title: 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.
authors.affiliation: Department of Chemistry, Brock University, 500 Glenridge Ave., St. Catharines, Ontario L2S 3A1, Canada.
authors.forename: Fatma
authors.initials: F
authors.lastname: Eljabu
authors.affiliation: Department of Chemistry, Brock University, 500 Glenridge Ave., St. Catharines, Ontario L2S 3A1, Canada.
authors.forename: Joshi
authors.initials: J
authors.lastname: Dhruval
authors.affiliation: Department of Chemistry, Brock University, 500 Glenridge Ave., St. Catharines, Ontario L2S 3A1, Canada. Electronic address: tyan@brocku.ca.
authors.forename: Hongbin
authors.initials: H
authors.lastname: Yan
mesh_terms: D001391:Azo Compounds / Q000737:chemistry*; D003500:Cyclization; D004247:DNA / Q000737:chemistry*; D008027:Light; D015394:Molecular Structure; D009693:Nucleic Acid Hybridization; D009838:Oligodeoxyribonucleotides / Q000737:chemistry*; D060327:Solid-Phase Synthesis Techniques / Q000379:methods
chemical_list: D001391:Azo Compounds; D009838:Oligodeoxyribonucleotides; D004247:DNA; C009850:azobenzene
keywords: Cyclic azobenzene; FRET; Hybridization; Photoisomerization; Spatiotemporal control