Brassinin and its derivatives as potential anticancer agents

Toxicology in Vitro

Volumn 28, Issue 5, 2014, Pages 909-915

  Chripkova, Martina ^a   Drutovic, David ^a   Pilatova, Martina ^a   Mikes, Jaromir ^a   Budovska, Mariana ^a   Vaskova, Janka ^a   Broggini, Massimo ^b   Mirossay, Ladislav ^a   Mojzis, Jan ^a  

^a P J AFÁRIK UNIVERSITY   (Slovakia)

^b MARIO NEGRI INSTITUTE FOR PHARMACOLOGICAL RESEARCH   (Italy)

Author keywords

Anti proliferative effect; Apoptosis; Brassinin; Indole phytoalexins

Indexed keywords

1 (2,3,4,6 TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSYL); 1 (2,3,5 TRI O ACETYL BETA DEXTRO RIBOFURANOSYL)BRASSININ; 1 (8 PHENYLMENTHOXYCARBONYL) BRASSININ; 1 (BETA DEXTRO GLUCOPYRANOSYL)BRASSININ; 1 (CAMPHOR 10 SULFONYL)BRASSININ; 1 (MENTHOXYCARBONYL)BRASSININ; 1 ACETYLBRASSININ; 1 BENZOYLBRASSININ; 1 METHOXYBRASSININ; 1 METHOXYCARBONYL BRASSININ; ANTINEOPLASTIC AGENT; BRASSININ; BRASSININ DERIVATIVE; CASPASE 3; CASPASE 7; GLUTATHIONE; METHYL 2 (1H INDOL 3 YL)ACETYLCARBAMODITHIOATE; N [(1 METHOXY INDOL 3 YL)METHYL] N' (4 CHLOROPHENYL)THIOUREA; N [(1 METHOXY INDOL 3 YL)METHYL] N' (4 METHOXYPHENYL)THIOUREA; N [(1 METHOXY INDOL 3 YL)METHYL] N' INDOL 3 YLMETHYLTHIOUREA; N [[(1 TERT BUTOXYCARBONYL)INDOL 3 YL]METHYL] N' (4 METHOXYPHENYL)THIOUREA; N [[(1 TERT BUTOXYCARBONYL)INDOL 3 YL]METHYL] N' (4 METHYLPHENYL)THIOUREA; N [[1 (TERT BUTOXYCARBONYL)INDOL 3 YL]METHYL] N' INDOL 3 YLMETHYLTHIOUREA; N [[1 (TERT BUTOXYCARBONYL)INDOL 3 YL]METHYL] N' METHYL N' PHENYLTHIOUREA; N [[1 (TERT BUTOXYCARBONYL)INDOL 3 YL]METHYL] N' PHENYLTHIOUREA; N [[1 (TERT BUTOXYCARBONYL)INDOL 3 YL]METHYL] N' [1 METHOXYINDOL 3 YLMETHYL]THIOUREA; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE; OXOBRASSININ; PROTEIN BAX; UNCLASSIFIED DRUG; INDOLE DERIVATIVE; PROTEIN BCL 2; THIOCARBAMIC ACID DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; BAX GENE; BCL XL GENE; BCL2 GENE; CACO 2 CELL LINE; CANCER CELL LINE; CELL CYCLE ARREST; CELL LEVEL; CONTROLLED STUDY; DNA FRAGMENTATION ASSAY; DRUG POTENCY; DRUG STRUCTURE; FLOW CYTOMETRY; GENE EXPRESSION REGULATION; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; PROTEIN CLEAVAGE; PROTEIN EXPRESSION; QUANTITATIVE ANALYSIS; REAL TIME POLYMERASE CHAIN REACTION; CELL CYCLE; CELL SURVIVAL; DRUG EFFECTS; GENETICS; HCT116 CELL LINE; HEPG2 CELL LINE; METABOLISM;

ANTINEOPLASTIC AGENTS; CACO-2 CELLS; CASPASE 3; CASPASE 7; CELL CYCLE; CELL SURVIVAL; GLUTATHIONE; HCT116 CELLS; HEP G2 CELLS; HUMANS; INDOLES; POLY(ADP-RIBOSE) POLYMERASES; PROTO-ONCOGENE PROTEINS C-BCL-2; THIOCARBAMATES;

EID: 84899844604     PISSN: 08872333     EISSN: 18793177     Source Type: Journal    
DOI: 10.1016/j.tiv.2014.04.002     Document Type: Article

References (37)

