Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

NMR Studies on Antitumor Drug Candidates, Berberine and Berberrubine

  • Published : 2002.03.20
Download PDF
⟨ Previous Next ⟩

Abstract

Berberine and berberrubine, which display antitumor activity, have also demonstrated distinct enzyme-poisoning activities by stabilizing topoisomerase Ⅱ-DNA cleavable complexes. The protoberberine berberrubine differs in chemical structure with berberine at only one position, however, it shows a prominent activity difference from berberine. Solution structures of berberine and berberrubine determined by NMR spectroscopy are similar, however, the minor structural rearrangement has been observed near 19 methoxy or hydroxyl group. We suggest that the DNA cleavage activities of topoisomerase Ⅱ poisons could be correlated with both chemical environments and minor structural change together with hydrophobicity of interacting side chains of drugs with DNA molecule.

Keywords

References

  1. Wang, J. C. Annu. Rev. Biochem. 1996, 65, 635-692. https://doi.org/10.1146/annurev.bi.65.070196.003223
  2. Watt, P. M.; Hickson, I. D. Biochem. J. 1994, 303, 681-695. https://doi.org/10.1042/bj3030681
  3. Corbett, A. H.; Osheroff, N. Chem. Res. Toxicol. 1993, 6, 585-597. https://doi.org/10.1021/tx00035a001
  4. Froelich-Ammon, S. J.; Osheroff, N. J. Biol. Chem. 1995, 270,21429-21432. https://doi.org/10.1074/jbc.270.37.21429
  5. Pommier, Y.; Leteurtre, F.; Fesen, M. R.; Fujimori, A.; Bertrand,R.; Soary, E.; Kohlhagen, G.; Kohn, K. W. Cancer Invest. 1994,12, 530-542. https://doi.org/10.3109/07357909409021413
  6. Berger, J. N.; Gamblin, S. J.; Harrison, S. C.; Wang, J. C. Nature1996, 379, 225-232. https://doi.org/10.1038/379225a0
  7. Osheroff, N. Pharmacol. Ther. 1989, 41, 223-241. https://doi.org/10.1016/0163-7258(89)90108-3
  8. Roca, J.; Wang, J. C. Cell 1994, 77, 609-616. https://doi.org/10.1016/0092-8674(94)90222-4
  9. Chen, A. Y.; Liu, L. F. Annu. Rev. Pharmacol. Toxicol. 1994, 34,191-218. https://doi.org/10.1146/annurev.pa.34.040194.001203
  10. Lin, J. G.; Chung, J. G.; Wu, L. T. Am. J. Chin. Med. 1999, 27,265-275. https://doi.org/10.1142/S0192415X99000306
  11. Fukuda, K.; Hibiya, Y.; Mutoh, M. J. Ethnopharmacol. 1999, 66,227-233. https://doi.org/10.1016/S0378-8741(98)00162-7
  12. Creasey, W. A. Biochem. Pharmacol. 1979, 28, 1081-1084. https://doi.org/10.1016/0006-2952(79)90308-3
  13. Hong, S. W.; Kim, S. H.; Jeun, J. A.; Lee, S. J.; Kim, J. H. PlantaMed. 2000, 66(4), 361-363. https://doi.org/10.1055/s-2000-8536
  14. Kim, S. A.; Kwon, Y.; Kim, J. H.; Muller, M. T.; Chung, I. K.Biochemistry 1998, 37, 16316-16324. https://doi.org/10.1021/bi9810961
  15. Hoshi, A.; Ikekawa, T.; Ikeda, Y.; Shirakawa, S.; Iigo, M.;Kuretani, K.; Fukuoka, F. Gann 1976, 67, 321-325.
  16. Ikekawa, T.; Ikeda, Y. J. Pharmacobio-Dyn. 1982, 5, 469-474. https://doi.org/10.1248/bpb1978.5.469
  17. Krishnan, P.; Bastow, K. F. Anticancer Drug Des. 2000, 15(4),255-264.
  18. Spath, E.; Polgar, N. Monatish. Chem. 1929, 52, 117-128. https://doi.org/10.1007/BF02715980
  19. Rance, M.; Sorensen, O. W.; Bodenhausen, G.; Wagner, G.; Ernst,R. R.; Wuthrich, K. Biochem. Biophys. Res. Commun. 1983, 117,479-485. https://doi.org/10.1016/0006-291X(83)91225-1
  20. Derome, A.; Davis, D. G. J. Magn. Reson. 1990, 88, 117-185.
  21. Bax, A.; Davis, D. G. J. Magn. Reson. 1985, 63, 207-213.
  22. Bax, A.; Summers, M. F. J. Am. Chem. Soc. 1986, 108, 2093-2094. https://doi.org/10.1021/ja00268a061
  23. Scheucher, J.; Schwendinger, M.; Sattler, M.; Schmidt, P.;Schedletzky, O.; Glaser, S. J.; Sorensen, O. W.; Griesinger, C. J.Biomol. NMR 1994, 4, 301-306.
  24. Kleywegt, G. J.; Jones, T. A. Acta Crystallogr. 1998, D54, 1119-1131.
  25. Lee, C. H.; Hong, H. D.; Shin, J.; Jung, M. K.; Shin, I. J., Yoon, J.B.; Lee, W. Biochem. Biophys. Res. Commun. 2000, 274, 359-369. https://doi.org/10.1006/bbrc.2000.3086

