PMID- 27072397
OWN - NLM
STAT- MEDLINE
DCOM- 20170209
LR  - 20191027
IS  - 1875-5550 (Electronic)
IS  - 1389-2037 (Linking)
VI  - 18
IP  - 1
DP  - 2017
TI  - Enantioselective Biotransformation of Chiral Persistent Organic Pollutants.
PG  - 48-56
AB  - BACKGROUND: Enantiomers of chiral compounds commonly undergo enantioselective 
      transformation in most biologically mediated processes. As chiral persistent 
      organic pollutants (POPs) are extensively distributed in the environment, 
      differences between enantiomers in biotransformation should be carefully 
      considered to obtain exact enrichment and specific health risks. This review 
      provides an overview of in vivo biotransformation of chiral POPs currently 
      indicated in the Stockholm Convention and their chiral metabolites. METHODS: 
      Peer-reviewed journal articles focused on the research question were thoroughly 
      searched. A set of inclusion and exclusion criteria were developed to identify 
      relevant studies. We mainly compared the results from different animal models 
      under controlled laboratory conditions to show the difference between enantiomers 
      in terms of distinct transformation potential. Interactions with enzymes involved 
      in enantioselective biotransformation, especially cytochrome P450 (CYP), were 
      discussed. Further research areas regarding this issue were proposed. RESULTS: 
      Limited evidence for a few POPs has been found in 30 studies. Enantioselective 
      biotransformation of alpha-hexachlorocyclohexane (alpha-HCH), chlordane, 
      dichlorodiphenyltrichloroethane (DDT), heptachlor, hexabromocyclododecane (HBCD), 
      polychlorinated biphenyls (PCBs), and toxaphene, has been investigated using 
      laboratory mammal, fish, bird, and worm models. Tissue and excreta distributions, 
      as well as bioaccumulation and elimination kinetics after administration of 
      racemate and pure enantiomers, have been analyzed in these studies. Changes in 
      enantiomeric fractions have been considered as an indicator of enantioselective 
      biotransformation of chiral POPs in most studies. Results of different laboratory 
      animal models revealed that chiral POP biotransformation is seriously affected by 
      chirality. Pronounced results of species-, tissue-, gender-, and 
      individual-dependent differences are observed in in vivo biotransformation of 
      chiral POPs. Enantioselective biotransformation of chiral POPs is dependent on 
      enzyme amounts and activities. However, the role of cytochrome P450 in 
      enantioselective biotransformation has not yet been confirmed. CONCLUSION: 
      Currently available data on biotransformation of chiral POPs provide a 
      preliminary understanding of the fate of chiral compounds in organisms. Further 
      detailed studies of species-dependent biotransformation pathway and molecular 
      mechanism in various animal models should be performed to comprehensively 
      understand chiral POP biotransformation.
FAU - Zhang, Ying
AU  - Zhang Y
AD  - School of Ecological and Environmental Science, East China Normal University, 
      Shanghai 200241, China.
FAU - Ye, Jing
AU  - Ye J
FAU - Liu, Min
AU  - Liu M
LA  - eng
PT  - Journal Article
PT  - Review
PL  - United Arab Emirates
TA  - Curr Protein Pept Sci
JT  - Current protein & peptide science
JID - 100960529
RN  - 0 (Environmental Pollutants)
RN  - 0 (Organic Chemicals)
RN  - 9035-51-2 (Cytochrome P-450 Enzyme System)
SB  - IM
MH  - Animals
MH  - *Biotransformation
MH  - Cytochrome P-450 Enzyme System/metabolism
MH  - Environmental Pollutants/chemistry/*metabolism
MH  - *Green Chemistry Technology
MH  - Humans
MH  - Organic Chemicals/chemistry/*metabolism
EDAT- 2016/04/14 06:00
MHDA- 2017/02/10 06:00
CRDT- 2016/04/14 06:00
PHST- 2016/01/26 00:00 [received]
PHST- 2016/03/30 00:00 [revised]
PHST- 2016/04/30 00:00 [accepted]
PHST- 2016/04/14 06:00 [pubmed]
PHST- 2017/02/10 06:00 [medline]
PHST- 2016/04/14 06:00 [entrez]
AID - CPPS-EPUB-74936 [pii]
AID - 10.2174/1389203717666160413124027 [doi]
PST - ppublish
SO  - Curr Protein Pept Sci. 2017;18(1):48-56. doi: 10.2174/1389203717666160413124027.