1. Banerjee T., Duhadaway J.B., Gaspari P., Sutanto-Ward E., Munn D.H., Mellor A.L., Malachowski W.P., Prendergast G.C., Muller A.J. A key in vivo antitumor mechanism of action of natural product-based brassinin is inhibition of indoleamine 2,3-dioxygenase. Oncogene 2008, 27:2581-2587.
2. Budovska M., Kutschy P., Kozar T., Gondova T., Petrovaj J. Synthesis of spiroindoline phytoalexin (S)-(-)-spirobrassinin and its unnatural (R)-(+)-enantiomer. Tetrahedron 2013, 69:1092-1104.
3. Budovska M., Pilatova M., Varinska L., Mojzis J., Mezencev R. The synthesis and anticancer activity of analogs of the indole phytoalexins brassinin, 1-methoxyspirobrassinol methyl ether and cyclobrassinin. Bioorg. Med. Chem. 2013, 21:6623-6633.
4. Calvert P., Yao K.S., Hamilton T.C., O'Dwyer P.J. Clinical studies of reversal of drug resistance based on glutathione. Chem. Biol. Interact. 1998, 111-112:213-224.
5. Ebel J. Phytoalexin synthesis: the biochemical analysis of the induction process. Phytopathology 1986, 24:235-264.
6. Estrela J.M., Ortega A., Obrador E. Glutathione in cancer biology and therapy. Crit. Rev. Clin. Lab. Sci. 2006, 43:143-181.
7. Floreani M., Petrone M., Debetto P., Palatini P. A comparison between different methods for the determination of reduced and oxidized glutathione in mammalian tissues. Free Rad. Res. 1997, 26:449-455.
8. Gerhäuser C., You M., Liu J., Moriarty R.M., Hawthorne M., Mehta R.G., Moon R.C., Pezzuto J.M. Cancer chemopreventive potential of sulforamate, a novel analogue of sulforaphane that induces phase 2 drug-metabolizing enzymes. Cancer Res. 1997, 57:272-278.
9. Izutani Y., Yogosawa S., Sowa Y., Sakai T. Brassinin induces G1 phase arrest through increase of p21 and p27 by inhibition of the phosphatidylinositol 3-kinase signaling pathway in human colon cancer cells. Int. J. Oncol. 2012, 40:816-824.
10. Kim S.M., Park J.H., Kim K.D., Nam D., Shim B.S., Kim S.H., Ahn K.S., Choi S.H., Ahn K.S. Brassinin induces apoptosis in PC-3 human prostate cancer cells through the suppression of PI3K/Akt/mTOR/S6K1 signaling cascades. Phytother. Res. 2014, 28:423-431.
11. Kinghorn A.D., Su B.N., Jang D.S., Chang L.C., Lee D., Gu J.Q., Carcache-Blanco E.J., Pawlus A.D., Lee S.K., Park E.J., Cuendet M., Gills J.J., Bhat K., Park H.S., Mata-Greenwood E., Song L.L., Jang M., Pezzuto J.M. Natural inhibitors of carcinogenesis. Planta Med. 2004, 70:691-705.
12. Kutschy P., Sabol M., Maruskova R., Curillova Z., Dzurilla M., Geci I., Alföldi J., Kovacik V. A linear synthesis of 1-(β-D-Glucopyranosyl)brassinin, -brassenin A, -brassenin B and 9-(β-D-Glucopyranosyl)cyclobrassinin. Coll. Czech. Chem. Comm. 2004, 69:850-866.
13. Kutschy P., Sykora A., Curillova Z., Repovska M., Pilatova M., Mojzis J., Mezencev R., Pazdera P., Hromjakova T. Glyoxyl analogs of indole phytoalexins: synthesis and anticancer activity. Coll. Czech. Chem. Comm. 2010, 75:887-903.
14. Limame R., Wouters A., Pauwels B., Fransen E., Peeters M., Lardon F., De Wever O., Pauwels P. Comparative analysis of dynamic cell viability, migration and invasion assessments by novel real-time technology and classic endpoint assays. PLoS ONE 2012, 7:1-12.
15. MacManus J.P., Linnik M.D. Gene expression induced by cerebral ischemia: an apoptotic perspective. J. Cereb. Blood Flow Metab. 1997, 17:815-832.
16. Mehta R.G., Liu J., Constantinou A., Thomas C.F., Hawthorne M., You M., Gerhüser C., Pezzuto J.M., Moon R.C., Moriarty R.M. Cancer chemopreventive activity of brassinin, a phytoalexin from Cabbage. Carcinogenesis 1995, 16:399-404.
17. Mezencev R., Mojzis J., Pilatova M., Kutschy P. Antiproliferative and cancer chemopreventive activity of phytoalexins: focus on indole phytoalexins from crucifers. Neoplasma 2003, 50:239-245.
