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Journal articles on the topic 'Tributyltin'

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Published: 4 June 2021

Last updated: 1 August 2024

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1

Stefanizzi, Valeria, Antonella Minutolo, Elena Valletta, Martina Carlini, Franca M. Cordero, Anna Ranzenigo, Salvatore Pasquale Prete, et al. "Biological Evaluation of Triorganotin Derivatives as Potential Anticancer Agents." Molecules 28, no. 9 (May 2, 2023): 3856. http://dx.doi.org/10.3390/molecules28093856.

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Metal-derived platinum complexes are widely used to treat solid tumors. However, systemic toxicity and tumor resistance to these drugs encourage further research into similarly effective compounds. Among others, organotin compounds have been shown to inhibit cell growth and induce cell death and autophagy. Nevertheless, the impact of the ligand structure and mechanisms involved in the toxicity of organotin compounds have not been clarified. In the present study, the biological activities of commercially available bis(tributyltin) oxide and tributyltin chloride, in comparison to those of specially synthesized tributyltin trifluoroacetate (TBT-OCOCF3) and of cisplatin, were assessed using cells with different levels of tumorigenicity. The results show that tributyltins were more cytotoxic than cisplatin in all the tested cell lines. NMR revealed that this was not related to the interaction with DNA but to the inhibition of glucose uptake into the cells. Moreover, highly tumorigenic cells were less susceptible than nontumorigenic cells to the nonunique pattern of death induced by TBT-OCOCF3. Nevertheless, tumorigenic cells became sensitive when cotreated with wortmannin and TBT-OCOCF3, although no concomitant induction of autophagy by the compound was detected. Thus, TBT-OCOCF3 might be the prototype of a family of potential anticancer agents.

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2

Alzieu, Claude. "Tributyltin." Ocean & Coastal Management 40, no. 1 (July 1998): 23–36. http://dx.doi.org/10.1016/s0964-5691(98)00036-2.

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3

Maguire, R. J. "Environmental Assessment of Tributyltin in Canada." Water Science and Technology 25, no. 11 (June 1, 1992): 125–32. http://dx.doi.org/10.2166/wst.1992.0283.

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The aquatic chemistry, fate and toxicity of tributyltin are reviewed. A summary is given of investigations of the occurrence and persistence of tributyltin and its less toxic degradation products in water and sediment in Canada. Tributyltin was mainly found in areas of heavy boating or shipping traffic, which was consistent with its use as an antifouling agent. In about 8% of the 269 locations across Canada at which samples were collected, tributyltin was found in water at concentrations which could cause chronic toxicity in a sensitive species, rainbow trout. Tributyltin was occasionally found in the surface microlayer of fresh water at much higher concentrations than in subsurface water. It was also found in about 30% of sediment samples collected across Canada. The few fish analyzed that contained tributyltin were from harbours, a finding consistent with findings in water and sediment. Biological degradation in water and sediment appears to be the most important factor limiting the persistence of tributyltin in aquatic ecosystems. Estimates of the half-life of biological degradation of tributyltin in fresh water and sediment in Canada are in the range of a few weeks to 4-5 months, respectively. Recent Canadian regulations of tributyltin are discussed as well as the current Canadian Environmental Protection Act review of non-pesticidal organotins.

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4

Maguire, R. James, and Richard J. Tkacz. "Concentration of Tributyltin in the Surface Microlayer of Natural Waters." Water Quality Research Journal 22, no. 2 (May 1, 1987): 227–33. http://dx.doi.org/10.2166/wqrj.1987.017.

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Abstract High concentrations of the very toxic antifouling agent tributyltin have been found in 24 surface microlayer samples in a survey of 74 locations in Ontario, Quebec, and New York State. In 6 of these 24 locations the concentration of tributyltin in the surface microlayer exceeded the 24-hr LC-50 value for adult rainbow trout. The most heavily contaminated area was the mouth of the Moira River at Belleville, Ontario, where the concentration of tributyltin in the surface microlayer was 42 times the 24-hr LC-50 value for trout. The concentration of tributyltin in the surface microlayer was occasionally so much greater than that in subsurface water that the microlayer contained a significant amount of tributyltin relative to that in the whole depth of the subsurface water. Similar findings were observed for the less toxic degradation products of tributyltin - dibutyltin, monobutyltin and inorganic tin.

