Novel dithiolethione-modified nonsteroidal anti-inflammatory drugs in human hepatoma HepG2 and colon LS180 cells

Clinical Cancer Research

Volumn 15, Issue 6, 2009, Pages 1964-1972

  Bass, Sara E ^a   Sienkiewicz, Pawel ^b   MacDonald, Christopher J ^b   Cheng, Robert Y S ^b   Sparatore, Anna ^c   Soldato, Piero Del ^d   Roberts, David D ^e   Moody, Terry W ^e   Wink, David A ^e   Chaoyeh, Grace ^b,e  

^a SAIC FREDERICK INC   (United States)

^b NATIONAL CANCER INSTITUTE   (United States)

^c UNIVERSITY OF MILAN   (Italy)

^d Sulfidris   (Italy)

^e NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBON RECEPTOR; CARCINOGEN; CYTOCHROME P450 1A1; DICLOFENAC; GLUTAMATE CYSTEINE LIGASE; GLUTATHIONE; GLUTATHIONE REDUCTASE; GLUTATHIONE TRANSFERASE A2; NONSTEROID ANTIINFLAMMATORY AGENT; NUCLEAR RNA; SULINDAC;

ARTICLE; CARCINOGENESIS; CELL STRAIN HEPG2; CELL TRANSFORMATION; CHROMATIN IMMUNOPRECIPITATION; COLON ADENOCARCINOMA; DETOXIFICATION; DNA RESPONSIVE ELEMENT; DRUG STRUCTURE; ENZYME INHIBITION; GENE MUTATION; GENETIC TRANSCRIPTION; HUMAN; HUMAN CELL; LIVER CELL CARCINOMA; PRIORITY JOURNAL; PROTEIN EXPRESSION; RECEPTOR UPREGULATION; SIGNAL TRANSDUCTION; TRANSCRIPTION INITIATION; TRANSCRIPTION REGULATION; XENOBIOTIC RESPONSIVE ELEMENT;

ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ANTICARCINOGENIC AGENTS; CELL LINE, TUMOR; COLORECTAL NEOPLASMS; CYTOCHROME P-450 CYP1A1; DICLOFENAC; HUMANS; LIVER NEOPLASMS; RECEPTORS, ARYL HYDROCARBON; RNA, MESSENGER; SULINDAC; TETRACHLORODIBENZODIOXIN; THIONES;

EID: 63549098125     PISSN: 10780432     EISSN: None     Source Type: Journal    
DOI: 10.1158/1078-0432.CCR-08-1870     Document Type: Article

References (48)

