed]
  5. Antiestrogens inhibit xenoestrogen-induced brain aromatase activity but do not prevent xenoestrogen-induced feminization in Japanese medaka (Oryzias latipes). Kuhl, A.J., Brouwer, M. Environ. Health Perspect. (2006) [Pubmed]
  6. 2',3'=Carbonates in the synthesis of uridine 5'-deoxy and 2',5'-dideoxy derivatives. Hein, L., Draser, P., Beránek, J. Nucleic Acids Res. (1976) [Pubmed]
  7. On membrane motor activity and chloride flux in the outer hair cell: lessons learned from the environmental toxin tributyltin. Song, L., Seeger, A., Santos-Sacchi, J. Biophys. J. (2005) [Pubmed]
  8. Mechanism of entry into the cytosol of poliovirus type 1: requirement for low pH. Madshus, I.H., Olsnes, S., Sandvig, K. J. Cell Biol. (1984) [Pubmed]
  9. Sponge Bcl-2 homologous protein (BHP2-GC) confers distinct stress resistance to human HEK-293 cells. Wiens, M., Diehl-Seifert, B., Müller, W.E. Cell Death Differ. (2001) [Pubmed]
  10. Prodigiosins as a new group of H+/Cl- symporters that uncouple proton translocators. Sato, T., Konno, H., Tanaka, Y., Kataoka, T., Nagai, K., Wasserman, H.H., Ohkuma, S. J. Biol. Chem. (1998) [Pubmed]
  11. Mechanisms for the transport of alpha,omega-dicarboxylates through the mitochondrial inner membrane. Liu, G., Hinch, B., Beavis, A.D. J. Biol. Chem. (1996) [Pubmed]
  12. Stimulation by ATP of proinsulin to insulin conversion in isolated rat pancreatic islet secretory granules. Association with the ATP-dependent proton pump. Rhodes, C.J., Lucas, C.A., Mutkoski, R.L., Orci, L., Halban, P.A. J. Biol. Chem. (1987) [Pubmed]
  13. pH dependence of the partitioning of triphenyltin and tributyltin between phosphatidylcholine liposomes and water. Hunziker, R.W., Escher, B.I., Schwarzenbach, R.P. Environ. Sci. Technol. (2001) [Pubmed]
  14. Toxicity of dibutyltin, tributyltin and other organotin compounds to humans and to experimental animals. Boyer, I.J. Toxicology (1989) [Pubmed]
  15. Development of a biosensor for the detection of tributyltin. Horry, H., Durand, M.J., Picart, P., Bendriaa, L., Daniel, P., Thouand, G. Environ. Toxicol. (2004) [Pubmed]
  16. Interaction of tributyltin with 3,3',4,4',5-pentachlorobiphenyl-induced ethoxyresorufin O-deethylase activity in rat hepatoma cells. Kannan, K., Villeneuve, D.L., Blankenship, A.L., Giesy, J.P. J. Toxicol. Environ. Health Part A (1998) [Pubmed]
  17. Differential gliotoxicity of organotins. Karpiak, V.C., Eyer, C.L. Cell Biol. Toxicol. (1999) [Pubmed]
  18. Enantioselective alkylations of tributyltin enolates catalyzed by Cr(salen)Cl: access to enantiomerically enriched all-carbon quaternary centers. Doyle, A.G., Jacobsen, E.N. J. Am. Chem. Soc. (2005) [Pubmed]
  19. Endocrine-disrupting organotin compounds are potent inducers of adipogenesis in vertebrates. Grün, F., Watanabe, H., Zamanian, Z., Maeda, L., Arima, K., Cubacha, R., Gardiner, D.M., Kanno, J., Iguchi, T., Blumberg, B. Mol. Endocrinol. (2006) [Pubmed]
  20. Benzylidene acetal fragmentation route to 6-deoxy sugars: direct reductive cleavage in the presence of ether protecting groups, permitting the efficient, highly stereocontrolled synthesis of beta-D-rhamnosides from D-mannosyl glycosyl donors. Total synthesis of alpha-D-Gal-(1-->3)-alpha-D-Rha-(1-->3)- beta-D-Rha-(1-->4)-beta-D-Glu-OMe, the repeating unit of the antigenic lipopolysaccharide from Escherichia hermannii ATCC 33650 and 33652. Crich, D., Yao, Q. J. Am. Chem. Soc. (2004) [Pubmed]
