β-中-苯基胆绿素IXα和N-苯基原卟啉IX，苯肼与氧合血红蛋白反应的产物。
beta-meso-Phenylbiliverdin IX alpha and N-phenylprotoporphyrin IX, products of the reaction of phenylhydrazine with oxyhemoproteins.
作者信息
Saito S, Itano H A
出版信息
Proc Natl Acad Sci U S A. 1981 Sep;78(9):5508-12. doi: 10.1073/pnas.78.9.5508.
Abstract
Oxyhemoglobin and oxymyoglobin 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 zinc complex suggested binding of the phenyl group to one of the two 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 hemoglobin molecule by the replacement of heme with phenyl adducts of biliverdin and protoporphyrin.
摘要
使氧合血红蛋白和氧合肌红蛋白与苯肼和对甲苯肼进行需氧反应。每个反应混合物的氯仿提取物经硫酸/甲醇处理后，产生一种蓝色色素和一种绿色色素，通过电子吸收、质谱和质子核磁共振光谱分别鉴定为β-中位-芳基胆绿素IXα和N-芳基原卟啉IX的二甲酯。N-苯基原卟啉IX二甲酯与Zn2+、Cd2+和Hg2+形成络合物，但不与其他阳离子形成络合物。锌络合物的质子核磁共振光谱表明苯基与原卟啉IX的两个吡咯环之一结合，该吡咯环带有丙酸取代基。苯肼作为海因茨小体形成诱导剂的有效性可能是由于血红蛋白分子被胆绿素和原卟啉的苯基加合物取代血红素而变得不稳定。
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