Dimethyl-celecoxib (DMC), a derivative of celecoxib that lacks cyclooxygenase-2-inhibitory function, potently mimics the anti-tumor effects of celecoxib on Burkitt's lymphoma in vitro and in vivo

Cancer Biology and Therapy

Volumn 4, Issue 5, 2005, Pages 571-582

  Kardosh, Adel ^a   Wang, Weijun ^b   Uddin, Jasim ^b   Petasis, Nicos A ^b   Hofman, Florence M ^b   Chen, Thomas C ^b   Schönthal, Axel H ^a,c  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

^b UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

^c NONE   (United States)

Author keywords

Bextra; Burkitt's lymphoma; CDK; Celebrex; Celecoxib; Cell cycle; Cyclins; DMC; Flurbiprofen; Indomethacin; Lymphoma; NSAIDs; Raji; Ramos; Rofecoxib; Sulindac; Valdecoxib; Vioxx

Indexed keywords

CELECOXIB; CYCLOOXYGENASE 2 INHIBITOR; DIMETHYLCELECOXIB; ROFECOXIB; UNCLASSIFIED DRUG; VALDECOXIB;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; BURKITT LYMPHOMA; CELL CULTURE; CELL PROLIFERATION; CONTROLLED STUDY; DOWN REGULATION; DRUG EFFECT; DRUG POTENCY; ENZYME ACTIVITY; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; LYMPHOMA CELL; MOUSE; NONHUMAN; STATISTICAL SIGNIFICANCE; TUMOR GROWTH;

EID: 25144506566     PISSN: 15384047     EISSN: 15558576     Source Type: Journal    
DOI: 10.4161/cbt.4.5.1699     Document Type: Article

References (92)

