Apoptotic effect of ethyl-4-isothiocyanatobutanoate is associated with DNA damage, proteasomal activity and induction of p53 and p21cip1/waf1

Apoptosis

Volumn 11, Issue 8, 2006, Pages 1299-1310

  Bodo, Juraj ^a   Jakubikova, Jana ^a   Chalupa, Ivan ^a   Bartosova, Zdena ^a   Horakova, Katarina ^b   Floch, Lubomir ^b   Sedlak, Jan ^a  

^a CANCER RESEARCH INSTITUTE   (Slovakia)

^b SLOVAK UNIVERSITY OF TECHNOLOGY   (Slovakia)

Author keywords

Apoptosis; Double strand breaks; Isothiocyanate E 4IB; Mismatch repair; Mitotic block

Indexed keywords

BENZYLOXYCARBONYLLEUCYLLEUCYLLEUCINAL; BENZYLOXYCARBONYLVALYLALANYLASPARTYL FLUOROMETHYL KETONE; CAFFEINE; CASPASE INHIBITOR; CLASTOGEN; CYCLIN DEPENDENT KINASE INHIBITOR 1; ETHYL 4 ISOTHIOCYANATOBUTANOATE; GROWTH ARREST AND DNA DAMAGE INDUCIBLE PROTEIN 45; ISOTHIOCYANIC ACID; ISOTHIOCYANIC ACID DERIVATIVE; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE; PROTEIN P53; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; CELL CYCLE REGULATION; CELL NUCLEUS; CELL SURVIVAL; CHROMOSOME ABERRATION; DNA DAMAGE; DNA STRAND BREAKAGE; DRUG EFFECT; ENZYME ACTIVATION; ENZYME ACTIVITY; FRAGMENTATION REACTION; HUMAN; HUMAN CELL; MEMBRANE POTENTIAL; METAPHASE; MISMATCH REPAIR; MITOCHONDRIAL MEMBRANE; MITOSIS; PRIORITY JOURNAL; PROTEIN DEGRADATION; PROTEIN EXPRESSION; PROTEIN INDUCTION; WESTERN BLOTTING;

AMINO ACID CHLOROMETHYL KETONES; APOPTOSIS; BUTYRATES; CAFFEINE; CELL CYCLE; CELL CYCLE PROTEINS; CELL LINE; CHROMOSOME ABERRATIONS; CYCLIN-DEPENDENT KINASE INHIBITOR P21; DNA DAMAGE; FLOW CYTOMETRY; HUMANS; ISOTHIOCYANATES; LEUPEPTINS; MEMBRANE POTENTIAL, MITOCHONDRIAL; PROTEASOME ENDOPEPTIDASE COMPLEX; PROTEIN-SERINE-THREONINE KINASES; TUMOR SUPPRESSOR PROTEIN P53;

EID: 33745869508     PISSN: 13608185     EISSN: 1573675X     Source Type: Journal    
DOI: 10.1007/s10495-006-8760-5     Document Type: Article

References (64)

