B-9-3, a novel β-carboline derivative exhibits anti-cancer activity via induction of apoptosis and inhibition of cell migration in vitro

European Journal of Pharmacology

Volumn 724, Issue 1, 2014, Pages 219-230

  Daoud, Abdelkader ^a   Song, Jing ^a   Xiao, Feiyang ^a   Shang, Jing ^a  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

Anti tumor; Harmane; Necro apoptosis; Peganum harmala L

Indexed keywords

ANTINEOPLASTIC AGENT; B 9 3; UNCLASSIFIED DRUG;

ANTIANGIOGENIC ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CANCER INHIBITION; CELL CYCLE G0 PHASE; CELL VIABILITY; CONTROLLED STUDY; DRUG STRUCTURE; FLOW CYTOMETRY; G2 PHASE CELL CYCLE CHECKPOINT; HOECHST STAINING; HUMAN; HUMAN CELL; HUMAN UMBILICAL VASCULAR ENDOTHELIAL CELL; IN VITRO STUDY; MIGRATION INHIBITION; NECROPTOSIS; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; S PHASE CELL CYCLE CHECKPOINT; STAINING; VASCULAR ENDOTHELIUM; WESTERN BLOTTING;

ANTI-TUMOR; HARMANE; NECRO-APOPTOSIS; PEGANUM HARMALA L;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; APOPTOSIS; CARBOLINES; CELL LINE, TUMOR; CELL MOVEMENT; HUMANS; PEGANUM;

EID: 84892737335     PISSN: 00142999     EISSN: 18790712     Source Type: Journal    
DOI: 10.1016/j.ejphar.2013.12.038     Document Type: Article

References (46)

