Multiple effects of berberine derivatives on colon cancer cells

BioMed Research International

Volumn 2014, Issue , 2014, Pages

  Guamán Ortiz, Luis Miguel ^a,b   Tillhon, Micol ^a   Parks, Michael ^a   Dutto, Ilaria ^a   Prosperi, Ennio ^a   Savio, Monica ^c   Arcamone, Andrea G ^d   Buzzetti, Franco ^d   Lombardi, Paolo ^d   Scovassi, Anna Ivana ^a  

^a CNR   (Italy)

^b UNIVERSIDAD TÉCNICA PARTICULAR DE LOJA   (Ecuador)

^c UNIVERSITY OF PAVIA   (Italy)

^d Naxospharma Srl   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; BERBERINE DERIVATIVE; DSA NAX 012; DSA NAX 014; DSA NAX 018; NAX 012; NAX 014; NAX018; UNCLASSIFIED DRUG; BERBERINE; PROTEIN P53;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; AUTOPHAGY; CANCER CELL; CELL CYCLE ARREST; CELL PROLIFERATION; CELL STRUCTURE; CELL VIABILITY; COLON CANCER; CONTROLLED STUDY; DRUG SYNTHESIS; GENE; GENE MUTATION; HCT116 CELL LINE; HUMAN; HUMAN CELL; P53 GENE; ANALOGS AND DERIVATIVES; COLONIC NEOPLASMS; DRUG EFFECTS; GENETICS; PATHOLOGY; SYNTHESIS;

ANTINEOPLASTIC AGENTS; APOPTOSIS; AUTOPHAGY; BERBERINE; CELL PROLIFERATION; COLONIC NEOPLASMS; HCT116 CELLS; HUMANS; TUMOR SUPPRESSOR PROTEIN P53;

EID: 84904170644     PISSN: 23146133     EISSN: 23146141     Source Type: Journal    
DOI: 10.1155/2014/924585     Document Type: Article

References (56)

