Oxidation of 9-alkylanthracenes by cytochrome P450 2B1, horseradish peroxidase, and iron tetraphenylporphine/iodosylbenzene systems: anaerobic and aerobic mechanisms

Biochemistry
P AnzenbacherF Peter Guengerich

Abstract

Variously substituted alkylanthracenes were studied as models for polycyclic hydrocarbon oxidations. 9-Methylanthracene was oxidized to 9-(hydroxymethyl)anthracene, 10-methyl-10-hydroxy-9-anthrone, and anthraquinone in several systems, including (i) NADPH- and O2-fortified rat liver microsomes, (ii) cytochrome P450 (P450) 2B1 Supported by either iodosylbenzene (PhIO) or a mixture of NADPH-P450 reductase, NADPH, and O2, (iii) horseradish peroxidase and either H2O2 or ethyl hydroperoxide, and (iv) a mixture of iron tetraphenylporphine (FeTPP) and PhIO (in anhydrous CH2Cl2/MeOH). The microsomal system also formed dihydrodiols from 9-methyl- and 9-ethylanthracenes. The formation of the three oxidized products by the P450/NADPH/O2 system was dependent upon O2 label from 18O2 was incorporated into the products, and no label from H2(18O) was incorporated. No label from 18O2 was incorporated into the three products in the FeTPP/PhIO system. In the horseradish peroxidase/H2O2 system, the formation of the three products was decreased when O2 was omitted, and label from both H2(18)O and 18O2 was incorporated into all three products. The results are interpreted in terms of three mechanisms. One is used by the FeTPP and P450 systems, with a...Continue Reading

References

May 1, 1990·FASEB Journal : Official Publication of the Federation of American Societies for Experimental Biology·F P Guengerich, T L MacDonald

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Citations

May 29, 2010·Applied Microbiology and Biotechnology·Nomathemba Loice ChiguHiroyuki Wariishi
Dec 5, 2002·Archives of Biochemistry and Biophysics·F Peter Guengerich
Apr 3, 2003·Rapid Communications in Mass Spectrometry : RCM·Ulrik JurvaAndries P Bruins
Oct 29, 1998·Biochemical and Biophysical Research Communications·J W FlesherA F Lehner
Feb 26, 2000·Carcinogenesis·F P Guengerich
Mar 20, 2018·Archives of Environmental Contamination and Toxicology·Jennifer J TrowellChristopher J Kennedy
Feb 26, 2019·Science Advances·Ankita DasJyotishman Dasgupta
Jun 23, 2018·Chemical Reviews·F Peter Guengerich, Francis K Yoshimoto

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