  21. Tributyltin interacts with mitochondria and induces cytochrome c release. Nishikimi, A., Kira, Y., Kasahara, E., Sato, E.F., Kanno, T., Utsumi, K., Inoue, M. Biochem. J. (2001) [Pubmed]
  22. Tributyltin is a potent inducer of the heat shock response in human diploid fibroblasts. Zhang, H., Liu, A.Y. J. Cell. Physiol. (1992) [Pubmed]
  23. Trialkyltin compounds enhance human CG secretion and aromatase activity in human placental choriocarcinoma cells. Nakanishi, T., Kohroki, J., Suzuki, S., Ishizaki, J., Hiromori, Y., Takasuga, S., Itoh, N., Watanabe, Y., Utoguchi, N., Tanaka, K. J. Clin. Endocrinol. Metab. (2002) [Pubmed]
  24. Stereocontrolled synthesis of the D- and L-glycero-beta-D-manno-heptopyranosides and their 6-deoxy analogues. Synthesis of methyl alpha-l-rhamno-pyranosyl-(1-->3)-D-glycero-beta-D-manno-heptopyranosyl- (1-->3)-6-deoxy-glycero-beta-D-manno-heptopyranosyl-(1-->4)-alpha-L- rhamno-pyranoside, a tetrasaccharide subunit of the lipopolysaccharide from Plesimonas shigelloides. Crich, D., Banerjee, A. J. Am. Chem. Soc. (2006) [Pubmed]
  25. The decrease of mitochondrial substrate uptake caused by trialkyltin and trialkyl-lead compounds in chloride media and its relevance to inhibition of oxidative phosphorylation. Skilleter, D.N. Biochem. J. (1975) [Pubmed]
  26. Inability of tributyltin-induced chloride/hydroxyl exchange to stimulate calcium transport in mitochondria isolated from flight muscle of the sheep blowfly Lucilia cuprina. Bygrave, F.L., Smith, R.L. Biochem. J. (1978) [Pubmed]
  27. Fluorescence measurement of chloride transport in monolayer cultured cells. Mechanisms of chloride transport in fibroblasts. Chao, A.C., Dix, J.A., Sellers, M.C., Verkman, A.S. Biophys. J. (1989) [Pubmed]
  28. Activation of mitogen-activated protein kinases by tributyltin in CCRF-CEM cells: role of intracellular Ca(2+). Yu, Z.P., Matsuoka, M., Wispriyono, B., Iryo, Y., Igisu, H. Toxicol. Appl. Pharmacol. (2000) [Pubmed]
  29. Expression of CD16, CD18 and CD56 in tributyltin-exposed human natural killer cells. Whalen, M.M., Ghazi, S., Loganathan, B.G., Hatcher, F. Chem. Biol. Interact. (2002) [Pubmed]
  30. In vitro metabolism of tributyltin and triphenyltin by human cytochrome P-450 isoforms. Ohhira, S., Enomoto, M., Matsui, H. Toxicology (2006) [Pubmed]
  31. Steady-state fluorescence and circular dichroism of trout hemoglobins I and IV interacting with tributyltin. Zolese, G., Gabbianelli, R., Caulini, G.C., Bertoli, E., Falcioni, G. Proteins (1999) [Pubmed]
  32. Is there a causal association between genotoxicity and the imposex effect? Hagger, J.A., Depledge, M.H., Oehlmann, J., Jobling, S., Galloway, T.S. Environ. Health Perspect. (2006) [Pubmed]
  33. Reduced sperm counts in guppies (Poecilia reticulata) following exposure to low levels of tributyltin and bisphenol A. Haubruge, E., Petit, F., Gage, M.J. Proc. Biol. Sci. (2000) [Pubmed]
  34. Simultaneous determination of mono-, di- and tributyltin in environmental samples using isotope dilution gas chromatography mass spectrometry. Centineo, G., Rodríguez-González, P., Blanco González, E., García Alonso, J.I., Sanz-Medel, A. Journal of mass spectrometry : JMS. (2004) [Pubmed]
  35. Determination of tributyltin ions in estuarine waters by high-performance liquid chromatography with fluorimetric detection using morin in a micellar solution. Ebdon, L., Garcia Alonso, J.I. The Analyst. (1987) [Pubmed]
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