1. Vuddanda P. R., Chakraborty S., Singh S., Berberine: a potential phytochemical with multispectrum therapeutic activities. Expert Opinion on Investigational Drugs 2010 19 10 1297 1307 2-s2.0-77956589652 10.1517/13543784.2010.517745
2. Huang Z.-J., Zeng Y., Lan P., Sun P.-H., Chen W.-M., Advances in structural modifications and biological activities of berberine: an active compound in traditional Chinese medicine. Mini-Reviews in Medicinal Chemistry 2011 11 13 1122 1129 2-s2.0-80054055026 10.2174/138955711797655362
3. Tillhon M., Guamán Ortiz L. M., Lombardi P., Scovassi A. I., Berberine: new perspectives for old remedies. Biochemical Pharmacology 2012 84 10 1260 1267 2-s2.0-84867846281 10.1016/j.bcp.2012.07.018
4. Derosa G., Maffioli P., Alkaloids in the nature: pharmacological applications in clinical practice of berberine and mate tea. Current Topics in Medicinal Chemistry 2014 14 2 200 206
5. Tan W., Li Y., Chen M., Wang Y., Berberine hydrochloride: anticancer activity and nanoparticulate delivery system. International Journal of Nanomedicine 2011 6 1773 1777 2-s2.0-84862832826
6. Lu J.-J., Bao J.-L., Chen X.-P., Huang M., Wang Y.-T., Alkaloids isolated from natural herbs as the anticancer agents. Evidence-Based Complementary and Alternative Medicine 2012 2012 12 2-s2.0-84866981349 10.1155/2012/485042 485042
7. Wang Y., Liu Q., Liu Z., Li B., Sun Z., Zhou H., Zhang X., Gong Y., Shao C., Berberine, a genotoxic alkaloid, induces ATM-Chk1 mediated G2 arrest in prostate cancer cells. Mutation Research 2012 734 1-2 20 29 2-s2.0-84862006905 10.1016/j.mrfmmm.2012.04.005
8. Wang J., Liu Q., Yang Q., Radiosensitization effects of berberine on human breast cancer cells. International Journal of Molecular Medicine 2012 30 5 1166 1172 2-s2.0-84866623599 10.3892/ijmm.2012.1095
9. Cai Y., Xia Q., Luo R., Huang P., Sun Y., Shi Y., Jiang W., Berberine inhibits the growth of human colorectal adenocarcinoma in vitro and in vivo. Journal of Natural Medicines 2013 68 1 53 62 2-s2.0-84876165965 10.1007/s11418-013-0766-z
10. Li J., Gu L., Zhang H., Liu T., Tian D., Zhou M., Zhou S., Berberine represses DAXX gene transcription and induces cancer cell apoptosis. Laboratory Investigation 2013 93 3 354 364 2-s2.0-84874591642 10.1038/labinvest.2012.172
11. Marverti G., Ligabue A., Lombardi P., Ferrari S., Monti M. G., Frassineti C., Costi M. P., Modulation of the expression of folate cycle enzymes and polyamine metabolism by berberine in cisplatin-sensitive and-resistant human ovarian cancer cells. International Journal of Oncology 2013 43 4 1269 1280 2-s2.0-84882447813 10.3892/ijo.2013.2045
12. Singh I. P., Mahajan S., Berberine and its derivatives: a patent review (2009-2012). Expert Opinion on Therapeutic Patents 2013 23 2 215 231 2-s2.0-84872724395 10.1517/13543776.2013.746314
13. Bhadra K., Kumar G. S., Therapeutic potential of nucleic acid-binding isoquinoline alkaloids: binding aspects and implications for drug design. Medicinal Research Reviews 2011 31 6 821 862 2-s2.0-79953751999 10.1002/med.20202
14. Kumar G. S., RNA targeting by small molecules: binding of protoberberine, benzophenanthridine and aristolochia alkaloids to various RNA structures. Journal of Biosciences 2012 37 3 539 552 2-s2.0-84864364001 10.1007/s12038-012- 9217-3
15. Bhowmik D., Das S., Hossain M., Haq L., Suresh Kumar G., Biophysical characterization of the strong stabilization of the RNA triplex poly(U)•poly(A) poly(U) by 9-O-(ω -amino) alkyl ether berberine analogs. PLoS ONE 2012 7 5 2-s2.0-84861556509 10.1371/journal.pone.0037939 e37939
