Spacer length and attaching position-dependent binding of synthesized protoberberine dimers to double-stranded DNA

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 13, 2006, Pages 4670-4676

  Long, Yu Hua ^a   Bai, Li Ping ^b   Qin, Yong ^b   Pang, Ji Yan ^a   Chen, Wen Hua ^a   Cai, Zongwei ^b   Xu, Zun Le ^a   Jiang, Zhi Hong ^b  

^a SUN YAT SEN UNIVERSITY   (China)

^b HONG KONG BAPTIST UNIVERSITY   (Hong Kong)

Author keywords

Dimerization; DNA binding; Jatrorrhizine; Protoberberine; Synthesis

Indexed keywords

9 O (OMEGA BROMOALKYL)BERBERINE DERIVATIVE; ALANINE DERIVATIVE; ALANYLALANYLGLYCYLALANYLALANYLTHREONYLTHREONYLCYSTEINYLTHREONYLTHREONINE; ALKANE DERIVATIVE; ALPHA OMEGA DIBROMOALKANE DERIVATIVE; BERBERINE; DOUBLE STRANDED DNA; HETERODIMER; HOMODIMER; JATRORRHIZINE; OLIGODEOXYNUCLEOTIDE DERIVATIVE; PROTOBERBERINE DERIVATIVE; PROTOBERBERINE DIMER DERIVATIVE; SPACER DNA; THREONINE; THREONYLALANYLALANYLGLYCYLALANYLALANYLTHREONYLTHREONYLCYSTEINYLTHREONYLTHREONYLALANINE; THREONYLTHREONYLALANYLALANYLGLYCYLALANYLALANYLTHREONYLTHREONYLCYSTEINYLTHREONYLTHREONYLALANYLALANINE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; DNA BINDING; PROTEIN INTERACTION; SPECTROFLUOROMETRY; SPECTROPHOTOMETRY; SYNTHESIS;

BERBERINE; BERBERINE ALKALOIDS; DIMERIZATION; DNA;

EID: 33646576228     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.03.004     Document Type: Article

References (35)

1. Some reviews on the noncovalent interactions of small molecules with DNA:. Dervan P.B., Poulin-Kerstien A.T., Fechter E.J., and Edelson B.S. Top. Curr. Chem. 253 (2005) 1
2. Armitage B.A. Top. Curr. Chem. 253 (2005) 55
3. Ihmels H., Faulhaber K., and Viola G. Evaluation of the DNA-Binding Properties of Cationic Dyes by Absorption and Emission Spectroscopy. In: Schmuck C., and Wennemers H. (Eds). Highlights in Bioorganic Chemistry: Methods and Applications (2004), Wiley-VCH, Weinheim
4. Gallmeier H.-C., and Konig B. Eur. J. Org. Chem. (2003) 3473
5. Dervan P.B. Bioorg. Med. Chem. 9 (2001) 2215
6. Barton J.K. Science 233 (1986) 727
7. Chrisey L.A., Bonjar G.H.S., and Hecht S.M. J. Am. Chem. Soc. 110 (1988) 644
8. Zein N., Sinha A.M., McGarhren W.J., and Ellestad G.A. Science 240 (1988) 1198
9. Wolkenberg S.E., and Bogor D.L. Chem. Rev. 102 (2002) 2477
10. Creasey W.A. Biochem. Pharmacol. 28 (1979) 1081
11. Birdsall T.C., and Kelley G.S. Altern. Med. Rev. 2 (1997) 94
12. Lau C.W., Yao X.Q., Chen Z.Y., Kou W.H., and Huang Y. Cardiovasc. Drug Rev. 19 (2001) 234
13. Vollekova A., Kostalova D., Kettmann V., and Toth J. Phytother. Res. 17 (2003) 834
14. Kuo C.L., Chou C.C., and Yung B.Y.M. Cancer Lett. 93 (1995) 193
15. Mutoh M., Koshiji M., Akao S., and Fujiwara H. J. Ethnopharmacol. 66 (1999) 227
16. Lin J.G., Chung J.G., Wu L.T., Chen G.W., Chang H.L., and Wang T.F. Am. J. Chin. Med. 27 (1999) 265
17. Krishnan P.K., and Bastow K.F. Anti-Cancer Drug Des. 15 (2000) 255
18. Fukuda K., Hibiya Y., Iizuka N., Miyamoto K., Hazama S., Yoshino S., Yoshimura K., Okita K., Fukumoto T., Yamamoto S., Tangoku A., and Oka M. Cancer Lett. 158 (2000) 35
19. Krey A.K., and Halm F.E. Science 166 (1969) 755
20. Kluza J., Baldeyron B., Colson P., Rasoanaivo P., Mambu L., Frappier F., and Bailly C. Eur. J. Pharm. Sci. 20 (2003) 383
21. Mazzini S., Bellucci M.C., and Mondelli R. Bioorg. Med. Chem. 11 (2003) 505
22. Yadav R.C., Kumar G.S., Bhadra K., Giri P., Sinha R., Pal S., and Maiti M. Bioorg. Med. Chem. 13 (2005) 165
23. Chen W.-H., Chan C.-L., Cai Z., Luo G.-A., and Jiang Z.-H. Bioorg. Med. Chem. Lett. 14 (2004) 4955
24. Chen W.-H., Qin Y., Cai Z.-W., Chan C.-L., Luo G.-A., and Jiang Z.-H. Bioorg. Med. Chem. 13 (2005) 1859
25. Pang J.-Y., Qin Y., Chen W.-H., Luo G.-A., and Jiang Z.-H. Bioorg. Med. Chem. 13 (2005) 5835
26. Chen W.-H., Pang J.-Y., Qin Y., Peng Q., Cai Z., and Jiang Z.-H. Bioorg. Med. Chem. Lett. 15 (2005) 2689
27. Qin Y., Pang J.-Y., Chen W.-H., Cai Z., and Jiang Z.-H. Bioorg. Med. Chem. 14 (2006) 25
28. Hirakawa K., Kawanishi S., and Hirano T. Chem. Res. Toxicol. 18 (2005) 1545
29. Iwasa K., Kamigauchi M., Ueki M., and Taniguchi M. Eur. J. Med. Chem. 31 (1996) 469
30. Gaugain B., Barbet J., Capelle N., Roques B.P., Le Pecq J.B., and Le Bert M. Biochemistry 17 (1978) 5078
31. Le Pecq J.B., Le Bert M., Barbet J., and Roques B.P. Proc. Natl. Acad. Sci. U.S.A. 72 (1975) 2915
32. Long E.C., and Barton J.K. Acc. Chem. Res. 23 (1990) 271
33. Pyle C.V., Rehmann J.P., Meshoyrer R., Kumer C.V., Turro N.J., and Barton J.K. J. Am. Chem. Soc. 111 (1989) 3051
34. Palmatine, berberine, and berberine homodimers are reported to interact with double-stranded DNA in an intercalating mode. See Refs. 5b and 7b.
35. Schneider H.-J., and Yatsimirski A.K. Principles and Methods in Supramolecular Chemistry (2000), J. Wiley, New York 137-143