Organotins: A review of their reproductive toxicity, biochemistry, and environmental fate

Hoch, 2001, Organotin compounds in the environment – an overview, Applied Geochemistry, 16, 719, 10.1016/S0883-2927(00)00067-6 Meng, 2009, Aquatic organotin pollution in Taiwan, Journal of Environmental Management, 90, 8, 10.1016/j.jenvman.2008.06.008 Choi, 2009, Butyltin contamination in industrialized bays associated with intensive marine activities in Korea, Archives of Environmental Contamination and Toxicology, 57, 77, 10.1007/s00244-008-9235-1 Rudel, 2003, Case study: bioavailability of tin and tin compounds, Ecotoxicology and Environmental Safety, 56, 180, 10.1016/S0147-6513(03)00061-7 Oliveira, 2010, Occurrence and chemical speciation analysis of organotin compounds in the environment: a review, Talanta, 82, 9, 10.1016/j.talanta.2010.04.046 Pinochet, 2009, Butyltin compounds and their relation with organic matter in marine sediments from San Vicente Bay-Chile, Environmental Monitoring and Assessment, 155, 341, 10.1007/s10661-008-0439-7 Santos, 2010, Occurrence and behaviour of butyltins in intertidal and shallow subtidal surface sediments of an estuarine beach under different sampling conditions, Estuarian Coastal Shelf Science, 88, 322, 10.1016/j.ecss.2010.04.009 Grün, 2006, Endocrinedisrupting organotin compounds are potent inducers of adipogenesis in vertebrates, Molecular Endocrinology (Baltimore, Md.), 20, 2141, 10.1210/me.2005-0367 Delgado Filho, 2011, Triorganotin as a compound with potential reproductive toxicity in mammals, Brazilian Journal of Medical and Biological Research, 44, 958, 10.1590/S0100-879X2011007500110 Fent, 2003, Ecotoxicological problems associated with contaminated sites, Toxicology Letters, 140–141, 353, 10.1016/S0378-4274(03)00032-8 Fent, 1996, Ecotoxicology of organotin compounds, Critical Reviews in Toxicology, 26, 1, 10.3109/10408449609089891 Oberdõrster, 2000, The neuropeptide APGWamide induces imposex in the mud snail, Ilyanassa obsolete, Peptides, 21, 1323, 10.1016/S0196-9781(00)00274-6 Oehlmann, 1998, Imposex development in response to TBT pollution in Hinia incrassata (Ström, 1768) (Prosobranchia, Stenoglossa), Aquatic Toxicology (Amsterdam, Netherlands), 43, 239, 10.1016/S0166-445X(98)00058-7 Smith, 1996, Selective decline in imposex levels in the dog-whelk Lepsiella scobina following a ban on the use of TBT antifoulants in New Zealand, Marine Pollution Bulletin, 32, 362, 10.1016/0025-326X(96)84830-2 Keithly, 1999, Tributyltin in seafood from Asia, Australia, Europe, and North America: assessment of human health risks, Human and Ecological Risk Assessment: An International Journal, 5, 337, 10.1080/10807039991289473 Grote, 2004, Effects of organotin compounds on pubertal male rats, Toxicology, 202, 145, 10.1016/j.tox.2004.05.003 Grote, 2006, Effects of peripubertal exposure to triphenyltin on female sexual development of the rat, Toxicology, 222, 17, 10.1016/j.tox.2006.01.008 Dorneles, 2008, Evaluation of cetacean exposure to organotin compounds in Brazilian waters through hepatic total tin concentrations, Environmental Pollution, 156, 1268, 10.1016/j.envpol.2008.03.007 Nakanishi, 2002, Trialkyltin compounds enhance human CG secretion and aromatase activity in human placental choriocarcinoma cells, The Journal of Clinical Endocrinology and Metabolism, 87, 2830, 10.1210/jc.87.6.2830 Lo, 2003, Dithioerythritol (DTE) prevents inhibitory effects of triphenyltin (TPT) on the key enzymes of the human sex steroid hormone metabolism, The Journal of Steroid Biochemistry and Molecular Biology, 84, 569, 10.1016/S0960-0760(03)00074-8 Omura, 2001, Two-generation reproductive toxicity study of tributyltin chloride in male rats, Toxicological Sciences: an Official Journal of the Society of Toxicology, 64, 224, 10.1093/toxsci/64.2.224 Ogata, 2001, Two-generation reproductive toxicity study of tributyltin chloride in female rats, Journal of Toxicology and Environmental Health. Part A, 63, 127, 10.1080/15287390151126469 Tontonoz, 2008, Fat and beyond: the diverse biology of PPARgamma, Annual Review of Biochemistry, 77, 289, 10.1146/annurev.biochem.77.061307.091829 Godoi, 2003, Environmental contamination for organotin compounds, Quimica Nova, 26, 708, 