Induction Stabilization and Fluorescence-based Switch-on Detection of G-Quadruplex by Zinc (II)-salen Complex
Received date: 2017-04-13
Online published: 2017-05-09
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
Wang Yafen , Zhang Xiong , Liu Chaoxing , Zhou Xiang . Induction Stabilization and Fluorescence-based Switch-on Detection of G-Quadruplex by Zinc (II)-salen Complex[J]. Acta Chimica Sinica, 2017 , 75(7) : 692 -698 . DOI: 10.6023/A17040162
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