Related Experiment Video
Updated: Aug 18, 2026

Mass Spectrometry and Luminogenic-based Approaches to Characterize Phase I Metabolic Competency of In Vitro Cell Cultures
Published on: March 28, 2017
3-Hydroxymethylcholanthrene: metabolic formation from 3-methylcholanthrene and stereoselective metabolism by rat
1Department of Pharmacology, F. Edward Hébert School of Medicine, Uniformed Services University of the Health Sciences, Bethesda, MD 20814-4799, USA.
Abstract:
3-Hydroxymethylcholanthrene (3-OHMC) was identified as one of the three initial hydroxylation products formed in the metabolism at the aliphatic carbons of 3-methylcholanthrene (3MC) by rat liver microsomes. The 3-OHMC formed in 3MC metabolism by liver microsomes prepared from untreated (control) rats, and rats treated with phenobarbital, 3MC, and polychlorinated biphenyls (Aroclor 1254) was determined by HPLC analysis and the effect of enzyme inducers on its formation was phenobarbital > polychlorinated biphenyls > 3MC > control. Incubation of 3-OHMC with rat liver microsomes produced the following identifiable products: 1-hydroxy-3-hydroxymethylcholanthrene (enriched in 1S-enantiomer, enantiomer excess 14-50%), 2-hydroxy-3-hydroxymethylcholanthrene (enriched in 2S-enantiomer, enantiomer excess 30-92%), 3-hydroxymethylcholanthrene-1-one, 3-hydroxymethylcholanthrene-2-one, 8-hydroxy-3-hydroxymethylcholanthrene, 3-hydroxymethylcholanthrene trans-9,10-dihydrodiol (enriched in 9R,10R-enantiomer, enantiomer excess 64-86%), 3-hydroxymethylcholanthrene trans-7,8-dihydrodiol (enriched in 7R,8R-enantiomer), and 3-hydroxymethylcholanthrene trans-11,12-dihydrodiol (enriched in 11R,12R-enantiomer). The enantiomer compositions were determined by circular dichroism spectral analysis and/or chiral stationary phase HPLC analysis.
More Related Videos
09:33Formation of Covalent DNA Adducts by Enzymatically Activated Carcinogens and Drugs In Vitro and Their Determination by 32P-postlabeling
Published on: March 20, 2018
10:03Isolation, Propagation, and Identification of Bacterial Species with Hydrocarbon Metabolizing Properties from Aquatic Habitats
Published on: December 7, 2021
Related Concept Videos
Prochirality
Radical Halogenation: Stereochemistry
Halogenation to form a new chiral center:
Radical Anti-Markovnikov Addition to Alkenes: Overview
Drug Metabolism: Phase I Reactions
Phase I Reactions: Oxidation of Aliphatic and Aromatic Carbon-Containing Systems
Oxidation reactions are fundamental in aromatic carbon-containing systems. An example is the hydroxylation of phenobarbital, a process that transforms it into...
Phase II Reactions: Methylation Reactions
The mechanism of methylation unfolds in two stages. The first stage sees a methyltransferase enzyme facilitating the transfer of a methyl group from S-adenosylmethionine (SAM) to the substrate, forming S-adenosylhomocysteine (SAH). The second stage involves further metabolism of SAH into homocysteine, which can be recycled...