NEW PEPTIDYL-ANTHRAQUINONES - SYNTHESIS AND DNA-BINDING

Aminoacyl- hydroxy-anthraquinones bearing glicyl, valyl, lysyl and try ptophanyl residues in the side-chain were synthesized as new potential DNA-directed drugs. These compounds bind very tightly to double-stran ded DNA by intercalating their planar portion into the nucleic acid an d further stabilizing the complex through electrostatic contacts with the backbone phosphates. All protonated groups in the side-chains part icipate in the latter process. The free energy of DNA-binding correcte d for the electrostatic contribution is similar for the lysyl and glic yl derivatives, which points to a common geometry of intercalation.