Effect of ajoene, a natural antitumor small molecule, on human 20S proteasome activity in vitro and in human leukemic HL60 cells

Fundamental and Clinical Pharmacology

Volumn 18, Issue 2, 2004, Pages 171-180

  Xu, Bo ^a,b   Monsarrat, Bernard ^c   Gairin, Jean Edouard ^a   Girbal Neuhauser, Elisabeth ^a  

^a INSTITUT DE RECHERCHE PIERRE FABRE   (France)

^b PEKING UNIVERSITY   (China)

^c INSTITUT DE PHARMACOLOGIE ET DE BIOLOGIE STRUCTURALE   (France)

Author keywords

Ajoene; Proteasome; Proteasome inhibitor

Indexed keywords

AJOENE; ANTINEOPLASTIC AGENT; CHYMOTRYPSIN; PEPTIDE; PROTEASOME; TRYPTASE;

ARTICLE; CANCER CELL CULTURE; CELL CYCLE G2 PHASE; CELL STRAIN HL 60; CONTROLLED STUDY; CYTOSOL; DRUG EFFECT; DRUG SCREENING; ENZYME ACTIVITY; ENZYME DEGRADATION; ENZYME INHIBITION; ENZYME PURIFICATION; ENZYME STABILITY; ENZYME SUBSTRATE; ERYTHROCYTE; HUMAN; HUMAN CELL; HYDROLYSIS; IN VITRO STUDY; INHIBITION KINETICS; LEUKEMIA CELL; MOLECULAR SIZE; PRIORITY JOURNAL;

ACETYLCYSTEINE; ANTINEOPLASTIC AGENTS; CELL DIVISION; CHYMOTRYPSIN; DISULFIDES; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; G2 PHASE; GARLIC; HL-60 CELLS; HUMANS; HYBRIDOMAS; OVALBUMIN; PEPTIDES; PLANT EXTRACTS; PLANT STEMS; PROTEASOME ENDOPEPTIDASE COMPLEX; TIME FACTORS; TRYPSIN;

EID: 1842833496     PISSN: 07673981     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1472-8206.2004.00219.x     Document Type: Article

References (48)