10.1590/S0100-40422003000500015 Abalos, 1997, Analytical procedures for the determination of organotin compounds in sediment and biota: a critical review, Journal of Chromatography. A, 788, 1, 10.1016/S0021-9673(97)00733-4 Dietz, 2007, Current perspectives in analyte extraction strategies for tin and arsenic speciation, Journal of Chromatography. A, 1153, 114, 10.1016/j.chroma.2006.11.064 Gómez-Ariza, 1997, Spatial distribution of butyltin and phenyltin compounds on the Huelva Coast (Southwest Spain), Chemosphere, 31, 937 Zhai, 2009, Rapid and direct speciation of methyltins in seawater by an on-line coupled high performance liquid chromatography–hydride generation–ICP/MS system, Talanta, 77, 1273, 10.1016/j.talanta.2008.08.032 Attar, 1996, Analytical methods for speciation of organotins in the environment, Applied Organometallic Chemistry, 10, 317, 10.1002/(SICI)1099-0739(199606)10:5<317::AID-AOC485>3.0.CO;2-4 Ebdon, 1985, Speciation of tin in natural-waters using coupled high-performance liquid chromatography flame atomic-absorption spectrometry, Analyst, 110, 515, 10.1039/an9851000515 Kumar, 1993, Supercritical fluid extraction of organotins from biological samples and speciation by liquid chromatography and inductively coupled plasma mass spectrometry, Journal of Chromatography. Part A, 655, 340, 10.1016/0021-9673(93)83242-K Thomas, 2000, Antifouling paint booster biocide contamination in UK marine sediments, Marine Pollution Bulletin, 40, 739, 10.1016/S0025-326X(00)00010-2 Ugarte, 2009, Solid phase microextraction coupled to liquid chromatography-inductively coupled plasma mass spectrometry for the speciation of organotin compounds in water samples, Journal of Analytical Atomic Spectrometry, 24, 347, 10.1039/B810786F Garcia-Alonso, 1993, Determination of butylin ion species by ion-exchange chromatography with inductively coupled plasma mass spectrometric and spectrofluorimetric detection, Analytica Chimica Acta, 283, 261, 10.1016/0003-2670(93)85231-8 Quevauviller, 2000, Collaborative evaluation of methods for tributyltin determinations in sediment and mussel tissue, Trends in Analytical Chemistry, 19, 180, 10.1016/S0165-9936(99)00203-4 Castro, 2012, Organotin contamination in South American coastal areas, Environmental Monitoring and Assessment, 184, 1781, 10.1007/s10661-011-2078-7 Dirkx, 1994, Speciation analysis of organotin in water and sediments by gas chromatography with optical spectrometric detection after extraction separation, Analytica Chimica Acta, 286, 309, 10.1016/0003-2670(94)85077-1 Braithwaite, 1985 Jacobsen, 1997, Organotin speciation in environmental sample by capillary gas chromatography and pulsed flame photometric detection (PFPD), Applied Organometallic Chemistry, 11, 737, 10.1002/(SICI)1099-0739(199709)11:9<737::AID-AOC640>3.0.CO;2-L Godoi, 2003, GC analysis of organotin compounds using pulsed flame photometric detection and conventional flame photometric detection, Chromatographia, 58, 97, 10.1365/s10337-003-0010-1 Godoi, 2003, Determination of butyltin compounds in surface sediments from the São Paulo State coast (Brazil) by gas chromatography–pulsed flame photometric detection, Journal of Chromatography. Part A, 985, 205, 10.1016/S0021-9673(02)01456-5 Santos, 2009, Organotin compounds in the Paranaguá Estuarine Complex, Paraná, Brazil: evaluation of biological effects, surface sediment and suspended particulate matter, Marine Pollution Bulletin, 58, 1926, 10.1016/j.marpolbul.2009.09.004 Whitehead, 2006, Endocrine-disrupting chemicals as modulators of sex steroid synthesis, Best Practice & Research. Clinical Endocrinology & Metabolism, 20, 45, 10.1016/j.beem.2005.09.003 Matthiessen, 1998, Critical appraisal of the evidence for tributyltin-mediated endocrine disruption in mollusks, Environmental Toxicology and Chemistry, 17, 37, 10.1002/etc.5620170106 Bettin, 1996, TBT-induced imposex in marine neogastropods is mediated by an increasing androgen level, Helgol Meeresunters, 50, 299, 10.1007/BF02367105 Cooke, 2002, Effect of organotins on human aromatase activity in vitro, Toxicology Letters, 126, 121, 10.1016/S0378-4274(01)00451-9 Saitoh, 2001, Tributyltin or triphenyltin inhibits aromatase activity in the human granulosa-like tumor cell line KGN, Biochemical and