Organic copper complexes as a new class of proteasome inhibitors and apoptosis inducers in human cancer cells

Biochemical Pharmacology

Volumn 67, Issue 6, 2004, Pages 1139-1151

  Daniel, Kenyon G ^a   Gupta, Puja ^a   Harbach, R Hope ^b   Guida, Wayne C ^a,b   Dou, Q Ping ^a,c  

^a UNIVERSITY OF SOUTH FLORIDA   (United States)

^b ECKERD COLLEGE   (United States)

^c WAYNE STATE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

8 hydroxyquinoline hemisulfate; 8 OHQ; 8 OHQ 5 sulfonic acid; Cu D PA; Cu TM; Cu trientine Cl2; D PA; D PA copper complex; D penicillamine; Tetrathiomolybdate; TM; TM copper complex; Trientine; Trientine copper complex; Triethylenetetramine

Indexed keywords

8 QUINOLINOL; BIS(8 HYDROXYQUINOLINE)COPPERDRUG DEVELOPMENT; CHYMOTRYPSIN; COPPER DERIVATIVE; CUPRIC CHLORIDE; HYDROGEN PEROXIDE; NCI 109268; NICKEL CHLORIDE; PROTEASOME; PROTEASOME INHIBITOR; REDUCING AGENT; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; CANCER CELL; CANCER CELL CULTURE; CELL IMMORTALIZATION; CONTROLLED STUDY; DRUG POTENCY; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; LEUKEMIA CELL; LIGAND BINDING; NATURAL KILLER CELL; OXIDATIVE STRESS; PRIORITY JOURNAL; PROSTATE CANCER;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL LINE, TRANSFORMED; CHYMOTRYPSIN; COPPER; CYSTEINE ENDOPEPTIDASES; HUMANS; JURKAT CELLS; MULTIENZYME COMPLEXES; OXYQUINOLINE; PROTEASOME ENDOPEPTIDASE COMPLEX; TUMOR CELLS, CULTURED;

EID: 1542270307     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2003.10.031     Document Type: Article

References (59)

