5-羟色胺和5,7-二羟色胺的氧化。一种新的氧化途径及一种新型神经毒素的形成。

Oxidation of 5-hydroxytryptamine and 5,7-dihydroxytryptamine. A new oxidation pathway and formation of a novel neurotoxin.

作者信息

Wrona M Z, Lemordant D, Lin L, Blank C L, Dryhurst G

出版信息

J Med Chem. 1986 Apr;29(4):499-505. doi: 10.1021/jm00154a013.

Abstract

The electrochemical oxidation of 5-hydroxytryptamine (5-HT) in acidic solution proceeds through a minor route leading first to 5,7-dihydroxytryptamine (5,7-DHT) then to 4,5,7-trihydroxytryptamine and finally to 5-hydroxytryptamine-4,7-dione. The latter compound is a major electrochemical oxidation product of 5,7-DHT at pH 2 and 7 and a major autoxidation product at pH greater than or equal to 6. Preliminary biological results indicate that 5-hydroxytryptamine-4,7-dione is a more potent central nervous system toxin than 5,7-DHT. These results show for the first time a chemical pathway from 5-HT to 5,7-DHT and suggest possible minor metabolic oxidative pathways for the neurotransmitter 5-HT to at least two powerful neurotoxins.

摘要

5-羟色胺（5-HT）在酸性溶液中的电化学氧化通过一条次要途径进行，首先生成5,7-二羟基色胺（5,7-DHT），然后生成4,5,7-三羟基色胺，最后生成5-羟色胺-4,7-二酮。后一种化合物是5,7-DHT在pH值为2和7时的主要电化学氧化产物，也是pH值大于或等于6时的主要自氧化产物。初步生物学结果表明，5-羟色胺-4,7-二酮是一种比5,7-DHT更强效的中枢神经系统毒素。这些结果首次展示了从5-HT到5,7-DHT的化学途径，并提示了神经递质5-HT至少向两种强大神经毒素的可能次要代谢氧化途径。