title: Lysinyl macrocyclic hexaoxazoles: synthesis and selective G-quadruplex stabilizing properties.
abstract: Macrocyclic hexaoxazoles having one or two lysinyl side chains in which the terminal nitrogen is either a primary amine, N,N-dimethylamine, or an acetamide have been synthesized. Sodium ion has been found to be beneficial to the macrocyclization step by acting as a template around which the linear polyoxazole can organize. Each of the targeted compounds selectivity stabilizes G-quadruplex versus duplex DNA. Compounds with one valine and one lysine residue display the best combination of G-quadruplex stabilizing ability with no detectable stabilization of duplex DNA.
authors.affiliation: Department of Pharmaceutical Chemistry, Ernest Mario School of Pharmacy, Rutgers, The State University of New Jersey, 160 Frelinghuysen Road, Piscataway, NJ 08854-8020, USA.
authors.forename: Suzanne G
authors.initials: SG
authors.lastname: Rzuczek
authors.forename: Daniel S
authors.initials: DS
authors.lastname: Pilch
authors.forename: Edmond J
authors.initials: EJ
authors.lastname: LaVoie
authors.forename: Joseph E
authors.initials: JE
authors.lastname: Rice
mesh_terms: D004247:DNA / Q000187:drug effects*; D015195:Drug Design; D054856:G-Quadruplexes; D008239:Lysine / Q000737:chemistry* / Q000494:pharmacology*; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D047028:Macrocyclic Compounds; D010080:Oxazoles; D004247:DNA; D008239:Lysine