1. Thun MJ, Henley SJ, Patrono C. Nonsteroidal anti-inflammatory drugs as anticancer agents: mechanistic, pharmacologic, and clinical issues. J Natl Cancer Inst 2002; 94:252-66.
2. Parente L, Perretti M. Advances in the pathophysiology of constitutive and inducible cyclooxygenases: two enzymes in the spotlight. Biochem Pharmacol 2003; 65:153-9.
3. Howe LR, Dannenberg AJ. A role for cyclooxygenase-2 inhibitors in the prevention and treatment of cancer. Semin Oncol 2002; 29:111-9.
4. FitzGerald GA. COX-2 and beyond: Approaches to prostaglandin inhibition in human disease. Nat Rev Drug Discov 2003; 2:879-90.
5. Dannenberg AJ, Subbaramaiah K. Targeting cyclooxygenase-2 in human neoplasia: rationale and promise. Cancer Cell 2003; 4:431-436.
6. Hawk ET, Viner JL, Dannenberg A, DuBois RN. COX-2 in cancer - a player that's defining the rules. J Natl Cancer Inst 2002; 94:545-6.
7. Keller JJ, Giardiello FM. Chemoprevention strategies using NSAIDs and COX-2 inhibitors. Cancer Biol Ther 2003; 2:S140-9.
8. Marnett LJ, Kalgutkar AS. Cyclooxygenase 2 inhibitors: discovery, selectivity and the future. Trends Pharmacol Sci 1999; 20:465-9.
9. Rao CV, Reddy BS. NSAIDs and chemoprevention. Curr Cancer Drug Targets 2004; 4:29-42.
10. Koehne CH, Dubois RN. COX-2 inhibition and colorectal cancer. Semin Oncol 2004; 31:12-21.
11. Chun KS, Surh YJ. Signal transduction pathways regulating cyclooxygenase-2 expression: potential molecular targets for chemoprevention. Biochem Pharmacol 2004; 68:1089-100.
12. Diperna CA, Bart RD, Sievers EM, Ma Y, Starnes VA, Bremner RM. Cyclooxygenase-2 inhibition decreases primary and metastatic tumor burden in a murine model of orthotopic lung adenocarcinoma. J Thorac Cardiovasc Surg 2003; 126:1129-33.
13. Gupta S, Adhami VM, Subbarayan M, MacLennan GT, Lewin JS, Hafeli UO, Fu P, Mukhtar H. Suppression of prostate carcinogenesis by dietary supplementation of celecoxib in transgenic adenocarcinoma of the mouse prostate model. Cancer Res 2004; 64:3334-43.
14. Masferrer JL, Leahy KM, Koki AT, Zweifel BS, Settle SL, Woerner BM, Edwards DA, Flickinger AG, Moore RJ, Seibert K. Antiangiogenic and antitumor activities of cyclooxygenase-2 inhibitors. Cancer Res 2000; 60:1306-11.
15. Reddy BS, Hirose Y, Lubet R, Steele V, Kelloff G, Paulson S, Seibert K, Rao CV. Chemoprevention of colon cancer by specific cyclooxygenase-2 inhibitor, celecoxib, administered during different stages of carcinogenesis. Cancer Res 2000; 60:293-7.
16. Roh JL, Sung MW, Park SW, Heo DS, Lee DW, Kim KH. Celecoxib can prevent tumor growth and distant metastasis in postoperative setting. Cancer Res 2004; 64:3230-5.
17. Trifan OC, Durham WF, Salazar VS, Horton J, Levine BD, Zweifel BS, Davis TW, Masferrer JL. Cyclooxygenase-2 inhibition with celecoxib enhances antitumor efficacy and reduces diarrhea side effect of CPT-11. Cancer Res 2002; 62:5778-84.
18. Williams CS, Watson AJ, Sheng H, Helou R, Shao J, DuBois RN. Celecoxib prevents tumor growth in vivo without toxicity to normal gut: lack of correlation between in vitro and in vivo models. Cancer Res 2000; 60:6045-51.
19. Zweifel BS, Davis TW, Ornberg RL, Masferrer JL. Direct evidence for a role of cyclooxygenase 2-derived prostaglandin E2 in human head and neck xenograff tumors. Cancer Res 2002; 62:6706-11.
20. Tegeder I, Pfeilschifter J, Geisslinger G. Cyclooxygenase-independent actions of cyclooxygenase inhibitors. Faseb J 2001; 15:2057-72.