1. Banerjee S.K., Mukherjee P.K., Maulik S.K. Garlic as an antioxidant: the good, the bad and the ugly. Phytother. Res. (2003) 17 97-106.
2. Fleischauer A.T., Arab L. Garlic and cancer: a critical review of the epidemiologic literature. J. Nutr. (2001) 131 1032S-1040S.
3. Milner J.A. A historical perspective on garlic and cancer. J. Nutr. (2001) 131 1027S-1031S.
4. Tadi P.P., Teel R.W., Lau B.H. Organosulfur compounds of garlic modulate mutagenesis, metabolism, and DNA binding of aflatoxin B1. Nutr. Cancer (1991) 15 87-95.
5. Ishikawa K., Naganawa R., Yoshida H. et al. Antimutagenic effects of ajoene, an organosulfur compound derived from garlic. Biosci. Biotechnol. Biochem. (1996) 60 2086-2088.
6. Nishikawa T., Yamada N., Hattori A. et al. Inhibition by ajoene of skin-tumor promotion in mice. Biosci. Biotechnol. Biochem. (2002) 66 2221-2223.
7. Li M., Ciu J.R., Ye Y. et al. Antitumor activity of Z-ajoene, a natural compound purified from garlic: antimitotic and microtubule-interaction properties. Carcinogenesis (2002) 23 573-579.
8. Dirsch V.M., Gerbes A.L., Vollmar A.M. Ajoene, a compound of garlic, induces apoptosis in human promyeloleukemic cells, accompanied by generation of reactive oxygen species and activation of nuclear factor kappa B. Mol. Pharmacol. (1998) 53 402-407.
9. Antlsperger D.S., Dirsch V.M., Ferreira D. et al. Ajoene-induced cell death in human promyeloleukemic cells does not require JNK but is amplified by the inhibition of ERK. Oncogene (2003) 22 582-589.
10. Li M., Min J.M., Cui J.R. et al. Z-ajoene induces apoptosis of HL-60 cells: involvement of Bcl-2 cleavage. Nutr. Cancer (2002) 42 241-247.
11. Dirsch V.M., Antlsperger D.S., Hentze H. et al. Ajoene, an experimental anti-leukemic drug: mechanism of cell death. Leukemia (2002) 16 74-83.
12. Kisselev A.F., Goldberg A.L. Proteasome inhibitors: from research tools to drug candidates. Chem. Biol. (2001) 8 739-758.
13. Unno M., Mizushima T., Morimoto Y. et al. The structure of the mammalian 20S proteasome at 2.75. A resolution. Structure (Camb.) (2002) 10 609-618.
14. Groll M., Ditzel L., Lowe J. et al. Structure of 20S proteasome from yeast at 2.4. A resolution. Nature (1997) 386 463-471.
15. Groll M., Bajorek M., Kohler A. et al. A gated channel into the proteasome core particle. Nat. Struct. Biol. (2000) 7 1062-1067.
16. Orlowski M., Wilk S. Catalytic activities of the 20S proteasome, a multicatalytic proteinase complex. Arch. Biochem. Biophys. (2000) 383 1-16.
17. Ichihara A., Tanaka K. Roles of proteasomes in cell growth. Mol. Biol. Rep. (1995) 21 49-52.
18. Adams J. Proteasome inhibition: a novel approach to cancer therapy. Trends Mol. Med. (2002) 8 S49-S54.
19. Elliott P.J., Ross J.S. The proteasome: a new target for novel drug therapies. Am. J. Clin. Pathol. (2001) 116 637-646.
20. Murray R.Z., Norbury C. Proteasome inhibitors as anti-cancer agents. Anticancer Drugs (2000) 11 407-117.
21. Almond J.B., Cohen G.M. The proteasome: a novel target for cancer chemotherapy. Leukemia (2002) 16 433-443.
22. Delcros J.G., Floc'h M.B., Prigent C. et al. Proteasome inhibitors as therapeutic agents: current and future strategies. Curr. Med. Chem. (2003) 10 479-503.
23. Adams J. The proteasome: structure, function, and role in the cell. Cancer Treat. Rev. (2003) 29(Suppl. 1) 3-9.
24. Adams J., Palombella V.J., Sausville E.A. et al. Proteasome inhibitors: a novel class of potent and effective antitumor agents. Cancer Res. (1999) 59 2615-2622.
25. Nawrocki S.T., Bruns C.J., Harbison M.T. et al. Effects of the proteasome inhibitor PS-341 on apoptosis and angiogenesis in orthotopic human pancreatic tumor xenografts. Mol. Cancer Ther. (2002) 1 1243-1253.
26. Ling Y.H., Liebes L., Jiang J.D. et al. Mechanisms of proteasome inhibitor PS-341-induced G(2)-M-Phase arrest and apoptosis in human non-small cell lung cancer cell lines. Clin. Cancer Res. (2003) 9 1145-1154.
27. Ling Y.H., Liebes L., Ng B. et al. PS-341, a novel proteasome inhibitor, induces Bcl-2 phosphorylation and cleavage in association with G2-M phase arrest and apoptosis. Mol. Cancer Ther. (2002) 1 841-849.
28. Hideshima T., Mitsiades C., Akiyama M. et al. Molecular mechanisms mediating antimyeloma activity of proteasome inhibitor PS-341. Blood (2003) 101 1530-1534.