16. Xiao N., Chen S., Ma Y., Qiu J., Tan J.-H., Ou T.-M., Gu L.-Q., Huang Z.-S., Li D., Interaction of Berberine derivative with protein POT1 affect telomere function in cancer cells. Biochemical and Biophysical Research Communications 2012 419 3 567 572 2-s2.0-84862805273 10.1016/j.bbrc.2012.02.063
17. Wang Y., Kheir M. M., Chai Y., Hu J., Xing D., Lei F., Du L., Comprehensive study in the inhibitory effect of berberine on gene transcription, including TATA box. PLoS ONE 2011 6 8 2-s2.0-80051951301 10.1371/journal.pone. 0023495 e23495
18. Choi M. S., Oh J. H., Kim S. M., Jung H. Y., Yoo H. S., Lee Y. M., Moon D. C., Han S. B., Hong J. T., Berberine inhibits p53-dependent cell growth through induction of apoptosis of prostate cancer cells. International Journal of Oncology 2009 34 5 1221 1230 2-s2.0-67649438659 10.3892/ijo-00000250
19. Yang X., Huang N., InvesBerberine induces selective apoptosis through the AMPK-mediated mitochondrial/caspase pathway in hepatocellular carcinoma. Molecular Medicine Reports 2013 8 2 505 510 2-s2.0-84879901015 10.3892/mmr.2013.1506
20. Kim H.-S., Kim M.-J., Kim E. J., Yang Y., Lee M.-S., Lim J.-S., Berberine-induced AMPK activation inhibits the metastatic potential of melanoma cells via reduction of ERK activity and COX-2 protein expression. Biochemical Pharmacology 2012 83 3 385 394 2-s2.0-84455208086 10.1016/j.bcp.2011.11.008
21. Fu L., Chen W., Guo W., Wang J., Tian Y., Shi D., Zhang X., Qiu H., Xiao X., Kang T., Huang W., Wang S., Deng W., Berberine targets AP-2/hTERT, NF- B/COX-2, HIF-1 /VEGF and cytochrome-c/caspase signaling to suppress human cancer cell growth. PLoS ONE 2013 8 7 2-s2.0-84880252424 10.1371/journal.pone.0069240 e69240
22. Wang N., Feng Y., Zhu M., Tsang C.-M., Man K., Tong Y., Tsao S.-W., Berberine induces autophagic cell death and mitochondrial apoptosis in liver cancer cells: the cellular mechanism. Journal of Cellular Biochemistry 2010 111 6 1426 1436 2-s2.0-78649775152 10.1002/jcb.22869
23. Waters M. L., Aromatic interactions in model systems. Current Opinion in Chemical Biology 2002 6 6 736 741 2-s2.0-0036897848 10.1016/S1367-5931(02)00359- 9 (Pubitemid 35449331)
24. Bhowmik D., Buzzetti F., Fiorillo G., Lombardi P., Suresh Kumar G., Spectroscopic studies on the binding interaction of novel 13-phenylalkyl analogs of the natural alkaloid berberine to nucleic acid triplexes. Spectrochimica Acta Part A 2014 120 257 264
25. Donzelli M., Bernardi R., Negri C., Prosperi E., Padovan L., Lavialle C., Brison O., Scovassi A. I., Apoptosis-prone phenotype of human colon carcinoma cells with a high level amplification of the c-myc gene. Oncogene 1999 18 2 439 448 2-s2.0-0033552956 10.1038/sj.onc.1202309 (Pubitemid 29060619)
26. + antiporter inhibitor HMA on cancer cells. Apoptosis 2013 18 12 1586 1598 2-s2.0-84883109960 10.1007/s10495-013-0898-3
27. Carpignano F., Silva G., Surdo S., Leva V., Montecucco A., Aredia F., Scovassi A. I., Merlo S., Barillaro G., Mazzini G., A new cell-selective three-dimensional microincubator based on silicon photonic crystals. PLoS ONE 2012 7 11 2-s2.0-84874368576 10.1371/journal.pone.0048556 e48556
28. Giansanti V., Camboni T., Piscitelli F., Prosperi E., La Regina G., Lazzè M. C., Santin G., Silvestri R., Scovassi A. I., Study of the effects of a new pyrazolecarboxamide: changes in mitochondria and induction of apoptosis. International Journal of Biochemistry and Cell Biology 2009 41 10 1890 1898 2-s2.0-68949092046 10.1016/j.biocel.2009.04.008
