SULFONATION OF ENVIRONMENTAL CHEMICALS AND THEIR METABOLITES IN THE POLAR BEAR (Ursus maritimus)
Although its habitat comprises mostly remote regions of the Arctic, the polar bear is subject to bioaccumulation of persistent environmental pollutants. Along with their phase I metabolites, they are potential substrates for detoxification via sulfonation and glucuronidation. The capability of polar...
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| Published in | Drug metabolism and disposition Vol. 33; no. 9; pp. 1341 - 1348 |
|---|---|
| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
Bethesda, MD
Elsevier Inc
01.09.2005
American Society for Pharmacology and Experimental Therapeutics |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0090-9556 1521-009X |
| DOI | 10.1124/dmd.105.004648 |
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| Abstract | Although its habitat comprises mostly remote regions of the Arctic, the polar bear is subject to bioaccumulation of persistent environmental pollutants. Along with their phase I metabolites, they are potential substrates for detoxification via sulfonation and glucuronidation. The capability of polar bear liver to sulfonate a structurally diverse group of environmental chemicals, that is, 3-hydroxybenzo[a]pyrene (3-OH-B[a]P), triclosan, 4′-hydroxy-3,3′,4,5′-tetrachlorobiphenyl (4′OH-PCB79), 4′-hydroxy-2,3,3′,4,5,5′-hexachlorobiphenyl (4′-OH-PCB159), 4′-hydroxy-2,3,3′,5,5′,6-hexachlorobiphenyl (4′-OH-PCB165), the methoxychlor metabolite 2-(4-methoxyphenyl)-2-(4-hydroxyphenyl)-1,1,1-trichloroethane (OHMXC), tris(4-chlorophenyl)-methanol (TCPM), and pentachlorophenol (PCP) was investigated. The glucuronidation of 3-OH-B[a]P was also studied. Enzyme activity was assayed by incubation of liver cytosol or microsomes derived from three adult male polar bears with 3′-phosphoadenosine-5′-phosphosulfate or uridine 5′-diphosphoglucuronic acid and substrate, followed by fluorometric or radiochemical thin-layer chromatographic analysis. The efficiency of sulfonation decreased in the order 3-OH-B[a]P ⋙ triclosan ≫ 4′-OH-PCB79 > OHMXC > 4′-OH-PCB165 > TCPM > 4′-OH-PCB159 > PCP, all of which produced detectable sulfate conjugates. The 3-OH-B[a]P substrate was readily sulfonated and glucuronidated (apparent Km 0.41, 1.4 μM, and apparent Vmax 0.50, 3.00 nmol/min/mg, respectively). UDP-glucuronic acid kinetics suggested the presence of multiple enzymes glucuronidating 3-OH-B[a]P. Substrate inhibition was observed for the sulfonation of 3-OH-B[a]P and 4′OH-PCB79 (Ki 1.0 and 217 μM, respectively). Triclosan was the most rapidly sulfated (apparent Vmax 1008 pmol/min/mg) of the substrates tested. Since sulfonation of an acyclic tertiary alcoholic group, as in TCPM, has not previously been reported, we also examined TCPM conjugation in humans and catfish, both of which formed TCPM-sulfate. The hexachlorinated polychlorinated biphenylols, TCPM, and PCP were poor substrates for sulfonation, suggesting that this may be one reason why these substances and structurally similar xenobiotics persist in polar bears. |
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| AbstractList | Although its habitat comprises mostly remote regions of the Arctic, the polar bear is subject to bioaccumulation of persistent environmental pollutants. Along with their phase I metabolites, they are potential substrates for detoxification via sulfonation and glucuronidation. The capability of polar bear liver to sulfonate a structurally diverse group of environmental chemicals, that is, 3-hydroxybenzo[a]pyrene (3-OH-B[a]P), triclosan, 4'-hydroxy-3,3',4,5'-tetrachlorobiphenyl (4'OH-PCB79), 4'-hydroxy-2,3,3',4,5,5'-hexachlorobiphenyl (4'-OH-PCB159), 4'-hydroxy-2,3,3',5,5',6-hexachlorobiphenyl (4'-OH-PCB165), the methoxychlor metabolite 2-(4-methoxyphenyl)-2-(4-hydroxyphenyl)-1,1,1-trichloroethane (OHMXC), tris(4-chlorophenyl)-methanol (TCPM), and pentachlorophenol (PCP) was investigated. The glucuronidation of 3-OH-B[a]P was also studied. Enzyme activity was assayed by incubation of liver cytosol or microsomes derived from three adult male polar bears with 3'-phosphoadenosine-5'-phosphosulfate or uridine 5'-diphosphoglucuronic acid and substrate, followed by fluorometric or radiochemical thin-layer chromatographic analysis. The efficiency of sulfonation decreased in the order 3-OH-B[a]P >>> triclosan >> 4'-OH-PCB79 > OHMXC > 4'-OH-PCB165 > TCPM > 4'-OH-PCB159 > PCP, all of which produced detectable sulfate conjugates. The 3-OH-B[a]P substrate was readily sulfonated and glucuronidated (apparent K(m) 0.41, 1.4 microM, and apparent V(max) 0.50, 3.00 nmol/min/mg, respectively). UDP-glucuronic acid kinetics suggested the presence of multiple enzymes glucuronidating 3-OH-B[a]P. Substrate inhibition was observed for the sulfonation of 3-OH-B[a]P and 4'OH-PCB79 (K(i) 1.0 and 217 microM, respectively). Triclosan was the most rapidly sulfated (apparent V(max) 1008 pmol/min/mg) of the substrates tested. Since sulfonation of an acyclic tertiary alcoholic group, as in TCPM, has not previously been reported, we also examined TCPM conjugation in humans and catfish, both of which formed TCPM-sulfate. The hexachlorinated polychlorinated biphenylols, TCPM, and PCP were poor substrates for sulfonation, suggesting that this may be one reason why these substances and structurally similar xenobiotics persist in polar bears. Although its habitat comprises mostly remote regions of the Arctic, the polar bear is subject to bioaccumulation of persistent environmental pollutants. Along with their phase I metabolites, they are potential substrates for detoxification via sulfonation and glucuronidation. The capability of polar bear liver to sulfonate a structurally diverse group of environmental chemicals, that is, 3-hydroxybenzo[a]pyrene (3-OH-B[a]P), triclosan, 4'-hydroxy-3,3',4,5'-tetrachlorobiphenyl (4'OH-PCB79), 4'-hydroxy-2,3,3',4,5,5'-hexachlorobiphenyl (4'-OH-PCB159), 4'-hydroxy-2,3,3',5,5',6-hexachlorobiphenyl (4'-OH-PCB165), the methoxychlor metabolite 2-(4-methoxyphenyl)-2-(4-hydroxyphenyl)-1,1,1-trichloroethane (OHMXC), tris(4-chlorophenyl)-methanol (TCPM), and pentachlorophenol (PCP) was investigated. The glucuronidation of 3-OH-B[a]P was also studied. Enzyme activity was assayed by incubation of liver cytosol or microsomes derived from three adult male polar bears with 3'-phosphoadenosine-5'-phosphosulfate or uridine 5'-diphosphoglucuronic acid and substrate, followed by fluorometric or radiochemical thin-layer chromatographic analysis. The efficiency of sulfonation decreased in the order 3-OH-B[a]P >>> triclosan >> 4'-OH-PCB79 > OHMXC > 4'-OH-PCB165 > TCPM > 4'-OH-PCB159 > PCP, all of which produced detectable sulfate conjugates. The 3-OH-B[a]P substrate was readily sulfonated and glucuronidated (apparent K(m) 0.41, 1.4 microM, and apparent V(max) 0.50, 3.00 nmol/min/mg, respectively). UDP-glucuronic acid kinetics suggested the presence of multiple enzymes glucuronidating 3-OH-B[a]P. Substrate inhibition was observed for the sulfonation of 3-OH-B[a]P and 4'OH-PCB79 (K(i) 1.0 and 217 microM, respectively). Triclosan was the most rapidly sulfated (apparent V(max) 1008 pmol/min/mg) of the substrates tested. Since sulfonation of an acyclic tertiary alcoholic group, as in TCPM, has not previously been reported, we also examined TCPM conjugation in humans and catfish, both of which formed TCPM-sulfate. The hexachlorinated polychlorinated biphenylols, TCPM, and PCP were poor