21. Hanif R, Pittas A, Feng Y, Koutsos MI, Qiao L, Staiano-Coico L, Shiff SI, Rigas B. Effects of nonsteroidal anti-inflammatory drugs on proliferation and on induction of apoptosis in colon cancer cells by a prostaglandin-independent pathway. Biochem Pharmacol 1996; 52:237-45.
22. Shureiqi I, Chen D, Lotan R, Yang P, Newman RA, Fischer SM, Lippman SM. 15-Lipoxygenase-1 mediates nonsteroidal anti-inflammatory drug-induced apoptosis independently of cyclooxygenase-2 in colon cancer cells. Cancer Res 2000; 60:6846-50.
23. Blumenthal RD, Waskewich C, Goldenberg DM, Lew W, Flefleh C, Burton J. Chronotherapy and chronotoxicity of the cyclooxygenase-2 inhibitor, celecoxib, in athymic mice bearing human breast cancer xenograffs. Clin Cancer Res 2001; 7:3178-85.
24. Zhang X, Morham SG, Langenbach R, Young DA. Malignant transformation and antineoplastic actions of nonsteroidal antiinflammatory drugs (NSAIDs) on cyclooxygenase-null embryo fibroblasts. J Exp Med 1999; 190:451-59.
25. Arico S, Pattingre S, Bauvy C, Gane P, Barbat A, Codogno P, Ogier-Denis E. Celecoxib induces apoptosis by inhibiting 3-phosphoinositide-dependent protein kinase-1 activity in the human colon cancer HT-29 cell line. J Biol Chem 2002; 277:27613-21.
26. Kulp SK, Yang YT, Hung CC, Chen KF, Lai JP, Tseng PH, Fowble JW, Ward PJ, Chen CS. 3-phosphoinositide-dependent protein kinase-1/Akt signaling represents a major cyclooxygenase-2-independent target for celecoxib in prostate cancer cells. Cancer Res 2004; 64:1444-51.
27. Gupta RA, DuBois RN. Colorectal cancer prevention and treatment by inhibition of cyclooxygenase. Nature Rev Cancer 2001; 1:11-21.
28. Grosch S, Tegeder I, Niederberger E, Brautigam L, Geisslinger G. COX-2 independent induction of cell cycle arrest and apoptosis in colon cancer cells by the selective COX-2 inhibitor celecoxib. Faseb J 2001; 15:2742-4.
29. Kardosh A, Blumenthal M, Wang WJ, Chen TC, Schönthal AH. Differential Effects of Selective COX-2 Inhibitors on Cell Cycle Regulation and Proliferation of Glioblastoma Cell Lines. Cancer Biol Ther 2004; 3:9-16.
30. Narayanan BA, Condon MS, Bosland MC, Narayanan NK, Reddy BS. Suppression of N-methyl-N-nitrosourea/testosterone-induced rat prostate cancer growth by celecoxib: effects on cyclooxygenase-2, cell cycle regulation, and apoptosis mechanism(s). Clin Cancer Res 2003; 9:3503-13.
31. Waskewich C, Blumenthal RD, Li H, Stein R, Goldenberg DM, Burton J. Celecoxib exhibits the greatest potency amongst cyclooxygenase (COX) inhibitors for growth inhibition of COX-2-negative hematopoietic and epithelial cell lines. Cancer Res 2002; 62:2029-33.
32. Yamazaki R, Kusunoki N, Matsuzaki T, Hashimoto S, Kawai S. Selective cyclooxygenase-2 inhibitors show a differential ability to inhibit proliferation and induce apoptosis of colon adenocarcinoma cells. FEBS Lett 2002; 531:278-84.
33. Davies NM, McLachlan AJ, Day RO, Williams KM. Clinical pharmacokinetics and pharmacodynamics of celecoxib: a selective cyclo-oxygenase-2 inhibitor. Clin Pharmacokinet 2000; 38:225-42.
34. Paulson SK, Kaprak TA, Gresk CJ, Fast DM, Baratta MT, Burton EG, Breau AP, Karim A. Plasma protein binding of celecoxib in mice, rat, rabbit, dog and human. Biopharm Drug Dispos 1999; 20:293-9.
35. Penning TD, Talley JJ, Bertenshaw SR, Carter JS, Collins PW, Docter S, Graneto MJ, Lee LF, Malecha JW, Miyashiro JM, Rogers RS, Rogier DJ, Yu SS, AndersonGd, Burton EG, Cogburn JN, Gregory SA, Koboldt CM, Perkins WE, Seibert K, Veenhuizen AW, Zhang YY, Isakson PC. Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benze nesulfonamide (SC-58635, celecoxib). J Med Chem 1997; 40:1347-65.
