nteractions between DNA and Psoralenamines Studied with Dichroism Techniques

Journal article, 1986

The interaction of a series of water-soluble mono- and bis-psoralenamines with calf thymus DNA has been studied with flow UV linear dichroism (LD), circular dichroism (CD) and equilibrium techniques. The positive charge of a protonated amino group strongly enhances the DNA affinity compared to that of the parent compound, 8-methoxypsoralen. The orientation of the psoralen when bound to DNA, depends on the position of the amino substituent. With amino substituents in the 5-position (on the‘hydrophobic edge’of psoralen) psoralenamines tend to bind with a considerable tilt relative to the average orientation of the DNA base-pairs. The tilt generally increases with an increased psoralen: base-pair ratio, indicating a more random, nonintercalated binding. With the amino substituents in the 8-position the psoralen binds with its plane parallel to that of the DNA bases as expected for intercalation. The DNA CD supports that these psoralenamines induce a considerable perturbation of the DNA structure, and the CD induced in the psoralen chromophore is in qualitative agreement with intercalation. The study also includes a theoretical and an experimental determination of the UV transition moments of the psoralen chromophore.