• Title/Summary/Keyword: tributyltin

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Mechanistic Studies on the Reactions of 1-[(Aryl)(phenylseleno)methyl]benzotriazoles and 6-Aryl-6-(benzotriazol-1-yl)-1-hexenyl Phenyl Selenides with Tributyltin Hydride (1-[(아릴)(페닐셀레노)메틸]벤조트리아졸과 셀렌화 6-아릴-6-(벤조트리아졸-1-일)-1-헥센일 페닐의 삼부틸틴 수소화물과의 반응메카니즘에 관한 연구)

  • Kang, Yoon Ho;Kim, Kyong Tae
    • Journal of the Korean Chemical Society
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    • v.43 no.1
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    • pp.74-84
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    • 1999
  • Most of the reactions involving benzotriazoles as a synthetic auxiliary have been explained by ionic mechanisms, whereas benzotriazole-mediated radical reactions have received little attention. The reaction of 1-[(aryl)(phenylseleno)methyl]benzotriazole with $Bu_3$SnH in the presence of AIBN in benzene at reflux gave 2-aminodiphenyl selenide (16-29%), 2-aminobiphenyl (9-15%), diphenyl diselenide (30-93%), 1-(arylmethyl) benzotriazole (9-39%) and tributyltin-phenyl selenide (10-36%), whereas the compounds were treated with excess molar amount of $Bu_3$SnH in the absence of AIBN to afford N-(arylmethyl)anilines (44-66%) along with diphenyl diselenide (53-100%), benzotriazole (27-35%) and 1-(arylmethyl)benzotriazole (16-33%). Similarly, treatment of 6-aryl-6-(benzotriazol-1-yl)-1-hexenyl phenyl selenides with $Bu_3$SnH in the presence of AIBN gave 6-aryl-6-phenylamino-1-hexene (9-31%) and 1-aryl-1-oxo-5-pentene (15-44%). A mechanism for the formation of the products is proposed.

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Effects of Tributyltin in vitro on Hepatic Monooxygenase System in Marine Fishes (유기주석화합물이 해산 어류의 간장 MFO 효소계에 미치는 영향)

  • 전중균;이미희;이지선;심원준;이수형;허형택
    • Korean Journal of Environmental Biology
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    • v.21 no.1
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    • pp.18-25
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    • 2003
  • Effects of tributyltin chloride (TBTC) in vitro on mixed function oxygenase (MFO) system on liver microsome of eight marine fish species were investigated. To determine the effects on MFO system, cytochrome P45O (CYP) and cytochrome b5 con-tents, activities of two reductases (NADH-cytochrome b5 reductase and NADPH-cy-tochrome P450 reductase) and four dealkylation enzymes (EROD, PROD, MROD and ECOD) were measured in fish microsoms exposed to TBTC for 20 min. The WP content was reduced to 10% of the control group in 6 out of 8 species exposed to TBTC, whereas there was no significant change in the cytochrome bs content. the response of NAD(P)H dependant reductases depended on fish species. The dealkylation enzyme activities in microsome were also apparently inhibited by TBTC. The degree of inhibition was different among fish species and four enzymes. The EROD activities in eight species were decreased to the range of 1∼65% of control group.

Ultrastructural Changes in digestive gland and Lipofuscin Accumulation of the Equilateral Venus, Gomphina veneriformis (Bivalvia: Veneridae) on Tributyltin chloride (TBTCl) Toxicity (TBTCl 독성에 의한 대복, Gomphina veneriformis 소화선의 미세구조적 변화 및 지방갈색소 축적)

