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Photoswitching properties of hairpin ODNs with azobenzene derivatives at the loop position
Wu, Li1,2; Wu, Ya3; Jin, Hongwei2; Zhang, Liangren2; He, Yujian1,2; Tang, Xinjing2
刊名MEDCHEMCOMM
2015
DOI10.1039/c4md00378k
6期:3页:461-468
收录类别SCI
文章类型Article
WOS标题词Science & Technology
类目[WOS]Biochemistry & Molecular Biology ; Chemistry, Medicinal
研究领域[WOS]Biochemistry & Molecular Biology ; Pharmacology & Pharmacy
关键词[WOS]THERMODYNAMIC PARAMETERS ; PREDICT STABILITY ; PHOTO-REGULATION ; GENE-EXPRESSION ; MOLECULAR GLUE ; DNA ; PHOTOREGULATION ; LINKER ; LIGHT ; OLIGONUCLEOTIDES
英文摘要

We report herein the possibility of modulating the structure of hairpin oligonucleotides (ODNs) by light exposure. By using 4,4′-dihydroxyl azobenzene derivatives as suitable linker units, the hairpin conformation can be photocontrolled in a reversible manner. To determine which cross-links show the largest photo-switching effect, 4,4′-bis(hydroxymethyl) azobenzene (Az1) and 4,4′-bis(hydroxyethyl) azobenzene (Az2) were designed and used to replace the loops of ODN hairpins. When Az1 was introduced to the loop of ODN hairpins with 4, 5 and 6 base pairs, the thermodynamic stability of the ODN hairpins decreased and the differences in T-m values from trans to cis were 12.1-24.1 degrees C, although this did not happen for Az2-ODN hairpins. CD results indicated that the azobenzene-modified hairpins displayed strong induced CD signals in the range of 300-350 nm and 400-450 nm. Thermodynamic parameters showed that the enthalpic change (-Delta H degrees) and the entropic change (-T Delta S degrees) for trans to cis isomerization of Az1-ODNs 5a, 6a and 8a significantly decreased with a decrease in T-m values, whereas -Delta H degrees and -T Delta S degrees for Az2-ODNs 5b and 6b clearly increased in spite of little change in T-m values. Quantum chemical calculation further explained that the stabilities of the trans form are much higher than their cis form for Az1-ODNs, but not for Az2-ODNs.

语种英语
WOS记录号WOS:000351095400011
项目编号21302008 ; 21272263 ; K20140212 ; K20130206
资助机构Chinese Nature Science Foundation ; State Key Laboratory of Natural and Biomimetic Drugs, Peking University
引用统计
被引频次:5[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/65382
专题北京大学药学院
北京大学医学部管理机构_医学部
北京大学药学院_天然药物与仿生药物国家重点实验室
北京大学药学院_药物化学系
作者单位1.Univ Chinese Acad Sci, Coll Chem Chem Engn, Beijing 100049, Peoples R China
2.Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
3.Xian Shiyou Univ, Coll Chem & Chem Engn, Xian 710062, Peoples R China
推荐引用方式
GB/T 7714
Wu, Li,Wu, Ya,Jin, Hongwei,et al. Photoswitching properties of hairpin ODNs with azobenzene derivatives at the loop position[J]. MEDCHEMCOMM,2015,6(3):461-468.
APA Wu, Li,Wu, Ya,Jin, Hongwei,Zhang, Liangren,He, Yujian,&Tang, Xinjing.(2015).Photoswitching properties of hairpin ODNs with azobenzene derivatives at the loop position.MEDCHEMCOMM,6(3),461-468.
MLA Wu, Li,et al."Photoswitching properties of hairpin ODNs with azobenzene derivatives at the loop position".MEDCHEMCOMM 6.3(2015):461-468.
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