Biophysical Research Communications, 289, 198, 10.1006/bbrc.2001.5952 Heidrich, 2001, Inhibition of human cytochrome P450 aromatase activity by butyltins, Steroids, 66, 763, 10.1016/S0039-128X(01)00108-8 Nakanishi, 2006, Organotin compounds enhance 17beta-hydroxysteroid dehydrogenase type I activity in human choriocarcinoma JAr cells: potential promotion of 17beta-estradiol biosynthesis in human placenta, Biochemical Pharmacology, 71, 1349, 10.1016/j.bcp.2006.01.014 Doering, 2002, Effects of butyltins on human 5alpha-reductase type 1 and type 2 activity, Steroids, 67, 859, 10.1016/S0039-128X(02)00051-X McVey, 2003, Inhibition of rat testis microsomal 3beta-hydroxysteroid dehydrogenase activity by tributyltin, The Journal of Steroid Biochemistry and Molecular Biology, 86, 99, 10.1016/S0960-0760(03)00256-5 Ohno, 2005, Triphenyltin and tributyltin inhibit pig testicular 17beta-hydroxysteroid dehydrogenase activity and suppress testicular testosterone biosynthesis, Steroids, 70, 645, 10.1016/j.steroids.2005.03.005 Escriva, 2000, Ligand binding and nuclear receptor evolution, BioEssays: News and Reviews in Molecular, Cellular and Developmental Biology, 22, 717, 10.1002/1521-1878(200008)22:8<717::AID-BIES5>3.0.CO;2-I Escriva, 1997, Ligand binding was acquired during evolution of nuclear receptors, Proceedings of the National Academy of Sciences of the United States of America, 94, 6803, 10.1073/pnas.94.13.6803 Nakanishi, 2008, Endocrine disruption induced by organotin compounds; organotins function as a powerful agonist for nuclear receptors rather than an aromatase inhibitor, The Journal of Toxicological Sciences, 33, 269, 10.2131/jts.33.269 Alzieu, 1998, Tributyltin case study of a chronic contaminant in the coastal environment, Ocean Coast Management, 40, 23, 10.1016/S0964-5691(98)00036-2 Clark, 1988, The fate of tributyltin in the aquatic environment – a look at the data, Environmental Science & Technology, 22, 600, 10.1021/es00171a001 Guérin, 2007, Organotin levels in seafood and its implications for health risk in high-seafood consumers, The Science of the Total Environment, 388, 66, 10.1016/j.scitotenv.2007.08.027 Iwata, 1994, Detection of butyltin compound residues in the blubber of marine mammals, Marine Pollution Bulletin, 28, 607, 10.1016/0025-326X(94)90362-X Ruiz, 1996, Three decades of tributyltin in the coastal environment with emphasis on Arcachon bay, France, Environmental Pollution, 93, 195, 10.1016/0269-7491(96)00029-2 Chien, 2002, Daily intake of TBT, Cu, Zn, Cd and As for fishermen in Taiwan, The Science of the Total Environment, 285, 177, 10.1016/S0048-9697(01)00916-0 Blaber, 1971, The occurrence of penis-like outgrowth behind the right tentacle in spent females of Nucella lapillus, Journal of Molluscan Studies, 39, 435 Smith, 1971, Sexuality in the American mud snail, Nassarius obsoletus (Say), Proceedings of the Malacological Society London, 39, 377 Alzieu, 1986, Tin contamination in Arcachon Bay: effects on oyster shell anomalies, Marine Pollution Bulletin, 17, 494, 10.1016/0025-326X(86)90636-3 Alzieu, 2000, Impact of tributyltin on marine invertebrates, Ecotoxicology, 9, 71, 10.1023/A:1008968229409 Alzieu, 1989 De Mora, 2003, Assessment of organotin contamination in marine sediments and biota from the Gulf and adjacent region, Marine Pollution Bulletin, 46, 401, 10.1016/S0025-326X(02)00481-2 Marsot, 1995, Effect of triphenyltin chloride on growth of the marine microalgae Parilora lutheri in continuous culture, Bulletin of Environmental Contamination and Toxicology, 54, 389, 10.1007/BF00195110 Titley-O’Neal, 2011, The effects of organotin on female gastropods, Journal of Environmental Monitoring: JEM, 13, 2360, 10.1039/c1em10011d Gooding, 2003, The biocide tributyltin reduces the accumulation of testosterone as fatty acid esters in the mud snail (Ilyanassa obsoleta), Environmental Health Perspectives, 111, 426, 10.1289/ehp.5779 Roni, 1996, The metabolism of testosterone by the periwinkle (Littorina zittorea) in vitro and in viva: effects of Tributyltin, Marine Environmental Research, 42, 161, 10.1016/0141-1136(95)00069-0 Nishikawa, 2004, Involvement of the retinoid X receptor in the development of imposex caused by Organotins in gastropods, Environmental Science & Technology, 38, 6271, 10.1021/es049593u Gibbs, 1987, TBT paints and the demise of the Dog-whelk, Nucella lapillus (Gastropoda), Proceedings Oceans, 4, 1482 Oehlmann, 1991, The morphological expression of imposex in Nucella lapillus (Linnaeus) (Gastropoda: Muricidae), Journal of Molluscan Studies, 57, 375, 10.1093/mollus/57.3.375 Bauer, 1995, TBT effects on the female genital systen of Littorina littorea: a possible indicator fr tributyltin pollution, Hydrobiology, 309, 15, 10.1007/BF00014468 Bauer, 1997, The use of Littorina littorea for tributyltin (TBT) effect monitoring-results from the german TBT survey 1994/1995 and laboratory experiments, Environmental Pollution, 96, 299, 10.1016/S0269-7491(97)00049-3 Horiguchi, 2000, Ovo-testis and disturbed reproductive cycle in the giant abalone, Haliotis madaka: possible linkage with organotin contamination in a site of population decline, Marine Environmental Research, 50, 223, 10.1016/S0141-1136(00)00071-4 Santos, 2011, Contamination and impact of organotin compounds on the Brazilian coast, 31 Kotrikla, 2009, Environmental management aspects for TBT antifouling wastes from the shipyards, Journal of Environmental Management, 90, 77, 10.1016/j.jenvman.2008.07.017 Castro, 2011, Butyltin compounds and imposex levels in Ecuador, Archives of Environmental Contamination and Toxicology, 61, 1 Bigatti, 2009, Biomonitoring of TBT contamination and imposex incidence along 4700km of Argentinean shoreline (SW Atlantic: From 38S to 54S), Marine Pollution Bulletin, 58, 695, 10.1016/j.marpolbul.2009.01.001 Galante-Oliveira, 2009, Imposex levels and tributyltin pollution in Ria de Aveiro (NW Portugal) between 1997 and 2007: evaluation of legislation effectiveness, Journal of Environmental Monitoring, 11, 1405, 10.1039/b900723g Martí, 2009, Occurrence of priority pollutants in WWTP effluents and Mediterranean coastal waters of Spain, 2011, Marine Pollution Bulletin, 62, 615, 10.1016/j.marpolbul.2011.01.010 Fernandez-Alba, 2002, Toxicity evaluation of single and mixed antifouling biocides measured with acute toxicity bioassays, Analytica Chimica Acta, 456, 303, 10.1016/S0003-2670(02)00037-5 Fernandez, 2007, New approaches for monitoring the marine environment: the case of antifouling paints, International Journal of Environment and Health, 1, 427, 10.1504/IJENVH.2007.017875 Guomundsdottir, 2011, Long-term temporal treand (1992–2008) of imposex status associated with organotin contamination in the dogwhelk Nucella lapillus along the Icelandic coast, Marine Pollution Bulletin, 63, 500, 10.1016/j.marpolbul.2011.02.012 Toste, 2011, Organotin pollution at arraial do Cabo, Rio de Janeiro State, Brazil: increasing levels after the TBT ban, Brazilian Journal of Oceanography, 59, 111, 10.1590/S1679-87592011000100008 Furdek, 2012, Organotin compounds in seawater and Mytilus galloprovincialis mussels along the Croatian Adriatic Coast, Marine Pollution Bulletin, 64, 189, 10.1016/j.marpolbul.2011.12.009 Marti, 2011, Occurrence of priority pollutants in WWTP effluents and Mediterranean coastal waters of Spain, Marine Pollution Bulletin, 62, 615, 10.1016/j.marpolbul.2011.01.010 Cardwell, 1999, Tributyltin in U.S. market-bought seafood and assessment of human risks, Human and Ecological Risk Assessment, 5, 317, 10.1080/10807039991289464 Fernandez, 2005, Preliminary evaluation of human health risks from ingestion of organotin contaminated seafood in Brazil, Brazilian Journal of Oceanography, 53, 75, 10.1590/S1679-87592005000100008 Filicori, 1986, Characterization of the physiological pattern of episodic gonadotropin secretion throughout the human menstrual cycle, The Journal of Clinical Endocrinology and Metabolism, 62, 1136, 10.1210/jcem-62-6-1136 Piprek, 2009, Genetic mechanisms underlying male sex determination in mammals, Journal of Applied Genetics, 50, 347, 10.1007/BF03195693 Adeeko, 2003, Effects of in utero tributyltin chloride exposure in the rat on pregnancy outcome, Toxicological Sciences: an Official Journal of the Society of Toxicology, 74, 407, 10.1093/toxsci/kfg131 Chen, 2008, Reduction of spermatogenesis in mice after tributyltin administration, Toxicology, 251, 21, 10.1016/j.tox.2008.06.015 Kishta, 2007, In utero exposure to tributyltin chloride differentially