• Title/Summary/Keyword: tributyltin

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In vitro Effects of TBT, TPhT and Aroclor 1254 on Oocyte Maturation and Ovulation in O1ive Flounder (Paralichthys olivaceus) (넙치 (Paralichthys olivaceus)의 in vitro 난모세포 성숙과 배란에 미치는 TBT, TPhT 및 Aroclor 1254의 영향)

  • BAEK Hea-Ja;JUNG Jee-Hyun;JEON Joong-Kyun
    • Korean Journal of Fisheries and Aquatic Sciences
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    • v.34 no.6
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    • pp.584-587
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    • 2001
  • The effects of tributyltin (TBT), triphenyltin (TPhT) and Aroclor 1254 on germinal vesicle breakdown (GVBD) and ovulation of olive flounder (Paralichthys olivaceus) were investigated in in vitro bioassay. TBT, TPhT and Aroclor 1254 showed the inhibition effects on GVBD and ovulation in response to HCG. The oocyte response appeared to be more sensitive to TBT than Aroclor 1254. TBT was more effective in inhibition GVBD at concentrations of 0.1 and 1 ppm. However, no significant inhibition was obseued in concentrations tested ($0.0001\~1\;ppm$). Significant inhibition of ovulation in response to HCG occurred at TBT (0.01, 0.1, 1 ppm), TPhT (0.01, 0.1, 1 ppm) and Aroclor 1254 (0.01, 1 ppm, except 0,1 ppm), compared to HCG control, The lowest ovulation rate was measured at 1 ppm TBT, These data suggest that TBT (or TPhT) could possibly interfere the actions of progestogens to induce GVBD and ovulation in in vitro bioassay system.

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Disproportionation/Dehydrocoupling of Endocrine Disruptor, Tributyltin Hydride to Polystannanes Using Cp2TiCl2/N-Selectride (Cp' = Cp' = C5H5, Cp; Me-C5H4, Me-Cp; Me5C5, Cp*) Catalyst

  • Park, Jaeyoung;Kim, Seongsim;Lee, Beomgi;Cheong, Hyeonsook;Lee, Ki Bok;Woo, Hee-Gweon
    • Journal of Integrative Natural Science
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    • v.6 no.1
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    • pp.34-38
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    • 2013
  • Tributyltin hydride ($n-Bu_3SnH$), an endocrine disruptor, was slowly polymerized by the group 4 ${Cp^{\prime}}_2TiCl_2/N$-selectride (Cp' = $C_5H_5$, Cp; $Me-C_5H_4$, Me-Cp; $Me_5C_5$, $Cp^*$) catalyst combination to give two phases of products: one is an insoluble cross-linked solid, polystannane in 3-25% yield as minor product via disproportionation/dehydrocoupling combination process, and the other is an oil, hexabutyldistannane in 65-90% yield as major product via simple dehydrocoupling process. Disproportionation/dehydrocoupling process first produced a low-molecular-weight oligostannane possessing partial backbone Sn-H bonds which then underwent an extensive cross-linking reaction of backbone Sn-H bonds, resulting in the formation of an insoluble polystannane. The disproportionation/dehydrocoupling of a tertiary hydrostannane mediated by early transition metallocene/inorganic hydride is quite unusual and applicable.

Mechanisms of Tributyltin-induced Leydig Cell Apoptosis (유기주석화합물이 웅성생식세포주에 미치는 영향)