1. M.L. Alomar, F.A. Rasse-Suriani, A. Ganuza, V.M. Coceres, F.M. Cabrerizo, and S.O. Angel In vitro evaluation of beta-carboline alkaloids as potential anti-Toxoplasma agents BMC Res. Notes 6 2013 193
2. J.R., F. Asgarpanah Chemistry, pharmacology and medicinal properties of Peganum harmala L Afr. J. Pharm. Pharmacol. 6 2012 1573 1580
3. E. Augustin, A. Mos-Rompa, D. Nowak-Ziatyk, and J. Konopa Antitumor 1-nitroacridine derivative C-1748, induces apoptosis, necrosis or senescence in human colon carcinoma HCT8 and HT29 cells Biochem. Pharmacol. 79 2010 1231 1241
4. D.L. Bemis, J.L. Capodice, P. Gorroochurn, A.E. Katz, and R. Buttyan Anti-prostate cancer activity of a beta-carboline alkaloid enriched extract from Rauwolfia vomitoria Int. J. Oncol. 29 2006 1065 1073
5. R. Cao, W. Peng, Z. Wang, and A. Xu beta-Carboline alkaloids: biochemical and pharmacological functions Curr. Med. Chem. 14 2007 479 500
6. Cordell, G.A., 2008. The alkaloids: chemistry and biology. Preface. The Alkaloids. Chemistry and Biology 65, ix. Elsevier Science, Amsterdam.
7. P. Cumming, and S.R. Vincent Inhibition of histamine-N-methyltransferase (HNMT) by fragments of 9-amino-1,2,3,4-tetrahydroacridine (tacrine) and by beta-carbolines Biochem. Pharmacol. 44 1992 989 992
8. C. Di Giorgio, F. Delmas, E. Ollivier, R. Elias, G. Balansard, and P. Timon-David In vitro activity of the beta-carboline alkaloids harmane, harmine, and harmaline toward parasites of the species Leishmania infantum Exp. Parasitol. 106 2004 67 74 (Pubitemid 38686275)
9. X. Di, R.P. Shiu, I.F. Newsham, and D.A. Gewirtz Apoptosis, autophagy, accelerated senescence and reactive oxygen in the response of human breast tumor cells to adriamycin Biochem. Pharmacol. 77 2009 1139 1150
10. J. Ferlay, H.R. Shin, F. Bray, C. Mathers, and D.M. Parkin GLOBOCAN 2008 cancer incidence and mortality worldwide: IARC CancerBase no. 10 2008 International Agency for Research on Cancer Lyon, France
11. J. Gerardy Effect of moclobemide on rat brain monoamine oxidase A and B: comparison with harmaline and clorgyline Prog. Neuropsychopharmacol. Biol. Psychiatry 18 1994 793 802
12. P. Golstein, and G. Kroemer Cell death by necrosis: towards a molecular definition Trends Biochem. Sci. 32 2007 37 43 (Pubitemid 46043552)
13. T.P. Hamsa, and G. Kuttan Harmine activates intrinsic and extrinsic pathways of apoptosis in B16F-10 melanoma Chin. Med. 6 2011 11
14. X. Han, J. Zhang, L. Guo, R. Cao, Y. Li, N. Li, Q. Ma, J. Wu, Y. Wang, and S. Si A series of beta-carboline derivatives inhibit the kinase activity of PLKs PloS One 7 2012 e46546
15. Y.A. Hannun Apoptosis and the dilemma of cancer chemotherapy Blood 89 1997 1845 1853 (Pubitemid 27132097)
16. C. Huisman, C.G. Ferreira, L.E. Broker, J.A. Rodriguez, E.F. Smit, P.E. Postmus, F.A. Kruyt, and G. Giaccone Paclitaxel triggers cell death primarily via caspase-independent routes in the non-small cell lung cancer cell line NCI-H460 Clin. Cancer Res. Off. J. Am. Assoc. Cancer Res. 8 2002 596 606 (Pubitemid 34193982)
17. R. Ikeda, T. Iwaki, T. Iida, T. Okabayashi, E. Nishi, M. Kurosawa, N. Sakai, and T. Konakahara 3-benzylamino-beta-carboline derivatives induce apoptosis through G2/M arrest in human carcinoma cells HeLa S-3 Eur. J. Med. Chem. 46 2011 636 646
18. R. Ikeda, T. Kimura, T. Tsutsumi, S. Tamura, N. Sakai, and T. Konakahara Structure-activity relationship in the antitumor activity of 6-, 8- or 6,8-substituted 3-benzylamino-beta-carboline derivatives Bioorg. Med. Chem. Lett. 22 2012 3506 3515
19. J. Ishida, H.K. Wang, K.F. Bastow, C.Q. Hu, and K.H. Lee Antitumor agents 201. Cytotoxicity of harmine and beta-carboline analogs Bioorg. Med. Chem. Lett. 9 1999 3319 3324
20. F. Jahaniani, S.A. Ebrahimi, N. Rahbar-Roshandel, and M. Mahmoudian Xanthomicrol is the main cytotoxic component of Dracocephalum kotschyii and a potential anti-cancer agent Phytochemistry 66 2005 1581 1592 (Pubitemid 40950551)
21. M. Kartal, M.L. Altun, and S. Kurucu HPLC method for the analysis of harmol, harmalol, harmine and harmaline in the seeds of Peganum harmala L J. Pharm. Biomed. Anal. 31 2003 263 269 (Pubitemid 36254808)
22. M. Kong, J. Fan, A. Dong, H. Cheng, and R. Xu Effects of polyphyllin I on growth inhibition of human non-small lung cancer cells and in xenograft Acta Biochim. Biophys. Sin. 42 2010 827 833
23. W. Kuhn, T. Muller, H. Grosse, T. Dierks, and H. Rommelspacher Plasma levels of the beta-carbolines harman and norharman in Parkinson×s disease Acta Neurol. Scand. 92 1995 451 454 (Pubitemid 3008315)
24. F. Lamchi, A. Settaf, Y. Cherrah, M. Zemzami, B. Lyoussi, A. Zaid, N. Atif, and M. Hassar Antitumour principles from Peganum harmala seeds Therapie 54 1999 753 758 (Pubitemid 30085378)