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5

NISHIKIMI, Akihiko, Yukimi KIRA, Emiko KASAHARA, Eisuke F. SATO, Tomoko KANNO, Kozo UTSUMI, and Masayasu INOUE. "Tributyltin interacts with mitochondria and induces cytochrome c release." Biochemical Journal 356, no. 2 (May 24, 2001): 621–26. http://dx.doi.org/10.1042/bj3560621.

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Although triorganotins are potent inducers of apoptosis in various cell types, the critical targets of these compounds and the mechanisms by which they lead to cell death remain to be elucidated. There are two major pathways by which apoptotic cell death occurs: one is triggered by a cytokine mediator and the other is by a mitochondrion-dependent mechanism. To elucidate the mechanism of triorganotin-induced apoptosis, we studied the effect of tributyltin on mitochondrial function. We found that moderately low doses of tributyltin decrease mitochondrial membrane potential and induce cytochrome c release by a mechanism inhibited by cyclosporine A and bongkrekic acid. Tributyltin-induced cytochrome c release is also prevented by dithiols such as dithiothreitol and 2,3-dimercaptopropanol but not by monothiols such as GSH, N-acetyl-l-cysteine, l-cysteine and 2-mercaptoethanol. Further studies with phenylarsine oxide agarose revealed that tributyltin interacts with the adenine nucleotide translocator, a functional constituent of the mitochondrial permeability transition pore, which is selectively inhibited by dithiothreitol. These results suggest that, at low doses, tributyltin interacts selectively with critical thiol residues in the adenine nucleotide translocator and opens the permeability transition pore, thereby decreasing membrane potential and releasing cytochrome c from mitochondria, a series of events consistent with established mechanistic models of apoptosis.

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6

Ambrosini, Annarina, Enrico Bertoli, Giovanna Zolese, and Fabio Tanfani. "Interaction of tributylin acetate and tributyltin chloride with dipalmitoyl phosphatidylcholine model membrane." Chemistry and Physics of Lipids 58, no. 1-2 (May 1991): 73–80. http://dx.doi.org/10.1016/0009-3084(91)90113-p.

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7

Jayanthi, Arumugam. "Tributyltin Hydride (Bu3SnH)." Synlett 2007, no. 1 (January 2007): 0173–74. http://dx.doi.org/10.1055/s-2006-958426.

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8

Simmonds, Mark. "Tributyltin—new legislation." Oryx 21, no. 2 (April 1987): 113. http://dx.doi.org/10.1017/s0030605300026685.

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9

Darwish, Alla, and J. Michael Chong. "Synthesis of Hexabutylditin from Tributyltin Hydride and bis(Tributyltin)oxide." Synthetic Communications 34, no. 10 (December 31, 2004): 1885–90. http://dx.doi.org/10.1081/scc-120034172.

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10

Mimura, Haruo, Ryusei Sato, Yuichi Furuyama, Akira Taniike, Masahiro Yagi, Kazutoshi Yoshida, and Akira Kitamura. "Adsorption of tributyltin by tributyltin resistant marine Pseudoalteromonas sp. cells." Marine Pollution Bulletin 57, no. 6-12 (January 2008): 877–82. http://dx.doi.org/10.1016/j.marpolbul.2008.03.029.

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11

Kizlink, Juraj, and Vladimír Rattay. "Organotin derivatives of alkanedisulfonic acids." Collection of Czechoslovak Chemical Communications 52, no. 6 (1987): 1514–19. http://dx.doi.org/10.1135/cccc19871514.

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The preparation of dibutyltin and tributyltin alkanedisulfonates from alkyltin oxides and the corresponding alkanedisulfonic acids has been studied. The products, obtained in 56 – 74% yield, were tested as biocides against bacteria, yeasts, and moulds as well as fungicides against wood rot and their activity was compared with that of bis(tributyltin) oxide.

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12

Yaqin, Khusnul. "DNA damage and shell malformation in Blue Mussel, Mytilus edulis." Akuatikisle: Jurnal Akuakultur, Pesisir dan Pulau-Pulau Kecil 6, no. 1 (May 18, 2022): 65–74. http://dx.doi.org/10.29239/j.akuatikisle.6.1.65-74.

