Synthesis and human telomeric G-quadruplex DNA-binding activity of glucosaminosides of shikonin/alkannin

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 4, 2012, Pages 1582-1586

  He, Hao ^b   Bai, Li Ping ^a,b   Jiang, Zhi Hong ^a,b  

^a MACAU UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Macao)

^b HONG KONG BAPTIST UNIVERSITY   (Hong Kong)

Author keywords

Alkannin; G quadruplex; Glycosylation; Shikonin; Telomeric

Indexed keywords

ALKANNIN; ALKANNIN N ACETYL BETA GLUCOSAMINOSIDE; GUANINE QUADRUPLEX; N ACETYL GLUCOSAMINOSIDE DERIVATIVE; SHIKONIN DERIVATIVE; SHIKONIN N ACETYL BETA GLUCOSAMINOSIDE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BINDING KINETICS; CONTROLLED STUDY; DRUG DNA BINDING; DRUG SYNTHESIS; ELECTROSPRAY MASS SPECTROMETRY; GLYCOSYLATION; NONHUMAN; TIME OF FLIGHT MASS SPECTROMETRY;

EID: 84856678408     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.12.143     Document Type: Article

References (43)

1. Papageorgiou, V. P.; Assimopoulou, A. N.; Couladouros, E. A.; Hepworth, D.; Nicolaou, K. C. Angew. Chem., Int. Ed. 1999, 38, 270.
2. Papageorgiou, V. P.; Assimopoulou, A. N.; Samanidou, V. F.; Papadoyannis, I. N. Curr. Org. Chem. 2006, 10, 2123.
3. Papageorgiou, V.P.; Assimopoulou, A. N.; Ballis, A. C. Curr. Med. Chem. 2008, 15, 3248.
4. Tanaka, S.; Tajima, M.; Tsukada, M.; Tabata, M. J. Nat. Prod. 1986, 49, 466.
5. Sankawa, U.; Ebizuka, Y.; Miyazaki, T.; Isomura, Y.; Otsuka, H.; Shibata, S.; Inomata, M.; Fukuoka, F. Chem. Pharm. Bull. 1977, 25, 2392.
6. Bhakuni, D. S.; Dhar, M. L.; Dhar, M. M.; Dhawn, B. N.; Mehrotra, B. N.; Indian, J. Exp. Biol. 1969, 7, 250.
7. Driscoll, J. S.; Hazard, G. F.; Wood, H. B., Jr.; Goldin, A., Jr. Cancer Chemother. Rep. Part 2 1974, 4, 1.
8. Miler, M. G.; Rodgers, A.; Cohen, G. M. Biochem. Pharmacol. 1986, 35, 1177.
9. Mao, X.; Yu, C. R.; Li, W. H.; Li, W. X. Cell Res. 2008, 18, 879.
10. Liu, J.; Zhou, W.; Li, S. S.; Sun, Z.; Lin, B.; Lang, Y. Y.; He, J. Y.; Cao, X.; Yan, T.; Wang, L.; Lu, J.; Han, Y. H.; Cao, Y.; Zhang, X. K.; Zeng, J. Z. Cancer Res. 2008, 68, 8871.
11. Hu, X.; Han, W.; Li, L. Autophagy 2007, 3, 490.
12. Han, W.; Li, L.; Qiu, S.; Lu, Q.; Pan, Q.; Gu, Y.; Luo, J.; Hu, X. Mol. Cancer Ther. 2007, 6, 1641.
13. Hisa, T.; Kimura, Y.; Takada, K.; Suzuki, F.; Takigawa, M. Anticancer Res. 1998, 18, 783.
14. Komi, Y.; Suzuki, Y.; Shimamura, M.; Kajimoto, S.; Nakajo, S.; Masuda, M.; Shibuya, M.; Itabe, H.; Shimokado, K.; Oettgen, P.; Nakaya, K.; Kojima, S. Cancer Sci. 2009, 100, 269.
15. Ahn, B.-Z.; Baik, K.-U.; Kweon, G.-R.; Lim, K.; Hwang, B.-D. J. Med. Chem. 1995, 38, 1044.
16. Yang, F.; Chen, Y.; Duan, W.; Zhang, C.; Zhu, H.; Ding, J. Int. J. Cancer 2006, 119, 1184.