18. Mezencev R., Kutschy P., Salayova A., Curillova Z., Mojzis J., Pilatova M., McDonald J. Anticancer properties of 2-piperidyl analogues of the natural indole phytoalexin 1-methoxyspirobrassinol. Chemotherapy 2008, 54:372-378.
19. Mezencev R., Galizzi M., Kutschy P., Docampo R. Trypanosoma cruzi: antiproliferative effect of indole phytoalexins on intracellular amastigotes in vitro. Exp. Parasitol. 2009, 122:66-69.
20. Mezencev R., Updegrove T., Kutschy P., Repovska M., McDonald J.F. Camalexin induces apoptosis in T-leukemia Jurkat cells by increased concentration of reactive oxygen species and activation of caspase-8 and caspase-9. J. Nat. Med. 2011, 65:488-499.
21. Mosmann T. Rapid colorimetric assay for cellular growth and survival:application to proliferation and cytotoxicity assays. J. Immunol. Methods 1983, 65:55-63.
22. Oliver F.J., de la Rubia G., Rolli V., Ruiz-Ruiz M.C., de Murcia G., Murcia J.M. Importance of poly(ADP-ribose) polymerase and its cleavage in apoptosis. Lesson from an uncleavable mutant. J. Biol. Chem. 1998, 273:33533-33539.
23. Oltvai Z., Milliman C., Korsmeyer S.J. Bcl-2 heterodimerizes in vivo with a conversed homolog, Bax, that accelerates programmed cell death. Cell 1993, 74:609-619.
24. Pedras M.S.C., Yaya E.E. Phytoalexins from Brassicaceae: news from the front. Phytochemistry 2010, 71:1191-1197.
25. Pedras M.S., Okanga F.I., Zaharia I.L., Khan A.Q. Phytoalexins from crucifers: synthesis, biosynthesis and biotransformation. Phytochemistry 2000, 53:161-176.
26. Pedras M.S.C., Montaut S., Suchy M. Phytoalexins from the crucifer rutabaga: structures, syntheses, biosyntheses, and antifungal activity. J. Org. Chem. 2004, 69:4471-4476.
27. Pedras M.S., Yaya E.E., Glawischnig E. The phytoalexins from cultivated and wild crucifers: chemistry and biology. Nat. Prod. Rep. 2011, 28:1381-1405.
28. Peitsh M.C., Muüller C.H., Tschopp J. DNA fragmentation during apoptosis is caused by frequent single-strand cuts. Nucleic Acids Res. 1993, 21:4206-4209.
29. Pilatova M., Sarissky M., Kutschy P., Mirossay A., Mezencev R., Curillova Z., Suchy M., Monde K., Mirossay L., Mojzis J. Cruciferous phytoalexins: antiproliferative effects in T-Jurkat leukemic cells. Leukemia Res. 2005, 29:415-421.
30. Pilatova M., Ivanova L., Kutschy P., Varinska L., Saxunova L., Repovska M., Sarissky M., Seliga R., Mirossay L., Mojzis J. In vitro toxicity of camalexin derivatives in human cancer and non-cancer cells. Tox. In Vitro. 2013, 27:939-944.
31. Rudel T. Caspase inhibitors in prevention of apoptosis. Herz 1999, 24:236-241.
32. Sabol M., Kutschy P., Siegfried L., Mirossay A., Suchy M., Hrbkova H., Dzurilla M., Maruskova R., Starkova J., Paulikova E. Cytotoxic effect of cruciferous phytoalexins against murine L1210 leukemia and B16 melanoma. Biologia 2000, 55:701-707.
33. Takasugi M., Katsui N., Shirata A. Isolation of three novel sulfur-containing phytoalexins from the Chinese cabbage Brassica campestris L. Ssp. Pekinensis (Cruciferae). J. Chem. Soc. - Ser. Chem. Comm. 1986, 14:1077-1078.
34. Virág L., Szabó C. The therapeutic potential of poly(ADP-Ribose) polymerase inhibitors. Pharmacol. Rev. 2002, 54:375-429.
35. Wyllie A., Kerr J.F.R., Currie A.R. Cell death: the significance of apoptosis. Int. Rev. Cytol. 1980, 68:251-306.
36. Yang E., Korsmeyer S. Molecular thanatopics: a discourse on the BCL2 family and cell death. Blood 1996, 88:386-401.
37. Zhu H., Ding W.J., Wu R., Weng Q.J., Lov J.S., Jin R.J., Lu W., Yang B., He Q.J. Synergistic anti-cancer activity by the combination of TRAIL/APO-2L and celastrol. Cancer Invest. 2010, 28:23-32.