PHOTOCHEMISTRY OF THE PSORALENS
PHOTOCHEMISTRY OF THE PSORALENS
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DOI：
10.1021/tx00008a001
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发表时间：
1989-03-01
影响因子：
4.1
通讯作者：
HEARST, JE
中科院分区：
文献类型：
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作者：
HEARST, JE
自有文字记载以来，含有补骨脂素的植物一直被用于治疗各种皮肤病。考虑到大量含有补骨脂素的植物，这并不令人惊讶。这些疗法中活跃的植物的发现和对阳光需求的认识实际上发生在很晚的时间，可能是在公元前300年到公元600年之间(1)。这个化合物家族的生理活性显然在阿拉伯古代文献(公元前1400年)中被描述过，其中提到了将山葵果实用作治疗白皮病的药物(2)。纯化的化合物用于治疗牛皮癣和白癜风(2，3)。当补骨脂素局部或口服给药时，它们会使皮肤对近紫外光敏感，导致皮肤晒黑和晒伤。这种治疗可以缓解牛皮癣的症状。补骨脂素与DNA发生光反应并导致DNA螺旋的两条链发生交叉连接的说法最早出现在1971年(4，5)。合成补骨脂素的合成有机化学已得到广泛应用(6)。最常用的补骨脂素如图1所示。HMT中的羟甲基取代和AMT中的氨甲基取代在水中提供了更大的溶解度，这是使这些化合物相对于天然产物具有更高的光化学效率的主要因素。艾萨克斯等人(6)
Psoralen-containing plants have been used since the be-ginnings of written history in the cures of various skin disorders. This is not terribly surprising, considering the large numbers of plants that contain psoralens. Identi-fication of the active plantsin these cures and recognition of the need for the use of sunlight actually occurred much later, perhaps between 300 BC and 600 AD (1). The physiological activity of this family of compounds was apparently described in old Arabic literature (1400 BC), where reference was made to the use of fruits of Ammi majus as a remedy for leukoderma (2). The purified compounds are used in the treatment of psoriasis and vitiligo (2, 3). When psoralens are administered, either topically to the skin or orally, they sensitize the skin to near-ultraviolet light, inducing tanning and sunburn. Such treatment results in remission of the symptoms of psoriasis. The suggestion that psoralens photoreact with DNA and result in the cross-linkage of the two strands of the DNA helix first appeared in 1971 (4, 5). The synthetic organic chemistry resulting in modified psoralens has been ex-tensive (6). The most commonly used psoralens are shown in Figure 1. The greater solubilities in water provided by the hydroxymethyl substitution in HMT and the amino-methyl substitution in AMT are major factors in the greater efficiency of the photochemistry using these com-pounds relative to thenatural products. Isaacs et al.(6)