alters male and female fetal gonad morphology and gene expression profiles in the Sprague-Dawley rat, Reproductive Toxicology, 23, 1, 10.1016/j.reprotox.2006.08.014 Wang, 2006, Effects of tributyltin chloride (TBT) and triphenyltin chloride (TPT) on rat testicular Leydig cells, Zhonghua nan ke xue = National Journal of Andrology, 12, 516 Yu, 2003, Spermatogenetic disorders in adult rats exposed to tributyltin chloride during puberty, The Journal of Veterinary Medical Science, 65, 1331, 10.1292/jvms.65.1331 Yu, 2003, Effects of tributyltin chloride on the reproductive system in pubertal male rats, The Journal of Veterinary Medical Science, 4, 29 Zhang, 2009, Inhibition of thyroidal status related to depression of testicular development in Sebastiscus marmoratus exposed to tributyltin, Aquatic Toxicology (Amsterdam, Netherlands), 94, 62, 10.1016/j.aquatox.2009.06.003 Zhang, 2009, Effect of tributyltin on testicular development in Sebastiscus marmoratus and the mechanism involved, Environmental Toxicology and Chemistry, 28, 1528, 10.1897/08-347.1 Robertson, 1999, Impairment of spermatogenesis in mice lacking a functional aromatase (cyp 19) gene, Proceedings of the National Academy of Sciences of the United States of America, 96, 7986, 10.1073/pnas.96.14.7986 Shetty, 1998, Effect of long-term treatment with aromatase inhibitor on testicular function of adult male bonnet monkeys (M. radiata), Steroids, 63, 414, 10.1016/S0039-128X(98)00042-7 Habenicht, 1986, Development of a model for the induction of estrogen-related prostatic hyperplasia in the dog and its response to the aromatase inhibitor 4-hydroxy-4-androstene-3,17-dione: preliminary results, Prostate, 8, 181, 10.1002/pros.2990080208 Suzuki, 1996, Effect of aromatase inhibitor, TZA-2209, on the prostate of androstenedione-treated castrated dogs: changes in prostate volume and histopathological findings, Prostate, 28, 328, 10.1002/(SICI)1097-0045(199605)28:5<328::AID-PROS10>3.0.CO;2-L Bouton, 1981, Estrogen regulation of rat prostate androgen receptor, The Journal of Steroid Biochemistry, 15, 403, 10.1016/0022-4731(81)90305-8 Dhar, 1998, Estrogen, androgen and antiestrogen responses in the accessory organs of male rats during different phases of life, Endocrine Research, 24, 159, 10.1080/07435809809135525 Cooke, 2008, Organotin speciation and tissue distribution in rat dams, fetuses, and neonates following oral administration of tributyltin chloride, Journal of Toxicology and Environmental Health. Part A, 71, 384, 10.1080/15287390701801653 Grote, 2009, Sex differences in effects on sexual development in rat offspring after pre- and postnatal exposure to triphenyltin chloride, Toxicology, 260, 53, 10.1016/j.tox.2009.03.006 Harazono, 1996, Pre-implantation embryonic loss induced by tributyltin chloride in rats, Toxicology Letters, 89, 185, 10.1016/S0378-4274(96)03805-2 Nakanishi, 2005, Trialkyltin compounds bind retinoid X receptor to alter human placental endocrine functions, Molecular Endocrinology, 19, 2502, 10.1210/me.2004-0397 Ema, 1997, Effects of triphenyltin chloride on implantation and pregnancy in rats, Reproductive Toxicology, 11, 201, 10.1016/S0890-6238(97)00007-5 Harazono, 1998, Evaluation of malnutrition as a cause of tributyltin-induced pregnancy failure in rats, Bulletin of Environmental Contamination and Toxicology, 61, 224, 10.1007/s001289900752 Podratz, 2012, Tributyltin impairs the reproductive cycle in female rats, Journal of Toxicology and Environmental Health. Part A, 75, 1035, 10.1080/15287394.2012.697826 Itami, 1990, Teratogenic evaluation of tributyltin chloride in rats following oral exposure, Drug and Chemical Toxicology, 13, 283, 10.3109/01480549009032287 Ema, 2007, Developmental toxicity of dibutyltin dichloride in cynomolgus monkeys, Reproductive Toxicology, 23, 12, 10.1016/j.reprotox.2006.09.003 Ema, 2009, Developmental toxicity of dibutyltin dichloride given on three consecutive days during organogenesis in cynomolgus monkeys, Drug and Chemical Toxicology, 32, 150, 10.1080/01480540802594327 Bryan, 1986, The decline of the gastropod Nucella lapillus around south-west England: evidence for the effect of tributyltin from anti-fouling paints, Journal of Marine Biological Association of United Kingdom, 