フロクマリン類の光化学
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概要
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Psoralens are one isomeric form of furocoumarins whose photochemical reactivity toward DNA has long been used in the treatment of skin disorders such as psoriasis and vitiligo. Upon irradiation, consecutive addition reactions at the two reactive sites of a psoralen molecule toward two thymine residues of different strands of DNA result in the cross-linking of DNA, which is one of the most important outcomes for the therapeutic effectiveness of psoralen. However, this cross-linking is also considered mainly responsible for some undesired side effects such as skin cancer. Therefore, one of the important lines of current research in the field of psoralen photochemotherapy consists of developing effective monofunctional furocoumarins capable of modifying DNA without cross-linking two strands.<BR>Interestingly, the site-selectivity (chemoselectivity) of two reactive sites in a photo-excited psoralen in DNA is different from that in solution. Such a remarkable difference in the site-selectivity in different environments strongly indicates an important role of intercalation into DNA in controlling psoralens site selectivity. In this article, through the analysis of the nature of this intercalation step, several ideas are presented to develop new and more effective monofunctional molecules that would photochemically modify DNA. This approach should provide us a better basis for understanding the psoralens photochemotherapy and developing medicinally as well as chemically useful furocoumarins and the related compounds.
- 社団法人 有機合成化学協会の論文