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Directing quadruplex-stabilizing drugs to the telomere: Synthesis and properties of acridine - Oligonucleotide conjugates

Directing quadruplex-stabilizing drugs to the telomere: Synthesis and properties of acridine - Oligonucleotide conjugates
Directing quadruplex-stabilizing drugs to the telomere: Synthesis and properties of acridine - Oligonucleotide conjugates
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.
1043-1802
1351-1359
Casals, J.
dad31e18-b6ea-4c8e-817e-187be4cca333
Debethune, L.
30e81484-5ab6-40cf-92b4-c411155ce7f7
Alvarez, K.
70a80f2f-ea30-49e4-acc1-be1fdd453e70
Risitano, A.
cf59ac40-0ade-4e18-ab7e-354b4026b8a3
Fox, K.R.
9da5debc-4e45-473e-ab8c-550d1104659f
Grandas, A.
0d1e9e9d-fc0e-4273-b623-237992674f2d
Pedroso, E.
d35758b4-c758-4fea-ba18-b68d3014c565
Casals, J.
dad31e18-b6ea-4c8e-817e-187be4cca333
Debethune, L.
30e81484-5ab6-40cf-92b4-c411155ce7f7
Alvarez, K.
70a80f2f-ea30-49e4-acc1-be1fdd453e70
Risitano, A.
cf59ac40-0ade-4e18-ab7e-354b4026b8a3
Fox, K.R.
9da5debc-4e45-473e-ab8c-550d1104659f
Grandas, A.
0d1e9e9d-fc0e-4273-b623-237992674f2d
Pedroso, E.
d35758b4-c758-4fea-ba18-b68d3014c565

Casals, J., Debethune, L., Alvarez, K., Risitano, A., Fox, K.R., Grandas, A. and Pedroso, E. (2006) Directing quadruplex-stabilizing drugs to the telomere: Synthesis and properties of acridine - Oligonucleotide conjugates. Bioconjugate Chemistry, 17, 1351-1359. (doi:10.1021/bc060194t).

Record type: Article

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.

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Published date: 2 September 2006

Identifiers

Local EPrints ID: 56009
URI: http://eprints.soton.ac.uk/id/eprint/56009
ISSN: 1043-1802
PURE UUID: 85b82e31-3a1e-49f8-8ab4-2b79aa51397a
ORCID for K.R. Fox: ORCID iD orcid.org/0000-0002-2925-7315

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Date deposited: 07 Aug 2008
Last modified: 03 Dec 2019 02:07

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