66, 611, 10.1017/S0025315400042247 Oehlmann, 1996, Tributyltin (TBT) effects on Ocinebrina aciculata (Gastropoda: Muricidae): imposex development, sterilization, sex change and population decline, The Science of the Total Environment, 188, 205, 10.1016/0048-9697(96)05173-X Golub, 2004, Triphenyltin as a potential human endocrine disruptor, Journal of Toxicology and Environmental Health. Part B, Critical Reviews, 7, 281, 10.1080/10937400490452705 Cooke, 2006, Toxicology of tributyltin in mammalian animal models, Immunology, Endocrine & Metabolic Agents in Medicinal Chemistry, 6, 63, 10.2174/187152206775528815 Grün, 2006, Environmental obesogens: organotins and endocrine disruption via nuclear receptor signaling, Endocrinology, 147, 50, 10.1210/en.2005-1129 Grün, 2009, Minireview: the case for obesogens, Molecular and Cellular Endocrinology, 23, 1127, 10.1210/me.2008-0485 Grün, 2009, Endocrine disrupters as obesogens, Molecular and Cellular Endocrinology, 304, 19, 10.1016/j.mce.2009.02.018 Ema, 2000, Adverse effects of dibutyltin dichloride on initiation and maintenance of rat pregnancy, Reproductive Toxicology, 14, 451, 10.1016/S0890-6238(00)00095-2 Newbold, 2009, Environmental estrogens and obesity, Molecular and Cellular Endocrinology, 304, 84, 10.1016/j.mce.2009.02.024 Rubin, 2009, Bisphenol A: perinatal exposure and body weight, Molecular and Cellular Endocrinology, 304, 55, 10.1016/j.mce.2009.02.023 Penza, 2011, The environmental chemical tributyltin chloride (TBT) shows both estrogenic and adipogenicactivities in mice which might depend on the exposure dose, Toxicology and Applied Pharmacology, 255, 65, 10.1016/j.taap.2011.05.017 Evans, 2004, PPARs and the complex journey to obesity, Nature Medicine, 10, 355, 10.1038/nm1025 Reddy, 2001, Peroxisomal beta-oxidation and peroxisome proliferator-activated receptor alpha: an adaptive metabolic system, Annual Review of Nutrition, 21, 193, 10.1146/annurev.nutr.21.1.193 Kim, 2003, Peroxisome proliferator-activated receptor-alpha agonist treatment in a transgenic model of type 2 diabetes reverses the lipotoxic state and improves glucose homeostasis, Diabetes, 52, 1770, 10.2337/diabetes.52.7.1770 Rosen, 2000, Transcriptional regulation of adipogenesis, Genes & Development, 14, 1293, 10.1101/gad.14.11.1293 Tontonoz, 1994, Stimulation of adipogenesis in fibroblasts by PPAR gamma 2, a lipid-activated transcription factor, Cell, 79, 1147, 10.1016/0092-8674(94)90006-X Carfi’, 2008, TBTC induces adipocyte differentiation in human bone marrow long term culture, Toxicology, 249, 11, 10.1016/j.tox.2008.03.025 Li, 2011, The environmental obesogen tributyltin chloride acts via peroxisome proliferator activated receptor gamma to induce adipogenesis in murine 3T3-L1 preadipocytes, The Journal of Steroid Biochemistry and Molecular Biology, 127, 9, 10.1016/j.jsbmb.2011.03.012 Martin, 2000, Induction of the fatty acid transport protein 1 and acyl-CoA synthase genes by dimer-selective rexinoids suggests that the peroxisome proliferator-activated receptor-retinoid X receptor heterodimer is their molecular target, The Journal of Biological Chemistry, 275, 12612, 10.1074/jbc.275.17.12612 Tontonoz, 1995, PPAR g 2 regulates adipose expression of the phosphoenolpyruvate carboxykinase gene, Molecular and Cellular Biology, 15, 351, 10.1128/MCB.15.1.351 Magana, 1997, Sterol regulation of acetyl coenzyme A carboxylase promoter requires two interdependent binding sites for sterol regulatory element binding proteins, Journal of Lipid Research, 38, 1630, 10.1016/S0022-2275(20)37181-9 Schadinger, 2005, PPARγ2 regulates lipogenesis and lipid accumulation in steatotic hepatocytes, American Journal of Physiology. Endocrinology and Metabolism, 288, 1195, 10.1152/ajpendo.00513.2004 Tontonoz, 1993, ADD1: a novel helix-loop-helix transcription factor associated with adipocyte determination and differentiation, Molecular and Cellular Biology, 13, 4753, 10.1128/MCB.13.8.4753 Kim, 1996, ADD1/SREBP1 promotes adipocyte differentiation and gene expression linked to fatty acid metabolism, Genes & Development, 10, 1096, 10.1101/gad.10.9.1096 Joseph, 2002, Direct and indirect mechanisms for regulation of fatty acid synthase gene expression by liver X receptors, The Journal of Biological