substrates for sulfonation, suggesting that this may be one reason why these substances and structurally similar xenobiotics persist in polar bears.Although its habitat comprises mostly remote regions of the Arctic, the polar bear is subject to bioaccumulation of persistent environmental pollutants. Along with their phase I metabolites, they are potential substrates for detoxification via sulfonation and glucuronidation. The capability of polar bear liver to sulfonate a structurally diverse group of environmental chemicals, that is, 3-hydroxybenzo[a]pyrene (3-OH-B[a]P), triclosan, 4'-hydroxy-3,3',4,5'-tetrachlorobiphenyl (4'OH-PCB79), 4'-hydroxy-2,3,3',4,5,5'-hexachlorobiphenyl (4'-OH-PCB159), 4'-hydroxy-2,3,3',5,5',6-hexachlorobiphenyl (4'-OH-PCB165), the methoxychlor metabolite 2-(4-methoxyphenyl)-2-(4-hydroxyphenyl)-1,1,1-trichloroethane (OHMXC), tris(4-chlorophenyl)-methanol (TCPM), and pentachlorophenol (PCP) was investigated. The glucuronidation of 3-OH-B[a]P was also studied. Enzyme activity was assayed by incubation of liver cytosol or microsomes derived from three adult male polar bears with 3'-phosphoadenosine-5'-phosphosulfate or uridine 5'-diphosphoglucuronic acid and substrate, followed by fluorometric or radiochemical thin-layer chromatographic analysis. The efficiency of sulfonation decreased in the order 3-OH-B[a]P >>> triclosan >> 4'-OH-PCB79 > OHMXC > 4'-OH-PCB165 > TCPM > 4'-OH-PCB159 > PCP, all of which produced detectable sulfate conjugates. The 3-OH-B[a]P substrate was readily sulfonated and glucuronidated (apparent K(m) 0.41, 1.4 microM, and apparent V(max) 0.50, 3.00 nmol/min/mg, respectively). UDP-glucuronic acid kinetics suggested the presence of multiple enzymes glucuronidating 3-OH-B[a]P. Substrate inhibition was observed for the sulfonation of 3-OH-B[a]P and 4'OH-PCB79 (K(i) 1.0 and 217 microM, respectively). Triclosan was the most rapidly sulfated (apparent V(max) 1008 pmol/min/mg) of the substrates tested. Since sulfonation of an acyclic tertiary alcoholic group, as in TCPM, has not previously been reported, we also examined TCPM conjugation in humans and catfish, both of which formed TCPM-sulfate. The hexachlorinated polychlorinated biphenylols, TCPM, and PCP were poor substrates for sulfonation, suggesting that this may be one reason why these substances and structurally similar xenobiotics persist in polar bears. Although its habitat comprises mostly remote regions of the Arctic, the polar bear is subject to bioaccumulation of persistent environmental pollutants. Along with their phase I metabolites, they are potential substrates for detoxification via sulfonation and glucuronidation. The capability of polar bear liver to sulfonate a structurally diverse group of environmental chemicals, that is, 3-hydroxybenzo[ a ]pyrene (3-OH-B[a]P), triclosan, 4â²-hydroxy-3,3â²,4,5â²-tetrachlorobiphenyl (4â²OH-PCB79), 4â²-hydroxy-2,3,3â²,4,5,5â²-hexachlorobiphenyl (4â²-OH-PCB159), 4â²-hydroxy-2,3,3â²,5,5â²,6-hexachlorobiphenyl (4â²-OH-PCB165), the methoxychlor metabolite 2-(4-methoxyphenyl)-2-(4-hydroxyphenyl)-1,1,1-trichloroethane (OHMXC), tris(4-chlorophenyl)-methanol (TCPM), and pentachlorophenol (PCP) was investigated. The glucuronidation of 3-OH-B[a]P was also studied. Enzyme activity was assayed by incubation of liver cytosol or microsomes derived from three adult male polar bears with 3â²-phosphoadenosine-5â²-phosphosulfate or uridine 5â²-diphosphoglucuronic acid and substrate, followed by fluorometric or radiochemical thin-layer chromatographic analysis. The efficiency of sulfonation decreased in the order 3-OH-B[a]P â triclosan â« 4â²-OH-PCB79 > OHMXC > 4â²-OH-PCB165 > TCPM > 4â²-OH-PCB159 > PCP, all of which produced detectable sulfate conjugates. The 