Literature DB >> 24361551

Functional characterization of cytochromes P450 2B from the desert woodrat Neotoma lepida.

P Ross Wilderman1, Hyun-Hee Jang2, Jael R Malenke3, Mariam Salib2, Elisabeth Angermeier2, Sonia Lamime2, M Denise Dearing3, James R Halpert2.   

Abstract

Mammalian detoxification processes have been the focus of intense research, but little is known about how wild herbivores process plant secondary compounds, many of which have medicinal value or are drugs. cDNA sequences that code for three enzymes of the cytochrome P450 (CYP) 2B subfamily, here termed 2B35, 2B36, and 2B37 have been recently identified from a wild rodent, the desert woodrat (Malenke et al., 2012). Two variant clones of each enzyme were engineered to increase protein solubility and to facilitate purification, as reported for CYP2B enzymes from multiple species. When expressed in Escherichia coli each of the woodrat proteins gave the characteristic maximum at 450nm in a reduced carbon monoxide difference spectrum but generally expressed at lower levels than rat CYP2B1. Two enzymes, 2B36 and 2B37, showed dealkylation activity with the model substrates 7-ethoxy-4-(trifluoromethyl)coumarin and 7-benzyloxyresorufin, whereas 2B35 was inactive. Binding of the monoterpene (+)-α-pinene produced a Type I shift in the absorbance spectrum of each enzyme. Mutation of 2B37 at residues 114, 262, or 480, key residues governing ligand interactions with other CYP2B enzymes, did not significantly change expression levels or produce the expected functional changes. In summary, two catalytic and one ligand-binding assay are sufficient to distinguish among CYP2B35, 2B36, and 2B37. Differences in functional profiles between 2B36 and 2B37 are partially explained by changes in substrate recognition site residue 114, but not 480. The results advance our understanding of the mechanisms of detoxification in wild mammalian herbivores and highlight the complexity of this system.
Copyright © 2013 Elsevier Inc. All rights reserved.

Entities:  

Keywords:  2-mercaptoethanol; 2BXdH; 3-[(3-cholamidopropyl)dimethylammonio]-1-propanesulfonate; 7-BR; 7-EFC; 7-benzyloxyresorufin; 7-ethoxy-4-(trifluoromethyl)coumarin; BME; Biotransformation; CHAPS; CYP; Cytochrome P450; DTT; DXMS; Detoxification; EDTA; HS(P450); ITC; Juniper; PMSF; PSC; Woodrats; an N-terminally truncated and modified 2B enzyme with a C-terminal tetra-His tag to facilitate purification; cytochrome P450-dependent monooxygenases; dithiotheitol; ethylenediaminetetraacetic acid; high spin P450; hydrogen–deuterium exchange coupled to mass spectrometry; isothermal titration calorimetry; phenylmethanesulfonyl fluoride; plant secondary compound or plant specialized compound

Mesh:

Substances:

Year:  2013        PMID: 24361551      PMCID: PMC3970846          DOI: 10.1016/j.taap.2013.12.005

Source DB:  PubMed          Journal:  Toxicol Appl Pharmacol        ISSN: 0041-008X            Impact factor:   4.219


  68 in total

1.  Rational engineering of human cytochrome P450 2B6 for enhanced expression and stability: importance of a Leu264->Phe substitution.

Authors:  Santosh Kumar; Yonghong Zhao; Ling Sun; Surendra S Negi; James R Halpert; B K Muralidhara
Journal:  Mol Pharmacol       Date:  2007-08-22       Impact factor: 4.436

2.  Alanine-scanning mutagenesis of a putative substrate recognition site in human cytochrome P450 3A4. Role of residues 210 and 211 in flavonoid activation and substrate specificity.

Authors:  G R Harlow; J R Halpert
Journal:  J Biol Chem       Date:  1997-02-28       Impact factor: 5.157

Review 3.  Plasticity of CYP2B enzymes: structural and solution biophysical methods.

Authors:  P Ross Wilderman; James R Halpert
Journal:  Curr Drug Metab       Date:  2012-02       Impact factor: 3.731

4.  Induction of xenobiotic metabolising enzymes in the common brushtail possum, Trichosurus vulpecula, by Eucalyptus terpenes.