Chemistry, 277, 11019, 10.1074/jbc.M111041200 Seo, 2004, Activated liver X receptors stimulate adipocyte differentiation through induction of peroxisome proliferator-activated receptor γ expression, Molecular and Cellular Biology, 24, 3430, 10.1128/MCB.24.8.3430-3444.2004 Zuo, 2009, Tributyltin causes obesity and hepatic steatosis in male mice, Environmental Toxicology, 26, 79, 10.1002/tox.20531 Asakawa, 2010, Enhanced inhibitory effects of TBT chloride on the development of F1 rats, Archives of Environmental Contamination and Toxicology, 58, 1065, 10.1007/s00244-009-9421-9 Cooke, 2004, Oral (gavage), in utero and postnatal exposure of Sprague-Dawley rats to low doses of tributyltin chloride. Part 1: toxicology, histopathology and clinical chemistry, Food and Chemical Toxicology: An International Journal Published for the British Industrial Biological Research Association, 42, 211, 10.1016/j.fct.2003.09.003 Kirchner, 2010, Prenatal exposure to the environmental obesogen tributyltin predisposes multipotent stem cells to become adipocytes, Molecular Endocrinology, 24, 526, 10.1210/me.2009-0261 Tonk, 2011, Developmental immunotoxicity of di-n-octyltin dichloride (DOTC) in an extended one-generationreproductive toxicity study, Toxicology Letters, 204, 156, 10.1016/j.toxlet.2011.04.027 Ravanan, 2011, Exposure to an organometal compound stimulates adipokine and cytokine expression in whiteadipose tissue, Cytokine, 53, 355, 10.1016/j.cyto.2010.11.015 Tryphonas, 2004, Oral (gavage), in utero and post-natal exposure of Sprague-Dawley rats to low doses of tributyltin chloride, Part II: effects on the immune system, Food and Chemical Toxicology: An International Journal Published for the British Industrial Biological Research Association, 42, 221, 10.1016/j.fct.2003.08.019 Abbas, 2000 Holladay, 2000, Development of the murine and human immune system: differential effects of immunotoxicants depend on time of exposure, Environmental Health Perspectives, 108, 463, 10.1289/ehp.00108s3463 Tonk, 2011, Developmental immunotoxicity in male rats after juvenile exposure to di-n-octyltin dichloride (DOTC), Reproductive Toxicology, 32, 341, 10.1016/j.reprotox.2011.08.005 Penninks, 1993, The evaluation of data-derived safety factors for bis(tri-nbutyltin) oxide, Food Additives and Contaminants, 10, 351, 10.1080/02652039309374157 Kimura, 2005, Effect of lactational exposure to tributyltin chloride on innate immunodefenses in the F1 generation in mice, Bioscience, Biotechnology, and Biochemistry, 69, 1104, 10.1271/bbb.69.1104 Gennari, 1997, Organotin-induced apoptosis as observed in vitro is not relevant for induction of thymus atrophy at antiproliferative doses, Toxicology and Applied Pharmacology, 147, 259, 10.1006/taap.1997.8265 Reader, 1999, Tributyltin triggers apoptosis in trout hepatocytes: the role of Ca2+, protein kinase C and proteases, Biochimica et Biophysica Acta, 1448, 473, 10.1016/S0167-4889(98)00166-9 Thompson, 1995, Apoptosis inthe pathogenesis and treatment of disease, Science, 267, 1456, 10.1126/science.7878464 Chen, 2011, Tributyltin chloride-induced immunotoxicity and thymocyte apoptosis are related to abnormal Fas expression, International Journal of Hygiene and Environmental Health, 214, 145, 10.1016/j.ijheh.2011.01.008 Ueno, 2009, Reduction in peripheral lymphocytes and thymus atrophy induced by organotin compounds in vivo, The Journal of Veterinary Medical Science, 71, 1041, 10.1292/jvms.71.1041 Carfi’, 2007, In vitro tests to evaluate immunotoxicity: a preliminary study, Toxicology, 229, 11, 10.1016/j.tox.2006.09.003 DeWitt, 2007, Immune function is not impaired in Sprague-Dawley rats exposed to dimethyltin dichloride (DMTC) during development or adulthood, Toxicology, 232, 303, 10.1016/j.tox.2007.01.017 Ahima, 2006, Adipose tissue as an endocrine organ, Obesity, 14, 242S, 10.1038/oby.2006.317 Weisberg, 2003, Obesity is associated with macrophage accumulation in adipose tissue, The Journal of Clinical Investigation, 112, 1796, 10.1172/JCI200319246 Lumeng, 2007, Obesity induces a phenotypic switch in adipose tissue macrophage polarization, The Journal of Clinical Investigation, 117, 175, 10.1172/JCI29881 Ley, 2006, Microbial ecology: human gut microbes associated with obesity, Nature, 