Synthesis and DNA-binding affinities of monomodified berberines

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 20, 2005, Pages 5835-5840

  Pang, Ji Yan ^a   Qin, Yong ^b   Chen, Wen Hua ^a   Luo, Guo An ^c   Jiang, Zhi Hong ^b  

^a SUN YAT SEN UNIVERSITY   (China)

^b HONG KONG BAPTIST UNIVERSITY   (Hong Kong)

^c TSINGHUA UNIVERSITY   (China)

Author keywords

Berberine; DNA binder; Spectrometry; Synthesis

Indexed keywords

9 O 2 (1' IMIDAZOLYLETHYL)BERBERINE; 9 O 2 (4' ETHYLPIPERAZINYLETHYL)BERBERINE; 9 O 2 AMINOETHYLBERBERINE; 9 O 2 HYDROXYETHYLBERBERINE; AMIDE; BERBERINE DERIVATIVE; DNA; ETHIDIUM BROMIDE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CATTLE; DNA BINDING; DRUG DNA BINDING; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; THYMUS; TITRIMETRY;

BERBERINE; BINDING, COMPETITIVE; DNA; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR STRUCTURE;

EID: 24344476072     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.05.048     Document Type: Article

References (29)

1. W.A. Creasey Biochem. Pharmacol. 28 1979 1081
2. T.C. Birdsall, and G.S. Kelley Altern. Med. Rev. 2 1997 94
3. C.W. Lau, X.Q. Yao, Z.Y. Chen, W.H. Kou, and Y. Huang Cardiovasc. Drug Rev. 19 2001 234
4. A.K. Krey, and F.E. Halm Science 166 1969 755
5. S. Mazzini, M.C. Bellucci, and R. Mondelli Bioorg. Med. Chem. 11 2003 505
6. J. Kluza, B. Baldeyron, P. Colson, P. Rasoanaivo, L. Mambu, F. Frappier, and C. Bailly Eur. J. Pharm. Sci. 20 2003 381
7. R.C. Yadav, G.S. Kumar, K. Bhadra, P. Giri, R. Sinha, S. Pal, and M. Maiti Bioorg. Med. Chem. 13 2005 165
8. W.-H. Chen, C.-L. Chan, Z. Cai, G.-A. Luo, and Z.-H. Jiang Bioorg. Med. Chem. Lett. 14 2004 4955
9. W.-H. Chen, Y. Qin, Z. Cai, C.-L. Chan, G.-A. Luo, and Z.-H. Jiang Bioorg. Med. Chem. 13 2005 1859
10. W.-H. Chen, J.-Y. Pang, Y. Qin, Q. Peng, Z. Cai, and Z.-H. Jiang Bioorg. Med. Chem. Lett. 15 2005 2689
11. C.L. Kuo, C.C. Chou, and B.Y.M. Yung Cancer Lett. 93 1995 193
12. H.L. Wu, C.Y. Hsu, W.H. Liu, and B.Y. Yung Int. J. Cancer 81 1999 293
13. G.S. Kumar, D. Debnath, A. Sen, and M. Maiti Biochem. Pharmacol. 46 1993 1665
14. T.-K. Li, E. Bathory, E.J. LaVoie, A.R. Srinivasan, W.K. Olson, and R.R. Sauer Biochemistry 39 2000 7107
15. P. Krishnan, and K.F. Bastow Anti-Cancer Drug Des. 15 2000 255
16. K. Iwasa, H.S. Kim, Y. Wataya, and D.U. Lee Eur. J. Med. Chem. 33 1998 65
17. K.R. Fox Drug-DNA interaction protocols 1997 Humana Press Totowa, New Jersey
18. H.J. Schneider, and A.K. Yatsimirski Principles and methods in supramolecular chemistry 2000 John Wiley New York pp 137-143.
19. (Poly)amine-modified DNA-binders have highly enhanced affinities toward DNA. See for examples: P. Laugaa, J. Markovits, A. Delbarre, J.-B. Le Pecq, and B.P. Roques Biochemistry 24 1985 5567
20. I.S. Blagbrough, S. Taylor, M.L. Carpenter, V. Novoselskiy, T. Shamma, and I.S. Haworth Chem. Commun. 1998 929
21. L. Wang, H.L. Price, J. Juusola, M. Kline, and O. Phanstiel IV J. Med. Chem. 44 2001 3682
22. E.C. Long, and J.K. Barton Acc. Chem. Res. 23 1990 271
23. C.V. Pyle, J.P. Rehmann, R. Meshoyrer, C.V. Kumer, N.J. Turro, and J.K. Barton J. Am. Chem. Soc. 111 1989 3051
24. H. Ihmels, K. Faulhaber, and G. Viola Evaluation of the DNA-binding properties of cationic dyes by absorption and emission spectroscopy C. Schmuck H. Wennemers Highlights in bioorganic chemistry: methods and applications 2004 Wiley-VCH Weinheim
25. R.F. Pasterack, E.J. Gibbs, and J.J. Villafranca Biochemistry 22 1983 2406
26. B. Juskowiak, E. Galezowska, and S. Takenaka Spectrochim. Acta Part A 2003 1083
27. D.L. Boger, B.E. Fink, S.R. Brunette, W.C. Tse, and M.P. Hedrick J. Am. Chem. Soc. 123 2001 5878
28. Under the same conditions, berberine can also displace EB from CT DNA-EB complexes, but to a much less extent. This may result from the weaker interaction of berberine with CT DNA.
29. K. Hamasaki, and R.R. Rando Anal. Biochem. 261 1998 183