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Pollutants in waters that cause DNA damage, such as tributyltin, have been known to cause malformations in the mussel shell, which need attention to be studied. Shell malformations or deformities of blue mussels were observed in Norsminde Fjord harbour. The mean shell thickness index of blue mussels from the polluted site was greater than it from expected clean waters. DNA damages detected using the versatile comet assay which expressed as tail length and olive tail moment were evaluated in blue mussels gill cells both in situ and in vitro. The results showed that the average of DNA damages in treatments, namely the polluted site, tributyltin chloride (TBTC) (10 g/l), and hydrogen peroxide (H2O2) (10 M) were different from the expected unpolluted site. Although comet assay is considered as an unspecific assay, the results proposed the similarity of DNA damage character of blue mussel gill cells when exposed to tributyltin chloride and taken directly from the polluted site. The data obtained are important for assessing the environmental risks created by genotoxic agents, e.g. tributyltin, used as antifouling agents in marine paints.

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13

Suzuki, S., T. Fukagawa, and K. Takama. "Occurrence of tributyltin-tolerant bacteria in tributyltin- or cadmium-containing seawater." Applied and Environmental Microbiology 58, no. 10 (1992): 3410–12. http://dx.doi.org/10.1128/aem.58.10.3410-3412.1992.

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14

Abubakar, Abdussamad, Garba Uba, and Hadiza Aliyu Biu. "Kinetics Modelling of Pseudomonas stutzeri strain DN2 Growth Behaviour in Tributyltin Chloride." Journal of Environmental Microbiology and Toxicology 9, no. 2 (December 31, 2021): 13–18. http://dx.doi.org/10.54987/jemat.v9i2.641.

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A predictive model was performed to describe Pseudomonas stutzeri strain DN2 growth behaviour in tributyltin chloride, using primary Modelling and a polynomial model as a secondary predictive model. In this investigation, data predicted using the modified Logistic (ML) was the most accurate. The Bias Factor (Bf) and Accuracy Factor (Af) values for the (ML) model were 1.39 and 1.51, indicating that the predictions were within a reliable range. The low RMSE value of 0.14, R2 and adj R2 (0.99) value closer to 1, showing that modified logistics is better than the other models at describing the growth behaviour of Pseudomonas stutzeri strain DN2 in toxic tributyltin chloride. Both the Aiba and Haldane models on the other hand, among the secondary model best fit the behaviours having low RMSE and MSE values and adjR2 value closer to 1. In this study, the primary and secondary kinetics of Pseudomonas stutzeri strain DN2 growth behaviour in tributyltin chloride was explored and it was shown in this study that the modified logistic and the Haldane models better suit the growth behavior of Pseudomonas stutzeri strain DN2 in tributyltin chloride. The parameters obtained from the modelling exercise will be very valuable in transferring the laboratory results to the field.

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15

Lee, W. K., K. W. Lee, E. J. Kwak, S. W. Yang, K. S. Yang, J. C. Park, H. S. Joo, W. J. Lee, and W. B. Lee. "Effects of environmental endocrine disruptors on the sex differentiation in Korean rockfish, Sebastes schlegeli." Water Science and Technology 47, no. 9 (May 1, 2003): 65–70. http://dx.doi.org/10.2166/wst.2003.0494.