444, 1022, 10.1038/4441022a Turnbaugh, 2009, A core gut microbiome in obese and lean twins, Nature, 457, 480, 10.1038/nature07540 Vijay-Kumar, 2010, Metabolic syndrome and altered gut microbiota in mice lacking Toll-like receptor 5, Science, 328, 228, 10.1126/science.1179721 Turnbaugh, 2006, An obesity-associated gut microbiome with increased capacity for energy harvest, Nature, 444, 1027, 10.1038/nature05414 Slack, 2009, Innate and adaptive immunity cooperate flexibly to maintain host-microbiota mutualism, Science, 325, 617, 10.1126/science.1172747 Singh, 1979, The action of tributyltin chloride on the uptake of proline and glutamine by intact cells of Escherichia coli, Canadian Journal of Biochemistry, 57, 1376, 10.1139/o79-183 Jude, 1996, Evaluation of tributyltin resistance in marine sediment bacteria, Canadian Journal of Microbiology, 42, 525, 10.1139/m96-071 Singh, 1979, The action of tributyltin chloride on energy-dependent transhydrogenation of NADP+ by NADH in membranes of Escherichia coli, Canadian Journal of Biochemistry, 57, 1384, 10.1139/o79-184 Azenha, 2002, Butyltin compounds in Portuguese wines, Journal of Agricultural and Food Chemistry, 50, 2713, 10.1021/jf0115544 Antizar-Ladislao, 2008, Environmental levels, toxicity and human expousure to tributiyltin (TBT)- contaminated marine environment. A review, Environment International, 34, 292, 10.1016/j.envint.2007.09.005 ATSDR. Agency for toxic substances and disease registry. Toxicological profile for tin and tin compounds. US Department of Health and Human Services; 2005. http://www.atsdr.cdc.gov/toxprofiles/tp55.pdf. Accessed: 2007. EU-SCOOP. Revised assessment of the risks to health and the environment associated with the use of the four organotin compounds TBT, DBT, DOT and TPT. Directorate General Health and Consumer Protection; 2006. http://ec.europa.eu/health/ph_risk_committees/04_scher/docs/scher_o_047.pdf. Accessed: 2007. Choi, 2012, Intake and potential health risk of butyltin compounds from seafood consumption in Korea, Archives of Environmental Contamination and Toxicology, 62, 333, 10.1007/s00244-011-9688-5 WHO-IPCS. World Health Organisation. International Programme on Chemical Safety. Concise International Chemical Assessment Document 14. Tributyltin oxide; 1999. http://www.inchem.org/documents/cicads/cicad14.htm. Accessed: 2007. Tsuda, 1995, Daily intakes of tributyltin and triphenyltin compounds from meals, Journal of AOAC International, 78, 941, 10.1093/jaoac/78.4.941 Airaksinen, 2010, Organotin intake through fish consumption in Finland, Environmental Research, 110, 544, 10.1016/j.envres.2010.06.004 Appel, 2004, Organotin compounds, toxicokinetic aspects, Drug Metabolism Reviews, 36, 763, 10.1081/DMR-200033490 Azenha, 2004, Estimation of the human intestinal permeability of butyltin species using the Caco-2 cell line model, Food and Chemical Toxicology: An International Journal Published for the British Industrial Biological Research Association, 42, 1431, 10.1016/j.fct.2004.04.004 Snoeij, 1987, Biological activity of organotin compounds – an overview, Environmental Research, 44, 335, 10.1016/S0013-9351(87)80242-6 Delie, 1997, A human colonic cell line sharing similarities with enterocytes as a model to examine oral absorption: advantages and limitations of the Caco-2 model, Critical Reviews in Therapeutic Drug Carrier Systems, 14, 221, 10.1615/CritRevTherDrugCarrierSyst.v14.i3.20 Heindel, 2003, Endocrine disruptors and the obesity epidemic, Toxicological Sciences: an Official Journal of the Society of Toxicology, 76, 247, 10.1093/toxsci/kfg255 Nilsson, 2000, Endocrine modulators in the food chain and environment, Toxicologic Pathology, 28, 420, 10.1177/019262330002800311 Toschke, 2002, Childhood obesity is associated with maternal smoking in pregnancy, European Journal of Pediatrics, 161, 445, 10.1007/s00431-002-0983-z Belfroid, 2000, Organotin levels in seafood, Marine Pollution Bulletin, 40, 226, 10.1016/S0025-326X(99)00241-6 Nakanishi, 2007, Potencial toxicity of organotin compound via nuclear receptor signaling in mammals, Journal of Health Sciences, 53, 1, 10.1248/jhs.53.1 Schulte-Oehlmann, 2006, COMPRENDO: focus and approach, Environmental Health Perspectives, 114, 98, 10.1289/ehp.8060