3-OH-B[a]P substrate was readily sulfonated and glucuronidated (apparent K m 0.41, 1.4 μM, and apparent V max 0.50, 3.00 nmol/min/mg, respectively). UDP-glucuronic acid kinetics suggested the presence of multiple enzymes glucuronidating 3-OH-B[a]P. Substrate inhibition was observed for the sulfonation of 3-OH-B[a]P and 4â²OH-PCB79 ( K i 1.0 and 217 μM, respectively). Triclosan was the most rapidly sulfated (apparent V max 1008 pmol/min/mg) of the substrates tested. Since sulfonation of an acyclic tertiary alcoholic group, as in TCPM, has not previously been reported, we also examined TCPM conjugation in humans and catfish, both of which formed TCPM-sulfate. The hexachlorinated polychlorinated biphenylols, TCPM, and PCP were poor substrates for sulfonation, suggesting that this may be one reason why these substances and structurally similar xenobiotics persist in polar bears. Although its habitat comprises mostly remote regions of the Arctic, the polar bear is subject to bioaccumulation of persistent environmental pollutants. Along with their phase I metabolites, they are potential substrates for detoxification via sulfonation and glucuronidation. The capability of polar bear liver to sulfonate a structurally diverse group of environmental chemicals, that is, 3-hydroxybenzo[a]pyrene (3-OH-B[a]P), triclosan, 4'-hydroxy-3,3',4,5'-tetrachlorobiphenyl (4'OH-PCB79), 4'-hydroxy-2,3,3',4,5,5'-hexachlorobiphenyl (4'-OH-PCB159), 4'-hydroxy-2,3,3',5,5',6-hexachlorobiphenyl (4'-OH-PCB165), the methoxychlor metabolite 2-(4-methoxyphenyl)-2-(4-hydroxyphenyl)-1,1,1-trichloroethane (OHMXC), tris(4-chlorophenyl)-methanol (TCPM), and pentachlorophenol (PCP) was investigated. The glucuronidation of 3-OH-B[a]P was also studied. Enzyme activity was assayed by incubation of liver cytosol or microsomes derived from three adult male polar bears with 3'-phosphoadenosine-5'-phosphosulfate or uridine 5'-diphosphoglucuronic acid and substrate, followed by fluorometric or radiochemical thin-layer chromatographic analysis. The efficiency of sulfonation decreased in the order 3-OH-B[a]P >>> triclosan >> 4'-OH-PCB79 > OHMXC > 4'-OH-PCB165 > TCPM > 4'-OH-PCB159 > PCP, all of which produced detectable sulfate conjugates. The 3-OH-B[a]P substrate was readily sulfonated and glucuronidated (apparent K sub(m) 0.41, 1.4 mu M, and apparent V sub(max) 0.50, 3.00 nmol/min/mg, respectively). UDP-glucuronic acid kinetics suggested the presence of multiple enzymes glucuronidating 3-OH-B[a]P. Substrate inhibition was observed for the sulfonation of 3-OH-B[a]P and 4'OH-PCB79 (K sub(i) 1.0 and 217 mu M, respectively). Triclosan was the most rapidly sulfated (apparent V sub(max) 1008 pmol/min/mg) of the substrates tested. Since sulfonation of an acyclic tertiary alcoholic group, as in TCPM, has not previously been reported, we also examined TCPM conjugation in humans and catfish, both of which formed TCPM-sulfate. The hexachlorinated polychlorinated biphenylols, TCPM, and PCP were poor substrates for sulfonation, suggesting that this may be one reason why these substances and structurally similar xenobiotics persist in polar bears. Although its habitat comprises mostly remote regions of the Arctic, the polar bear is subject to bioaccumulation of persistent environmental pollutants. Along with their phase I metabolites, they are potential substrates for detoxification via sulfonation and glucuronidation. The capability of polar bear liver to sulfonate a structurally diverse group of environmental chemicals, that is, 3-hydroxybenzo[a]pyrene (3-OH-B[a]P), triclosan, 4′-hydroxy-3,3′,4,5′-tetrachlorobiphenyl (4′OH-PCB79), 4′-hydroxy-2,3,3′,4,5,5′-hexachlorobiphenyl (4′-OH-PCB159), 4′-hydroxy-2,3,3′,5,5′,6-hexachlorobiphenyl (4′-OH-PCB165), the