beta-meso-Phenylbiliverdin IX alpha and N-phenylprotoporphyrin IX, products of the reaction of phenylhydrazine with oxyhemoproteins.
- 1 September 1981
- journal article
- research article
- Published by Proceedings of the National Academy of Sciences in Proceedings of the National Academy of Sciences
- Vol. 78 (9) , 5508-5512
- https://doi.org/10.1073/pnas.78.9.5508
Abstract
HbO2 [human] and oxymyoglobin [horse heart] were allowed to react aerobically with phenylhydrazine and p-tolylhydrazine. The chloroform extract of each reaction mixture, after treatment with H2SO4/methanol, yielded a blue pigment and a green pigment, which were identified by electronic absorption, mass, and proton NMR spectroscopy as the dimethyl esters of .beta.-meso-arylbiliverdin IX-.alpha. and N-arylprotoporphyrin IX, respectively. N-Phenylprotoporphyrin IX dimethyl ester formed complexes with Zn2+, Cd2+, and Hg2+ but not with other cations. The proton NMR spectrum of the Zn complex suggested binding of the phenyl group to 1 of the 2 pyrrole rings of protoporphyrin IX with a propionic acid substituent. The effectiveness of phenylhydrazine as an inducer of Heinz body formation may be due to destabilization of the Hb molecule by the replacement of heme with phenyl adducts of biliverdin and protoporphyrin.This publication has 18 references indexed in Scilit:
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