1. Jacobson M.D., Weil M., Raff M.C. Programmed cell death in animal development. Cell. 88:1997;347-354.
2. Song Z., Steller H. Death by design: mechanism and control of apoptosis. Trends Cell Biol. 9:1999;M49-M52.
3. Earnshaw W.C., Martins L.M., Kaufmann S.H. Mammalian caspases: structure, activation, substrates, and functions during apoptosis. Annu. Rev. Biochem. 68:1999;383-424.
4. Bratton S.B., MacFarlane M., Cain K., Cohen G.M. Protein complexes activate distinct caspase cascades in death receptor and stress-induced apoptosis. Exp. Cell Res. 256:2000;27-33.
5. Wyllie A.H., Kerr J.F., Currie A.R. Cell death: the significance of apoptosis. Int. Rev Cytol. 68:1980;251-306.
6. Green D.R., Reed J.C. Mitochondria and apoptosis. Science. 281:1998;1309-1312.
7. Adams J. Potential for proteasome inhibition in the treatment of cancer. Drug. Discov. Today. 8:2003;307-315.
8. Dou Q.P., Li B. Proteasome inhibitors as potential novel anticancer agents. Drug Resist. Update. 2:1999;215-223.
9. Almond J.B., Cohen G.M. The proteasome: a novel target for cancer chemotherapy. Leukemia. 16:2002;433-443.
10. Goldberg A.L. Functions of the proteasome: the lysis at the end of the tunnel. Science. 268:1995;522-523.
11. Dou QP, Smith DM, Daniel KG, Kazi A. Interruption of tumor cell cycle progression through proteasome inhibition: implications for cancer therapy. In: Meijer L, Jezequel A, Roberge M, editors. Progress in cell cycle research. Life in Progress ed. Roscoff; 2003. p. 441-6.
12. Lowe J., Stock D., Jap B., Zwickl P., Baumeister W., Huber R. Crystal structure of the 20S proteasome from the archaeon T. acidophilum at 3.4 A resolution. Science. 268:1995;533-539.
13. An B., Goldfarb R.H., Siman R., Dou Q.P. 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. 5:1998;1062-1075.
14. Lopes U.G., Erhardt P., Yao R., Cooper G.M. p53-dependent induction of apoptosis by proteasome inhibitors. J. Biol. Chem. 272:1997;12893-12896.
15. Adams J. Preclinical and clinical evaluation of proteasome inhibitor PS-341 for the treatment of cancer. Curr. Opin. Chem. Biol. 6:2002;493-500.
16. Dou Q.P., Goldfarb R.H. Bortezomib (Millennium Pharmaceuticals). IDrugs. 5:2002;828-834.
17. Twombly R. First proteasome inhibitor approved for multiple myeloma. J. Natl. Cancer Inst. 95:2003;845.
18. Adams J. The proteasome: structure, function, and role in the cell. Cancer Treat. Rev. 29:2003;3-9.
19. Eatock M.M., Schatzlein A., Kaye S.B. Tumour vasculature as a target for anticancer therapy. Cancer Treat. Rev. 26:2000;191-204.
20. Fox S.B., Gasparini G., Harris A.L. Angiogenesis: pathological, prognostic, and growth-factor pathways and their link to trial design and anticancer drugs. Lancet Oncol. 2:2001;278-289.
21. Brem S. Angiogenesis and cancer control: from concept to therapeutic trial. Cancer Control. 6:1999;436-458.
22. Brewer G.J. Copper control as an antiangiogenic anticancer therapy: lessons from treating Wilson's disease. Exp. Biol. Med. (Maywood). 226:2001;665-673.
23. Theophanides T., Anastassopoulou J. Copper and carcinogenesis. Crit. Rev. Oncol. Hematol. 42:2002;57-64.
24. Scanni A., Licciardello L., Trovato M., Tomirotti M., Biraghi M. Serum copper and ceruloplasmin levels in patients with neoplasias localized in the stomach, large intestine or lung. Tumori. 63:1977;175-180.
25. Zowczak M., Iskra M., Torlinski L., Cofta S. Analysis of serum copper and zinc concentrations in cancer patients. Biol. Trace Elem. Res. 82:2001;1-8.
26. Turecky L., Kalina P., Uhlikova E., Namerova S., Krizko J. Serum ceruloplasmin and copper levels in patients with primary brain tumors. Klin. Wochenschr. 62:1984;187-189.
27. Chan A., Wong F., Arumanayagam M. Serum ultrafiltrable copper, total copper and caeruloplasmin concentrations in gynaecological carcinomas. Ann. Clin. Biochem. 30:1993;545-549.
28. McAuslan B.R., Reilly W. Endothelial cell phagokinesis in response to specific metal ions. Exp. Cell Res. 130:1980;147-157.
29. Hu G.F. Copper stimulates proliferation of human endothelial cells under culture. J. Cell Biochem. 69:1998;326-335.
30. Pan Q., Kleer C.G., van Golen K.L., Irani J., Bottema K.M., Bias C., De Carvalho M., Mesri E.A., Robins D.M., Dick R.D., Brewer G.J., Merajver S.D. Copper deficiency induced by tetrathiomolybdate suppresses tumor growth and angiogenesis. Cancer Res. 62:2002;4854-4859.
31. Yoshii J., Yoshiji H., Kuriyama S., Ikenaka Y., Noguchi R., Okuda H., Tsujinoue H., Nakatani T., Kishida H., Nakae D., Gomez D.E., De Lorenzo M.S., Tejera A.M., Fukui H. The copper-chelating agent, trientine, suppresses tumor development and angiogenesis in the murine hepatocellular carcinoma cells. Int. J. Cancer. 94:2001;768-773.