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The effects of estradiol-17β, methyltestosterone, tributyltin, bisphenol A and 2,4-dinitrophenol on sex differentiation were investigated in the Korean rockfish, Sebastes schlegeli. The 51 day-old fry with undifferentiated gonads were fed with food containing the chemicals at 0.05, 0.5, 5, 50 and 100 μ/g diet for 29 days. Sex ratio and gonadal abnormality after the chemical treatment were determined by histological examination of gonads. In control group, the sex ratio of fry was 1:1.3 (female:male), and more males than females appeared. The sex of fry fed with estradiol-17β at 5, 50 and 100 μ/g diet was all females. Feminization of the fry was induced by exogenic estradiol-17β. In the methyltestosterone group, sex ratio of fry was 1:10.2 in 0.05 μ/g diet, 1:2.4 in 0.5 μ/g diet, 1:3.1 in 5 μ/g diet, 1:1.2 in 50 μ/g diet and 1:2.3 in 100 μ/g diet. Masculinization of the fry was induced by methyltestosterone at the lowest concentration. Furthermore, intersex of the fry was observed. The number of intersex fry was 23.3, 25.0 and 35.3 at 0.5, 5 and 50 μ/g diet of methyltestosterone, respectively. Sex ratio of bisphenol A group showed no difference with that of the control. The sex of fry fed with 2,4-dinitrophenol at 5, 50 and 100 μ/g diet was all females. 2,4-dinitrophenol should be considered as a new member of endocrine disruptors. In tributyltin group, the sex ratio of fry at 100 μ/g diet of tributyltin was 5.4:1. Tributyltin induced the feminization of the fry at the highest dose. Tributyltin showed an estrogenic effect in the Korean rockfish in contrast to an androgenic effect in gastropods.

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16

Benya, Theodore J. "Bis(Tributyltin) Oxide Toxicology." Drug Metabolism Reviews 29, no. 4 (January 1997): 1189–280. http://dx.doi.org/10.3109/03602539709002247.

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17

Simmonds, Mark. "The case against tributyltin." Oryx 20, no. 4 (October 1986): 217–20. http://dx.doi.org/10.1017/s0030605300020238.

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The use of paints containing tributyltin (TBT) to keep boat hulls clean is threatening marine life in some coastal regions, especially where boating for pleasure is popular. Research so far has shown that very low concentrations of the chemical have lethal or mutagenic effects on some marine invertebrates and stop the growth of phytoplankton. Legislation is being drawn up by many countries to control the use of these paints, but the author fears that it may be too little and too late for some populations of organisms.

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18

Korkalainen, Merja, Maria Herlin, Arja Tamminen, Helen Håkansson, and Matti Viluksela. "Tributyltin modulates osteoblast differentiation." Toxicology Letters 180 (October 2008): S187. http://dx.doi.org/10.1016/j.toxlet.2008.06.186.

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19

Maguire, R. James. "Environmental aspects of tributyltin." Applied Organometallic Chemistry 1, no. 6 (1987): 475–98. http://dx.doi.org/10.1002/aoc.590010602.

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20

Weis, Judith S., and Leonard A. Cole. "Tributyltin and public policy." Environmental Impact Assessment Review 9, no. 1 (January 1989): 33–47. http://dx.doi.org/10.1016/0195-9255(89)90017-6.

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21

Kubota, Naoyoshi, Haruo Mimura, Tomoya Yamauchi, and Akira Kitamura. "Accelerator analyses of tributyltin chloride associated with a tributyltin resistant marine microorganism." Marine Pollution Bulletin 48, no. 7-8 (April 2004): 800–805. http://dx.doi.org/10.1016/j.marpolbul.2004.01.002.

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22

Conway, RJ, JP Nagel, RV Stick, and DMG Tilbrook. "Further Aspects of the Reduction of Dithiocarbonates with Tributyltin Hydride and Deuteride." Australian Journal of Chemistry 38, no. 6 (1985): 939. http://dx.doi.org/10.1071/ch9850939.

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The reduction of 1,2:5,6-di-O-isopropylidene-3-O-(methylthio) thiocarbonyl-β-D-idose ,- talose, and -(3-2H) talose with tributyltin hydride and deuteride leads to the deoxy sugar and some deuterium-containing deoxy sugars. A modification of the normal procedure allows for reduction with tributyltin hydride generated in situ. As well, the reduction of some dithiocarbonates derived from glycosides of N-acetyl-D- glucosamine allows access to a variety of dideoxy and trideoxy sugars.

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23

Matsuo, Takashi, Kunihiko Komatsuzaki, Takanori Tsuji, and Takashi Hayashi. "Reaction of cobalt porphycene with hydride reagents: spectroscopic detection of Co–H porphycene species and formation of Co–SnR3 porphycene species." Journal of Porphyrins and Phthalocyanines 16, no. 05n06 (May 2012): 616–25. http://dx.doi.org/10.1142/s1088424612500587.

