View : 12 Download: 0

Using electronic theory to identify metabolites present in 17α-ethinylestradiol biotransformation pathways

Title
Using electronic theory to identify metabolites present in 17α-ethinylestradiol biotransformation pathways
Authors
Barr W.J.Yi T.Aga D.Acevedo O.Harper W.F.
Ewha Authors
이태우
Issue Date
2012
Journal Title
Environmental Science and Technology
ISSN
0013-936XJCR Link
Citation
vol. 46, no. 2, pp. 760 - 768
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
This research used electronic theory to model the biotransformation of 17α-ethinylestradiol (EE 2) under aerobic conditions in mixed culture. The methodology involved determining the Frontier Electron Density (FED) for EE 2 and various metabolites, as well as invoking well-established degradation rules to predict transformation pathways. We show that measured EE 2 metabolites are in good agreement with what is expected based on FED-based modeling. Initiating reactions occur at Ring A, producing metabolites that have been experimentally detected. When OH-EE 2 and 6AH-EE 2 are transformed, Ring A is cleaved before Ring B. The metabolites involved in these pathways have different estrogenic potentials, as implied by our analysis of the log P values and the hydrogen bonding characteristics. The OH-EE 2 and 6AH-EE 2 transformation pathways also show redox-induced electron rearrangement (RIER), where oxidation reactions lead to the reduction of carbon units present along the bond axis. Sulfo-EE 2 appears to be difficult to biotransform. These findings clarify theoretical and practical aspects of EE 2 biotransformation. © 2011 American Chemical Society.
DOI
10.1021/es201774r
Appears in Collections:
엘텍공과대학 > 환경공학전공 > Journal papers
Files in This Item:
There are no files associated with this item.
Export
RIS (EndNote)
XLS (Excel)
XML


qrcode

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.

BROWSE