Vedaldi D, Caffieri S, Frank S, Dall'Acqua F, Jakobs A, Piette J
Department of Pharmaceutical Sciences, University of Padova, Italy.
Farmaco. 1995 Jul-Aug;50(7-8):527-36.
Some heteropsoralens, obtained by replacing one or both the intracyclic oxygen atoms with sulphur and/or selenium, were studied. In preliminary tests, these compounds showed strong photobiological activity, in some cases more than two orders of magnitude higher than that of psoralen. Heteropsoralens containing sulphur undergo intercalation inside duplex DNA, showing evident affinity for the macromolecule; when selenium replaces furan oxygen, the psoralen isoster also undergoes intercalation but with lower efficiency, while psoralen isosters in which pyrone oxygen is replaced by selenium practically do not intercalate. Parallel behaviour was also observed for DNA photobinding and crosslink formation. The cycloadduct between furan selenium and pyrone sulphur isoster and thymine was isolated and characterized. The capacity of the various psoralen isosters to generate singlet oxygen and superoxide radical anion was studied. For the former the yield varies markedly for the various compounds, while for the latter the yield is similar for all compounds.
研究了一些通过用硫和/或硒取代一个或两个环内氧原子而获得的杂补骨脂素。在初步试验中，这些化合物表现出很强的光生物活性，在某些情况下比补骨脂素高出两个数量级以上。含硫的杂补骨脂素会插入双链DNA内部，对该大分子表现出明显的亲和力；当硒取代呋喃氧时，补骨脂素类似物也会发生插入，但效率较低，而其中吡喃酮氧被硒取代的补骨脂素类似物实际上不会发生插入。在DNA光结合和交联形成方面也观察到了类似的行为。呋喃硒和吡喃酮硫类似物与胸腺嘧啶之间的环加成物被分离并表征。研究了各种补骨脂素类似物产生单线态氧和超氧阴离子自由基的能力。对于前者，各种化合物的产率差异显著，而对于后者，所有化合物的产率相似。
