Reaction of cyclohexylamine with hypochlorite and enhancement of oxidation of plasma sulfhydryl groups by hypochlorite in vitro.

Reaction of cyclohexylamine with hypochlorite and enhancement of oxidation of plasma sulfhydryl groups by hypochlorite in vitro.
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环己胺与次氯酸盐的反应以及次氯酸盐在体外增强血浆硫氢基的氧化。

DOI:
10.1016/s0278-6915(98)00060-x
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发表时间:
1998
期刊:
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association
影响因子:
--
通讯作者:
H. Tsai
H. Tsai
中科院分区:
--
文献类型:
--
作者:
M. Hu;H. Tsai

文献摘要

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在本研究中,我们研究了甜蜜素及其主要代谢物环己胺(CyhNH2)与NaOCl的反应。允许100μm的NaOCl2与不同浓度的甜蜜素和氰化氢反应,并与还原型谷胱甘肽和抗坏血酸的反应活性进行了比较。结果表明,在浓度低于50μm时,CyhNH_2与NaO_1的反应弱于谷胱甘肽,但略高于抗坏血酸,在75和100μm时,Cyh_NH_2不能进一步降低NaO_2。甜蜜素的活性比CyhNH2低得多,在100μm甜蜜素的氯化钠中只有43%的损失。当人血浆与0.75μm NaOCl孵育时,CyhNH_2以浓度依赖的方式促进巯基的氧化,在7.5 mM的CyhNH_2时,SH基氧化完全。甜蜜素不起作用。CyhNH2的这种增强表明CyhNH2与NaOCl反应生成了反应产物。吸收光谱表明,在pH值为7.4时,CyhNH_2与NaOCl反应生成N-一氯胺,在245 nm处出现一个新的峰,而NaOCl在292 nm处的峰消失。甜蜜素含有氨基磺酸而不是伯胺,在pH 7.4时也与NaOCl反应,但反应不那么明显,产物可能不是一氯胺,因为峰在270 nm而不是245 nm。由于甜蜜素是许多国家糖尿病患者的重要甜味剂,CyhNH2可能会促进HOClOCL−对重要蛋白质的氧化。
In this study we investigated the reaction of cyclamate and its major metabolite, cyclohexylamine (CyhNH2), with NaOCl. NaOCl at 100 μm was allowed to react with various concentrations of cyclamate and CyhNH2, and the reactivity was compared with those of reduced glutathione (GSH) and ascorbic acid. The results showed that CyhNH2was less reactive with NaOCl than GSH but was slightly more reactive than ascorbic acid at concentrations below 50 μm. CyhNH2at 75 and 100 μmdid not further decrease NaOCl. Cyclamate was much less reactive than CyhNH2, with only 43% loss in NaOCl at 100 μm cyclamate. When human blood plasma was incubated with 0.75 μm NaOCl, inclusion of CyhNH2enhanced oxidation of sulfhydryl groups in a concentration-dependent manner, with complete oxidation of SH groups at 7.5mm CyhNH2. Cyclamate had no effect. This enhancement by CyhNH2suggests the formation of reactive products from the reaction of CyhNH2with NaOCl. Absorption spectra demonstrated that reaction of CyhNH2with NaOCl at pH7.4 produced N-monochloramine, as evidenced by the appearance of a new peak at 245nm and by the disappearance of the 292-nm peak of NaOCl. Cyclamate, which contains a sulfamic acid instead of a primary amine, also reacted with NaOCl at pH7.4, but the reaction was much less pronounced and the product was probably not monochloramine since the peak was at 270nm rather than at 245nm. Because cyclamate is an important sweetener in many countries for people with diabetes mellitus, the possibility exists that CyhNH2may enhance oxidation of important proteins by HOCl/OCl−.