methoxychlor metabolite 2-(4-methoxyphenyl)-2-(4-hydroxyphenyl)-1,1,1-trichloroethane (OHMXC), tris(4-chlorophenyl)-methanol (TCPM), and pentachlorophenol (PCP) was investigated. The glucuronidation of 3-OH-B[a]P was also studied. Enzyme activity was assayed by incubation of liver cytosol or microsomes derived from three adult male polar bears with 3′-phosphoadenosine-5′-phosphosulfate or uridine 5′-diphosphoglucuronic acid and substrate, followed by fluorometric or radiochemical thin-layer chromatographic analysis. The efficiency of sulfonation decreased in the order 3-OH-B[a]P ⋙ triclosan ≫ 4′-OH-PCB79 > OHMXC > 4′-OH-PCB165 > TCPM > 4′-OH-PCB159 > PCP, all of which produced detectable sulfate conjugates. The 3-OH-B[a]P substrate was readily sulfonated and glucuronidated (apparent Km 0.41, 1.4 μM, and apparent Vmax 0.50, 3.00 nmol/min/mg, respectively). UDP-glucuronic acid kinetics suggested the presence of multiple enzymes glucuronidating 3-OH-B[a]P. Substrate inhibition was observed for the sulfonation of 3-OH-B[a]P and 4′OH-PCB79 (Ki 1.0 and 217 μM, respectively). Triclosan was the most rapidly sulfated (apparent Vmax 1008 pmol/min/mg) of the substrates tested. Since sulfonation of an acyclic tertiary alcoholic group, as in TCPM, has not previously been reported, we also examined TCPM conjugation in humans and catfish, both of which formed TCPM-sulfate. The hexachlorinated polychlorinated biphenylols, TCPM, and PCP were poor substrates for sulfonation, suggesting that this may be one reason why these substances and structurally similar xenobiotics persist in polar bears. |
| Author | Sacco, James C. James, Margaret O. |
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| CitedBy_id | crossref_primary_10_1007_s11356_017_9694_x crossref_primary_10_1016_j_envint_2009_02_005 crossref_primary_10_1002_jat_1660 crossref_primary_10_1002_prp2_147 crossref_primary_10_1107_S1600536810012845 crossref_primary_10_1007_s00216_014_7922_5 crossref_primary_10_1016_j_aquatox_2012_07_009 crossref_primary_10_1016_j_aquatox_2017_08_009 crossref_primary_10_1016_j_jhazmat_2011_10_021 crossref_primary_10_1107_S1600536808038865 crossref_primary_10_1124_dmd_107_019596 crossref_primary_10_1016_j_dmpk_2014_10_004 crossref_primary_10_1016_j_cbpc_2007_11_009 crossref_primary_10_1107_S1600536810020362 crossref_primary_10_1021_tx800133d crossref_primary_10_1139_er_2016_0118 crossref_primary_10_1016_j_marenvres_2008_05_011 crossref_primary_10_1007_s11356_015_4987_4 crossref_primary_10_1021_es504766p crossref_primary_10_1021_es303807f crossref_primary_10_1016_j_scitotenv_2014_09_077 crossref_primary_10_1021_tx500150h crossref_primary_10_1016_j_aquatox_2007_11_003 crossref_primary_10_1002_rcm_4558 |
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| Snippet | Although its habitat comprises mostly remote regions of the Arctic, the polar bear is subject to bioaccumulation of persistent environmental pollutants. Along... Although its habitat comprises mostly remote regions of the Arctic, the polar bear is subject to bioaccumulation of persistent environmental pollutants. Along... |
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| SubjectTerms | Animals Biological and medical sciences Cells, Cultured Cytosol - enzymology Cytosol - metabolism Environmental Pollutants - metabolism Glucuronosyltransferase - metabolism Liver - enzymology Liver - metabolism Male Medical sciences Microsomes, Liver - enzymology Microsomes, Liver - metabolism Pharmacology. Drug treatments Sulfotransferases - metabolism Ursidae - metabolism Xenobiotics - metabolism |
| Title | SULFONATION OF ENVIRONMENTAL CHEMICALS AND THEIR METABOLITES IN THE POLAR BEAR (Ursus maritimus) |
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