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

详细信息    查看全文

• 作者：Fatma Eljabu ; Joshi Dhruval ; Hongbin Yan ; ^{tyan@brocku.ca" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Cyclic azobenzene ; FRET ; Hybridization ; Photoisomerization ; Spatiotemporal control
• 刊名：Bioorganic & Medicinal Chemistry Letters
• 出版年：2015
• 出版时间：1 December 2015
• 年：2015
• 卷：25
• 期：23
• 页码：5594-5596
• 全文大小：571 K

文摘

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.