Incorporation of cyclic azobenzene into oligodeoxynucleotides for the photo-regulation of DNA hybridization.

Abstract:

:Cyclic azobenzene carboxylic acid was synthesized using a shortened route. After reaction with D-threolinol, the resulting cyclic azobenzene-D-threolinol (cAB-Thr) building block was transformed into the corresponding DMTr-protected phosphoramidite, and incorporated into oligodeoxynucleotides at various positions and frequencies by solid phase synthesis. The melting temperatures of these modified oligonucleotides were determined by UV spectrometry. Photo-regulation of cAB-Thr-modified oligonucleotides with their complementary sequence was evaluated by Fluorescence Resonance Energy Transfer experiments using a fluorescein-Black Hole Quencher pair. Results suggest that while cis-cAB destabilizes DNA duplexes, trans-cAB can be accommodated in double stranded DNA.

journal_name

Bioorg Med Chem Lett

authors

Eljabu F,Dhruval J,Yan H

doi

10.1016/j.bmcl.2015.10.043

subject

Has Abstract

pub_date

2015-12-01 00:00:00

pages

5594-6

issue

23

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(15)30152-9

journal_volume

25

pub_type

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