1,2,4-Thiadiazolidine derivative inhibits nuclear transcription factor-κB and its dependent genes activation but induces apoptosis

International Journal of Cancer

Volumn 113, Issue 4, 2005, Pages 549-560

  Manna, Paresh ^a   Narang, Krishnan K ^a   Manna, Sunil K ^b  

^a BANARAS HINDU UNIVERSITY   (India)

^b CENTRE FOR DNA FINGERPRINTING AND DIAGNOSTICS   (India)

Author keywords

1,2,4 thiadiazolidine; Apoptosis; Cell signaling; NF B; Tumor

Indexed keywords

1,2,4 THIADIAZOLE DERIVATIVE; ANTIINFLAMMATORY AGENT; ANTINEOPLASTIC AGENT; CYCLOOXYGENASE 2; I KAPPA B KINASE; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE; TRANSCRIPTION FACTOR; TUMOR NECROSIS FACTOR;

ANALYTIC METHOD; ANIMAL CELL; ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CELL DEATH; CONTROLLED STUDY; DRUG POTENCY; DRUG SYNTHESIS; ENZYME ACTIVATION; ENZYME INHIBITION; EPITHELIUM CELL; GENE ACTIVATION; GENE EXPRESSION; HUMAN; HUMAN CELL; INFLAMMATION; NONHUMAN; PRIORITY JOURNAL; PROTEIN DEGRADATION; PROTEIN EXPRESSION; RAT; REPORTER GENE; T LYMPHOCYTE;

APOPTOSIS; CASPASES; CELL NUCLEUS; CELLS, CULTURED; CYCLOOXYGENASE 2; ENZYME ACTIVATION; EPITHELIAL CELLS; GENE EXPRESSION REGULATION; HUMANS; I-KAPPA B KINASE; I-KAPPA B PROTEINS; ISOENZYMES; LIPID PEROXIDATION; MEMBRANE PROTEINS; NF-KAPPA B; POLY(ADP-RIBOSE) POLYMERASES; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES; PROTEIN TRANSPORT; PROTEIN-SERINE-THREONINE KINASES; T-LYMPHOCYTES; THIADIAZOLES; TUMOR NECROSIS FACTOR-ALPHA;

EID: 11144335893     PISSN: 00207136     EISSN: None     Source Type: Journal    
DOI: 10.1002/ijc.20590     Document Type: Article

References (52)