29. Parks M., Tillhon M., Donà F., Prosperi E., Scovassi A. I., 2-methoxyestradiol: new perspectives in colon carcinoma treatment. Molecular and Cellular Endocrinology 2011 331 1 119 128 2-s2.0-78149406276 10.1016/j.mce.2010.08.017
30. Savio M., Cerri M., Cazzalini O., Perucca P., Stivala L. A., Pichierri P., Franchitto A., Meijer L., Prosperi E., Replication-dependent DNA damage response triggered by roscovitine induces an uncoupling of DNA replication proteins. Cell Cycle 2006 5 18 2153 2159 2-s2.0-33749658586 (Pubitemid 44553751)
31. Torriglia A., Negri C., Chaudun E., Prosperi E., Courtois Y., Counis M. F., Scovassi A. I., Differential involvement of DNases in HeLa cell apoptosis induced by etoposide and long term-culture. Cell Death and Differentiation 1999 6 3 234 244 2-s2.0-0033009872 (Pubitemid 29145827)
32. Lo C.-Y., Hsu L.-C., Chen M.-S., Lin Y.-J., Chen L.-G., Kuo C.-D., Wu J.-Y., Synthesis and anticancer activity of a novel series of 9-O-substituted berberine derivatives: a lipophilic substitute role. Bioorganic and Medicinal Chemistry Letters 2013 23 1 305 309 2-s2.0-84871020246 10.1016/j.bmcl.2012.10. 098
33. Bhowmik D., Hossain M., Buzzetti F., D'Auria R., Lombardi P., Kumar G. S., Biophysical studies on the effect of the 13 position substitution of the anticancer alkaloid berberine on its DNA binding. Journal of Physical Chemistry B 2012 116 7 2314 2324 2-s2.0-84857424138 10.1021/jp210072a
34. Zhang L., Li J., Ma F., Yao S., Li N., Wang J., Wang Y., Wang X., Yao Q., Synthesis and cytotoxicity evaluation of 13-n-alkyl berberine and palmatine analogues as anticancer agents. Molecules 2012 17 10 11294 11302 2-s2.0-84868088803 10.3390/molecules171011294
35. Muller P. A., Vousden K. H., Mutant p53 in cancer: new functions and therapeutic opportunities. Cancer Cell 2014 25 3 304 317 10.1016/j.ccr.2014.01. 021
36. + FEBS Journal 2005 272 18 4576 4589 2-s2.0-25444463296 10.1111/j.1742-4658.2005.04864.x (Pubitemid 41372054)
37. Marchenko N. D., Wolff S., Erster S., Becker K., Moll U. M., Monoubiquitylation promotes mitochondrial p53 translocation. The EMBO Journal 2007 26 4 923 934 2-s2.0-33847276654 10.1038/sj.emboj.7601560
38. Cornel A., Sorrentino G., Capaci V., Del Sal G., The cytoplasmic side of p53's oncosuppressive activities. FEBS Letters 2014 10.1016/j.febslet.2014.04. 015
39. Pierpaoli E., Arcamone A. G., Buzzetti F., Lombardi P., Salvatore C., Provinciali M., Antitumor effect of novel berberine derivatives in breast cancer cells. BioFactors 2013 39 6 672 679 2-s2.0-84883162448 10.1002/biof.1131
40. Albring K. F., Weidemüller J., Mittag S., Weiske J., Friedrich K., Geroni M. C., Lombardi P., Huber O., Berberine acts as a natural inhibitor of Wnt/ β -catenin signaling-Identification of more active 13-arylalkyl derivatives. BioFactors 2013 39 6 652 662 2-s2.0-84882521993 10.1002/biof.1133
41. He W., Wang B., Zhuang Y., Shao D., Sun K., Chen J., Berberine inhibits growth and induces G1 arrest and apoptosis in human cholangiocarcinoma QBC939 cells. Journal of Pharmacological Sciences 2012 119 4 341 348 2-s2.0-84865419415 10.1254/jphs.12052FP
42. Liu Z., Liu Q., Xu B., Wu J., Guo C., Zhu F., Yang Q., Gao G., Gong Y., Shao C., Berberine induces p53-dependent cell cycle arrest and apoptosis of human osteosarcoma cells by inflicting DNA damage. Mutation Research 2009 662 1-2 75 83 2-s2.0-60449106119 10.1016/j.mrfmmm.2008.12.009