1. Ruegg C, Zaric J, Stupp R. Non steroidal anti-inflammatory drugs and COX-2 inhibitors as anti-cancer therapeutics: hypes, hopes and reality. Ann Med 2003;35:476-87.
2. Hawkey CJ. Non-steroidal anti-inflammatory drug gastropathy: causes and treatment. Scand J Gastroenterol Suppl 1996;220:124-7.
3. Mukherjee D, Nissen SE,Topol EJ. Risk of cardiovascular events associated with selective COX-2 inhibitors. JAMA 2001;286:954-9.
4. Wallace JL, Reuter B, Cicala C, McKnight W, Grisham MB, Cirino G. Novel nonsteroidal anti-inflammatory drugderivatives with markedly reduced ulcerogenic properties in the rat. Gastroenterology 1994;107: 173-9.
5. Hawkey CJ, Jones JI, Atherton CT, et al. Gastrointestinal safety of AZD3582, a cyclooxygenase inhibiting nitric oxide donator: proof of concept study in humans. Gut 2003;52:1537-42.
6. Fiorucci S, Santucci L, Wallace JL, etal. Interaction of a selective cyclooxygenase-2 inhibitor with aspirin and NO-releasingaspirin in the human gastric mucosa. Proc Natl Acad Sci U S A 2003;100:10937-41.
7. Konturek PC, Kania J, Burnat G, Hahn EG. NO-releas- ingaspirin exerts stronger growth inhibitory effect on Barrett's adenocarcinoma cells than traditional aspirin. J Physiol Pharmacol 2006;57 Suppl 12:15-24.
8. WangR.Two's company, three's a crowd: can H2S be the third endogenous gaseous transmitter? FASEB J 2002;16:1792-8.
9. Fiorucci S, Distrutti E, Cirino G, Wallace JL. The emerging roles of hydrogen sulfide in the gastrointestinal tract and liver. Gastroenterology 2006;131: 259-71.
10. Distrutti E, Sediari L, Mencarelli A, et al. 5-Amino-2-hydroxybenzoic acid 4-(5-thioxo-5H-[1,2-3yl)- phenyl ester (ATB-429), a hydrogen sulfide-releasing derivative of mesalamine, exerts antinociceptive effects in a model of postinflammatory hypersensitivity. J Pharmacol ExpTher 2006;319:447-58.
11. Pan TT, FengZN, Lee SW, Moore PK, Bian JS. Endogenous hydrogen sulfide contributes to the cardio- protection by metabolic inhibition preconditioningin the rat ventricular myocytes. J Mol Cell Cardiol 2006; 40:119-30.
12. Li L, Rossoni G, SparatoreA, Lee LC, Del Soldato P, Moore PK. Anti-inflammatory and gastrointestinal effects of a novel diclofenac derivative. Free Radic Biol Med 2007;42:706-19.
13. Isenberg JS, JiaY, Field L, et al. Modulation of angiogenesis by dithiolethione-modified NSAIDs and valproicacid. Br J Pharmacol 2007;151:63-72.
14. Rossoni G, Sparatore A,Tazzari V, Manfredi B, Del Soldato P, Berti F. The hydrogen sulphide-releasing derivative of diclofenac protects against ischaemia-reperfusion injury in the isolated rabbit heart. Br J Pharmacol 2007.
15. Wallace JL, Caliendo G, Santagada V, Cirino G, Fiorucci S. Gastrointestinal safety and anti-inflammato- ryeffectsofahydrogen sulfide-releasing diclofenacde-rivative in the rat. Gastroenterology 2007;132:261 -71.
16. Winde G, Schmid KW, Schlegel W, Fischer R, Osswald H, Bunte H. Complete reversion and prevention of rectal adenomas in colectomized patients with familial adenomatous polyposis by rectal low-dose sulindac maintenance treatment. Advantages of a low-dose nonsteroidal anti-inflammatory drugregi- men in reversingadenomas exceeding 33 months. Dis Colon Rectum 1995;38:813-30.
17. Wargovich MJ, Jimenez A, McKee K, et al. Efficacy of potential chemopreventive agents on rat colon aberrant crypt formation and progression. Carcinogenesis 2000;21:1149-55.
18. Ciolino HP, MacDonald CJ, Memon OS, Bass SE, Yeh GC. Sulindac regulates the aryl hydrocarbon receptor-mediated expression of Phase 1 metabolic enzymes in vivo and in vitro. Carcinogenesis 2006; 27:1586-92.
19. Wattenberg LW. Chemoprevention of cancer. Cancer Res1985;45:1 -8.
20. YangCS, Smith TJ, Hong JY. Cytochrome P-450 enzymes as targets for chemoprevention against chemical carcinogenesis and toxicity: opportunities and limitations. Cancer Res 1994;54:1982-6s.
21. Elferink CJ, Reiners JJ, Jr. Quantitative RT-PCR on CYP1A1 heterogeneous nuclear RNA: a surrogate for the in vitro transcription run-on assay. Biotechniques 1996;20:470-7.
22. Guigal N, Seree E, Nguyen QB, Charvet B, Desobry A, BarraY. Serum induces a transcriptional activation of CYP1A1 gene in HepG2 independently of the AhR pathway. Life Sci 2001;68:2141 -50.
23. Ciolino HP, Bass SE, MacDonald CJ, Cheng RY, Yeh GC. Sulindac and its metabolites induce carcinogen metabolizing enzymes in human colon cancer cells. Int J Cancer 2008;122:990-8.
