Citation: 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 shu

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

Wang Yafen ^† ,
Zhang Xiong ^† ,
Liu Chaoxing ^† ,
Zhou Xiang ^*,,

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

Corresponding author: Zhou Xiang, xzhou@whu.edu.cn

^†

Received Date: 13 April 2017

Fund Project: the National Natural Science Foundation of China 21672167the National Natural Science Foundation of China 21432008the National Natural Science Foundation of China 91413109the National Natural Science Foundation of China 21672165

Figures(5)

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.
- Zinc (Ⅱ)-salen complex,
- selectivity,
- G-quadruplex,
- fluorescence,
- stability
1. [1]
  Bhasikuttan, A. C.; Mohanty, J. Chem. Commun. 2015, 51, 7581. doi: 10.1039/C4CC10030A
2. [2]
  Liu, C.; Chen, Y.; Wang, Y.; Wu, F.; Zhang, X.; Yang, W.; Wang, J.; Chen, Y.; He, Z.; Zou, G.; Wang, S.; Zhou, X. Nano Res. 2017, DOI:10.1007/s12274-017-1445-2. doi: 10.1007/s12274-017-1445-2
3. [3]
  Liu, C.; Wang, Y.; Zhang, X.; Wu, F.; Yang, W.; Zou, G.; Yao, Q.; Wang, J.; Chen, Y.; Wang, S.; Zhou, X. Chem. Sci. 2017, DOI:10.1039/C7SC00637C. doi: 10.1039/C7SC00637C
4. [4]
  Tian, T.; Xiao, H.; Weng, X.; Wang, S.; Zhou, X. Sci. Sin. Chim. 2013, 42, 1700(in Chinese).
5. [5]
  Biffi, G.; Tannahill, D.; McCafferty, J.; Balasubramanian, S. Nat. Chem. 2013, 5, 182. doi: 10.1038/nchem.1548
6. [6]
  Chen, S. B.; Hu, M. H.; Liu, G. C.; Wang, J.; Ou, T. M.; Gu, L. Q.; Huang, Z. S.; Tan, J. H. J. Am. Chem. Soc. 2016, 138, 10382. doi: 10.1021/jacs.6b04799
7. [7]
  Wang, S.; Min, Y.; Wang, J.; Liu, C.; Fu, B.; Wu, F., Wu, L; Qiao, Z.; Song, Y; Xu, G.; Wu, Z.; Huang, G.; Peng, N.; Huang, R.; Mao, W.; Peng, S.; Chen, Y.; Zhu, Y.; Tian, T.; Zhang, X.; Zhou, X. Sci. Adv. 2016, 2, e1501535 doi: 10.1126/sciadv.1501535
8. [8]
  Wang, S.; Zhang, Q.; Wang, J.; Ge, X.; Song, Y.; Wang, Y.; Li, X.; Fu, B.; Xu, G.; Shu, B.; Gong, P.; Zhang, B.; Tian, T.; Zhou, X. Cell Chem. Biol. 2016, 23, 1113. doi: 10.1016/j.chembiol.2016.07.019
9. [9]
  Zheng, X. H; Mu, G.; Tan, C. P.; Cao, G.; Mao, Z. W. Sci. Sin. Chim. 2014, 44, 484(in Chinese).
10. [10]
  Lin, S.; Xu, M.; Yuan, G. Chin. Chem. Lett. 2012, 23, 329. doi: 10.1016/j.cclet.2011.11.002
11. [11]
  Yan, J.; Guan, Y. Progr. Anatom. Sci. 2015, 21, 419.
12. [12]
  Zheng, X.; Liu, H.; Xia, L.; Mao, Z. Chin. Pharmacol. Bull. 2016, 32, 751(in Chinese). doi: 10.3969/j.issn.1001-1978.2016.06.003
13. [13]
  Müller, S.; Kumari, S.; Rodriguez, R.; Balasubramanian, S. Nat. Chem. 2010, 2, 1095. doi: 10.1038/nchem.842
14. [14]
  Zhang, C.; Wu, W.; Lu, Y.; Gu, L.; Huang, Z. S. Acta Chim. Sinica 2008, 66, 953(in Chinese). doi: 10.3321/j.issn:0567-7351.2008.08.020
15. [15]
  Zheng, K.; Zhang, D.; Zhang, L.; Hao, Y.; Zhou, X.; Tan, Z. J. Am. Chem. Soc. 2011, 133, 1475. doi: 10.1021/ja108972e
16. [16]
  Ou, Z. Z.; Ju, B. L.; Gao, Y. Y.; Wang, Z. C.; Huang, G.; Qian, Y. M. Acta Phys.-Chim. Sin. 2015, 31, 2386(in Chinese). doi: 10.3866/PKU.WHXB201510137