43. Myoung S. C., Dong Y. Y., Ju H. O., Hai Y. J., Sang B. H., Dong C. M., Jin T. H., Berberine inhibits human neuroblastoma cell growth through induction of p53-dependent apoptosis. Anticancer Research 2008 28 6 A 3777 3784 2-s2.0-58149163569
44. Yip N. K., Ho W. S., Berberine induces apoptosis via the mitochondrial pathway in liver cancer cells. Oncology Reports 2013 30 3 1107 1112 2-s2.0-84880592343 10.3892/or.2013.2543
45. Katiyar S. K., Meeran S. M., Katiyar N., Akhtar S., P53 cooperates berberine-induced growth inhibition and apoptosis of non-small cell human lung cancer cells in vitro and tumor xenograft growth in vivo. Molecular Carcinogenesis 2009 48 1 24 37 2-s2.0-58849122415 10.1002/mc.20453
46. Lee S.-J., Noh H.-J., Sung E.-G., Song I.-H., Kim J.-Y., Kwon T. K., Lee T.-J., Berberine sensitizes TRAIL-induced apoptosis through proteasome-mediated downregulation of c-FLIP and Mcl-1 proteins. International Journal of Oncology 2011 38 2 485 492 2-s2.0-78651254850 10.3892/ijo.2010.878
47. Goto H., Kariya R., Shimamoto M., Kudo E., Taura M., Katano H., Okada S., Antitumor effect of berberine against primary effusion lymphoma via inhibition of NF- B pathway. Cancer Science 2012 103 4 775 781 2-s2.0-84859005485 10.1111/j.1349-7006.2012.02212.x
48. Andrabi S. A., Dawson T. M., Dawson V. L., Mitochondrial and nuclear cross talk in cell death: parthanatos. Annals of the New York Academy of Sciences 2008 1147 233 241 2-s2.0-57649233085 10.1196/annals.1427.014
49. Wang L., Liu L., Shi Y., Cao H., Chaturvedi R., Calcutt M. W., Hu T., Ren X., Wilson K. T., Polk D. B., Yan F., Berberine induces caspase-independent cell death in colon tumor cells through activation of apoptosis-inducing factor. PLoS ONE 2012 7 5 2-s2.0-84860521181 10.1371/journal.pone.0036418 e36418
50. Peng P.-L., Kuo W.-H., Tseng H.-C., Chou F.-P., Synergistic tumor-killing effect of radiation and berberine combined treatment in lung cancer: the contribution of autophagic cell death. International Journal of Radiation Oncology Biology Physics 2008 70 2 529 542 2-s2.0-38149008948 10.1016/j.ijrobp.2007.08.034
51. Hou Q., Tang X., Liu H., Tang J., Yang Y., Jing X., Xiao Q., Wang W., Gou X., Wang Z., Berberine induces cell death in human hepatoma cells in vitro by downregulating CD147. Cancer Science 2011 102 7 1287 1292 2-s2.0-79959262084 10.1111/j.1349-7006.2011.01933.x
52. Giansanti V., Torriglia A., Scovassi A. I., Conversation between apoptosis and autophagy: is it your turn or mine? Apoptosis 2011 16 4 321 333 2-s2.0-79955755460 10.1007/s10495-011-0589-x
53. Chidambara Murthy K. N., Jayaprakasha G. K., Patil B. S., The natural alkaloid berberine targets multiple pathways to induce cell death in cultured human colon cancer cells. European Journal of Pharmacology 2012 688 1-3 14 21 2-s2.0-84863529339 10.1016/j.ejphar.2012.05.004
54. Teiten M.-H., Gaascht F., Dicato M., Diederich M., Anticancer bioactivity of compounds from medicinal plants used in European medieval traditions. Biochemical Pharmacology 2013 86 9 1239 1247 2-s2.0-84883466225 10.1016/j.bcp.2013.08.007
55. Guamán Ortiz L. M., Scovassi A. I., Traditional medicine: an ancient remedy rediscovered. Biochemistry & Pharmacology 2013 2 1 110 10.4172/2167-0501.1000110
56. Karaosmanoglu K., Sayar N. A., Kurnaz I. A., Akbulut B. S., Assessment of Berberine as a multi-target antimicrobial: a multi-omics study for drug discovery and repositioning. OMICS 2014 18 1 42 53 10.1089/omi.2013.0100