次氯酸和次溴酸与纯化的大肠杆菌磷脂的差异反应性:卤胺和卤醇的形成

Anitra C. Carr , Jeroen J.M. van den Berg , Christine C. Winterbourn
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引用次数: 51

摘要

次氯酸(HOCl)和次溴酸(HOBr)是由髓过氧化物酶和嗜酸性粒细胞过氧化物酶产生的强氧化剂,它们分别是中性粒细胞和嗜酸性粒细胞的主要抗菌酶。这些氧化剂与多种生物分子具有很强的活性。在生理pH下,HOCl和HOBr都很容易与胺反应生成卤代胺,并与脂肪酸的不饱和键反应生成卤代醇。我们已经研究了这些反应中的哪一个发生在磷脂酰乙醇胺(PE),大肠杆菌的主要磷脂。采用薄层色谱法和比色法测定卤胺的生成,采用薄层色谱法和气相色谱-质谱法测定卤醇的生成。对于HOCl,氯胺是首选产物,只有当HOCl超过将胺转化为二氯胺所需的量时,氯丙烷才会大量形成。在所有浓度的HOBr中,溴胺和溴丙烷同时生成,表明与不饱和脂肪酸的相对反应活性大于与HOCl的相对反应活性。聚乙烯的溴胺衍生物和其他伯胺,被发现比同等的氯胺反应性更强,并且能够溴化脂肪酸的不饱和键。因此,溴丙烷(直接形成或通过溴胺的作用形成)可能是体内产生HOBr的合适生物标志物。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Differential reactivities of hypochlorous and hypobromous acids with purified Escherichia coli phospholipid: formation of haloamines and halohydrins

Hypochlorous (HOCl) and hypobromous (HOBr) acids are strong oxidants derived from myeloperoxidase and eosinophil peroxidase, the major antimicrobial enzymes of neutrophils and eosinophils, respectively. These oxidants are highly reactive with a wide range of biomolecules. At physiological pH, both HOCl and HOBr react readily with amines to form haloamines and with the unsaturated bonds of fatty acids to form halohydrins. We have investigated which of these reactions occur with phosphatidylethanolamine (PE), the predominant phospholipid of Escherichia coli. The formation of haloamines was determined by TLC and colorimetrically and the formation of halohydrins was determined by TLC and GC-MS. With HOCl, chloramines were much the preferred product and chlorohydrins were formed in substantial amounts only when HOCl was in excess of the amount required to convert the amine to the dichloramine. With HOBr at all concentrations, bromamines and bromohydrins were formed concurrently, indicating a greater relative reactivity with unsaturated fatty acids than with HOCl. The bromamine derivatives of PE, and other primary amines, were found to be more reactive than the equivalent chloramines, and were able to brominate the unsaturated bonds of fatty acids. Bromohydrins (formed directly or through the action of bromamines) may, therefore, be suitable biomarkers for the production of HOBr in vivo.

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