PMID: 2497774Mar 7, 1989Paper

Oxidation of substituted N,N-dimethylanilines by cytochrome P-450: estimation of the effective oxidation-reduction potential of cytochrome P-450

Biochemistry
T L MacdonaldF P Guengerich

Abstract

Rates of N-demethylation of N,N-dimethylaniline and of eight meta- or para-substituted N,N-dimethylanilines by rat liver cytochrome P-450PB-B (P-450) were determined under conditions where oxidation was supported by iodosylbenzene or NADPH-P-450 reductase. The rates of dimethylaniline oxidation were found to correlate with the substrate oxidation-reduction potential within each series of substrates supported by a particular oxygen activation protocol; the kcat for each substrate studied was approximately 20-fold faster in the iodosylbenzene-supported system relative to the NADPH-P-450 reductase supported system. Since the N-demethylation of amines is believed to proceed via an initial electron-transfer step, a kinetic scheme for P-450 was proposed that enabled evaluation of the data according to theoretical treatments that correlate rates of electron transfer with extrakinetic parameters. In these analyses, the data could be fitted to the Rehm-Weller and Agmon-Levine equations, providing lambda values (for the energetics of enzyme-substrate reorganization) of 22-26 kcal mol-1 and apparent E1/2 (oxidation-reduction potentials) of 1.7-2.0 V (vs saturated calomel) for the oxidized enzyme. The apparent E1/2 for the enzyme is compos...Continue Reading

References

Jun 7, 1976·Biochemical and Biophysical Research Communications·F P GuengerichM J Coon
Mar 1, 1986·Proceedings of the National Academy of Sciences of the United States of America·E CheungJ R Miller
Jun 5, 1987·Journal of Molecular Biology·T L PoulosA J Howard
Aug 11, 1987·Biochemistry·S KobayashiA P Schaap
Nov 5, 1987·Nature·A Warshel
Nov 1, 1986·Biopolymers·M K Gilson, B H Honig
Jul 1, 1985·Proceedings of the National Academy of Sciences of the United States of America·W A LeeT C Bruice
Apr 1, 1986·Archives of Biochemistry and Biophysics·R E White, M B McCarthy
Aug 1, 1984·Quarterly Reviews of Biophysics·A Warshel, S T Russell
Sep 1, 1984·Journal of Medicinal Chemistry·F P Guengerich
Oct 1, 1984·European Journal of Drug Metabolism and Pharmacokinetics·G GallianiM Salmona
Nov 1, 1983·Proceedings of the National Academy of Sciences of the United States of America·L T BurkaT L Macdonald
Nov 1, 1983·Proceedings of the National Academy of Sciences of the United States of America·T E MeyerG Tollin
Jan 1, 1980·Annual Review of Biochemistry·R E White, M J Coon

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Citations

Dec 1, 1994·Cancer Metastasis Reviews·L J Marnett
Dec 29, 2007·Analytical and Bioanalytical Chemistry·Wiebke Lohmann, Uwe Karst
Jan 1, 1991·Pharmacology & Therapeutics·R E White
Jan 1, 1992·Pharmacology & Therapeutics·F P Guengerich
Jan 1, 1995·Biochimie·F P GuengerichO Okazaki
Apr 25, 2007·Journal of Toxicology and Environmental Health. Part a·Nam-Cheol KimKelly J Dix
Nov 28, 2002·Biological Chemistry·F Peter Guengerich
Apr 10, 2004·Drug Metabolism Reviews·Corwin HanschRajeshwar Prasad Verma
Jan 1, 1993·Drug Metabolism Reviews·C Hansch, L Zhang
Nov 1, 1996·Drug Metabolism Reviews·H Gao, C Hansch
Jan 1, 1990·Critical Reviews in Biochemistry and Molecular Biology·F P Guengerich
Jul 1, 1995·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·F P GuengerichT L Macdonald
Apr 3, 2003·Rapid Communications in Mass Spectrometry : RCM·Ulrik JurvaAndries P Bruins
Oct 16, 2007·Journal of Biochemical and Molecular Toxicology·F Peter Guengerich
Jan 27, 2005·Bioorganic & Medicinal Chemistry·Rajeshwar P VermaCorwin Hansch
Mar 19, 2015·Journal of Biological Inorganic Chemistry : JBIC : a Publication of the Society of Biological Inorganic Chemistry·Xiao-Xi LiYong Wang
Apr 2, 2011·The Journal of Organic Chemistry·Trisha L Andrew, Timothy M Swager
Sep 4, 2014·The Journal of Organic Chemistry·Pu LuoJoseph P Dinnocenzo
Jul 3, 2002·The Journal of Biological Chemistry·F Peter GuengerichMartha V Martin
Apr 25, 2007·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·H-J KimM-S Dong
May 19, 2006·Journal of Bacteriology·Julia S SabirovaPeter N Golyshin
Mar 7, 2003·Applied and Environmental Microbiology·Annett MikolaschFrieder Schauer
Oct 24, 2007·The Journal of Organic Chemistry·Enrico BaciocchiOsvaldo Lanzalunga
Jun 15, 2021·Chemical Science·Anne Roly Obah KossoJean-Philippe Goddard
Apr 13, 2018·The Journal of Organic Chemistry·Mina F ShehataJennifer L Roizen
May 21, 2019·ACS Catalysis·F Peter Guengerich

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