  • Park, Jung-Jun;Lee, Jung-Sick
    • The Korean Journal of Malacology
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    • v.26 no.1
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    • pp.63-78
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    • 2010
  • The purpose of this study was to investigate the effect of tributyltin (TBT) on histopathological and ultrastructural changes in the digestive gland structure of the equilateral venus, Gomphina veneriformis. Experimental period was 36 weeks. Experimental groups consist of control condition and 3 TBTCl exposure conditions (0.4, 0.6, $0.8\;TBTC\;{\mu}g\;L^{-1}$). Outer envelop of the visceral mass of G. veneriformis exposed to TBTCl was observed disappearance of microvilli and cilia, decrease of mucous cell and partially destruction of epithelium. In the digestive gland showed an increase of number of hemocyte and mucopolysaccaride near the digestive tubule at early time of the exposure. Especially, in $0.8\;TBTC\;{\mu}g\;L^{-1}$ group, collapse of digestive tubule with modification of epithelium was observed. TEM observation revealed the numerous glycogen granules in epithelium of the outer envelop and connective tissue. In the ciliated cell of the primary duct formed the cilia in cytoplasm. Basophilic cell was observed destruction of the rough endoplasmic reticulum and mitochondria. Also, nucleus in the epithelium of the digestive tubule was disappeared heterochromatin and nucleolus, and condense. As the concentration of TBTCl increased, the accumulation of lipofucin increased in the digestive gland, but the collapse of digestive tubule induced a decrease of accumulation of lipofuscin.

Analysis of butyltin compounds in Crassostrea gigas and Tapes philippinarum on the korean coast (한국연안의 참굴 및 바지락 속에 존재하는 부틸주석화합물의 분석)

  • Lee, Seongeon
    • Analytical Science and Technology
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    • v.22 no.5
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    • pp.360-368
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    • 2009
  • Tributyltin (TBT) use has been prohibited by the IMO (International Maritime Organization), as well as Korea, since 2003. This prohibition has affected a gradual reduction in TBT use in maritime environs (seawater, sediment, and biosamples) in several countries. In this study, Crassostrea gigas (oyster) and Tapes philippinarum (manila clam) were chosen and measured for butyltin compound concentrations to verify TBT pollution levels since its 2003 ban. Specimens were taken directly from farms for concentration measurement, where Crassostrea gigas and Tapes philippinarum are cultivated, as well as prevalent locations predicted to have been polluted. Concentrations of MBT, DBT, and TBT of Crassostrea gigas were measured to be N.D -N.D., N.D. -N.D., and N.D. -60.21 ng Sn $g^{-1}$ (wet wt), respectively. Regarding Tapes philippinarum, MBT, DBT, and TBT were N.D. -12.27 ng Sn $g^{-1}$ (wet wt), N.D. -45.95 ng Sn $g^{-1}$ (wet wt), and N.D.-7.30 ng Sn $g^{-1}$ (wet wt), respectively. For this research, a correlative study was conducted to determine butyltin compound concentration in Crassostrea gigas at the locations where measurements were made in 1994 to determine to what extent TBT pollution level decreased. A decrease in all 7 sites was observed. In 4 of the 7 samples, butyltin compounds were measured to be below the detection limit, while that of the Tapes philippinarum did not appear high compared to foreign research data.

Changes of hematological parameters and plasma constituents in the olive flounder Paralichthys olivaceus exposed to TBT (TBT 노출에 따른 넙치, Paralichthys olivaceus의 혈액학적 성상 및 혈장성분의 변화)

  • Kim, Shin-Hu;Hwang, In-Kim;Kang, Ju-Chan;Kim, Jun-Hwan
    • Journal of fish pathology
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    • v.28 no.2
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    • pp.87-92
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    • 2015
  • Juvenile Paralichthys olivaceus (mean length $17.3{\pm}2.2cm$, mean weight $46.5{\pm}6.3g$) were exposed for 10 days to tributyltin (TBT) at various concentrations (0, 1, 2, 4 and $8{\mu}g/L$). Hematological parameters, such as red blood cell (RBC) count, hematocrit (Ht), and hemoglobin (Hb) concentration, were considerably decreased by high TBT concentrations. In plasma constituents, inorganic components such calcium and magnesium were also significantly altered. Plasma calcium was notably decreased, whereas plasma magnesium was increased. The enzyme components, glutamic oxalate transaminase (GOT) and glutamic pyruvate transaminase (GPT), were significantly decreased by TBT exposure. The present findings suggest that TBT exposure can cause significant alterations in hematological parameters and plasma constituents of flatfish Paralichthys olivaceus.