1. Bostwick DG, Burke HB, Djakiew D et al (2004) Human prostate cancer risk factors. Cancer 101:2371-2490
2. Farmer PB, Singh R, Kaur B et al (2003) Molecular epidemiology studies of carcinogenic environmental pollutants. Effects of polycyclic aromatic hydrocarbons (PAHs) in environmental pollution on exogenous and oxidative DNA damage. Mutat Res 544:397-402
3. Giovannucci E, Rimm EB, Liu Y, Stampfer MJ, Willett WC (2003) A prospective study of cruciferous vegetables and prostate cancer. Cancer Epidemiol Biomarkers Prev 12:1403-1409
4. Rashidkhani B, Lindblad P, Wolk A (2005) Fruits, vegetables and risk of renal cell carcinoma: a prospective study of Swedish women. Int J Cancer 113:451-455
5. Nkondjock A, Krewski D, Johnson KC, Ghadirian P (2005) Dietary patterns and risk of pancreatic cancer. Int J Cancer 114:817-823
6. Cohen JH, Kristal AR, Stanford JL (2000) Fruit and vegetable intakes and prostate cancer risk. J Natl Cancer Inst 92:61-68
7. Gill S, Sinicrope FA (2005) Colorectal cancer prevention: is an ounce of prevention worth a pound of cure? Semin Oncol 32:24-34
8. Mathew A, Peters U, Chatterjee N, Kulldorff M, Sinha R (2004) Fat, fiber, fruits, vegetables, and risk of colorectal adenomas. Int J Cancer 108:287-292
9. Turner F, Smith G, Sachse C et al (2004) Vegetable, fruit and meat consumption and potential risk modifying genes in relation to colorectal cancer. Int J Cancer 112:259-264
10. Basten GP, Bao Y, Williamson G (2002) Sulforaphane and its glutathione conjugate but not sulforaphane nitrile induce UDP-glucuronosyl transferase (UGT1A1) and glutathione transferase (GSTA1) in cultured cells. Carcinogenesis 23:1399-1404
11. Bonnesen C, Eggleston IM, Hayes JD (2001) Dietary indoles and isothiocyanates that are generated from cruciferous vegetables can both stimulate apoptosis and confer protection against DNA damage in human colon cell lines. Cancer Res 61:6120-6130
12. Jakubikova J, Sedlak J, Mithen R, Bao Y (2005) Role of PI3K/Akt and MEK/ERK signaling pathways in sulforaphane-and erucin-induced phase II enzymes and MRP2 transcription, G(2)/M arrest and cell death in Caco-2 cells. Biochem Pharmacol 69:1543-1552
13. Maheo K, Morel F, Langouet S et al (1997) Inhibition of cytochromes P-450 and induction of glutathione S-transferases by sulforaphane in primary human and rat hepatocytes. Cancer Res 57:3649-3652
14. Svehlikova V, Wang S, Jakubikova J, Williamson G, Mithen R, Bao Y (2004) Interactions between sulforaphane and apigenin in the induction of UGT1A1 and GSTA1 in CaCo-2 cells. Carcinogenesis 25:1629-1637
15. Zhang Y, Talalay P (1998) Mechanism of differential potencies of isothiocyanates as inducers of anticarcinogenic Phase 2 enzymes. Cancer Res 58:4632-4639
16. Conaway CC, Krzeminski J, Amin S, Chung FL (2001) Decomposition rates of isothiocyanate conjugates determine their activity as inhibitors of cytochrome p450 enzymes. Chem Res Toxicol 14:1170-1176
17. Ye L, Dinkova-Kostova AT, Wade KL, Zhang Y, Shapiro TA, Talalay P (2002) Quantitative determination of dithiocarbamates in human plasma, serum, erythrocytes and urine: pharmacokinetics of broccoli sprout isothiocyanates in humans. Clin Chim Acta 316:43-53
18. Zhang Y (2001) Molecular mechanism of rapid cellular accumulation of anticarcinogenic isothiocyanates. Carcinogenesis 22:425-431
19. Chiao JW, Chung F, Krzeminski J et al (2000) Modulation of growth of human prostate cancer cells by the N-acetylcysteine conjugate of phenethyl isothiocyanate. Int J Oncol 16:1215-1219
20. Powolny A, Takahashi K, Hopkins RG, Loo G (2003) Induction of GADD gene expression by phenethylisothiocyanate in human colon adenocarcinoma cells. J Cell Biochem 90:1128-1139
21. Stoner GD, Morrissey DT, Heur YH, Daniel EM, Galati AJ, Wagner SA (1991) Inhibitory effects of phenethyl isothiocyanate on N-nitrosobenzylmethylamine carcinogenesis in the rat esophagus. Cancer Res 51:2063-2068
22. Rose P, Whiteman M, Huang SH, Halliwell B, Ong CN (2003) beta-Phenylethyl isothiocyanate-mediated apoptosis in hepatoma HepG2 cells. Cell Mol Life Sci 60:1489-1503
