title: Oxazole-based peptide macrocycles: a new class of G-quadruplex binding ligands.
abstract: Herein we report on the synthesis and DNA binding properties of a new class of water soluble oxazole-based peptide macrocycles that bind selectively to quadruplex DNA, with no detectable binding to duplex DNA. We have recently identified one quadruplex in the proto-oncogene c-kit that is suspected to act as a regulatory element for the expression of the c-kit gene. Here we provide the first example of a ligand binding to and stabilizing the c-kit quadruplex. Moreover, we show that these macrocycles show a preference for the c-kit quadruplex as compared to the human telomeric quadruplex.
authors.affiliation: The University Chemical Laboratory, University of Cambridge, UK.
authors.forename: Katja
authors.initials: K
authors.lastname: Jantos
authors.forename: Raphaël
authors.initials: R
authors.lastname: Rodriguez
authors.forename: Sylvain
authors.initials: S
authors.lastname: Ladame
authors.forename: Pravin S
authors.initials: PS
authors.lastname: Shirude
authors.forename: Shankar
authors.initials: S
authors.lastname: Balasubramanian
mesh_terms: D001483:Base Sequence; D001665:Binding Sites; D002942:Circular Dichroism; D004247:DNA / Q000737:chemistry*; D054856:G-Quadruplexes; D008024:Ligands; D047028:Macrocyclic Compounds / Q000737:chemistry*; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry*; D000090063:Proto-Oncogene Mas; D013237:Stereoisomerism
chemical_list: D008024:Ligands; C000715470:MAS1 protein, human; D047028:Macrocyclic Compounds; D010080:Oxazoles; D010455:Peptides; D000090063:Proto-Oncogene Mas; D004247:DNA