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首页> 外文期刊>Pigment cell research >Mechanistic studies of melanogenesis: the influence of N-substitution on dopamine quinone cyclization
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Mechanistic studies of melanogenesis: the influence of N-substitution on dopamine quinone cyclization

机译：黑色素生成的机理研究：N取代对多巴胺醌环化的影响

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The influence of side-chain structure on the mode of reaction of ortho-quinone amines has been investigated with a view, ultimately, to developing potential methods of therapeutic intervention by manipulating the early stages of melanogenesis. Four N-substituted dopamine derivatives have been prepared and quinone formation studied using pulse radiolysis and tyrosinase-oximetry. Ortho-quinones with an amide or urea side chain were relatively stable, although evidence for slow formation of isomeric para-quinomethanes was observed. A thiourea derivative cyclized fairly rapidly (k = 1.7/s) to a product containing a seven-membered ring, whereas a related amidine gave more rapidly (k similar to 2.5 x 10(2)/s) a stable spirocyclic product. The results suggest that cyclization of amides, ureas and carbamates (NHCO-X; X = R, NHR or OR) does not occur and is not, therefore, a viable approach to the formation of tyrosinase-activated antimelanoma prodrugs. It is also concluded that for N-acetyldopamine spontaneous ortho-quinone to para-quinomethane isomerization is slow.
机译：已经研究了侧链结构对邻苯二甲胺反应模式的影响，以期最终通过操纵黑色素生成的早期阶段发展潜在的治疗干预方法。已经制备了四种N-取代的多巴胺衍生物，并使用脉冲放射分解和酪氨酸酶-血氧测定法研究了醌的形成。尽管观察到异构体对喹啉甲烷缓慢形成的证据，但具有酰胺或脲侧链的邻醌相对稳定。硫脲衍生物相当快地环化（k = 1.7 / s）到含有七元环的产物，而相关的idine使更快地（k类似于2.5 x 10（2）/ s）形成稳定的螺环产物。结果表明，不会发生酰胺，脲和氨基甲酸酯（NHCO-X; X = R，NHR或OR）的环化，因此不是形成酪氨酸酶激活的炭疽杆菌前药的可行方法。还得出结论，对于N-乙酰基多巴胺，自发的邻醌到对喹啉甲烷的异构化是缓慢的。

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