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[硫代亚硝酸盐作为一氧化氮的有效供体:S-亚硝基-和S,S'-二亚硝基二氢硫辛酸的示例]

[Thionitrites as potent donors of nitric oxide: example of S-nitroso- and S,S'-dinitroso-dihydrolipoic acids].

作者信息

Petit C, Hoffmann P, Souchard J P, Nepveu F, Labidalle S

机构信息

Laboratoire de Synthèse, Physico-Chimie et Radiobiologie-JE 175, Université Paul-Sabatier, Faculté des Sciences Pharmaceutiques, Toulouse, France.

出版信息

C R Seances Soc Biol Fil. 1996;190(5-6):641-50.

PMID:9074729
Abstract

Until recently, nitric oxide (NO.) was considered as a toxic radical, but it appears now as an essential messenger implicated in a wide range of biological processes, including immune system, cardiovascular system, and nervous system. An aspect of NO. metabolism in vivo is the formation of a variety of high and low molecular weight nitrosothiols. S-nitrosocysteine and S-nitrosoglutathione are among the biologically derived S-nitrosothiols that are postulated to be carriers of NO.. Although most of the S-nitrosothiols are unstable and spontaneously break down to produce NO. and a disulfide, some of them, including protein thiols, can show significant stability. These molecules are able to convey nitric oxide, that is, to keep, to carry, and then to generate NO. in physiological media, and might display pharmacological effects as potential vasodilators or neuroprotectors. Here, we present the development of new thionitrites R-S-NO having intrinsic antioxidant properties. We report the preparation, the characterization, and the stability studies in aqueous solutions of S-nitroso derivatives of dihydro-alpha-lipoic acid, known for its antioxidant properties.

摘要

直到最近,一氧化氮(NO.)还被认为是一种有毒的自由基,但现在它似乎是一种重要的信使,参与包括免疫系统、心血管系统和神经系统在内的广泛生物过程。体内NO.代谢的一个方面是形成各种高分子量和低分子量的亚硝基硫醇。S-亚硝基半胱氨酸和S-亚硝基谷胱甘肽是推测为NO.载体的生物衍生亚硝基硫醇。尽管大多数亚硝基硫醇不稳定,会自发分解产生NO.和二硫化物,但其中一些,包括蛋白质硫醇,可表现出显著的稳定性。这些分子能够传递一氧化氮,即在生理介质中保存、携带并随后产生NO.,并且可能作为潜在的血管舒张剂或神经保护剂发挥药理作用。在此,我们展示了具有内在抗氧化特性的新型硫亚硝酸盐R-S-NO的研发情况。我们报告了以其抗氧化特性而闻名的二氢-α-硫辛酸的S-亚硝基衍生物在水溶液中的制备、表征和稳定性研究。

相似文献

1
[Thionitrites as potent donors of nitric oxide: example of S-nitroso- and S,S'-dinitroso-dihydrolipoic acids].[硫代亚硝酸盐作为一氧化氮的有效供体:S-亚硝基-和S,S'-二亚硝基二氢硫辛酸的示例]
C R Seances Soc Biol Fil. 1996;190(5-6):641-50.
2
Electrochemical determination of S-nitrosothiols with a Clark-type nitric oxide electrode.用克拉克型一氧化氮电极电化学测定S-亚硝基硫醇
Anal Biochem. 1998 Apr 10;258(1):68-73. doi: 10.1006/abio.1998.2562.
3
Thioredoxin and lipoic acid catalyze the denitrosation of low molecular weight and protein S-nitrosothiols.硫氧还蛋白和硫辛酸催化低分子量和蛋白质S-亚硝基硫醇的脱亚硝基反应。
J Am Chem Soc. 2005 Nov 16;127(45):15815-23. doi: 10.1021/ja0529135.
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The reaction of S-nitrosoglutathione with superoxide.S-亚硝基谷胱甘肽与超氧化物的反应。
Biochem Biophys Res Commun. 1998 Mar 17;244(2):525-30. doi: 10.1006/bbrc.1998.8227.
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Decomposition of alpha-lipoic acid derivatives by photoirradiation-formation of dihydrolipoic acid from alpha-lipoic acid-.通过光照射分解α-硫辛酸衍生物——从α-硫辛酸形成二氢硫辛酸。
Biochem Mol Biol Int. 1996 Feb;38(1):51-9.
6
Peroxynitrite-derived carbonate and nitrogen dioxide radicals readily react with lipoic and dihydrolipoic acid.过氧亚硝酸盐衍生的碳酸根和二氧化氮自由基很容易与硫辛酸和二氢硫辛酸发生反应。
Free Radic Biol Med. 2005 Jul 15;39(2):279-88. doi: 10.1016/j.freeradbiomed.2005.03.014. Epub 2005 Apr 5.
7
NO+, NO, and NO- donation by S-nitrosothiols: implications for regulation of physiological functions by S-nitrosylation and acceleration of disulfide formation.亚硝基硫醇的NO⁺、NO和NO⁻释放:对通过亚硝基化调节生理功能及加速二硫键形成的影响。
Arch Biochem Biophys. 1995 Apr 20;318(2):279-85. doi: 10.1006/abbi.1995.1231.
8
S-Nitrosothiols: a class of nitric oxide-donor drugs.S-亚硝基硫醇:一类一氧化氮供体药物。
Clin Sci (Lond). 2000 May;98(5):507-20.
9
S-nitrosothiols and the nitrergic neurotransmitter in the rat gastric fundus: effect of antioxidants and metal chelation.大鼠胃底中的S-亚硝基硫醇与氮能神经递质:抗氧化剂和金属螯合的作用
Br J Pharmacol. 1998 Mar;123(6):1039-46. doi: 10.1038/sj.bjp.0701692.
10
[NO-release ability and DNA-damage activity of aromatic N-nitroso compounds].[芳香族N-亚硝基化合物的一氧化氮释放能力及DNA损伤活性]
Kokuritsu Iyakuhin Shokuhin Eisei Kenkyusho Hokoku. 2004(122):10-5.

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