36. Song X, Lin HP, Johnson AJ, Tseng PH, Yang YT, Kulp SK, Chen CS. Cyclooxygenase-2, player or spectator in cyclooxygenase-2 inhibitor-induced apoptosis in prostate cancer cells. J Natl Cancer Inst 2002; 94:585-91.
37. Zhu J, Song X, Lin HP, Young DC, Yan S, Marquez VE, Chen CS. Using cyclooxygenase-2 inhibitors as molecular platforms to develop a new class of apoptosis-inducing agents. J Natl Cancer Inst 2002; 94:1745-57.
38. Talley JJ, Brown DL, Carter JS, Graneto MJ, Koboldt CM, Masferrer JL, Perkins WE, Rogers RS, Shaffer AF, Zhang YY, Zweifel BS, Seibert K. 4-[5-Methyl-3-phenylisoxazol-4-yl]- benzenesulfonamide, valdecoxib: a potent and selective inhibitor of COX-2. J Med Chem 2000; 43:775-777.
39. Ehrich EW, Dallob A, De Lepeleire I, Van Hecken A, Riendeau D, Yuan W, Porras A, Wittreich J, Seibold JR, De Schepper P, Mehlisch DR, Gertz BJ. Characterization of rofecoxib as a cyclooxygenase-2 isoform inhibitor and demonstration of analgesia in the dental pain model. Clin Pharmacol Ther 1999; 65:336-347.
40. Masood R, McGarvey ME, Zheng T, Cai J, Arora N, Smith DL, Sloane N, Gill PS. Antineoplastic urinary protein inhibits Kaposi's sarcoma and angiogenesis in vitro and in vivo. Blood 1999; 93:1038-1044.
41. Harlow E, Lane D. Antibodies: A Laboratory Manual. Cold Spring Harbor, NY:Cold Spring Harbor Laboratory, 1988.
42. Wu R-C, Schönthal AH. Activation of p53-p21 waf1 pathway in response to disruption of cell-matrix interactions. J Biol Chem 1997; 272:29091-29098.
43. Schönthal AH. Measuring cyclin-dependent kinase activity. In: Schönthal AH, ed. Checkpoint Controls and Cancer, Totowa, NJ:Humana Press, 2004:105-124.
44. Bain J, McLauchlan H, Elliott M, Cohen P. The specificities of protein kinase inhibitors: an update. Biochem J 2003; 371:199-204.
45. Davies SP, Reddy H, Caivano M, Cohen P. Specificity and mechanism of action of some commonly used protein kinase inhibitors. Biochem J 2000; 351:95-105.
46. Ohsugi Y, Gershwin ME, Owens RB, Nelson-Rees WA. Tumorigenicity of human malignant lymphoblasts: comparative study with unmanipulated nude mice, antilymphocyte serum-treated nude mice, and X-irradiated nude mice. J Natl Cancer Inst 1980; 65:715-8.
47. Watanabe S, Shimosato Y, Kuroki M, Sato Y, Nakajima T. Transplantability of human lymphoid cell line, lymphoma, and leukemia in splenectomized and/or irradiated nude mice. Cancer Res 1980; 40:2588-95.
48. McCarty KS, Jr., Szabo E, Flowers JL, Cox EB, Leight GS, Miller L, Konrath J, Soper JT, Budwit DA, Creasman WT, et al. Use of a monoclonal anti-estrogen receptor antibody in the immunohistochemical evaluation of human tumors. Cancer Res 1986; 46:4244s-8s.
49. Fischer SM, Lo HH, Gordon GB, Seibert K, Kelloff G, Lubet RA, Conti CJ. Chemopreventive activity of celecoxib, a specific cyclooxygenase-2 inhibitor, and indomethacin against ultraviolet light-induced skin carcinogenesis. Mol Carcinogenesis 1999; 25:231-40.
50. Grubbs CJ, Lubet RA, Koki AT, Leahy KM, Masferrer JL, Steele VE, Kellorf GJ, Hill DL, Seibert K. Celecoxib inhibits N-butyl-N-(4-hydroxybutyl)- nitrosamine-induced urinary bladder cancers in male B6D2F1 mice and female Fischer-344 rats. Cancer Res 2000; 60:5599-602.
51. Wun T, McKnight H, Tuscano JM. Increased cyclooxygenase-2 (COX-2): a potential role in the pathogenesis of lymphoma. Leuk Res 2004; 28:179-90.
52. Morgan DO. Principles of CDK regulation. Nature 1997; 374:131-34.
53. Harper JW, Adams PD. Cyclin-dependent kinases. Chem Rev 2001; 101:2511-26.
54. Alessi DR, James SR, Downes CP, Holmes AB, Gaffney PR, Reese CB, Cohen P. Characterization of a 3-phosphoinositide-dependent protein kinase which phosphorylates and activates protein kinase Balpha. Curr Biol 1997; 7:261-9.
