5-Methoxypsoralen photoadduct formation: conversion of monoadducts to crosslinks

5-Methoxypsoralen is often substituted for 8-methoxypsoralen in the photochemotherapy of psoriasis even though the nature of the resulting photadducts in cellular DNA has not been determined. A recent molecular mechanics study with a model oligonucleotide predicted that intercalated 5-methoxypsoralen molecules would tend to favor the preferential formation of 3,4-monoadducts. Such a result would be contrary to the photoadduct patterns observed with other psoralens. In this study we show that 5-methoxypsoralen photoadducts formation is, in fact, very similar to that for other psoralens, i.e., the primary photoadduct is the 4',5'-monoadduct which can be quantitatively converted to crosslink.