Chiral analysis of pesticides and drugs of environmental concern: biodegradation and enantiomeric fraction

Alexandra S. Maia; Ana R. Ribeiro; Paula M. L. Castro; Maria Elizabeth Tiritan

doi:10.3390/sym9090196

Chiral analysis of pesticides and drugs of environmental concern: biodegradation and enantiomeric fraction

Alexandra S. Maia, Ana R. Ribeiro, Paula M. L. Castro, Maria Elizabeth Tiritan^*

^*Corresponding author for this work

Research output: Contribution to journal › Review article › peer-review

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Abstract

The importance of stereochemistry for medicinal chemistry and pharmacology is well recognized and the dissimilar behavior of enantiomers is fully documented. Regarding the environment, the significance is equivalent since enantiomers of chiral organic pollutants can also differ in biodegradation processes and fate, as well as in ecotoxicity. This review comprises designed biodegradation studies of several chiral drugs and pesticides followed by enantioselective analytical methodologies to accurately measure the enantiomeric fraction (EF). The enantioselective monitoring of microcosms and laboratory-scale experiments with different environmental matrices is herein reported. Thus, this review focuses on the importance of evaluating the EF variation during biodegradation studies of chiral pharmaceuticals, drugs of abuse, and agrochemicals and has implications for the understanding of the environmental fate of chiral pollutants.

Original language	English
Article number	196
Pages (from-to)	1-29
Number of pages	29
Journal	Symmetry
Volume	9
Issue number	9
DOIs	https://doi.org/10.3390/sym9090196
Publication status	Published - 1 Sept 2017

Keywords

Biodegradation
Chiral analysis
Enantiomeric fraction (EF)
Enantioselectivity
Pesticides
Pharmaceuticals

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19808772Final published version, 1.49 MBLicence: CC BY

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@article{64ef552b4309489cbcbddd83ce16e638,

title = "Chiral analysis of pesticides and drugs of environmental concern: biodegradation and enantiomeric fraction",

abstract = "The importance of stereochemistry for medicinal chemistry and pharmacology is well recognized and the dissimilar behavior of enantiomers is fully documented. Regarding the environment, the significance is equivalent since enantiomers of chiral organic pollutants can also differ in biodegradation processes and fate, as well as in ecotoxicity. This review comprises designed biodegradation studies of several chiral drugs and pesticides followed by enantioselective analytical methodologies to accurately measure the enantiomeric fraction (EF). The enantioselective monitoring of microcosms and laboratory-scale experiments with different environmental matrices is herein reported. Thus, this review focuses on the importance of evaluating the EF variation during biodegradation studies of chiral pharmaceuticals, drugs of abuse, and agrochemicals and has implications for the understanding of the environmental fate of chiral pollutants.",

keywords = "Biodegradation, Chiral analysis, Enantiomeric fraction (EF), Enantioselectivity, Pesticides, Pharmaceuticals",

author = "Maia, {Alexandra S.} and Ribeiro, {Ana R.} and Castro, {Paula M. L.} and Tiritan, {Maria Elizabeth}",

note = "Funding Information: The authors wish to thank Funda{\c c}{\~a}o para a Ci{\^e}ncia e Tecnologia-FCT for financial support under the project Fluoropharma PTDC/EBB-EBI/111699/2009, the PhD grant attributed to Alexandra S. Maia SFRH/BD/86939/2012, QREN-POPH, European Social Fund, MCTES, PEst FCOMP-01-0124-FEDER-022718; PEst-OE/EQB/LA0016/2011, PEst-OE/SAU/UI4040/2014. This research was partially supported by the Strategic Funding UID/Multi/04423/2013 through national funds provided by FCT-Funda{\c c}{\~a}o para a Ci{\^e}ncia e Tecnologia and European Regional Development Fund (ERDF), in the framework of the program PT2020 and by CESPU (ChiralDrugs_CESPU_2017). Publisher Copyright: {\textcopyright} 2017 by the authors.",

year = "2017",

month = sep,

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doi = "10.3390/sym9090196",

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T2 - biodegradation and enantiomeric fraction

AU - Maia, Alexandra S.

AU - Ribeiro, Ana R.

AU - Castro, Paula M. L.

AU - Tiritan, Maria Elizabeth

N1 - Funding Information: The authors wish to thank Fundação para a Ciência e Tecnologia-FCT for financial support under the project Fluoropharma PTDC/EBB-EBI/111699/2009, the PhD grant attributed to Alexandra S. Maia SFRH/BD/86939/2012, QREN-POPH, European Social Fund, MCTES, PEst FCOMP-01-0124-FEDER-022718; PEst-OE/EQB/LA0016/2011, PEst-OE/SAU/UI4040/2014. This research was partially supported by the Strategic Funding UID/Multi/04423/2013 through national funds provided by FCT-Fundação para a Ciência e Tecnologia and European Regional Development Fund (ERDF), in the framework of the program PT2020 and by CESPU (ChiralDrugs_CESPU_2017). Publisher Copyright: © 2017 by the authors.

PY - 2017/9/1

Y1 - 2017/9/1

N2 - The importance of stereochemistry for medicinal chemistry and pharmacology is well recognized and the dissimilar behavior of enantiomers is fully documented. Regarding the environment, the significance is equivalent since enantiomers of chiral organic pollutants can also differ in biodegradation processes and fate, as well as in ecotoxicity. This review comprises designed biodegradation studies of several chiral drugs and pesticides followed by enantioselective analytical methodologies to accurately measure the enantiomeric fraction (EF). The enantioselective monitoring of microcosms and laboratory-scale experiments with different environmental matrices is herein reported. Thus, this review focuses on the importance of evaluating the EF variation during biodegradation studies of chiral pharmaceuticals, drugs of abuse, and agrochemicals and has implications for the understanding of the environmental fate of chiral pollutants.

AB - The importance of stereochemistry for medicinal chemistry and pharmacology is well recognized and the dissimilar behavior of enantiomers is fully documented. Regarding the environment, the significance is equivalent since enantiomers of chiral organic pollutants can also differ in biodegradation processes and fate, as well as in ecotoxicity. This review comprises designed biodegradation studies of several chiral drugs and pesticides followed by enantioselective analytical methodologies to accurately measure the enantiomeric fraction (EF). The enantioselective monitoring of microcosms and laboratory-scale experiments with different environmental matrices is herein reported. Thus, this review focuses on the importance of evaluating the EF variation during biodegradation studies of chiral pharmaceuticals, drugs of abuse, and agrochemicals and has implications for the understanding of the environmental fate of chiral pollutants.

KW - Biodegradation

KW - Chiral analysis

KW - Enantiomeric fraction (EF)

KW - Enantioselectivity

KW - Pesticides

KW - Pharmaceuticals

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JO - Symmetry

JF - Symmetry

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ER -

Chiral analysis of pesticides and drugs of environmental concern: biodegradation and enantiomeric fraction

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