CHEMICAL MECHANISMS UNDERLYING THE VASODILATOR AND PLATELET ANTI-AGGREGATING PROPERTIES OF S-NITROSO-N-ACETYL-DL-PENICILLAMINE AND S-NITROSOGLUTATHIONE
CHEMICAL MECHANISMS UNDERLYING THE VASODILATOR AND PLATELET ANTI-AGGREGATING PROPERTIES OF S-NITROSO-N-ACETYL-DL-PENICILLAMINE AND S-NITROSOGLUTATHIONE
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DOI：
10.1016/0968-0896(94)00139-t
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发表时间：
1995-01-01
影响因子：
3.5
通讯作者：
MEGSON, IL
中科院分区：
文献类型：
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作者：
ASKEW, SC;BUTLER, AR;MEGSON, IL
S-亚硝基-DL-青霉胺 (SNAP) 和 S-亚硝基谷胱甘肽 (GSNO) 的化学性质与其松弛血管平滑肌和防止血小板聚集的能力相关。金属离子催化大大加速了SNAP的分解，但对GSNO影响不大。相反，从 GSNO 释放 NO 是通过 NO 转移到游离硫醇（例如半胱氨酸）或通过谷氨酰-胱基肽键的酶裂解来实现的。在这两种情况下，产生的亚硝基硫醇（即分别为 S-亚硝基半胱氨酸和 S-亚硝基半胱氨酸）容易受到金属离子催化的 NO 释放的影响。我们得出的结论是，转亚硝化或酶裂解是 GSNO 释放 NO 的机制中的必要步骤，而 SNAP 仅需要金属离子的存在即可影响该过程。 NO 产生的不同模式可能会在一定程度上提高这些 S-亚硝基硫醇作为血管舒张剂和血小板聚集抑制剂的有效性。
The chemistries of S-nitroso-DL-penicillamine (SNAP) and S-nitrosoglutathione (GSNO) in relation to their ability to relax vascular smooth muscle and prevent platelet aggregation have been investigated. Metal ion catalysis greatly accelerates the decomposition of SNAP, but has little effect on GSNO. Instead, NO release from GSNO is effected either by NO transfer to a free thiol (e.g. cysteine), or by enzymatic cleavage of the glutamyl-cystyl peptide bond. In both cases the resulting nitrosothiol (i.e. S-nitrosocysteine and S-nitrosocystylglycine, respectively) is susceptible to metal ion catalysed NO release. We conclude that transnitrosation or enzymatic cleavage are obligatory steps in the mechanism of NO release from GSNO, whereas SNAP needs only the presence of metal ions to effect this process. The different modes of NO production may go some way towards effectiveness of these S-nitrosothiols as vasodilators and inhibitors of platelet aggregation.