title: Interaction of cationic nickel and manganese porphyrins with the minor groove of DNA.
abstract: The capacity of a series of new cationic nickel and manganese metalloporphyrins to bind in the minor groove of DNA was evaluated by binding competition experiments with manganese(III)-bis-aqua-meso-tetrakis(4-N-methylpyridiniumyl)porphyrin, Mn-TMPyP, a powerful artificial nuclease when associated with KHSO(5). The four N-methylpyridiniumyl substituents on this porphyrin macrocycle are responsible for a strong binding affinity for the minor groove of AT-rich DNA. The inhibition of DNA cleavage mediated by Mn-TMPyP/KHSO(5) by the various tested porphyrins correlated with their competitive occupancy of the minor groove site of Mn-TMPyP. Introduction of long and flexible cationic substituents at the periphery of the porphyrin macrocycle precluded the interaction of the porphyrin derivative in the minor groove and resulted in low affinity for DNA. On the other hand, introduction of phenylpyridiniumyl substituents on the porphyrin macrocycle surprisingly conferred the new porphyrin derivative with a tight binding in the minor groove of a six consecutive AT base pairs sequence. These data on structural requirements for minor groove DNA binding will help the rational design of porphyrin derivatives for selective targeting of quadruplex DNA versus double-stranded DNA.
authors: CNRS, Laboratoire de Chimie de Coordination, 205 route de Narbonne, F-31077 Toulouse, France.
authors: Carmen
authors: C
authors: Romera
authors: Laurent
authors: L
authors: Sabater
authors: Antonio
authors: A
authors: Garofalo
authors: Isabelle
authors: I
authors: M Dixon
authors: Geneviève
authors: G
authors: Pratviel
mesh_terms: D020029:Base Pairing; D001483:Base Sequence; D001667:Binding, Competitive; D004247:DNA / Q000737:chemistry* / Q000235:genetics / Q000378:metabolism*; D020862:GC Rich Sequence; D057927:Hydrophobic and Hydrophilic Interactions; D008345:Manganese / Q000737:chemistry*; D008665:Metalloporphyrins / Q000737:chemistry* / Q000378:metabolism*; D009532:Nickel / Q000737:chemistry*; D009690:Nucleic Acid Conformation; D010084:Oxidation-Reduction; D020349:Surface Plasmon Resonance
chemical_list: D008665:Metalloporphyrins; D008345:Manganese; D009532:Nickel; D004247:DNA