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The reaction of tetrapropylporphycenatocobalt(III) with tributyltin hydride generates a cobalt(III)–hydride porphycene detectable by UV-vis spectroscopy under diluted conditions, whereas it is impossible to characterize hydride species of cobalt porphyrins. One of the reasons for the stability of the porphycene hydride species is that the porphycene ring has a lower LUMO energy level due to the decrease in the symmetry of the ligand character. However, the hydride species in a highly concentrated solution of the complex is easily converted into the cobalt(II) species via dimerization or reaction of the hydride with excess tributyltin hydride through hemolysis of the Sn–H/Co–H bonds. When the Co(III) porphycene is reacted with LiBHEt3 , the final product is the cobalt(III)–ethyl complex formed by β-rearrangement during the reaction of the hydride species and diethylborane in a solvent cage. In the reaction of tetrakistrifluoromethylporphycenatocobalt(III) with tributyltin hydride, the dominant reaction pathway includes one-electron reduction of the porphycene ring together with radical coupling of the tin reagent rather than the net hydride transfer. This finding suggests that the delicate control of the LUMO energy level influences the stability of the hydride species. The tetrapropylporphycenatocobalt(III) complex with tributyltin or triphenyltin hydride in the presence of AIBN produces the corresponding Co(III)– trialkyltin complex. This complex was characterized by 1H NMR spectroscopy.

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24

FUKUZUMI, SHUNICHI, and SOUTA NOURA. "Cobalt(III) Porphyrin-catalysed Hydride Reduction of 10-Methylacridinium ion and Hydrometallation of Alkenes and Alkynes by Tributyltin Hydride." Journal of Porphyrins and Phthalocyanines 01, no. 03 (July 1997): 251–58. http://dx.doi.org/10.1002/(sici)1099-1409(199707)1:3<251::aid-jpp24>3.0.co;2-p.

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Cobalt(III) tetraphenylporphyrin catalyses a hydride transfer reaction from tributyltin hydride to 10-methylacridinium ion via the formation of hydridocobalt(III) tetraphenylporphyrin, which is the rate-determining step, followed by facile hydride transfer from the hydridocobalt(III) porphyrin to 10-methylacridinium ion in acetonitrile. Tributyltin hydride is also effective for the hydrometallation of alkenes and alkynes with cobalt(III) tetraphenylporphyrin to yield the corresponding organocobalt(III) porphyrins regioselectively. The hydrometallation is suggested to proceed via the hydride transfer from tributyltin hydride to cobalt(III) tetraphenylporphyrin to give the hydridocobalt(III) porphyrin, followed by the hydrogen transfer from hydridocobalt(III) porphyrin to alkenes and alkynes to yield the corresponding organocobalt(III) porphyrins. The regioselectivities are consistent with the stabilities of radicals generated by the hydrogen transfer from hydridocobalt(III) porphyrin to alkenes and alkynes. The rates of the electrophilic cleavage of cobalt-carbon bonds of organocobalt(III) porphyrins by trifluoroacetic acid in MeCN are also reported.

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25

Ruiz, JM, M. Quintela, and R. Barreiro. "Tributyltin and imposex:no uncertainty shown." Marine Ecology Progress Series 170 (1998): 293–94. http://dx.doi.org/10.3354/meps170293.

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26

Ten Hallers-Tjabbes, C. C. "Tributyltin and Policies for Antifouling." Environmental Technology 18, no. 12 (December 1997): 1265–68. http://dx.doi.org/10.1080/09593331808616648.

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27

Osmekhin, S., A. Caló, V. Kisand, E. Nõmmiste, H. Kotilainen, H. Aksela, and S. Aksela. "Fragmentation of molecular tributyltin chloride." International Journal of Mass Spectrometry 273, no. 1-2 (June 2008): 48–52. http://dx.doi.org/10.1016/j.ijms.2008.02.012.

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28

Sturgeon, R., and R. Wahlen. "CCQM-P18: Tributyltin in sediment." Metrologia 39, no. 1A (January 2002): 08003. http://dx.doi.org/10.1088/0026-1394/39/1a/21.

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29

Briche, Céline S. J. Wolff, Raimund Wahlen, and Ralph E. Sturgeon. "CCQM-K28: Tributyltin in sediment." Metrologia 43, no. 1A (January 2006): 08001. http://dx.doi.org/10.1088/0026-1394/43/1a/08001.