23. Singh AV, Xiao D, Lew KL, Dhir R, Singh SV (2004) Sulforaphane induces caspase-mediated apoptosis in cultured PC-3 human prostate cancer cells and retards growth of PC-3 xenografts in vivo. Carcinogenesis 25:83-90
24. Singh SV, Srivastava SK, Choi S et al (2005) Sulforaphane-induced cell death in human prostate cancer cells is initiated by reactive oxygen species. J Biol Chem 280:19911-19924
25. Xu K, Thornalley PJ (2001) Signal transduction activated by the cancer chemopreventive isothiocyanates: cleavage of BID protein, tyrosine phosphorylation and activation of JNK. Br J Cancer 84:670-673
26. Horakova K, Strakova Z, Jantova S, Muckova M, Floch L (1989) Biological effects of 2-isothiocyanatecarboxylic acid esters: I. Cytotoxic, antimicrobial and genotoxic streening of aminoacid isothiocyanate derivatives. [in Slovak]. Biologia 44:637-646
27. Sovcikova A, Mikulasova M, Horakova K, Floch L (2001) Antibacterial and mutagenic activities of new isothiocyanate derivatives. Folia Microbiol (Praha) 46:113-117
28. Tulinska J, Sovcikova A, Liskova A, Kubova J, Horakova K (2000) Immunotoxicity of ethyl-4-isothiocyanatobutanoate in male Wistar rats. Toxicology 145:217-225
29. Horakova K, Jantova S, Stred'ansky M, Novotna L, Floch L (1993) Ethyl 4-isothiocyanatobutanoate-antiproliferative activity in vitro and in vivo. Anticancer Drugs 4:369-375
30. Bodo J, Chovancova J, Hunakova L, Sedlak J (2005) Enhanced sensitivity of human ovarian carcinoma cell lines A2780 and A2780/CP to the combination of cisplatin and synthetic isothiocyanate ethyl 4-isothiocyanatobutanoate E-4IB. Neoplasma 52:510-516
31. Leach FS, Nicolaides NC, Papadopoulos N et al (1993) Mutations of a mutS homolog in hereditary nonpolyposis colorectal cancer. Cell 75:1215-1225
32. Miyaki M, Konishi M, Tanaka K et al (1997) Germline mutation of MSH6 as the cause of hereditary nonpolyposis colorectal cancer. Nat Genet 17:271-272
33. Papadopoulos N, Nicolaides NC, Wei YF et al (1994) Mutation of a mutL homolog in hereditary colon cancer. Science 263:1625-1629
34. O'Brien V, Brown R (2005) Signalling cell cycle arrest and cell death through the MMR system. Carcinogenesis 27:682-692
35. Vernole P, Tedeschi B, Tentori L et al (2006) Role of the mismatch repair system and p53 in the clastogenicity and cytotoxicity induced by bleomycin. Mutat Res 594:63-77
36. Goldmacher VS, Cuzick RA, Jr., Thilly WG (1986) Isolation and partial characterization of human cell mutants differing in sensitivity to killing and mutation by methylnitrosourea and N-methyl-N′-nitro-N-nitrosoguanidine. J Biol Chem 261:12462-12471
37. Szadkowski M, Iaccarino I, Heinimann K, Marra G, Jiricny J (2005) Characterization of the mismatch repair defect in the human lymphoblastoid MT1 cells. Cancer Res 65:4525-4529
38. Floch L, Gogova A, Jakubik T, Pronayova N (1997) Synthesis of ethyl 4-isothiocyanatobutanoate derivates. Chem Papers 51:416-420
39. Mosmann T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65:55-63
40. Bartkowiak D, Hogner S, Baust H, Nothdurft W, Rottinger EM (1999) Comparative analysis of apoptosis in HL60 detected by annexin-V and fluorescein-diacetate. Cytometry 37:191-196
41. ISCN (1978) An International System for Human Cytogenetic Nomenclature. Cytogenet Cell Genet 21:309-404
42. Venitt S, Parry JM (1984) Mutagenicity Testing: A Practical Approach. IRL Press, Oxford, Washington, DC, pp 353
43. Horakova K, Drobnica L, Nemec P, Antos A, Kristian P (1968) Cytotoxic and cancerostatis activity of isothiocyanates and related compounds. I. Activity of some naturally occurring isothiocyanates and their synthetic analogues on HeLa-cells. Neoplasma 15:169-176
44. Miyoshi N, Uchida K, Osawa T, Nakamura Y (2004) A link between benzyl isothiocyanate-induced cell cycle arrest and apoptosis: involvement of mitogen-activated protein kinases in the Bcl-2 phosphorylation. Cancer Res 64:2134-2142