24. Hestermann EV, Brown M. Agonist and chemopre- ventativeligands induce differential transcriptional co- factor recruitment by aryl hydrocarbon receptor. Mol Cell Biol 2003;23:7920-5.
25. Denison MS, Nagy SR. Activation of the aryl hydrocarbon receptor by structurally diverse exogenous and endogenous chemicals. Annu Rev Pharmacol Toxicol 2003;43:309-34.
26. TsuchiyaY, Nakajima M,YokoiT. Critical enhancer region to which AhR/ARNTand Sp1 bind in the human CYP1B1 gene. J Biochem (Tokyo) 2003;133:583-92.
27. Jiang Z, Dalton TP, Jin L, et al. Toward the evaluation of function in genetic variability: characterizing human SNP frequencies and establishing BAC-transgenic mice carryingthe human CYP1A1-CYP1A2 locus. Hum Mutat 2005;25:196-206.
28. Ueda R, Iketaki H, Nagata K, et al. A common regu- latoryregion functions bidirectionallyin transcriptional activation of the human CYP1A1 and CYP1A2 genes. Mol Pharmacol 2006;69:1924-30.
29. Doostdar H, Burke MD, Mayer RT. Bioflavonoids: selective substrates and inhibitors for cytochrome P450 CYP1A and CYP1B1. Toxicology 2000;144: 31-8.
30. Talalay P, Fahey JW. Phytochemicals from cruciferous plants protect against cancer by modulating carcinogen metabolism. J Nutr 2001;131:3027-33S.
31. Ansher SS, Dolan P, BuedingE. Biochemical effects of dithiolthiones. Food Chem Toxicol 1986; 24:405-15.
32. Kwak MK, Ramos-Gomez M, Wakabayashi N, Kensler TW. Chemoprevention by 1,2-dithiole-3-thio- nes through induction of NQO1 and other phase 2 enzymes. Methods Enzymol 2004;382:414-23.
33. MacDonald CJ, Ciolino HP,Yeh GC.The drugsalicy- lamide is an antagonistof the aryl hydrocarbon receptor that inhibits signal transduction induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin. Cancer Res 2004;64:429-34.
34. Huggins C, Grand LC, Brillantes FP. Mammary cancer induced by a single feeding of polymucular hydrocarbons, and its suppression. Nature 1961;189: 204-7.
35. Thompson HJ, JiangC, Lu J, et al. Sulfone metabolite of sulindac inhibits mammary carcinogenesis. Cancer Res 1997;57:267-71.
36. Takahashi Y, Itoh S, ShimojimaT, KamatakiT. Characterization of Ah receptor promoter in human liver cell line, HepG2. Pharmacogenetics 1994;4:219-22.
37. Harper PA, Prokipcak RD, Bush LE, Golas CL, Okey AB. Detection and characterization of the Ah receptor for 2,3,7,8-tetrachlorodibenzo-p-dioxin in the human colon adenocarcinoma cell line LS180. Arch Biochem Biophys 1991;290:27-36.
38. Bhatia M, Sidhapuriwala JN, Sparatore A, Moore PK. Treatment with H2s-releasingdiclofenac protects mice against acute pancreatitis-associated lung injury. Shock 2008;29:84-8.
39. Liu YL, Roebuck BD, Yager JD, Groopman JD, KenslerTW. Protection by 5-(2-pyrazinyl)-4-methyl- 1,2-dithiol-3-thione(oltipraz) against thehepatotoxic- ity of aflatoxin B1 in the rat. Toxicol Appl Pharmacol 1988;93:442-51.
40. Gupta E, Olopade OI, Ratain MJ, et al. Pharma- cokinetics and pharmacodynamics of oltipraz as a chemopreventive agent. Clin Cancer Res 1995;1: 1133-8.
41. Khanna S, Sen CK, Roy S, Christen MO, Packer L. Protective effects of anethole dithiolethione against oxidative stress-induced cytotoxicity in human Jurkat Tcells. Biochem Pharmacol 1998;56:61 -9.
42. Kwak MK, Egner PA, Dolan PM, et al. Role of phase 2 enzyme induction in chemoprotection by dithiole- thiones. Mutat Res 2001;480-481:305-15.
43. Yan SK, ChangT, Wang H, Wu L, Wang R, Meng QH. Effects of hydrogen sulfide on homocysteine- induced oxidative stress in vascular smooth muscle cells. Biochem Biophys Res Commun 2006;351: 485-91.
44. Sen CK,Traber KE, Packer L. Inhibition of NF-κBac- tivation in human T-cell lines by anetholdithiolthione. Biochem Biophys Res Commun 1996;218:148-53.
45. Stohs SJ. Oxidative stress induced by 2,3,7,8- tetrachlorodibenzo-p- dioxin (TCDD). Free Radic Biol Med 1990;9:79-90.
46. Alsharif NZ, LawsonT, Stohs SJ. Oxidative stress induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin is mediated by the aryl hydrocarbon (Ah) receptor complex. Toxicology 1994;92:39-51.
47. Vogel CF, Li W, Sciullo E, et al. Pathogenesis of aryl hydrocarbon receptor-mediated development of lymphoma is associated with increased cyclooxygenase-2 expression. Am J Pathol 2007;171:1538-48.
48. Martey CA, Baglole CJ, GasiewiczTA, Sime PJ, Phipps RP. The aryl hydrocarbon receptor is a regulator of cigarette smoke induction of the cyclooxygenase and prostaglandin pathways in human lung fibroblasts.Am J PhysiolLungCell MolPhysiol 2005;289:L391-9.