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30

Joshi, Ravi R., and Sudhir K. Gupta. "Biotoxicity of tributyltin acrylate polymers." Toxicity Assessment 5, no. 4 (November 1990): 389–93. http://dx.doi.org/10.1002/tox.2540050406.

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31

Shimasaki, Yohei, Takeshi Kitano,, Yuji Oshima, Suguru Inoue, Nobuyoshi Imada, and Tsuneo Honjo. "Tributyltin causes masculinization in fish." Environmental Toxicology and Chemistry 22, no. 1 (January 2003): 141–44. http://dx.doi.org/10.1002/etc.5620220118.

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32

Ambrosini, Annarina, Enrico Bertoli, Fabio Tanfani, and Giovanna Zolese. "Effect of the fungicides tributyltin acetate and tributyltin chloride on multilamellar liposomes: fluorescence studies." Chemistry and Physics of Lipids 59, no. 2 (September 1991): 189–97. http://dx.doi.org/10.1016/0009-3084(91)90007-x.

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33

Blunden, S. J., and R. Hill. "Bis(tributyltin) oxide as a wood preservative: Its conversion to tributyltin carboxylates inPinus sylvestris." Applied Organometallic Chemistry 4, no. 1 (January 1990): 63–68. http://dx.doi.org/10.1002/aoc.590040111.

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34

Lébl, Tomáš, Jaroslav Holeček, Marek Dymák, and Dirk Steinborn. "Reinvestigation of Reaction of (2-Ethoxyvinyl)stannanes with Acetyl Bromide." Collection of Czechoslovak Chemical Communications 67, no. 5 (2002): 587–95. http://dx.doi.org/10.1135/cccc20020587.

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Four analogous (2-ethoxyvinyl)stannanes (E/Z)-Bu3SnC(R)=CHOEt (R = Bu, H) were prepared and characterised using 1H, 13C, 119Sn, 1H-13C HMQC, 1H-13C HMBC, and 1H-119Sn HMQC NMR spectroscopy. The course of their reactions with acetyl bromide was studied by NMR spectroscopy. Although tributyltin bromide, ethyl acetate and the coresponding alkyne were identified as reaction products, this present reinvestigation showed unambiguously that heterolytic fragementation reactions, as stated previously, did not take place. Acetyl bromide cleaves the Sn-C= bond yielding tributyltin bromide and vinyl ethers. Subsequent decomposition of vinyl ethers and impurities in the starting stannane is the source of ethyl acetate and the alkyne, respectively.

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35

Veiga, Alexandra, Ana Ferreira Pinto, and Maria C. Loureiro-Dias. "Tributyltin oxide affects energy production in the yeast Rhodotorula ferulica, a utilizer of phenolic compounds." Canadian Journal of Microbiology 43, no. 7 (July 1, 1997): 683–87. http://dx.doi.org/10.1139/m97-097.

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Rhodotorula ferulica, a yeast able to utilize phenolic compounds, was chosen for evaluating the effects of tributyltin oxide (TBTO) on this utilization. TBTO reduced respiratory capacity when vanillic or benzoic acid was the energy source. The ATP level of the cells was severely affected by 2 μM TBTO. The mitochondrial ATPase was strongly inhibited by 0.5 μM TBTO, whereas the activity of the plasma membrane ATPase was not affected by concentrations of TBTO up to 30 μM. Our data support the hypothesis that the target for TBTO action is the mitochondrial ATPase, resulting in a severe disturbance of the yeast utilization of aromatic compounds.Key words: TBTO, tributyltin, yeast, Rhodotorula ferulica, respiration, ATPase.

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36

Harino, H., S. C. M. O'Hara, G. R. Burt, N. D. Pope, B. S. Chesman, and W. J. Langston. "Butyltin and phenyltin compounds in eels (Anguilla anguilla)." Journal of the Marine Biological Association of the United Kingdom 82, no. 5 (October 2002): 893–901. http://dx.doi.org/10.1017/s0025315402006318.