  • Lee, Kyung-Jin;Kim, Deok-Song;Ra, Myung-Suk;Wui, Seong-Uk;Im, Wook-Bin;Park, Hueng-Sik;Lee, Jong-Bin
    • Environmental Analysis Health and Toxicology
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    • v.18 no.2
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    • pp.89-94
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    • 2003
  • Tributyltin (TBT) used world-wide in antifouling paints for ships is a widespread environmental pollutant and cause reproductive organs atrophy in rodents. At low doses, antiproliferative modes of action have been shown to be involved, whereas at higher doses apoptosis seems to be the mechanism of toxicity in reproductive organs by TBT. In this study, we investigated that the mechanisms underlying DNA fragmentation induced by TBT in the rat leyding cell line, R2C. Effects of TBT on intracellular Ca$\^$2+/ level and reactive oxygen species (ROS) were investigated in R2C cells by fluorescence detector. TBT significantly induced intracellular Ca$\^$2+/ level in a time-dependent manner. The rise in intracellular Ca$\^$2+/ level was followed by a time-dependent generation of reactive oxygen species (ROS) at the cytosol level. Simultaneously, TBT induced the release of cytochrome c from the mitochondrial membrane into the cytosol. Furthermore, ROS production and the release of cytochrome c were reduced by BAPTA, an intracellular Ca$\^$2+/ chelator, indicating the important role of Ca$\^$2+/ in R2C during these early intracellular events. In addition, Z-DEVD FMK, a caspase-3 inhibitor, decreased apoptosis by TBT. Taken together, the present results indicated that the apoptotic pathway by TBT might start with an increase in intracellular Ca$\^$2+/ level, continues with release of ROS and cytochrome c from mitochondria, activation of caspases,and finally results in DNA fragmentation.

Butyltins in Surface Sediments of Kyeonggi Bay, Korea

  • Kim, Gi-Beum;Tanabe, Shinsuke;Koh, Chul-Hwan
    • Journal of the korean society of oceanography
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    • v.33 no.3
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    • pp.64-70
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    • 1998
  • Forty sediment samples from Kyeonggi Bay, Korea were analyzed for butyltins, including tributyltin (TBT), dibutyltin (DBT), and monobutyltin (MBT) to determine their distribution and source in this area. Total butyltin concentrations in Kyeonggi Bay sediments ranged from 0.8 to 297 ng/g dry wt. with a mean value of 38 ng/g. The highest butyltin concentration was found in the innermost site in Incheon Harbor basin. The mouth of Han River had higher butyltin levels in sediments compared to open ocean. Butyltin levels correlated well with organic carbon content of sediment, but the major factor was the distance from the source area where antifouling paints were used for vessels and marine structures. Butyltin concentrations in the study area were lower than those reported for bays in other parts of the world. Considering the high toxic potential and sediment/water partition coefficient of TBT, further studies are needed to assess its biological effect in the marine ecosystem of Kyeonggi Bay.

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Study on Electrochemical Properties of TBT(Tributyltin)

  • Park, Chil-Nam;Yang, Hyo-Kyung
    • Environmental Sciences Bulletin of The Korean Environmental Sciences Society
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    • v.10 no.S_4
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    • pp.173-179
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    • 2001
  • The chemical behavior and properties of the redox state of environmental pollutants was investigated using electrochemical methods. The purpose was to measure the variations in the redox reaction of differential pulse polarograms and cyclic voltammograms. The results observed the influences on redox potential and current of various factors including concentration, temperature, salt, and pH. These were established factors as the effect of the redox reaction. It can be clearly recognized that the electrode reaction are from reversible to irreversible processes. Also, it was mixing with reaction current controlled.

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광양만의 유기주석화합물 오염과 생물농축

  • 심원준;김남숙;임운혁;홍상희;오재룡
    • Proceedings of the Korea Society of Environmental Biology Conference
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    • 2002.11a
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    • pp.25-32
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    • 2002
  • 유기주석화합물은 선박방오도료에 살생물제로 쓰이는 독성이 강한 물질로서 내분비계장애물질의 일종으로 알려지고 있다. 광양만에서 유기주석화합물의 오염현황을 파악하고자 표층퇴적물 및 생물체 중의 농도를 정성 및 정량분석하였으며, 생물에 미치는 영향을 파악하고자 복족류의 임포섹스(암컷에서 수컷의 성기가 발현되는 현상)를 측정하였다. 표층퇴적물 및 생물체 체내에서 phenyltin은 일부 정점을 제외하고는 모두 검출한계 이하의 값을 보였으나, butyltin은 대부분의 정점에서 검출되었다. 표층퇴적물, 참굴, 대수리 체내의 tributyltin (TBT)의 농도는 각각 미검출-29 ng/g, 178-2458 ng/g, 47-236 ng/g 범위를 보였다. TBT 화합물의 공간적인 분포는 선박활동과 밀접한 관련이 있었으며, 항구가 위치한 여수 인근을 제외하고는 광양내만에서 상대적으로 높은 값을 보였다. 한편 대수리 중의 임포섹스는 11개 정점에서 모두 관찰되었으며, 상대성기길이 지수는 47.9-107.8%의 범위를 보였다.