Distribution of Butyltin Compounds in Surface Sediments inside Hallim Harbor of Jeiu Island, Korea (제주도 한림항내 표층퇴적물 중의 부틸주석화합물의 분포)

  • 감상규;김현정;허철구;최영찬;이민규
    • Journal of Environmental Science International
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    • v.12 no.7
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    • pp.753-762
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    • 2003
  • Butyltin compounds (BTs), namely tributyltin (TBT), dibutyltin (DBT) and monobutyltin (MBT), were measured in surface sediments collected in 2001 inside Hallim Harbor where a lot of shipping occurs as one of major harbors of Jeju Island, in order to evaluate their distribution. BTs were detected in surface sediments of all stations and their concentrations were comparable to those in surface sediments of other sites of domestic and foreign countries. The main species among BTs was MBT, although there was a little difference with a survey site. No correlations were obtained between organic matter or particles size of surface sediments and total BTs, indicating that these factors did not affect on the distribution of BTs. It was estimated that more complex factors including BTs loads and surrounding sedimentary environments, affected on the distribution of BTs. The high correlations between BTs indicated that DBT and MBT were mainly degraded from TBT based on antifouling paints of vessel etc. and other sources, such as DBT and MBT, could be ignored. The butyltin degradation indexes ([DBT] + [MBT]/[TBT]) Ivere in the range of 1.5∼3.3 (mean 2.5), indicating that the parent compound, TBT, were inflowed into the surface sediments a long years ago and degraded.

Contamination of Butyltin Compounds in Sediments inside Jeju Harbor of Jeju Island (제주도 제주항내 퇴적물 중의 부틸주석화합물의 오염)

  • Kam, Sang-Kyu;Hu, Chul-Goo;Lee, Min-Gyu
    • Journal of Environmental Science International
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    • v.20 no.5
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    • pp.655-665
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    • 2011
  • Contamination of butyltin compounds (BTs), namely tributyltin (TBT), dibutyltin (DBT) and monobutyltin (MBT), was evaluated in sediments collected inside Jeju Harbor in 2001. The concentrations of BTs in surface sediments were comparable to those in other sites of domestic and foreign countries. The high correlations between BTs in surface ($r^2$ = 0.83~0.91) and core ($r^2$ = 0.70~0.79) sediments and the significant correlations between BTs concentrations and the number of incoming and outgoing vessels indicated that DBT and MBT were mainly degraded from TBT based on antifouling paints of vessels etc. and other sources, such as DBT and MBT, could be ignored. The butyltin degradation indices ([DBT] + [MBT]/[TBT]) in surface sediments were in the range of 2.2~3.6 (mean 2.7), indicating that the parent compound, TBT, was inflowed into the surface sediments a long ago, degraded and deposited. The sedimentation age of BTs contaminated core sediments could not estimated because the content of $^{210}Pb$ activity was nearly all the same and so the sedimentation rate could not obtained.

Effect of TBT and PAHs on CYP1A, AhR and Vitellogenin Gene Expression in the Japanese Eel, Anguilla japonica

