Environmental biotransformation of chiral polychlorinated biphenyls and their metabolites
This dissertation combines laboratory and field experiments to investigate the mechanisms of atropisomer enrichment for chiral polychlorinated biphenyls (PCBs) and their metabolites in organisms. Stereoselective biotransformation and bioaccumulation were identified as two major reasons for the diffe...
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ftunivmanitoba:oai:mspace.lib.umanitoba.ca:1993/22286 2023-06-18T03:39:38+02:00 Environmental biotransformation of chiral polychlorinated biphenyls and their metabolites Lv, Zhe Wong, Charles S. (Chemistry) Wang, Feiyue (Chemistry) McKenna, Sean (Chemistry) Farenhorst, Annemieke (Soil Science) Wania, Frank (Physical and Environmental Sciences,University of Toronto Scarborough) 2013 application/pdf http://hdl.handle.net/1993/22286 eng eng ACS Publications Elsevier Lehmler, H.-J., Harrad, S. J., Hühnerfuss, H., Kania-Korwel, I., Lee, C. M., Lu, Z., Wong. C. S. 2010. Chiral polychlorinated biphenyl transport, metabolism, and distribution: a review. Environmental Science & Technology.44 (8): 2757-2766. (DOI:10.1021/es902208u) Lu, Z. and Wong, C. S. 2011. Factors affecting phase I stereoselective biotransformation of chiral polychlorinated biphenyls (PCBs) by rat cytochrome P-450 2B1 isozyme. Environmental Science & Technology. 45 (19), 8298-8305. (DOI:10.1021/es200673q) Lu, Z., Ma, G. B. Veinot, J.G.C., Wong, C. S. 2013. Disruption of biomolecule function by nanoparticles: How do gold nanoparticles affect phase I biotransformation of persistent organic pollutants? Chemosphere. 93,123-132. (DOI:10.1016/j.chemosphere.2013.05.004) Lu, Z., Kania-Korwel, I., Lehmler, H.-J., Wong. C. S. 2013. Stereoselective formation of mono- and di-hydroxylated polychlorinated biphenyls by rat cytochrome P450 2B1. Environmental Science & Technology. Accepted for publication on September 23. (DOI:10.1021/es402838f) http://hdl.handle.net/1993/22286 open access Chiral polychlorinated biphenyls Biotransformation Cytochrome P-450 isozymes Nanoparticles Greenland shark Arctic food web Metabolites Bioaccumulation doctoral thesis 2013 ftunivmanitoba 2023-06-04T17:36:06Z This dissertation combines laboratory and field experiments to investigate the mechanisms of atropisomer enrichment for chiral polychlorinated biphenyls (PCBs) and their metabolites in organisms. Stereoselective biotransformation and bioaccumulation were identified as two major reasons for the different environmental fate of PCB atropisomers. Other affecting factors, such as presence of nanoparticles and changes in feeding ecology of organisms, also affect the fate of chiral contaminants. In vitro incubations of rat cytochrome P-450 2B1 (CYP2B1) isozyme with chiral PCBs indicated that different biotransformation kinetics and competition among PCB congeners or between atropisomers were two main factors affecting atropisomer enrichment. Different interactions between chiral PCB congeners or atropisomers with rat CYP2B1 may occur at the molecular level. Non-racemic meta-hydroxylated-PCBs (5-OH-PCBs) were the major metabolites. CYP-mediated stereoselective formation of dihydroxylated PCBs from OH-PCBs was observed. Gold nanoparticles affected biotransformation activity of rat CYP2B1 and changed PCB atropisomeric composition, directly by electrostatic interaction, or indirectly by changes to the surrounding ionic strength. Thus, stereoselective metabolism of chiral PCBs and OH-PCBs by CYPs is a major mechanism for atropisomer enrichment of PCBs and their metabolites in the environment, with the degree of enrichment dependent, at least in part, on charged nanoparticles and stereoselective interference of atropisomers with each other at the enzyme level. The atropisomer compositions of chiral PCBs were measured in the marine biota of Cumberland Sound (Canada) and Svalbard (Norway). High trophic level organisms, including harp seal, beluga, and narwhal reported for the first time, had species-specific atropisomer signatures, likely due to a combination of in vivo biotransformation and trophic transfer. PCB chiral signatures in Greenland sharks supported the hypothesis that some of these PCB atropisomer compositions ... Doctoral or Postdoctoral Thesis Arctic Beluga Beluga* Cumberland Sound Greenland Harp Seal narwhal* Svalbard MSpace at the University of Manitoba Arctic Canada Cumberland Sound ENVELOPE(-66.014,-66.014,65.334,65.334) Greenland Norway Svalbard |
institution |
Open Polar |
collection |
MSpace at the University of Manitoba |
op_collection_id |
ftunivmanitoba |
language |
English |
topic |
Chiral polychlorinated biphenyls Biotransformation Cytochrome P-450 isozymes Nanoparticles Greenland shark Arctic food web Metabolites Bioaccumulation |
spellingShingle |
Chiral polychlorinated biphenyls Biotransformation Cytochrome P-450 isozymes Nanoparticles Greenland shark Arctic food web Metabolites Bioaccumulation Lv, Zhe Environmental biotransformation of chiral polychlorinated biphenyls and their metabolites |