45. Gamet-Payrastre L, Li P, Lumeau S et al (2000) Sulforaphane, a naturally occurring isothiocyanate, induces cell cycle arrest and apoptosis in HT29 human colon cancer cells. Cancer Res 60:1426-1433
46. Hasegawa T, Nishino H, Iwashima A (1993) Isothiocyanates inhibit cell cycle progression of HeLa cells at G2/M phase. Anticancer Drugs 4:273-279
47. Singh SV, Herman-Antosiewicz A, Singh AV et al (2004) Sulforaphane-induced G2/M phase cell cycle arrest involves checkpoint kinase 2-mediated phosphorylation of cell division cycle 25C. J Biol Chem 279:25813-25822
48. Chiao JW, Chung FL, Kancherla R, Ahmed T, Mittelman A, Conaway CC (2002) Sulforaphane and its metabolite mediate growth arrest and apoptosis in human prostate cancer cells. Int J Oncol 20:631-636
49. Jakubikova J, Sedlak J, Bacon J, Goldson A, Bao Y (2005) Effects of MEK1 and PI3K inhibitors on allyl-, benzyl-and phenylethylisothiocyanate-induced G2/M arrest and cell death in Caco-2 cells. Int J Oncol 27:1449-1458
50. Jakubikova J, Sedlak J, Bod'o J, Bao Y (2006) Effect of isothiocyanates on nuclear accumulation of NF-kappaB, Nrf2, and thioredoxin in caco-2 cells. J Agric Food Chem 54:1656-1662
51. Kwon SH, Ahn SH, Kim YK et al (2002) Apicidin, a histone deacetylase inhibitor, induces apoptosis and Fas/Fas ligand expression in human acute promyelocytic leukemia cells. J Biol Chem 277:2073-2080
52. Pappa G, Lichtenberg M, Iori R, Barillari J, Bartsch H, Gerhauser C (2006) Comparison of growth inhibition profiles and mechanisms of apoptosis induction in human colon cancer cell lines by isothiocyanates and indoles from Brassicaceae. Mutat Res Feb 22; [Epub ahead of print]
53. Xiao D, Singh SV (2002) Phenethyl isothiocyanate-induced apoptosis in p53-deficient PC-3 human prostate cancer cell line is mediated by extracellular signal-regulated kinases. Cancer Res 62:3615-3619
54. Nakamura Y, Kawakami M, Yoshihiro A et al (2002) Involvement of the mitochondrial death pathway in chemopreventive benzyl isothiocyanate-induced apoptosis. J Biol Chem 277:8492-8499
55. Ripple MO, Kalmadi S, Eastman A (2005) Inhibition of either phosphatidylinositol 3-kinase/Akt or the mitogen/extracellular-regulated kinase, MEK/ERK, signaling pathways suppress growth of breast cancer cell lines, but MEK/ERK signaling is critical for cell survival. Breast Cancer Res Treat 93:177-188
56. Parnaud G, Li P, Cassar G et al (2004) Mechanism of sulforaphane-induced cell cycle arrest and apoptosis in human colon cancer cells. NutrCancer 48:198-206
57. Xu K, Thornalley PJ (2000) Studies on the mechanism of the inhibition of human leukaemia cell growth by dietary isothiocyanates and their cysteine adducts in vitro. Biochem Pharmacol 60:221-231
58. Xiao D, Johnson CS, Trump DL, Singh SV (2004) Proteasome-mediated degradation of cell division cycle 25C and cyclin-dependent kinase 1 in phenethyl isothiocyanate-induced G2-M-phase cell cycle arrest in PC-3 human prostate cancer cells. MolCancer Ther 3:567-575
59. Brown KD, Rathi A, Kamath R et al (2003) The mismatch repair system is required for S-phase checkpoint activation. Nat Genet 33:80-84
60. Fishel R (2001) The selection for mismatch repair defects in hereditary nonpolyposis colorectal cancer: revising the mutator hypothesis. Cancer Res 61:7369-7374
61. Stojic L, Cejka P, Jiricny J (2005) High doses of SN1 type methylating agents activate DNA damage signaling cascades that are largely independent of mismatch repair. Cell Cycle 4:473-477
62. Kassie F, Knasmuller S (2000) Genotoxic effects of allyl isothiocyanate (AITC) and phenethyl isothiocyanate (PEITC). Chem Biol Interact 127:163-180
63. Fimognari C, Berti F, Cantelli-Forti G, Hrelia P (2005) Effect of sulforaphane on micronucleus inductionin cultured human lymphocytes by four different mutagens. Environ Mol Mutagen 46:260-267
64. Fimognari C, Berti F, Iori R, Cantelli-Forti G, Hrelia P (2005) Micronucleus formation and induction of apoptosis by different isothiocyanates and a mixture of isothiocyanates in human lymphocyte cultures. Mutat Res 582:1-10