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Aromatic hydroxylation of ellipticine in rats: Lack of an NIH shift
Author(s) -
Reinhold Ver N.,
Bruni Robert J.
Publication year - 1976
Publication title -
biomedical mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0306-042X
DOI - 10.1002/bms.1200030612
Subject(s) - hydroxylation , chemistry , pharmacology , stereochemistry , biochemistry , biology , enzyme
Abstract Metabolites of the antitumor agent, ellipticine (NSC 71795), are mainly secreted in rat bile as two conjugates of hydroxylated ellipticine. The possible involvement of an arene oxide intermediate prior to hydroxylation and conjugation has been studied using 7,9‐dideutero‐ellipticine and by determining the conservation of deuterium in the phenolic products. The deuterated drug was synthesized by acid catalyzed exchange and was characterized by nuclear magnetic resonance and high and low resolution mass spectrometry. Mass spectra of two conjugated metabolites from rat bile showed a mass ion at m / e 263 (singly deuterated hydroxylated ellipticine). There was no evidence for conservation of deuterium at the position of hydroxylation ( m / e 264). These results indicate that the major pathway of metabolism for this cancer chemotherapeutic drug, prior to conjugation and excretion in rat bile, proceeds by aromatic hydroxylation apparently without involving an arene oxide/NIH shift mechanism.