17. [17]
  Meng, C.; Wang, S.; Zhang, K.; Jin, H.; Chen, X.; Hu, M.; Xiong, J. Acta Chim. Sinica 2011, 69, 1173(in Chinese).
18. [18]
  Reed, J. E.; Arnal, A. A.; Neidle, S.; Vilar, R. J. Am. Chem. Soc. 2006, 128, 5992. doi: 10.1021/ja058509n
19. [19]
  Xu, L.; Wu, W.; Ding, J.; Feng, S.; Xing, X.; Deng, M.; Zhou, X. RSC Adv. 2012, 2, 894. doi: 10.1039/C1RA00851J
20. [20]
  Yu, L.; Gai, W.; Yang, Q.; Xiang, J.; Sun, H.; Li, Q.; Wang, L.; Guan, A.; Tang, Y. Chin. Chem. Lett. 2015, 26, 705. doi: 10.1016/j.cclet.2015.02.002
21. [21]
  Wu, F.; Liu, C.; Chen, Y.; Yang, S.; Xu, J.; Huang, R.; Wang, X.; Li, M.; Liu, W.; Mao, W.; Zhou, X. Sens. Actuators, B 2016, 236, 268. doi: 10.1016/j.snb.2016.05.162
22. [22]
  Tera, M.; Iida, K.; Ikebukuro, K.; Seimiya, H.; Shin-ya, K.; Nagasawa, K. Org. Biomol. Chem. 2010, 8, 2749. doi: 10.1039/c002117b
23. [23]
  Chen, Y.; Yan, S.; Yuan, L.; Zhou, Y.; Song, Y.; Xiao, H.; Weng, X.; Zhou, X. Org. Chem. Front. 2014, 1, 267. doi: 10.1039/c3qo00048f
24. [24]
  Xu, S.; Li, Q.; Xiang, J.; Yang, Q.; Sun, H.; Guan, A.; Wang, L.; Liu, Y.; Yu, L.; Shi, Y.; Chen, H.; Tang, Y. Nucleic Acids Res. 2015, 43, 9575.
25. [25]
  Mohanty, J.; Barooah, N.; Dhamodharan, V.; Harikrishna, S.; Pradeepkumar, P. I.; Bhasikuttan, A. C. J. Am. Chem. Soc. 2013, 135, 367. doi: 10.1021/ja309588h
26. [26]
  Chen, S. B.; Wu, W. B.; Hu, M. H.; Ou, T. M.; Gu, L. Q.; Tan, J. H.; Huang, Z. S. Chem. Commun. 2014, 50, 12173. doi: 10.1039/C4CC05394J
27. [27]
  Lin, S.; Gao, W.; Tian, Z.; Yang, C.; Lu, L.; Mergny, J.; Leung, C.; Ma, D. Chem. Sci. 2015, 6, 4284. doi: 10.1039/C5SC01320H
28. [28]
  Ji, X.; Yao, C.; Wan, Y.; Song, H.; Xin, P.; Cui, H.; Zheng, C.; Deng, S. Chin. J. Chem. 2016, 34, 331. doi: 10.1002/cjoc.v34.3
29. [29]
  Liu, X.; Yang, Y.; Hua, X.; Feng, X.; Su, S.; Huang, Y.; Fan, Q.; Wang, L.; Huang, W. Chin. J. Chem. 2015, 33, 981. doi: 10.1002/cjoc.v33.8
30. [30]
  Shao, Y.; Li, C.; Zhou, X.; Chen, P.; Yang, Z.; Li, Z.; Liu, D. Acta Chim. Sinica 2015, 73, 815(in Chinese).
31. [31]
  Liu, X.; Wang, Y.; Huang, Y.; Feng, X.; Fan, Q.; Huang, W. Acta Chim. Sinica 2016, 74, 664(in Chinese).
32. [32]
  Zhou, J.; Yuan, G. Acta Chim. Sinica 2007, 65, 1728(in Chinese). doi: 10.3321/j.issn:0567-7351.2007.16.035
33. [33]
  Wei, Q.; Qu, F.; Gong, R. Prog. Biochem. Biophys. 2015, 42, 624(in Chinese).
34. [34]
  Rankin, S.; Reszka, A. P.; Huppert, J.; Zloh, M.; Parkinson, G. N.; Todd, A. K.; Ladame, S.; Balasubramanian, S.; Neidle, S. J. Am. Chem. Soc. 2005, 127, 10584. doi: 10.1021/ja050823u
35. [35]
  Chung, W. J.; Heddi, B.; Schmitt, E.; Lim, K. W.; Mechulam, Y.; Phan, A. T. Proc. Natl. Acad. Sci. U. S. A. 2015, 112, 2729. doi: 10.1073/pnas.1418718112
36. [36]
  Zhao, A.; Zhao, C.; Ren, J.; Qu, X. Chem. Commun. 2016, 52, 1365. doi: 10.1039/C5CC08401F
37. [37]
  Fu, B.; Huang, J.; Chen, Y.; Wang, Y.; Xue, T.; Xu, G.; Wang, S.; Zhou, X. Chem. Commun. 2016, 52, 10052. doi: 10.1039/C6CC04866H
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