25. T. Landemaine, A. Jackson, A. Bellahcene, N. Rucci, S. Sin, B.M. Abad, A. Sierra, A. Boudinet, J.M. Guinebretiere, E. Ricevuto, C. Nogues, M. Briffod, I. Bieche, P. Cherel, T. Garcia, V. Castronovo, A. Teti, R. Lidereau, and K. Driouch A six-gene signature predicting breast cancer lung metastasis Cancer Res. 68 2008 6092 6099
26. Y. Li, F. Liang, W. Jiang, F. Yu, R. Cao, Q. Ma, X. Dai, J. Jiang, Y. Wang, and S. Si DH334, a beta-carboline anti-cancer drug, inhibits the CDK activity of budding yeast Cancer Biol. Ther. 6 2007 1193 1199 (Pubitemid 351590371)
27. J. Liebl, S.B. Weitensteiner, G. Vereb, L. Takacs, R. Furst, A.M. Vollmar, and S. Zahler Cyclin-dependent kinase 5 regulates endothelial cell migration and angiogenesis J. Biol. Chem. 285 2010 35932 35943
28. B.P. Liu, E.Y. Chong, F.W. Cheung, J.A. Duan, C.T. Che, and W.K. Liu Tangutorine induces p21 expression and abnormal mitosis in human colon cancer HT-29 cells Biochem. Pharmacol. 70 2005 287 299 (Pubitemid 40814410)
29. J.S. Long, and K.M. Ryan New frontiers in promoting tumour cell death: targeting apoptosis, necroptosis and autophagy Oncogene 31 2012 5045 5060
30. E.J. Massaro Handbook of Neurotoxicology Vol. 2 2002 Humana Press
31. H.R. Monsef, A. Ghobadi, M. Iranshahi, and M. Abdollahi Antinociceptive effects of Peganum harmala L. alkaloid extract on mouse formalin test J. Pharm. Pharm. Sci. Publication Can. Soc. Pharm. Sci., Soc. Can. Sci. Pharm. 7 2004 65 69 (Pubitemid 38628938)
32. G. Nenaah Antibacterial and antifungal activities of (beta)-carboline alkaloids of Peganum harmala (L) seeds and their combination effects Fitoterapia 81 2010 779 782
33. Z. Pan, and L. Gollahon Taxol directly induces endoplasmic reticulum-associated calcium changes that promote apoptosis in breast cancer cells Breast J. 17 2011 56 70
34. W. Polanski, C. Enzensperger, H. Reichmann, and G. Gille The exceptional properties of 9-methyl-beta-carboline: stimulation, protection and regeneration of dopaminergic neurons coupled with anti-inflammatory effects J. Neurochem. 113 2010 1659 1675
35. W. Polanski, H. Reichmann, and G. Gille Stimulation, protection and regeneration of dopaminergic neurons by 9-methyl-beta-carboline: a new anti-Parkinson drug? Expert Rev. Neurother. 11 2011 845 860
36. L. Quan, A.P. Stassen, C.A. Ruivenkamp, T. van Wezel, R.J. Fijneman, A. Hutson, N. Kakarlapudi, A.A. Hart, and P. Demant Most lung and colon cancer susceptibility genes are pair-wise linked in mice, humans and rats PloS One 6 2011 e14727
37. E. Sahai Illuminating the metastatic process Nat. Rev. Cancer 7 2007 737 749 (Pubitemid 47463672)
38. A.M. Sobhani, S.A. Ebrahimi, and M. Mahmoudian An in vitro evaluation of human DNA topoisomerase I inhibition by Peganum harmala L. seeds extract and its beta-carboline alkaloids J. Pharm. Pharm. Sci. Publication Can. Soc. Pharm. Sci., Soc. Can. Sci. Pharm. 5 2002 19 23 (Pubitemid 34463347)
39. Y. Song, J. Wang, S.F. Teng, D. Kesuma, Y. Deng, J. Duan, J.H. Wang, R.Z. Qi, and M.M. Sim Beta-carbolines as specific inhibitors of cyclin-dependent kinases Bioorg. Med. Chem. Lett. 12 2002 1129 1132 (Pubitemid 34242818)
40. R. Supino, G. Petrangolini, G. Pratesi, M. Tortoreto, E. Favini, L.D. Bo, P. Casalini, E. Radaelli, A.C. Croce, G. Bottiroli, P. Misiano, C. Farina, and F. Zunino Antimetastatic effect of a small-molecule vacuolar H+-ATPase inhibitor in in vitro and in vivo preclinical studies J. Pharmacol. Exp. Ther. 324 2008 15 22 (Pubitemid 350294162)
41. R. Susilo, and H. Rommelspacher Formation of a beta-carboline (1,2,3,4-tetrahydro-1-methyl-beta-carboline-1-carboxylic acid) following intracerebroventricular injection of tryptamine and pyruvic acid Naunyn Schmiedebergs Arch. Pharmacol. 335 1987 70 76 (Pubitemid 17000919)
42. R. Tournaire, M.P. Simon, F. le Noble, A. Eichmann, P. England, and J. Pouyssegur A short synthetic peptide inhibits signal transduction, migration and angiogenesis mediated by Tie2 receptor EMBO Rep. 5 2004 262 267 (Pubitemid 38500105)
43. L. Weng, J. Brown, and C. Eng PTEN induces apoptosis and cell cycle arrest through phosphoinositol-3-kinase/Akt-dependent and -independent pathways Hum. Mol. Genet. 10 2001 237 242 (Pubitemid 32123982)
44. H. Yamaguchi, J. Wyckoff, and J. Condeelis Cell migration in tumors Curr. Opin. Cell. Biol. 17 2005 559 564 (Pubitemid 41267171)
45. L. Yu, H.Z. Li, S.M. Lu, W.W. Liu, J.F. Li, H.B. Wang, and W. Xu Alteration in TWIST expression: possible role in paclitaxel-induced apoptosis in human laryngeal carcinoma Hep-2 cell line Croat. Med. J. 50 2009 536 542
46. H. Zhang, H. Li, L. Yang, Z. Deng, H. Luo, D. Ye, Z. Bai, L. Zhu, W. Ye, L. Wang, and L. Chen The ClC-3 chloride channel associated with microtubules is a target of paclitaxel in its induced-apoptosis Sci. Rep. 3 2013 2615