17. Singh, F.; Gao, D.; Lebwohl, M. G.; Wei, H. Cancer Lett. 2003, 200, 115.
18. Nakaya, K.; Miyasaka, T. Anticancer Drugs 2003, 14, 683.
19. Lu, Q.; Liu, W.; Ding, J.; Cai, J.; Duan, W. Bioorg. Med. Chem. Lett. 2002, 12, 1375
20. Kim, N. W.; Piatyszek, M. A.; Prowse, K. R.; Harley, C. B.; West, M. D.; Ho, P. L.; Coviello, G. M.; Wright, W. E.; Weinrich, S. L.; Shay, J. W. Science 1994, 266, 2011.
21. Lipps, H. J.; Rhodes, D. Trends Cell Biol. 2009, 19, 414.
22. Zahler, A. M.; Williamson, J. R.; Cech, T. R.; Prescott, D. M. Nature 1991, 350, 718.
23. Sun, D.; Thompson, B.; Cathers, B. E.; Salazar, M.; Kerwin, S. M.; Trent, J. O.; Jenkins, T. C.; Neidle, S.; Hurley, L. H. J. Med. Chem. 1997, 40, 2113.
24. Dwek, R. A. Chem. Rev. 1996, 96, 683.
25. Bertozzi, C. R.; Kiessling, L. L. Science 2001, 291, 2357.
26. Su, Y.; Xie, J.; Wang, Y.; Hu, X.; Lin, X. Eur. J. Med. Chem. 2010, 45, 2713.
27. Xi, Z.; Hwang, G.-S.; Goldberg, I. H.; Harris, J. L.; Pennington, W. T.; Fouad, F. S.; Qabaja, G.; Wright, J. M.; Jones, G. B. Chem. Biol. 2002, 9, 925.
28. Daniel, J. M.; Friess, S. D.; Rajagopalan, S.; Wendt, S.; Zenobi, R. Int. J. Mass Spectrom. 2002, 216, 1.
29. Rueda, M.; Luque, F. J.; Orozco, M. J. Am. Chem. Soc. 2006, 128, 3608.
30. Rosu, F.; Gabelica, V.; Houssier, C.; Colson, P.; De Pauw, E. Rapid Commun. Mass Spectrom. 2002, 16, 1729.
31. Rosu, F.; De Pauw, E.; Guittat, L.; Alberti, P.; Lacroix, L.; Mailliet, P.; Riou, J.-F.; Mergny, J.-L. Biochemistry 2003, 42, 10361.
32. Chen, W.-H.; Chan, C.-L.; Cai, Z.; Luo, G.-A.; Jiang, Z.-H. Bioorg. Med. Chem. Lett. 2004, 14, 4955.
33. Bai, L.-P.; Hagihara, M.; Jiang, Z.-H.; Nakatani, K. ChemBioChem 2008, 9, 2583.
34. Bai, L.-P.; Cai, Z.; Zhao, Z.-Z.; Nakatani, K.; Jiang, Z.-H. Anal. Bioanal. Chem. 2008, 392, 709.
35. Gabelica, V.; Baker, E. S.; Teulade-Fichou, M.-P.; De Pauw, E.; Bowers, M. T. J. Am. Chem. Soc. 2007, 129, 895.
36. Qin, Y.; Pang, J.-Y.; Chen, W.-H.; Cai, Z.; Jiang, Z.-H. Bioorg. Med. Chem. 2006, 14, 25.
37. Chen, W.-H.; Pang, J.-Y.; Qin, Y.; Peng, Q.; Cai, Z.; Jiang, Z.-H. Bioorg. Med. Chem. Lett. 2005, 15, 2689.
38. Bhadra, K.; Kumar, G. S. Biochim. Biophys. Acta 1810, 2011, 485.
39. Bai, L.-P.; Zhao, Z.-Z.; Cai, Z.; Jiang, Z.-H. Bioorg. Med. Chem. 2006, 14, 5439.
40. Long, Y.-H.; Bai, L.-P.; Qin, Y.; Pang, J.-Y.; Chen, W.-H.; Cai, Z.; Xu, Z.-L.; Jiang, Z.-H. Bioorg. Med. Chem. 2006, 14, 4670.
41. Yu, H.; Wang, X.; Fu, M.; Ren, J.; Qu, X. Nucleic Acids Res. 2008, 36, 5695.
42. Yu, H.; Zhao, C.; Chen, Y.; Fu, M.; Ren, J.; Qu, X. J. Med. Chem. 2010, 53, 492.
43. Zhao, C.; Geng, J.; Feng, L.; Ren, J.; Qu, X. Chem. Eur. J. 2011, 17, 8209