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Molecular Pharmacology, Vol 12, 738-745, Copyright © 1976 by the American Society for Pharmacology and Experimental Therapeutics

Tautomerism and the Receptor Action of Histamine: a Mechanistic Model

HAREL WEINSTEIN 1, DAVID CHOU 1, CARL L. JOHNSON 1, SUNGZONG KANG 1, and JACK PETER GREEN 1

1 Department of Pharmacology, Mount Sinai School of Medicine of the City University of New York, New York 10029

The effect of deprotonation of histamine monocation on the dominant tautomeric forms of the molecule was analyzed theoretically from molecular orbital calculations ab initio. The electron charge redistribution caused by the interaction of the monocation with a negatively charged group. In both cases the result is a shift in the dominant tautomeric form caused by a change in the reactivity of the ring nitrogens, as demonstrated by the molecular electrostatic potentials and total molecular energies. A model for the role of this induced tautomerism in the activation of the histamine H2 receptor is proposed on the basis of these findings.

Note:
ACKNOWLEDGMENTS The computations were supported in part by a grant of computer time from the Central Computer Facility of the City University of New York. The authors are grateful to Dr. W. F. Raub and the Chemical/Biological Information-Handling Program, Division of Research, National Institutes of Health, for providing access to the PROPHET system computer.

Submitted on October 7, 1975
Accepted on April 2, 1976




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Copyright © 1976 by the American Society for Pharmacology and Experimental Therapeutics