1. Bhargawa PM, Chourasia MR. New local anesthetics Derivatives of 5-diethyl aminoactamido-2-arylimino-3-aryl-4-thiazolidones. J Pharm Sci 1969;58:896-8.
2. Abdel-Halin AM, Abdel-Aziz RM, El-Dein HS, El-Kafrawy AF. Synthesis and Biological activity of some 2-[Pyrimidin-2-yl] imino-thiazoalidin-4-one. Indian J Heterocyclic Chem 1994;4:45-50.
3. Rajeswaran WG, Yang C, Xi-Ping H, Elizabeth WM, Tracy C, Solina L, Fenghua L, Peter IN, James E, Beth AL, Karl HN, William SM Jr. Design, synthesis and biological characterization of bivalent 1-methyl-1,2,5,6-tetrahydropyridyl- 1,2,5-thiadiazole derivatives as selective muscarinic agonists. J Med Chem 2001;44:4563-76.
4. Geard C, Bernard B, Bertin E, Cristina De A, Simon LC, Dumas M, Jacques P. Synthesis and Biological Activity of Nitro Heterocycles analogous to Mega zol, a Tryopanocidal lead. J Med Chem 2003;46:427-40.
5. Jag M, Ashok K. Synthesis and Antimicrobial activity of imidazo [2,1-b]-1,3,4-thiadiazolo[2,3-c]-S-triazoles and S-triazolo [3,4,b]-1,3,4- thiadiazoles. Indian J Heterocyclic Chemistry 2003;12:189-92.
6. Archana, Srivastava VK, Kumar A. Synthesis of newer indolyl thiadiazoles and their thiazolidnones and formanzans as potential anti-convulsant agents. Indian J Pharm Sci 2003;65:358-62.
7. Ilies Marc A, Daniela V, Jaromir P, Andrea S, Monica I, Miron TC, Silvia P, Claudie TS. Carbonic anhydrase inhibitions, Inhibition of Tumor Associated Isozyme IX by Halogenosulfanilamide and Halogenophenylaminobenzolamide derivatives. J Med Chem 2003;43:2187-96.
8. Choubey AK, Tripathi AK, Singh R. Synthesis, antifungal and antibacterial activities of Some New 2-benzylideneamino-5-arylimino-3-oxo-1,2,4- thiadiazolidines. Indian J Chem 1998;37B:145-50.
9. Singh R, Choubey AK, Tripathi AK. Synthesis of novel 2-p- methoxybenzylideneimino-5-arylimno-3-oxo-l,2,4-thiadiazolidines. Indian J Heterocyclic Chem 1997;6:251-4.
10. Youichiro N, Fumihiko A, Shinji T, Takehiro O, Masahiko K, Hiroko N, Masanori S, Chikara F, Yoshio K. Synthesis and pharmacological activities of Triazole derivatives inhibiting Eosinophilia. J Med Chem 1996;39:3019-29.
11. Ali MR, Verma VK. One-pot Synthesis of 2-aryl-3-phenyl-5-phenylimino-1,2, 4-thiadiazolines using N-Chlorosuccinimide. Synthesis 1985;691-3.
12. Ali MR, Singh R, Verma VK. A new synthesis of 5-aryl-3-oxo-2-phynel -2H-3H- 1,2,4- thiadiazoles. Indian J Chem 1985;24B:977-8.
13. Pandey AK, Singh R, Verma VK. Synthesis of 2-phynel-3-oxo-4-arylimino-1, 2,4-thiadiazolidines. Indian J Chem 1986;25B:202-3.
14. Singh R, Choubey AK, Bhattacharya AA. Novel rout to the synthesis of 2-cyclohexylideneamino-5-arylamino-3-oxo-1,2,4-thiadiazolidines. J Indian Chem Soc 1998;75:430-1.
15. Pandey A.K, Singh R, Verma VK. Oxidative deallylation and cyclization of 2-S-allyl-1-aryl-5-isothiobiurates as an alternative route to the synthesis of the 5-arylimino-3-oxo-2-phynel-1,2,4-thiadiazolidines. Indian J Chem 1982;21B:150-2.
16. Pandey AK, Singh R, Verma VK. Synthesis of N,N-Disubstituted 3-oxo-2-phynel-2,3-dihydro-1,2,4-thiadiazoles. Synthesis 1982;12:1068-70.
17. Baldwin AS. The NF-kappa B and I kappa B proteins: new discoveries and insights. Annu Rev Immunol 1996;14:649-83.
18. Baeuerle PA, Baichwal VR. NF-κB as a frequent target for immunosuppressive and anti-inflammatory molecules. Adv Immunol 1997;65:111-37.
19. Baichwal VR, Baeuerle PA. Apoptosis: activate NF-κB or die? Curr Biol 1997;7:R94-6.
20. Manna SK, Zhang HJ, Yan T, Oberley LW, Aggarwal BB. Overexpression of Mn-superoxide dismutase suppresses TNF induced apoptosis and activation of nuclear transcription factor-B and activated protein-1. J Biol Chem 1998;273:13245-54.
21. Czaja MJ. Induction and regulation of hepatocyte apoptosis by oxidative stress. Antioxid Redox Signal 2002;4:759-67.
22. Kondo T, Suzuki Y, Kitano T, Iwai K, Watanabe M, Umehara H, Daido N, Domae N, Tashima M, Uchiyama T, Okazaki T. Vesnarinone causes oxidative damage by inhibiting catalase function through ceramide action in myeloid cell apoptosis. Mol Pharmacol 2002;61:620-7.
23. Darnay B, Ni J, Moore PA, Aggarwal BB. Activation of NF-κB by RANK requires TRAF6 and NF-κB-inducing kinase (NIK): identification of a novel TRAF6 interaction motif. J Biol Chem 1999;274:7724-31.
24. Sarkar A, Sreenivasan Y, Ramesh GT, Manna SK. Beta-D-glucoside suppresses TNF-induced activation of nuclear transcription factor kappaB but potentiates apoptosis. J Biol Chem 2004;279:33768-81.
25. Takada Y, Singh S, Aggarwal BB. Identification of a p65 peptide that selectively inhibits NF-kappa B activation induced by various inflammatory stimuli and its role in down-regulation of NF-kappaB-mediated gene expression and up-regulation of apoptosis. J Biol Chem 2004;279:15096-104.
26. 2 in NF-κB activation by either cytokine in both primary and transformed endothelial cells. J Biol Chem 1997;272:25941-50.
