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Triplex staples: DNA double-strand cross-linking at internal and terminal sites using psoralen-containing triplex-forming oligonucleotides

Triplex staples: DNA double-strand cross-linking at internal and terminal sites using psoralen-containing triplex-forming oligonucleotides
Triplex staples: DNA double-strand cross-linking at internal and terminal sites using psoralen-containing triplex-forming oligonucleotides
A method has been developed to attach 4'-(hydroxymethyl)-4,5',8-trimethylpsoralen to the 5 position of thymine bases during solid-phase oligonucleotide synthesis. UV irradiation of triplex-forming oligonucleotides (TFOs) containing internally attached psoralens produces photoadducts at TpA steps within target duplexes, thus relaxing the constraints on selection of psoralen target sequences. Photoreaction of TFOs containing two psoralens, located at the 5'- and 3'-ends, has been used to create double-strand cross-links (triplex staples) at both termini of the TFO. Such complexes have no free single-stranded ends. TFOs containing 4'-(hydroxymethyl)-4,5',8-trimethyl-psoralen, 3-methyl-2-aminopyridine, and 5-(3-aminoprop-2-ynyl)deoxyuridine formed photoadducts with target duplexes under near-physiological conditions.
1043-1802
1561-1567
Li, Hong
44d51d43-1fe5-4d15-820d-22d302b9e1a7
Broughton-Head, Victoria J.
d094aa77-c889-4747-84d2-55542805c67c
Peng, Guomei
5ed31240-5067-4da5-9e84-aaab79fa33cd
Powers, Vicki E.C.
0646d625-5039-454c-a8ad-0da6bc72ae8a
Ovens, Matthew J.
56733b2a-b768-4439-86d9-8e55303db343
Fox, Keith R..
9da5debc-4e45-473e-ab8c-550d1104659f
Brown, Tom
a64aae36-bb30-42df-88a2-11be394e8c89
Li, Hong
44d51d43-1fe5-4d15-820d-22d302b9e1a7
Broughton-Head, Victoria J.
d094aa77-c889-4747-84d2-55542805c67c
Peng, Guomei
5ed31240-5067-4da5-9e84-aaab79fa33cd
Powers, Vicki E.C.
0646d625-5039-454c-a8ad-0da6bc72ae8a
Ovens, Matthew J.
56733b2a-b768-4439-86d9-8e55303db343
Fox, Keith R..
9da5debc-4e45-473e-ab8c-550d1104659f
Brown, Tom
a64aae36-bb30-42df-88a2-11be394e8c89

Li, Hong, Broughton-Head, Victoria J., Peng, Guomei, Powers, Vicki E.C., Ovens, Matthew J., Fox, Keith R.. and Brown, Tom (2006) Triplex staples: DNA double-strand cross-linking at internal and terminal sites using psoralen-containing triplex-forming oligonucleotides. Bioconjugate Chemistry, 17 (6), 1561-1567. (doi:10.1021/bc0601875).

Record type: Article

Abstract

A method has been developed to attach 4'-(hydroxymethyl)-4,5',8-trimethylpsoralen to the 5 position of thymine bases during solid-phase oligonucleotide synthesis. UV irradiation of triplex-forming oligonucleotides (TFOs) containing internally attached psoralens produces photoadducts at TpA steps within target duplexes, thus relaxing the constraints on selection of psoralen target sequences. Photoreaction of TFOs containing two psoralens, located at the 5'- and 3'-ends, has been used to create double-strand cross-links (triplex staples) at both termini of the TFO. Such complexes have no free single-stranded ends. TFOs containing 4'-(hydroxymethyl)-4,5',8-trimethyl-psoralen, 3-methyl-2-aminopyridine, and 5-(3-aminoprop-2-ynyl)deoxyuridine formed photoadducts with target duplexes under near-physiological conditions.

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Published date: November 2006

Identifiers

Local EPrints ID: 56677
URI: http://eprints.soton.ac.uk/id/eprint/56677
ISSN: 1043-1802
PURE UUID: 52fac2db-3e67-47ea-872f-a7b8dd9a5d3a
ORCID for Keith 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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Contributors

Author: Hong Li
Author: Victoria J. Broughton-Head
Author: Guomei Peng
Author: Vicki E.C. Powers
Author: Matthew J. Ovens
Author: Keith R.. Fox ORCID iD
Author: Tom Brown

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