32. Brem S.S., Zagzag D., Tsanaclis A.M., Gately S., Elkouby M.P., Brien S.E. Inhibition of angiogenesis and tumor growth in the brain. Suppression of endothelial cell turnover by penicillamine and the depletion of copper, an angiogenic cofactor. Am. J. Pathol. 137:1990;1121-1142.
33. Sunwoo J.B., Chen Z., Dong G., Yeh N., Crowl Bancroft C., Sausville E., Adams J., Elliott P., Van Waes C. 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. 7:2001;1419-1428.
34. Oikawa T., Sasaki T., Nakamura M., Shimamura M., Tanahashi N., Omura S., Tanaka K. The proteasome is involved in angiogenesis. Biochem. Biophys. Res. Commun. 246:1998;243-248.
35. Kolthoff IMS, Sandell EB, Kolthoff IMS. Textbook of quantitative inorganic analysis. New York: The MacMillan Co.; 1959.
36. Ohkaku N., Nakamoto K. Metal isotope effect on metal-ligand vibrations VI. Metal complexes of 8-hydroxyquinoline. Inorg. Chem. 10:1971;798-805.
37. Fanning J.C., Jonassen H.B. The reaction of 8-quinolinol with copper(II) salts. J. Inorg. Nucl. Chem. 25:1963;29-35.
38. Bevan J, Graddon D, McConnell J. Crystal structures of bis-(salicylaldehydato)-copper(II) and bis-(8-hydroxyquinolinato)-copper(II). Nature 1963;363.
39. Ray N, Tyagi S, Hathaway B. The preparation and properties of [Cu(chelate)]X2 complexes. Crystal structure and electronic properties of bis(2-pyridylamine)dibromo-copper(II). J Chem Soc Dalt Trans: Inorg Chem 1982;143-6.
40. Siddiqi K.S., Aqra F.M.A.M., Shah S.A., Zaidi S.A.A. A transition metal complex as a ligand in the chemistry of group (IV) elements. Polyhedron. 12:1993;949-953.
41. Lakshmanan V., Nagaraja K.S., Udupa M.R. Synthesis and characterization of copper(I) tetrathiomolybdates. Ind. J. Chem. 33A:1994;772-774.
42. Conley RT. Infrared spectroscopy. Boston: Allyn and Bacon; 1966.
43. Binne W.P., Redman M.J., Mallio W.J. On the preparation, properties, and structure of cuprous ammonium thiomolybdate. Inorg. Chem. 9:1970;1449-1452.
44. Paul J.M., Birker W.L., Freeman H.C. Properties, and function of a copper(I)-copper(II) complex of D-penicillamine. J. Am. Chem. Soc. 33:1977;6890-6899.
45. Drexler H.G., Matsuo A.Y., MacLeod R.A. Continuous hematopoietic cell lines as model systems for leukemia-lymphoma research. Leuk. Res. 24:2000;881-911.
46. An B., Dou Q.P. Cleavage of retinoblastoma protein during apoptosis: an interleukin 1 beta-converting enzyme-like protease as candidate. Cancer Res. 56:1996;438-442.
47. 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. 276:2001;13322-13330.
48. Godfrey E.G., Stewart J., Dargie H.J., Reid J.L., Dominiczak M., Hamilton C.A., McMurray J. Effects of ACE inhibitors on oxidation of human low density lipoprotein. Br. J. Clin. Pharmacol. 37:1994;63-66.
49. Rattan A.K., Arad Y. Temporal and kinetic determinants of the inhibition of LDL oxidation by N-acetylcysteine (NAC). Atherosclerosis. 138:1998;319-327.
50. Chen S.H., Liu S.H., Liang Y.C., Lin J.K., Lin-Shiau S.Y. Death signaling pathway induced by pyrrolidine dithiocarbamate-Cu(2+) complex in the cultured rat cortical astrocytes. Glia. 31:2000;249-261.
51. Sakano K., Oikawa S., Hasegawa K., Kawanishi S. Hydroxyurea induces site-specific DNA damage via formation of hydrogen peroxide and nitric oxide. Jpn. J. Cancer Res. 92:2001;1166-1174.
52. Yang G., Liao J., Li C., Chung J., Yurkow E., Ho C., Yang C. Effect of black and green tea polyphenols on c-jun phosphorylation and H(2)O(2) production in transformed and non-transformed human bronchial cell lines: possible mechanisms of cell growth inhibition and apoptosis induction. Carcinogenesis. 21:2000;2035-2039.
53. Sakagami H., Arakawa H., Maeda M., Satoh K., Kadofuku T., Fukuchi K., Gomi K. Production of hydrogen peroxide and methionine sulfoxide by epigallocatechin gallate and antioxidants. Anticancer Res. 21:2001;2633-2641.
54. Stockert R.J., Grushoff P.S., Morell A.G., Bentley G.E., O'Brien H.A., Scheinberg I.H., Sternlieb I. Transport and intracellular distribution of copper in a human hepatoblastoma cell line, HepG2. Hepatology. 6:1986;60-64.
55. Zelenko O., Gallagher J., Xu Y., Sigman D.S. Chemical nuclease activity of 1,10-phenanthroline-copper. Isotopic probes of mechanism. Inorg. Chem. 37:1998;2198-2204.
56. 2+ ion in the presence of bisintercalator containing penta(ethylene glycol) connector chain. J. Mol. Recog. 3:1990;156-162.
57. Verma R., Aravind L., Oania R., McDonald W.H., Yates J.R. III, Koonin E.V., Deshaies R.J. Role of Rpn11 metalloprotease in deubiquitination and degradation by the 26S proteasome. Science. 298:2002;611-615.
58. Yao T., Cohen R.E. A cryptic protease couples deubiquitination and degradation by the proteasome. Nature. 419:2002;403-407.
59. Kobashi K., Horecher B. Reversible inactivation of rabbit muscle aldolase by ophenanthroline. Arch. Biochem. Biophys. 121:1967;178-186.