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Tributyltin (TBT) and its degradation products, dibutyltin (DBT) and monobutyltin (MBT), together with triphenyltin (TPT), were investigated in eels from the Thames Estuary and the Weston Canal (Merseyside). Within individual eels, the concentrations of organotin (OT) compounds varied considerably between tissues. Tributyltin concentrations were highest in heart and gall bladder and lowest in muscle and gonad. Tributyltin was generally the most predominant of butyltin (BT) compounds present in eel tissues and DBT the least. Phenyltins were detected in eels from both locations, notably the Weston Canal where TPT was present up to 0.367 μg g−1 (as Sn) in liver samples. Concentrations of OTs in liver (and muscle) were independent of weight and length in the eel populations examined. In a survey of OTs in eel populations along the Thames Estuary hepatic TBT levels ranged from 0.066–0.347 μg g−1 dry wt (as Sn) in liver of eels and were generally highest in the mid-section of the estuary, resembling the distribution pattern of TBT in sediment. Proportions of TBT to total BTs were also elevated in eel from this section of the waterway, consistent with continuing inputs in this region, albeit at relatively low levels. Major sewage treatment plants are sited here and may represent a possible source.

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37

Huang, Xian-Ju, Ming Shen, Lizhong Wang, Fengxiang Yu, Wangjun Wu, and Hong-lin Liu. "Effects of Tributyltin Chloride on Developing Mouse Oocytes and Preimplantation Embryos." Microscopy and Microanalysis 21, no. 2 (April 2015): 358–67. http://dx.doi.org/10.1017/s1431927615000161.

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AbstractTributyltin, an organotin, is ubiquitous in estuaries and freshwater systems. Previous reports suggest that tributyltin is an endocrine disruptor in many wildlife species and it inhibits aromatase in mammalian placental and granulosa-like tumor cell lines. However, no evidence showing the effects of tributyltin on oocytes or preimplantation embryonic developmental competence exists. Therefore, we investigated the role of tributyltin chloride (TBTCl) in the development of female oocytes and preimplantation embryos. Briefly, female ICR mice were gavaged with 0 (vehicle), 4, and 8 mg/kg of TBTCl each day for 18 days. The fluorescence intensity analysis showed that the 5-methylcytosine level decreased after TBTCl treatment, indicating that the general DNA methylation level decreased in the treated oocytes. Our results demonstrate that TBTCl treatment results in decreased mRNA levels of imprinted genes H19, Igf2r, and Peg3 during oocyte growth. The TBTCl-treated oocytes showed a significant increase in reactive oxygen species levels in germinal vesicle oocytes. In TBTCl-treated oocytes, there was no difference in GPx and Sod1 expression, but a decreased mRNA level of Cat occurred when compared with control. Moreover, the blastocysts with TBTCl exposure displayed higher apoptotic signals. These results suggest that TBTCl induces developmental defects in oocytes and preimplantation embryos.

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38

Zeldin, M., and J. J. Lin. "Synthesis of isotactic, syndiotactic, and heterotactic poly(tributyltin methacrylate) and poly(tributyltin methacrylate-co-styrene)." Journal of Polymer Science: Polymer Chemistry Edition 23, no. 9 (September 1985): 2333–40. http://dx.doi.org/10.1002/pol.1985.170230901.

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Agafonova, Anastasiya V., Ilia A. Smetanin, Nikolai V. Rostovskii, Alexander F. Khlebnikov, and Mikhail S. Novikov. "Expedient synthesis of 3-hydroxypyrrolesviaBu3SnH-triggered ionic 5-exo-trig-cyclization of 5-chloro-3-azamuconoate derivatives." Organic Chemistry Frontiers 5, no. 23 (2018): 3396–401. http://dx.doi.org/10.1039/c8qo00982a.

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40

Jeong, Seong-Yun, Hong-Joo Son, and Nam-Ho Jeoung. "Isolation and Degradation Activity of a TBTCl (Tributyltin Chloride) Resistant Bacteriain Gwangyang Bay." Korean Journal of Environmental Agriculture 30, no. 4 (December 31, 2011): 424–31. http://dx.doi.org/10.5338/kjea.2011.30.4.424.