topic_facet |
Chiral polychlorinated biphenyls Biotransformation Cytochrome P-450 isozymes Nanoparticles Greenland shark Arctic food web Metabolites Bioaccumulation |
description |
This dissertation combines laboratory and field experiments to investigate the mechanisms of atropisomer enrichment for chiral polychlorinated biphenyls (PCBs) and their metabolites in organisms. Stereoselective biotransformation and bioaccumulation were identified as two major reasons for the different environmental fate of PCB atropisomers. Other affecting factors, such as presence of nanoparticles and changes in feeding ecology of organisms, also affect the fate of chiral contaminants. In vitro incubations of rat cytochrome P-450 2B1 (CYP2B1) isozyme with chiral PCBs indicated that different biotransformation kinetics and competition among PCB congeners or between atropisomers were two main factors affecting atropisomer enrichment. Different interactions between chiral PCB congeners or atropisomers with rat CYP2B1 may occur at the molecular level. Non-racemic meta-hydroxylated-PCBs (5-OH-PCBs) were the major metabolites. CYP-mediated stereoselective formation of dihydroxylated PCBs from OH-PCBs was observed. Gold nanoparticles affected biotransformation activity of rat CYP2B1 and changed PCB atropisomeric composition, directly by electrostatic interaction, or indirectly by changes to the surrounding ionic strength. Thus, stereoselective metabolism of chiral PCBs and OH-PCBs by CYPs is a major mechanism for atropisomer enrichment of PCBs and their metabolites in the environment, with the degree of enrichment dependent, at least in part, on charged nanoparticles and stereoselective interference of atropisomers with each other at the enzyme level. The atropisomer compositions of chiral PCBs were measured in the marine biota of Cumberland Sound (Canada) and Svalbard (Norway). High trophic level organisms, including harp seal, beluga, and narwhal reported for the first time, had species-specific atropisomer signatures, likely due to a combination of in vivo biotransformation and trophic transfer. PCB chiral signatures in Greenland sharks supported the hypothesis that some of these PCB atropisomer compositions ... |
author2 |
Wong, Charles S. (Chemistry) Wang, Feiyue (Chemistry) McKenna, Sean (Chemistry) Farenhorst, Annemieke (Soil Science) Wania, Frank (Physical and Environmental Sciences,University of Toronto Scarborough) |
format |
Doctoral or Postdoctoral Thesis |
author |
Lv, Zhe |
author_facet |
Lv, Zhe |
author_sort |
Lv, Zhe |
title |
Environmental biotransformation of chiral polychlorinated biphenyls and their metabolites |
title_short |
Environmental biotransformation of chiral polychlorinated biphenyls and their metabolites |
title_full |
Environmental biotransformation of chiral polychlorinated biphenyls and their metabolites |
title_fullStr |
Environmental biotransformation of chiral polychlorinated biphenyls and their metabolites |
title_full_unstemmed |
Environmental biotransformation of chiral polychlorinated biphenyls and their metabolites |
title_sort |
environmental biotransformation of chiral polychlorinated biphenyls and their metabolites |
publisher |
ACS Publications |
publishDate |
2013 |
url |
http://hdl.handle.net/1993/22286 |
long_lat |
ENVELOPE(-66.014,-66.014,65.334,65.334) |
geographic |
Arctic Canada Cumberland Sound Greenland Norway Svalbard |
geographic_facet |
Arctic Canada Cumberland Sound Greenland Norway Svalbard |
genre |
Arctic Beluga Beluga* Cumberland Sound Greenland Harp Seal narwhal* Svalbard |
genre_facet |
Arctic Beluga Beluga* Cumberland Sound Greenland Harp Seal narwhal* Svalbard |
op_relation |
Lehmler, H.-J., Harrad, S. J., Hühnerfuss, H., Kania-Korwel, I., Lee, C. M., Lu, Z., Wong. C. S. 2010. Chiral polychlorinated biphenyl transport, metabolism, and distribution: a review. Environmental Science & Technology.44 (8): 2757-2766. (DOI:10.1021/es902208u) Lu, Z. and Wong, C. S. 2011. Factors affecting phase I stereoselective biotransformation of chiral polychlorinated biphenyls (PCBs) by rat cytochrome P-450 2B1 isozyme. Environmental Science & Technology. 45 (19), 8298-8305. (DOI:10.1021/es200673q) Lu, Z., Ma, G. B. Veinot, J.G.C., Wong, C. S. 2013. Disruption of biomolecule function by nanoparticles: How do gold nanoparticles affect phase I biotransformation of persistent organic pollutants? Chemosphere. 93,123-132. (DOI:10.1016/j.chemosphere.2013.05.004) Lu, Z., Kania-Korwel, I., Lehmler, H.-J., Wong. C. S. 2013. Stereoselective formation of mono- and di-hydroxylated polychlorinated biphenyls by rat cytochrome P450 2B1. Environmental Science & Technology. Accepted for publication on September 23. (DOI:10.1021/es402838f) http://hdl.handle.net/1993/22286 |
op_rights |
open access |
_version_ |
1769004349347856384 |