Authors:  G J Pass; S McLean; I Stupans
Journal:  Comp Biochem Physiol C Pharmacol Toxicol Endocrinol       Date:  1999-11

5.  Experience matters: prior exposure to plant toxins enhances diversity of gut microbes in herbivores.

Authors:  Kevin D Kohl; M D Dearing
Journal:  Ecol Lett       Date:  2012-06-20       Impact factor: 9.492

6.  In vitro inhibition of CYP2B1 monooxygenase by beta-myrcene and other monoterpenoid compounds.

Authors:  A C De-Oliveira; L F Ribeiro-Pinto; J R Paumgartten
Journal:  Toxicol Lett       Date:  1997-06-16       Impact factor: 4.372

7.  Decreased susceptibility of the cytochrome P450 2B6 variant K262R to inhibition by several clinically important drugs.

Authors:  Jyothi C Talakad; Santosh Kumar; James R Halpert
Journal:  Drug Metab Dispos       Date:  2008-12-12       Impact factor: 3.922

8.  Escherichia coli expression of site-directed mutants of cytochrome P450 2B1 from six substrate recognition sites: substrate specificity and inhibitor selectivity studies.

Authors:  Y Q He; Y A He; J R Halpert
Journal:  Chem Res Toxicol       Date:  1995-06       Impact factor: 3.739

9.  Expression of biotransformation genes in woodrat (Neotoma) herbivores on novel and ancestral diets: identification of candidate genes responsible for dietary shifts.

Authors:  E Magnanou; J R Malenke; M D Dearing
Journal:  Mol Ecol       Date:  2009-04-07       Impact factor: 6.185

Review 10.  Insights on cytochrome p450 enzymes and inhibitors obtained through QSAR studies.

Authors:  Jayalakshmi Sridhar; Jiawang Liu; Maryam Foroozesh; Cheryl L Klein Stevens
Journal:  Molecules       Date:  2012-08-03       Impact factor: 4.411

View more
  6 in total

1.  Effects of Urbanization and Landscape on Gut Microbiomes in White-Crowned Sparrows.

Authors:  Mae Berlow; Jennifer N Phillips; Elizabeth P Derryberry
Journal:  Microb Ecol       Date:  2020-08-16       Impact factor: 4.552

2.  So many roads traveled: A career in science and administration.

Authors:  James R Halpert
Journal:  J Biol Chem       Date:  2020-01-17       Impact factor: 5.157

3.  Using the Specialization Framework to Determine Degree of Dietary Specialization in a Herbivorous Woodrat.

Authors:  Michele M Skopec; Kevin D Kohl; Katharina Schramm; James R Halpert; M Denise Dearing
Journal:  J Chem Ecol       Date:  2015-12-02       Impact factor: 2.626

4.  Structure-Function Analysis of Mammalian CYP2B Enzymes Using 7-Substituted Coumarin Derivatives as Probes: Utility of Crystal Structures and Molecular Modeling in Understanding Xenobiotic Metabolism.

Authors:  Manish B Shah; Jingbao Liu; Lu Huo; Qinghai Zhang; M Denise Dearing; P Ross Wilderman; Grazyna D Szklarz; C David Stout; James R Halpert
Journal:  Mol Pharmacol       Date:  2016-01-29       Impact factor: 4.436

5.  Exploration of Stereoselectivity in Embryo-Larvae (Danio rerio) Induced by Chiral PCB149 at the Bioconcentration and Gene Expression Levels.

Authors:  Tingting Chai; Feng Cui; Xiyan Mu; Yang Yang; Chengju Wang; Jing Qiu
Journal:  PLoS One       Date:  2016-05-09       Impact factor: 3.240

6.  Crystal Structure of CYP2B6 in Complex with an Efavirenz Analog.

Authors:  Manish B Shah; Qinghai Zhang; James R Halpert
Journal:  Int J Mol Sci       Date:  2018-03-29       Impact factor: 5.923

  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.