Tuomisto J, Tuomisto L
J Neural Transm. 1987;68(3-4):191-6. doi: 10.1007/BF02098497.
Derivatives of trans-decalin with a dopamine moiety incorporated in different conformations were studied as inhibitors of dopamine and 5-HT uptake in rat brain synaptosomes. In three derivatives the relation of the catechol ring and the amino function was gauche, in one isomer it was anti. One of the gauche isomers, (+/-)-2(a)-amino-3(e)-3, 4-dihydroxyphenol-trans-decalin had an affinity to the dopamine uptake system which was about one fourth of that of dopamine itself. The inhibition was competitive. The affinity of other isomers was about ten per cent or less of the affinity of dopamine. The active isomer was identical in conformation to the most active isomer in respective noradrenaline-derivatives tested previously. These results favour the view that the dopamine uptake site is able to accept the substrate as the gauche rotamer. This was not true with 5-HT uptake, and requirements for these two uptake sites may be conformationally different.
研究了在不同构象中掺入多巴胺部分的反式十氢化萘衍生物作为大鼠脑突触体中多巴胺和5-羟色胺摄取抑制剂的情况。在三种衍生物中，儿茶酚环与氨基官能团的关系是邻位交叉的，在一种异构体中是反式的。其中一种邻位交叉异构体，(±)-2(a)-氨基-3(e)-3,4-二羟基苯酚-反式十氢化萘对多巴胺摄取系统的亲和力约为多巴胺本身的四分之一。抑制作用是竞争性的。其他异构体的亲和力约为多巴胺亲和力的10%或更低。活性异构体的构象与先前测试的相应去甲肾上腺素衍生物中最具活性的异构体相同。这些结果支持这样一种观点，即多巴胺摄取位点能够接受作为邻位交叉旋转异构体的底物。对于5-羟色胺摄取则并非如此，这两个摄取位点的要求在构象上可能不同。
