Towards sequence selective DNA binding: design, synthesis and DNA binding studies of novel bis-porphyrin peptidic nanostructures.
A new series of peptidic nanostructures bearing two intercalating moieties was designed and synthesized to achieve selective recognition of DNA sequences. A cationic porphyrin was attached to a glutamic acid side chain and the latter introduced into a peptidic sequence by standard solid-phase peptide synthesis methodology. Conformation of the hydrosoluble peptidic structures bearing two cationic porphyrins was studied by circular dichroism. Using UV-visible spectroscopy and induced circular dichroism, we demonstrate that the compounds are fully intercalated upon binding to double-stranded DNA and that the compounds exhibit a tremendous preference for GC over AT sequences for intercalation.
Biron
Eric
E
Département de chimie and CREFSIP, Faculté des sciences et de génie, Université Laval, Québec, Québec, Canada.
Voyer
Normand
N
D000595:Amino Acid Sequence; D001483:Base Sequence; D004247:DNA / Q000235:genetics / Q000378:metabolism*; D015195:Drug Design; D007364:Intercalating Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D008969:Molecular Sequence Data; D049329:Nanostructures / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D011166:Porphyrins / Q000737:chemistry*; D011487:Protein Conformation; D013379:Substrate Specificity
D007364:Intercalating Agents; D010455:Peptides; D011166:Porphyrins; C092399:meso-tetrakis(1-methyl-4-pyridiniumyl)porphyrin; D004247:DNA