title: Directing quadruplex-stabilizing drugs to the telomere: synthesis and properties of acridine-oligonucleotide conjugates.
abstract: Conjugates containing quadruplex-stabilizing acridines linked to oligonucleotides that are complementary to the G-rich human telomere sequence were synthesized. Acylation of 3,6-diaminoacridine followed by two Michael reactions provided derivatives suitable for conjugation, which were coupled to resin-linked amine-modified oligonucleotides by activating the carboxyl group with pentafluorophenyl 4-nitrobenzenesulfonate. After deprotection with aqueous ammonia at room temperature, conjugates incorporating different acridines, linkers, and oligonucleotide sequences were obtained. These were tested for their ability to stabilize intramolecular DNA quadruplexes that are based on the human telomeric repeat sequence (GGGTTA)(n).
authors.affiliation: Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1-11, E-08028 Barcelona, Spain.
authors.forename: Joan
authors.initials: J
authors.lastname: Casals
authors.forename: Laurent
authors.initials: L
authors.lastname: Debéthune
authors.forename: Karine
authors.initials: K
authors.lastname: Alvarez
authors.forename: Antonina
authors.initials: A
authors.lastname: Risitano
authors.forename: Keith R
authors.initials: KR
authors.lastname: Fox
authors.forename: Anna
authors.initials: A
authors.lastname: Grandas
authors.forename: Enrique
authors.initials: E
authors.lastname: Pedroso
mesh_terms: D000166:Acridines / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D006801:Humans; D015394:Molecular Structure; D009841:Oligonucleotides / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D016615:Telomere / Q000235:genetics / Q000378:metabolism*
chemical_list: D000166:Acridines; D009841:Oligonucleotides