27. Manna SK, Mukhopadhyay A, Van NT, Aggarwal BB. Silymarin suppresses TNF-induced activation of nuclear transcription factor-[{kappa}] B, c-Jun N terminal kinase, and apoptosis. J Immunol 1999;162:6800-9.
28. Sreenivasan Y, Sarkar A, Manna SK. Mechanism of Cytosine arabinoside mediated apoptosis: Role of Rel A (p65) dephosphorylation. Oncogene 2003;22:4356-69.
29. Bonizzi G, Piette J, Merville MP, Bours V. Distinct signal transduction pathways mediate nuclear factor-κ B induction by IL-1β in epithelial and lymphoid cells. J Immunol 1997;159:5264-72.
30. Li N, Karin M. Ionizing radiation and short wavelength UV activate NF-κB through two distinct mechanisms. Proc Natl Acad Sci U S A 1998;95:13012-7.
31. Imbert V, Rupec RA, Livolsi A, Pahl HL, Traenckner EB, Mueller-Dieckmann C, Farahifar D, Rossi B, Auberger P, Baeuerle PA, Peyron JF. Tyrosine phosphorylation of IkBa activates NF-κB without proteolytic degradation of IκBα. Cell 1996;86:787-98.
32. Rath PC, Aggarwal BB. TNF-induced signaling in apoptosis. J Clin Immunol 1999;19:350-64.
33. Singh S, Aggarwal BB. Activation of transcription factor NF-κB is suppressed by curcumin (Diferulolylmethane). J Biol Chem 1995;270:24995-5000.
34. Jobin C, Bradham CA, Russo MP, Juma B, Narula AS, Brenner DA, Sartor RB. Curcumin blocks cytokine-mediated NF-κB activation and proinflammatory gene expression by inhibiting inhibitory factor I-κB kinase activity. J Immunol 1999;163:3474-83.
35. Natarajan K, Singh S, Burke TR, Grunberger D Jr, Aggarwal BB. Caffeic acid phenethyl ester (CAPE) is a potent and specific inhibitor of activation of nuclear transcription factor NF-κB. Proc Natl Acad Sci U S A 1996;93:9090-5.
36. Egan LJ, Mays DC, Huntoon CJ, Bell MP, Pike MG, Sandborn WJ, Lipsky JJ, McKean DJ. Inhibition of interleukin-1-stimulated NF-κB RelA/p65 phosphorylation by mesalamine is accompanied by decreased transcriptional activity. J Biol Chem 1999;274:26448-53.
37. Manna SK, Mukhopadhyay A, Aggarwal BB. Resveratrol suppresses TNF-induced activation of nuclear transcription factors NF-kappa B, activator protein-1, and apoptosis: potential role of reactive oxygen intermediates and lipid peroxidation. J Immunol 2000;164:6509-19.
38. DiDonato JA, Hayakawa M, Rothwarf DM, Zandi E, Karin M. A cytokine-responsive IκB kinase that activates the transcription factor NF-κB. Nature 1997;388:548-54.
39. Zandi E, Rothwarf DM, Delhase M, Hayakawa M, Karin M. The IκB kinase complex (IKK) contains two kinase subunits, IKKα and IKKβ, necessary for IκB phosphorylation and NF-κB activation. Cell 1997;9:243-52.
40. Sizemore N, Leung S, Stark GR. Activation of phosphatidylinositol 3-kinase in response to interleukin-1 leads to phosphorylation and activation of the NF-κB p65/RelA subunit. Mol Cell Biol 1999;19:4798-805.
41. Mercurio F, Manning AM. Multiple signals converging on NF-κB. Curr Opin Cell Biol 1999;11:226-32.
42. Manna SK, Sah NK, Aggarwal BB. Protein tyrosine kinase p56lck is required for ceramide-induced but not tumor necrosis factor-induced activation of NF-kappa B, AP-1, JNK, and apoptosis. J Biol Chem 2000;275:13297-306.
43. Sreenivasan Y, Sarkar A, Manna SK. Oleandrin suppresses activation of nuclear transcription factor-kappaB and activator protein-1 and potentiates apoptosis induced by ceramide. Biochem Pharmacol 2003;66:2223-39.
44. Lee JI, Burckart GJ. Nuclear factor-κB: important transcription factor and therapeutic target. J Clin Pharmacol 1998;38:981-93.
45. Wang CY, Guttridge DC, Mayo MW, Baldwin AS Jr. NF-κB induces expression of the Bcl-2 homologue A1/Bfl-1 to preferentially suppress chemotherapy-induced apoptosis. Mol Cell Biol 1999;19:5923-9.
46. Waddick KG, Uckun FM. Innovative treatment programs against cancer. II. Nuclear factor-kappa B (NF-κB) as a molecular target. Biochem Pharmacol 1999;57:9-17.
47. Dong G, Chen Z, Kato T, Van Waes C. The host environment promotes the constitutive activation of nuclear factor-B and proinflammatory cytokine expression during metastatic tumor progression of murine squamous cell carcinoma. Cancer Res 1999;59:3495-504.
48. VonKnethen A, Callsen D, Brune B. Superoxide attenuates macrophage apoptosis by NF-κB and AP-1 activation that promotes cyclooxygenase-2 expression. J Immunol 1997;163:2858-66.
49. Sato H, Seiki M. Regulatory mechanism of 92 kDa type IV collagenase gene expression which is associated with invasiveness of tumor cells. Oncogene 1993;8:395-405.
50. Collins T, Read MA, Neish AS, Whitley MZ, Thanos D, Maniatis T. Transcriptional regulation of endothelial cell adhesion molecules: NF-κB and cytokine-inducible enhancers. FASEB J 1995;9:899-909.
51. Iademarco MF, McQuillan JJ, Rosen GD, Dean DC. Characterization of the promoter for vascular cell adhesion molecule-1 (VCAM-1). J Biol Chem 1992;267:16323-9.
52. Wunsch H. COX provides missing link in mechanism of aspirin in colon cancer. Lancet 1998;351:1864.