3-芳基-Δ3-吡咯啉对单胺氧化酶的基于机制的抑制作用。
Mechanism-based inhibition of monoamine oxidase by 3-aryl-Delta3-pyrrolines.
作者信息
Williams C H, Lawson J
机构信息
School of Biology and Biochemistry, Medical Biology Centre, Queens University, Belfast BT9 7BL, Northern Ireland, UK.
出版信息
Biochem J. 1998 Nov 15;336 ( Pt 1)(Pt 1):63-7. doi: 10.1042/bj3360063.
Abstract
The compound 1-methyl-3-phenyl-Delta3-pyrroline and its 4-chlorophenyl analogue appear to act as irreversible inhibitors of monoamine oxidase B (MAO B) in mitochondria of rat liver. The compounds are metabolized by MAO B and concomitantly inhibit the enzyme in what seems to be a two-step process. The metabolic end product of this process is the corresponding pyrrole. This inhibition process is considered in the light of possible intermediates formed during the enzymic oxidation, and comparisons are made with the structurally analogous neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine.
摘要
化合物1-甲基-3-苯基-Δ3-吡咯啉及其4-氯苯基类似物似乎是大鼠肝脏线粒体中单胺氧化酶B（MAO B）的不可逆抑制剂。这些化合物被MAO B代谢，并在一个似乎是两步的过程中同时抑制该酶。这个过程的代谢终产物是相应的吡咯。根据酶促氧化过程中可能形成的中间体来考虑这种抑制过程，并与结构类似的神经毒素1-甲基-4-苯基-1,2,3,6-四氢吡啶进行比较。
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1
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J Agric Food Chem. 1998 Feb 16;46(2):616-619. doi: 10.1021/jf9706437.
2
1-Methyl-3-pyrrolines and 2-methylisoindolines: new classes of cyclic tertiary amine monoamine oxidase B substrates.1-甲基-3-吡咯啉和2-甲基异吲哚啉：新型环状叔胺单胺氧化酶B底物
Bioorg Med Chem. 1998 Feb;6(2):143-9. doi: 10.1016/s0968-0896(97)10020-7.
3
Advances in our understanding of the mechanisms of the neurotoxicity of MPTP and related compounds.我们对MPTP及相关化合物神经毒性机制认识的进展。
J Neurochem. 1993 Oct;61(4):1191-206. doi: 10.1111/j.1471-4159.1993.tb13610.x.
4
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Biochem Biophys Res Commun. 1995 Jan 17;206(2):556-62. doi: 10.1006/bbrc.1995.1079.
5
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