Acta Chim. Sinica ›› 2017, Vol. 75 ›› Issue (7): 692-698.DOI: 10.6023/A17040162 Previous Articles     Next Articles

Article

锌配体化合物选择性诱导、稳定、荧光检测G-四联体

王雅芬, 张雄, 刘朝兴, 周翔   

  1. 武汉大学 化学与分子科学学院 生物医药高分子教育部重点实验室 高等研究院 湖北省过敏及免疫相关疾病 重点实验室 武汉 430072
  • 收稿日期:2017-04-13 出版日期:2017-07-15 发布日期:2017-05-09
  • 通讯作者: 周翔 E-mail:xzhou@whu.edu.cn
  • 基金资助:

    项目受国家自然科学基金(Nos.21432008,91413109,21672165 and 21672167)资助.

Induction Stabilization and Fluorescence-based Switch-on Detection of G-Quadruplex by Zinc (II)-salen Complex

Wang Yafen, Zhang Xiong, Liu Chaoxing, Zhou Xiang   

  1. College of Chemistry and Molecular Sciences, Key Laboratory of Biomedical Polymers of Ministry of Education, The Institute for Advanced Studies, Hubei Province Key Laboratory of Allergy and Immunology, Wuhan University, Wuhan 430072
  • Received:2017-04-13 Online:2017-07-15 Published:2017-05-09
  • Contact: 10.6023/A17040162 E-mail:xzhou@whu.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos.21432008,91413109,21672165 and 21672167).

G-quadruplexes play vital roles in telomere maintenance and other biological systems.An effective G-quadruplexes stabilizer can be a promising medicine for cancer therapy.Here,a Zinc (Ⅱ) with salen derivatives as ligands (ZSC) has been prepared through two simple steps syntheses.2,4-Dihydroxybenzaldehyde (1 equiv.),1-(2-chloroethyl) pyrrolidine hydrochloride (1 equiv.) and potassium carbonate (2 equiv.) were dissolved in 150 mL acetone.After reflux for 20 h in Ar atmosphere and purification,the product 2-hydroxy-4-(2-(pyrrolidin-1-yl) ethoxy) benzaldehyde was obtained to yield 3.24 g (68.8%) as a pale solid.For the other step,2-hydroxy-4-(2-(pyrrolidin-1-yl) ethoxy) benzaldehyde (2 equiv.) and diaminomaleonitrile (1 equiv.) were dissolved into 10 mL methanol.After 20 min stirring at 60℃ in dark atmosphere,the Zinc acetate dehydrate (1 equiv.) was added in the solution for further 2 h reaction time.The final product Zinc (Ⅱ)-salen Complex (ZSC) was purified to yield 245 mg (67.7%) as a red powder.The fluorescence,CD spectra are reported,giving insight into the intrinsic properties of the compound.The Zinc (Ⅱ)-salen Complex could simply discriminate G-quadruplex from other DNA conformations such as hairpin,double-stranded DNA and single-stranded DNA by using fluorescence spectra.To the best of our knowledge,ZSC is the first Zinc (Ⅱ)-salen Complex bearing features of inducing,stabilizing,fluorescence-based switch-on detecting G-quadruplex.In addition,ZSC can also change the Z G-quadruplex to parallel G-quadruplex.Such a sensitive and topology-specific probe is able to light up G-quadruplexes and gain an excellently quantitative detection of DNA bearing G-quadruplexes sequences.The detailed study of the interactions of ZSC with different topology DNAs has allowed us to build the most vital features that Zinc (Ⅱ)-salen Complex can be a potential anticancer drug and in application to other bioanalytes.In the future,we will use the Zinc (Ⅱ)-salen Complex to downstream the gene expression in the gene promoter area to help analyze more biological processes or use it to selectively inhibit viruses which containing G-quadruplexes.

Key words: Zinc (II)-salen complex, selectivity, G-quadruplex, fluorescence, stability