Cited by

  1. β-Phenylethylamines and the isoquinoline alkaloids vol.21, pp.3, 2004, https://doi.org/10.1039/B212259F
  2. Berberine and Its Metabolites: Relationship between Physicochemical Properties and Plasma Levels after Administration to Human Subjects vol.77, pp.4, 2014, https://doi.org/10.1021/np400607k
  3. Non-Targeted Secondary Metabolite Profile Study for Deciphering the Cosmeceutical Potential of Red Marine Macro Alga Jania rubens—An LCMS-Based Approach vol.4, pp.4, 2017, https://doi.org/10.3390/cosmetics4040045
  4. DNA-Binding Affinities and Sequence Specificities of Protoberberine Alkaloids and Their Demethylated Derivatives: A Comparative Study vol.4, pp.2, 2007, https://doi.org/10.1002/cbdv.200790019
  5. Quantum chemical and nuclear magnetic resonance spectral studies on molecular properties and electronic structure of berberine and berberrubine vol.45, pp.8, 2007, https://doi.org/10.1002/mrc.2019
  6. Analysis of major alkaloids inRhizoma coptidis by capillary electrophoresis-electrospray-time of flight mass spectrometry with different background electrolytes vol.29, pp.10, 2008, https://doi.org/10.1002/elps.200700797
  7. Based on Microcalorimetry vol.27, pp.6, 2009, https://doi.org/10.1002/cjoc.200990199
  8. Two New Furanocoumarins from the Roots of Angelica dahurica vol.24, pp.11, 2002, https://doi.org/10.5012/bkcs.2003.24.11.1699
  9. A Theoretical Study on the N-Alkylation of a Pyrimidine with a Cyclopropa[c]inden-5-one; A Model Pharmacophore of Duocarmycins and CC-1065 vol.25, pp.1, 2002, https://doi.org/10.5012/bkcs.2004.25.1.069
  10. New Isoflavone Glycoside from the Woods of Sophora japonica vol.25, pp.1, 2004, https://doi.org/10.5012/bkcs.2004.25.1.147
  11. Diarylheptanoids from the Roots of Juglans mandshurica vol.25, pp.3, 2002, https://doi.org/10.5012/bkcs.2004.25.3.397
  12. DNA Binding Mode of the Isoquinoline Alkaloid Berberine with the Deoxyoligonucleotide d(GCCGTCGTTTTACA)2 vol.25, pp.4, 2002, https://doi.org/10.5012/bkcs.2004.25.4.539
  13. Two New Diarylheptanoids from Juglans mandshurica vol.26, pp.11, 2002, https://doi.org/10.5012/bkcs.2005.26.11.1878
  14. Analysis of alkaloids in Coptis chinensis Franch by accelerated solvent extraction combined with ultra performance liquid chromatographic analysis with photodiode array and tandem mass spectrometry de vol.613, pp.2, 2002, https://doi.org/10.1016/j.aca.2008.02.060
  15. Spontaneous Formation of Fluorescent Nanofibers and Reticulated Solid from Berberine Palmitate: A New Example of Aggregation-Induced Emission Enhancement in Organic Ion Pairs vol.27, pp.6, 2002, https://doi.org/10.1021/la104302d
  16. A new quaternary protoberberine alkaloid isolated from Dicranostigma leptopodum (Maxim) Fedde vol.28, pp.8, 2002, https://doi.org/10.1080/14786419.2013.879586
  17. Effects of pectin and tomato paste as a natural antioxidant on inhibition of lipid oxidation and production of functional chicken breast sausage vol.40, pp.2, 2002, https://doi.org/10.1590/fst.26419
  18. The electronic states and vibronic absorption spectrum of berberine in aqueous solution vol.121, pp.6, 2002, https://doi.org/10.1002/qua.26537