55. Stephens L, Anderson K, Stokoe D, Erdjument-Bromage H, Painter GF, Holmes AB, Gaffney PR, Reese CB, McCormick F, Tempst P, Coadwell J, Hawkins PT. Protein kinase B kinases that mediate phosphatidylinositol 3,4,5-trisphosphate- dependent activation of protein kinase B. Science 1998; 279:710-4.
56. Liu CH, Chang SH, Narko K, Trifan OC, Wu MT, Smith E, Haudenschild C, Lane TF, Hla T. Overexpression of cyclooxygenase-2 is sufficient to induce tumorigenesis in transgenic mice. J Biol Chem 2001; 276:18563-9.
57. Evans JF, Kargman SL. Cancer and cyclooxygenase-2 (COX-2) inhibition. Curr Pharm Des 2004; 10:627-34.
58. Phipps RP, Ryan E, Bernstein SH. Inhibition of cyclooxygenase-2: a new targeted therapy for B-cell lymphoma? Leuk Res 2004; 28:109-11.
59. Johnson AJ, Hsu AL, Lin HP, Song X, Chen CS. The cyclo-oxygenase-2 inhibitor celecoxib perturbs intracellular calcium by inhibiting endoplasmic reticulum Ca2+-ATPases: a plausible link with its anti-tumour effect and cardiovascular risks. Biochem J 2002; 366:831-7.
60. Zhu J, Huang JW, Tseng PH, Yang YT, Fowble J, Shiau CW, Shaw YJ, Kulp SK, Chen CS. From the cyclooxygenase-2 inhibitor celecoxib to a novel class of 3-phosphoinositide-dependent protein kinase-1 inhibitors. Cancer Res 2004; 64:4309-18.
61. Flynn P, Wongdagger M, Zavar M, Dean NM, Stokoe D. Inhibition of PDK-1 activity causes a reduction in cell proliferation and survival. Curr Biol 2000; 10:1439-42.
62. Williams MR, Arthur JS, Balendran A, van der Kaay J, Poli V, Cohen P, Alessi DR. The role of 3-phosphoinositide-dependent protein kinase 1 in activating AGC kinases defined in embryonic stem cells. Curr Biol 2000; 10:439-48.
63. Hsu AL, Ching TT, Wang DS, Song X, Rangnekar VM, Chen CS. The cyclooxygenase-2 inhibitor celecoxib induces apoptosis by blocking Akt activation in human prostate cancer cells independently of Bcl-2. J Biol Chem 2000; 275:11397-403.
64. Wu T, Leng J, Han C, Demetris AJ. The cyclooxygenase-2 inhibitor celecoxib blocks phosphorylation of Akt and induces apoptosis in human cholangiocarcinoma cells. Mol Cancer Ther 2004; 3:299-307.
65. Leng J, Han C, Demetris AJ, Michalopoulos GK, Wu T. Cyclooxygenase-2 promotes hepatocellular carcinoma cell growth through Akt activation: evidence for Akt inhibition in celecoxib-induced apoptosis. Hepatology 2003; 38:756-68.
66. Zhang Z, Lai GH, Sirica AE. Celecoxib-induced apoptosis in rat cholangiocarcinoma cells mediated by Akt inactivation and Bax translocation. Hepatology 2004; 39:1028-37.
67. Johnson AJ, Song X, Hsu A, Chen C. Apoptosis signaling pathways mediated by cyclooxygenase-2 inhibitors in prostate cancer cells. Adv Enzyme Regul 2001; 41:221-35.
68. Lawlor MA, Mora A, Ashby PR, Williams MR, Murray-Tait V, Malone L, Prescott AR, Lucocq JM, Alessi DR. Essential role of PDK1 in regulating cell size and development in mice. Embo J 2002; 21:3728-38.
69. Chen YJ, Lin JK, Lin-Shiau SY. Proliferation arrest and induction of CDK inhibitors p21 and p27 by depleting the calcium store in cultured C6 glioma cells. Eur J Cell Biol 1999; 78:824-31.
70. Kundu N, Smyth MJ, Samsel L, Fulton AM. Cyclooxygenase inhibitors block cell growth, increase ceramide and inhibit cell cycle. Breast Cancer Res Treat 2002; 76:57-64.
71. Levitt RJ, Pollak M. Insulin-like growth factor-I antagonizes the antiproliferative effects of cyclooxygenase-2 inhibitors on BxPC-3 pancreatic cancer cells. Cancer Res 2002; 62:7372-6.