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41

Sein, Myint M., Torsten C. Schmidt, Alfred Golloch, and Clemens von Sonntag. "Oxidation of some typical wastewater contaminants (tributyltin, clarithromycin, metoprolol and diclofenac) by ozone." Water Science and Technology 59, no. 8 (April 1, 2009): 1479–85. http://dx.doi.org/10.2166/wst.2009.153.

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The rate constants of the reactions of O3 with some typical wastewater pollutants (tributyltin, the macrolide antibiotic clarithromycin, the beta blocker metoprolol and the analgesic diclofenac) were determined and some mechanistic aspects were elucidated. Except for tributyltin compounds that react only slowly with O3 (k=4–7 M−1 s−1), the compounds react fast (k>104 M−1 s−1) and can be eliminated at low O3 doses. Clarithromycin reacts at its dimethylamino group and yields the corresponding N-oxide that is no longer biologically active. The nitrogen is also the major site of O3 attack in diclofenac and in metoprolol. This gives rise to •OH radicals and these are the precursors of hydroxylated products and markedly contribute to chloride release in diclofenac.

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42

Kumar, A. Sanjeeva, Palakuri Ramesh, G. Santosh Kumar, A. Swetha, Jagadeesh Babu Nanubolu, and H. M. Meshram. "A Ru(iii) – catalyzed α-cross-coupling aldol type addition reaction of activated olefins with isatins." RSC Advances 6, no. 3 (2016): 1705–9. http://dx.doi.org/10.1039/c5ra14714j.

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43

Hanaoka, Saki, Keishi Ishida, Saki Tanaka, Shuichiro Sakamoto, Katsuhiro Okuda, Seigo Sanoh, Shigeru Ohta, and Yaichiro Kotake. "Tributyltin induces epigenetic changes and decreases the expression of nuclear respiratory factor-1." Metallomics 10, no. 2 (2018): 337–45. http://dx.doi.org/10.1039/c7mt00290d.

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The toxicity of tributyltin, an organotin environmental contaminant, is potentially mediated by epigenetic changes in the nuclear respiratory factor-1 (NRF-1) promoter region, leading to reduced mitochondrial membrane potential.

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44

Yuan, Ge-hui, Zhan Zhang, Xing-su Gao, Jun Zhu, Wen-hui Guo, Li Wang, Ping Ding, Ping Jiang, and Lei Li. "Gut microbiota-mediated tributyltin-induced metabolic disorder in rats." RSC Advances 10, no. 71 (2020): 43619–28. http://dx.doi.org/10.1039/d0ra07502g.

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Tributyltin (TBT), an environmental pollutant widely used in antifouling coatings, can cause multiple-organ toxicity and gut microbiome dysbiosis in organisms, and can even cause changes in the host metabolomic profiles.

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45

de Mora, S. J., and E. Pelletier. "Environmental Tributyltin Research: Past, Present, Future." Environmental Technology 18, no. 12 (December 1997): 1169–77. http://dx.doi.org/10.1080/09593331808616637.

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46

Sloman, K. A. "FISH BRAINS: NERVOUS ACCUMULATION OF TRIBUTYLTIN." Journal of Experimental Biology 207, no. 1 (January 1, 2004): 10. http://dx.doi.org/10.1242/jeb.00752.

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47

Inadera, Hidekuni, and Akiko Shimomura. "Environmental chemical tributyltin augments adipocyte differentiation." Toxicology Letters 159, no. 3 (December 2005): 226–34. http://dx.doi.org/10.1016/j.toxlet.2005.05.015.

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48

Hall, Lenwood W. "Tributyltin environmental studies in Chesapeake Bay." Marine Pollution Bulletin 19, no. 9 (September 1988): 431–38. http://dx.doi.org/10.1016/0025-326x(88)90398-0.

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49

Qucani, Giovannella, Hans Mosbæk, and Stefan Trapp. "Uptake of Tributyltin into Willow Trees." Environmental Science and Pollution Research 11, no. 4 (July 2004): 267–72. http://dx.doi.org/10.1007/bf02979636.

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Trapp, Stefan, Giovannella Ciucani, and Milos Sismilich. "Toxicity of tributyltin to willow trees." Environmental Science and Pollution Research 11, no. 5 (September 2004): 327–30. http://dx.doi.org/10.1007/bf02979647.

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