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Radical Polymerization of Vinyl Monomers to Poly(vinyl)s having nBu3Sn end Groups with Biological Activity

  • Park, Jaeyoung;Lee, Beomgi;Kim, Seongsim;Cheong, Hyeonsook;Gwak, Gyeongja;Lee, Ki Bok;Woo, Hee-Gweon
    • Journal of Integrative Natural Science
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    • v.6 no.2
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    • pp.71-75
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    • 2013
  • $Bu_3Sn$-endded poly(vinyl)s with biological activity were obtained by the radical polymerization of vinyl monomers using thianthrene cation radical/$^nBu_3H$. Thianthrene cation and stannyl radicals promoted the homopolymerization and copolymerization of styrene and ethyl vinyl ether having number average molecular weights of 2000-3100. Tributyltin hydride functions as a chain transfer agent. Such polymereization by cationic thianthrene and stannyl radicals could provide some clues for the biological reaction in living animals. Plausible polymerization mechanisms were suggested.

The Synthesis of Trifluoromethylated 1,2-Diphenylvinyl Sulfone and It's Synthetic Utilities

  • 정인화;차재돈;정우진
    • Bulletin of the Korean Chemical Society
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    • v.19 no.12
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    • pp.1355-1359
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    • 1998
  • The treatment of 1,1-bis(phenylthio)-2,2,3,3,3-pentafluoropropylbenzene (1) with 2 equiv. of phenyllithium in THF at -78 ℃ resulted in the formation of isomeric mixture (70: 30) of trifluoromethylated 1,2-diphenylvinyl sulfide 2 in 87% yield. The further oxidation of 2 with m-chloroperbenzoic acid in methylene chloride afforded isomeric mixture (70:30) of trifluoromethylated 1,2-diphenylvinyl sulfone 3 in 87% yield. When 3 was reacted with carbon nucleophiles such as methyllithium, n-butyllithium, phenyllithium and lithium octylide, the corresponding addition-elimination adducts 4, 5, 6 and 7 were obtained in moderate to good yields. The reaction of 3 with 4 equiv. of tributyltin hydride in benzene at reflux temperature provided isomeric mixture (90 : 10) of trifluoromethylated 1,2-diphenylvinyl stannane 8 in 41% yield. The reaction of 8 with methyllithium in the presence of trimethylsilyl chloride gave isomeric mixtures (90: 10) of trifluoromethylated 1,2-diphenylvinyl silane 9 in 88% yield. Finally, the treatment of 8 with Br2 and 12 resulted in the formation of isomeric mixtures (90: 10) of trifluoromethylated 1,2-diphenylvinyl bromide 10 and iodide 11 in 72% and 90% yields, respectively.

Free Radical-mediated Ring Expansion Reactions:Endocyclic Cleavage of Cyclopropylcarbinyl Radicals

  • Lee, Pil Ho;Lee, Byeong Cheol;Lee, Gu Yeon;Lee, Chang Hui;Jang, Suk Bok
    • Bulletin of the Korean Chemical Society
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    • v.21 no.6
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    • pp.595-603
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    • 2000
  • Ring expansion reactions via endocyclic cleavage of cyclopropylcarbinyl radicals derived from the reaction of [1-benzyloxycarbonylbicyclo[n. 1.O]alk-(n+l)-yl] -1-imidazolethiocarboxylates with tributyltin hydride/AIBN proceeded to produce 3-cycloalkenecarboxylates in good yields. Benzyl (5'-phenoxypentyl) -3-cyclohepten-1 -carboxylate was obtained in 33% yield from the reaction of benzyl 5-methylenebicyclo [4. 1.0]- 1-carboxylates with 4-phenoxybutyl iodide under radical conditions. Selective cleavage of endocyclic bond in cyclopropane to the cyclohexane, results from stabilization of the resultant radical by the carbonyl groups, such as the benzyloxycarbonyl group, which lower the transition state energy for the final cyclopropane cleavage in the ring expansion.