Synthesis of DNA conjugates with metalated tetracationic porphyrins by postsynthetic cycloadditions

Article abstract of DOI:10.1021/ol500364j

Tetracationic porphyrins of the TMPP (meso-tetra-(4-N-methylpyridyl) porphyrin) type, metalated with Cu(II) or with Au(III), were conjugated covalently to oligonucleotides. The Cu(I)-catalyzed cycloaddition (between an azide and an ethynyl group) and the Diels-Alder cycloaddition (between a furan and a maleimide functionality) were successfully applied as two alternative postsynthetic methods to modify the 2′-position of an internal uridine. Melting temperatures and UV/vis absorption properties were compared. CD measurements indicated that the type of conjugation chemistry determines the grade of intercalation of the attached and positively charged porphyrins.