29. Sunwoo J.B., Chen Z., Dong G. et al. Novel proteasome inhibitor PS-341 inhibits activation of nuclear factor-kappa B, cell survival, tumor growth, and angiogenesis in squamous cell carcinoma. Clin. Cancer Res. (2001) 7 1419-1428.
30. Nam S., Smith D.M., Dou Q.P. Ester bond-containing tea polyphenols potently inhibit proteasome activity in vitro and in vivo. J. Biol. Chem. (2001) 276 13322-13330.
31. Kroll M., Arenzana-Seisdedos F., Bachelerie F. et al. The secondary fungal metabolite gliotoxin targets proteolytic activities of the proteasome. Chem. Biol. (1999) 6 689-698.
32. Claverol S., Burlet-Schiltz O., Girbal-Neuhauser E. et al. Mapping and structural dissection of human 20S proteasome using proteomic approaches. Mol. Cell. Proteomics (2002) 1 567-578.
33. Schultz E.S., Chapiro J., Lurquin C. et al. The production of a new MAGE-3 peptide presented to cytolytic T lymphocytes by HLA-B40 requires the immunoproteasome. J. Exp. Med. (2002) 195 391-399.
34. Morel S., Levy F., Burlet-Schiltz O. et al. Processing of some antigens by the standard proteasome but not by the immunoproteasome results in poor presentation by dendritic cells. Immunity (2000) 12 107-117.
35. Niedermann G., King G., Butz S. et al. The proteolytic fragments generated by vertebrate proteasomes: structural relationships to major histocompatibility complex class I binding peptides. Proc. Natl. Acad. Sci. USA (1996) 93 8572-8577.
36. Craiu A., Gaczynska M., Akopian T. et al. Lactacystin and clasto-lactacystin beta-lactone modify multiple proteasome beta-subunits and inhibit intracellular protein degradation and major histocompatibility complex class I antigen presentation. J. Biol. Chem. (1997) 272 13437-13445.
37. Kiyomiya K., Kurebe M., Nakagawa H. et al. The role of the proteasome in apoptosis induced by anthracycline anticancer agents. Int. J. Oncol. (2002) 20 1205-1209.
38. Bogyo M., McMaster J.S., Gaczynska M. et al. Covalent modification of the active site threonine of proteasomal beta subunits and the Escherichia coli homolog HsIV by a new class of inhibitors. Proc. Natl. Acad. Sci. USA (1997) 94 6629-6634.
39. Gallwitz H., Bonse S., Martinez-Cruz A. et al. Ajoene is an inhibitor and subversive substrate of human glutathione reductase and Trypanosoma cruzi trypanothione reductase: crystallographic, kinetic, and spectroscopic studies. J. Med. Chem. (1999) 42 364-372.
40. Thomson M., Ali M. Garlic (Allium sativum): a review of its potential use as an anti-cancer agent. Curr. Cancer Drug Targets (2003) 3 67-81.
41. Ferri N., Yokoyama K., Sadilek M. et al. Ajoene, a garlic compound, inhibits protein prenylation and arterial smooth muscle cell proliferation. Br. J. Pharmacol. (2003) 138 811-818.
42. Dick L.R., Moomaw C.R., Pramanik B.C. et al. Identification and localization of a cysteinyl residue critical for the trypsin-like catalytic activity of the proteasome. Biochemistry (1992) 31 7347-7355.
43. Kisselev A.F., Akopian T.N., Castillo V. et al. Proteasome active sites allosterically regulate each other, suggesting a cyclical bite-chew mechanism for protein breakdown. Mol. Cell (1999) 4 395-402.
44. Myung J., Kim K.B., Lindsten K. et al. Lack of proteasome active site allostery as revealed by subunit-specific inhibitors. Mol. Cell (2001) 7 411-120.
45. An B., Goldfarb R.H., Siman R. et al. Novel dipeptidyl proteasome inhibitors overcome Bcl-2 protective function and selectively accumulate the cyclin-dependent kinase inhibitor p27 and induce apoptosis in transformed, but not normal, human fibroblasts. Cell Death Differ. (1998) 5 1062-1075.
46. Bulteau A.L., Lundberg K.C., Humphries K.M. et al. Oxidative modification and inactivation of the proteasome during coronary occlusion/reperfusion. J. Biol. Chem. (2001) 276 30057-30063.
47. Chondrogianni N., Stratford F.L., Trougakos I.P. et al. Central role of the proteasome in senescence and survival of human fibroblasts: induction of a senescence-like phenotype upon its inhibition and resistance to stress upon its activation. J. Biol. Chem. (2003) 7 7.
48. Meiners S., Heyken D., Weller A. et al. Inhibition of proteasome activity induces concerted expression of proteasome genes and de novo formation of mammalian proteasomes. J. Biol. Chem. (2003) 3 3.