72. Schroeder CP, Yang P, Newman RA, Lotan R. Eicosanoid metabolism in squamous cell carcinoma cell lines derived from primary and metastatic head and neck cancer and its modulation by celecoxib. Cancer Biol Ther 2004; 3:847-52.
73. Steinbach G, Lynch PM, Phillips RK, Wallace MH, Hawk E, Gordon GB, Wakabayashi N, Saunders B, Shen Y, Fujimura T, Su LK, Levin B. The effect of celecoxib, a cyclooxygenase-2 inhibitor, in familial adenomatous polyposis. N Engl J Med 2000; 342:1946-52.
74. Thun MJ, Namboodiri MM, Heath CW, Jr. Aspirin use and reduced risk of fatal colon cancer. N Engl J Med 1991; 325:1593-6.
75. Thun MJ, Calle EE, Namboodiri MM, Flanders WD, Coates RJ, Byers T, Boffetta P, Garfinkel L, Heath CW, Jr. Risk factors for fatal colon cancer in a large prospective study. J Natl Cancer Inst 1992; 84:1491-500.
76. DuBois RN, Giardiello FM, Smalley WE. Nonsteroidal anti-inflammatory drugs, eicosanoids, and colorectal cancer prevention. Gastroenterol Clin North Am 1996; 25:773-91.
77. Giovannucci E, Egan KM, Hunter DJ, Stampfer MJ, Colditz GA, Willett WC, Speizer FE. Aspirin and the risk of colorectal cancer in women. N Engl J Med 1995; 333:609-14.
78. Williams CS, Sheng H, Brockman JA, Armandla R, Shao J, Washington MK, Elkahloun AG, DuBois RN. A cyclooxygenase-2 inhibitor (SC-58125) blocks growth of established human colon cancer xenograffs. Neoplasia 2001; 3:428-36.
79. Sheng H, Shao J, Morrow JD, Beauchamp RD, DuBois RN. Modulation of apoptosis and Bcl-2 expression by prostaglandin E2 in human colon cancer cells. Cancer Res 1998; 58:362-6.
80. Reddy BS, Rao CV, Rivenson A, Kelloff G. Inhibitory effect of aspirin on azoxymethane-induced colon carcinogenesis in F344 rats. Carcinogenesis 1993; 14:1493-7.
81. Kawamori T, Rao CV, Seibert K, Reddy BS. Chemopreventive activity of celecoxib, a specific cyclooxygenase-2 inhibitor, against colon carcinogenesis. Cancer Res 1998; 58:409-12.
82. Williams CS, Tsujii M, Reese J, Dey SK, DuBois RN. Host cyclooxygenase-2 modulates carcinoma growth. J Clin Invest 2000; 105:1589-94.
83. Oshima M, Dinchuk JE, Kargman SL, Oshima H, Hancock B, Kwong E, Trzaskos JM, Evans JF, Taketo MM. Suppression of intestinal polyposis in Apc delta716 knockout mice by inhibition of cyclooxygenase 2 (COX-2). Cell 1996; 87:803-9.
84. Gately S, Li WW. Multiple roles of COX-2 in tumor angiogenesis: a target for antiangiogenic therapy. Semin Oncol 2004; 31:2-11.
85. Davis TW, O'Neal JM, Pagel MD, Zweifel BS, Mehta PP, Heuvelman DM, Masferrer JL. Synergy between celecoxib and radiotherapy results from inhibition of cyclooxygenase-2-derived prostaglandin E2, a survival factor for tumor and associated vasculature. Cancer Res 2004; 64:279-85.
86. Scheiman JM. Gastroduodenal safety of cyclooxygenase-2 inhibitors. Curr Pharm Des 2003; 9:2197-206.
87. Ahmad SR, Kortepeter C, Brinker A, Chen M, Beitz J. Renal failure associated with the use of celecoxib and rofecoxib. Drug Saf 2002; 25:537-44.
88. Florin TH. Lessons from early large-scale adoption of celecoxib and rofecoxib by Australian general practitioners. Med J Aust 2004; 180:310-2.
89. Olin JL, Chan A, Lazarus DS. Pulmonary edema and possible pneumonitis associated with celecoxib. Ann Pharmacother 2004; 38:1086.
90. Warner TD, Mitchell JA. Cyclooxygenases: new forms, new inhibitors, and lessons from the clinic. Faseb J 2004; 18:790-804.
91. Coulter DM, Clark DW, Savage RL. Celecoxib, rofecoxib, and acute temporary visual impairment. Bmj 2003; 327:1214-5.
92. Brewster UC, Perazella MA. Acute tubulointerstitial nephritis associated with celecoxib. Nephrol Dial Transplant 2004; 19:1017-8.