  • Choi, Min Seop;Kwon, Se Ryun;Choi, Seong Hee;Kwon, Hyuk Chu
    • Development and Reproduction
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    • v.16 no.4
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    • pp.289-294
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    • 2012
  • Gene expressions of cytochrome P4501A (CYP1A), aryl hydrocarbon receptor (AhR) and vitellogenin (Vg) by endocrine disruptors, benzo[${\alpha}$]pyrene (B[a]P) and tributyltin (TBT) were examined in cultured eel hepatocytes which were isolated from eels treated previously with B[a]P (10 mg/kg) or estradiol-$17{\beta}$ (20 mg/kg) in vivo, and the relationship between CYP1A, AhR and Vg genes were studied. When the cultured eel hepatocytes were treated with B[a]P ($10^{-6}-10^{-5}M$) the gene expressions of CYP1A and AhR were enhanced in a concentration-dependent manner. However, when treated with TBT ($10^{-9}-10^{-5}M$) the gene expressions of CYP1A and AhR were suppressed at high concentrations ($10^{-6}-10^{-5}M$), while having no effects at low concentrations ($10^{-9}-10^{-7}M$). Gene expression of Vg was also suppressed by TBT in a concentration-dependent manner in cultured eel hepatocytes which was previously treated in vivo with estradiol-$17{\beta}$.

Preliminary Study on the Toxicity and Transfer of Heavy Metals and Tributyltin to Seagrass Zostera marina (잘피의 광합성에 대한 중금속 및 TBT의 독성 영향과 중금속 흡수에 대한 연구)

  • Choi, Tae-Seob;Kim, Kwang-Young;Lee, Byeong-Gweon;Lee, Jung-Suk
    • ALGAE
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    • v.20 no.2
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    • pp.157-166
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    • 2005
  • Uptake kinetics of Cd and Zn by leaves and rhizome of the seagrass Zostera marina were examined in controlled laboratory radiotracer experiments. Subsequently, acute toxicity of Cd, Cu and TBT on photosynthetic quantum yield (ΔF/Fm’ of Z. marina were determined, and the differential sensitivities of rapid light curve (RLC) to those harmful substances were also compared. All measurements on photosynthetic activity were determined by chlorophyll a fluorescence method using pulse amplitude modulation (PAM). Metal uptake by Z. marina was saturated with increasing exposure time in leaves and rhizomes. Uptake of Zn by Z. marina was faster than that of Cd. Metal uptake rates in Z. marina decreased with the increase of dissolved metal concentrations and also with the increase of biomass. The adverse effect of TBT on effective quantum yield was stronger than other pollutants. Average acute toxicity on the RLC of the seagrass exposed to TBT and two heavy metals (Cd and Cu) was going to decrease as follows: TBT > Cd > Cu. Our preliminary results in this study suggested that Z. marina potentially can be used as a biomonitor of harmful substances contamination in coastal waters.

In vivo Comet Assay on Flounder and Clam Exposed to BaP and TBT (BaP 및 TBT에 노출된 넙치와 개조개의 in vivo Comet assay)

  • Kim, So-Jung;Chung, Young-Jae;Lee, Taek-Kyun
    • Ocean and Polar Research
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    • v.33 no.2
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    • pp.127-133
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    • 2011
  • The comet assay, also called single-cell electrophoresis (SCGE) assay, is a potential sensitive monitoring tool for DNA damage in cells. The primary objective of this study was to use comet assay to ascertain if the blood cells of flounder (Pleuronichthys olivaceus) and muscle cells of clam (Saxidomus purpurata) are suitable for genotoxicity screening. This was achieved by initially exposing blood and muscle cells under in vitro conditions to the reference genotoxin hydrogen peroxide ($H_2O_2$); strong correlation between $H_2O_2$ concentration and comet values were found. Subsequently, the identification of DNA damage in isolated cells from flounder and clam was performed under in vivo exposure to benzo(a)pyrene (BaP) and tributyltin (TBT). Flounder and clam were exposed to different concentrations (1, 10, 50, 100 ${\mu}g/L$) of BaP or TBT for 4 days. Regardless of treated chemicals, blood cells of flounder were more prone to DNA breakage compared to muscle cells of clam. In conclusion, in vivo genotoxicity of BaP and TBT can be biomonitored using the comet assay. This study suggests that flounder and clam do show potential as mediums for monitoring genotoxic damage by comet assay.