515
Views
7
CrossRef citations to date
0
Altmetric
Research Article

Chemopreventive potential of 3-[2,6-bis(4-fluorophenyl)-3-methylpiperidin-4-ylideneamino]-2-thioxoimidazolidin-4-one on 7,12-dimethylbenz[a]anthracene (DMBA) induced hamster buccal pouch carcinogenesis

, , &
Pages 836-843 | Received 13 Dec 2009, Accepted 12 Feb 2010, Published online: 07 Apr 2010

References

  • Cherouvrier JR, Carreaux F, Bazureau JP. Reactivity of 2-thiohydantoins towards various electrophilic reagents: Applications to the synthesis of new 2-ylidene-3,5-dihydro-4H-imidazol-4-ones. Molecules 2004;9:867–875.
  • Wang ZD, Sheikh SO, Zhang Y. A simple synthesis of 2-thiohydantoins. Molecules 2006;11:739–750.
  • Baliah V, Jeyaraman, R, Chandrasekaran L. Synthesis of 2,6-disubstituted piperidones, oxanes and thianes. Chem Rev 1983;83:379–423.
  • Noller CR, Baliah V. The preparation of some piperidine derivatives by the Mannich reaction. J Am Chem Soc 1948;70:3853–3854.
  • Angle SR, Breitenbucher JG. In: Atta-ur-Rahman, (ed.) Studies in Natural Products Chemistry, Stereoselective Synthesis Vol 16, New York: Elsevier, 1995:453.
  • Johnson NW. Epidemiology of Oral Cancer in Risk Markers of Oral Disease. In: Johnson NW, (ed.) Oral Cancer Vol 2. Cambridge: Cambridge University Press, 1991:3–26.
  • Boring CC, Squires TS, Tong T. Cancer statistics. CA Cancer J Clin 1992;42:19–38.
  • Slaughter DP, Southwick HW, Smejkal W. Field cancerization in oral stratified squamous epithelium: clinical implications of multicentric origin. Cancer 1953;6:963–968.
  • Licciardello JTW, Spitz MR, Hong WK. Multiple primary cancer of the head and neck, esophagus and lung. International J Rad Oncol Biol Physics 1989;17:467–476.
  • Gimenez-Conti IB, Slaga TJ. The hamster cheek pouch model of carcinogenesis and chemoprevention. Adv Expt Med Biol 1992:320:63–67.
  • Gimenez-Conti IB, Slaga TJ. The hamster cheek pouch carcinogenesis model. J Cell Biochem Suppl 1993;17F:83–90.
  • Solt DB, Shklar G. Rapid induction of gamma glutamyl transpeptidase rich intraepithelial clones in 7,12-dimethylbenz[a]anthracene treated hamster buccal pouch. Cancer Res 1982;45:285–291.
  • Kwong YY, Husain Z, Biswas DK. C-Ha-ras gene mutation and activation precede pathological changes in DMBA-induced in vivo carcinogenesis. Oncogene 1992;7:1481–1489.
  • Chang KW, Lin SC, Koos S, Pather K, Solt D. P53 and Ha-ras mutations in chemically induced hamster buccal pouch carcinomas. Carcinogenesis 1996;17:595–600.
  • Wattenberg LW. Chemoprevention of cancer. Cancer Res 1985;45:1–8.
  • Sharma S, Stutzman JD, Kelloff GJ, Steele VE. Screening of potential chemopreventive agents using bio chemical markers of carcinogenesis. Cancer Res 1994;54:5848–5855.
  • Anderson ME, Meister A. Transport and direct utilization of gamma-glutamyl cyst(e)ine for glutathione synthesis. Proc Natl Acad Sci USA 1983;80:707–711.
  • Ketterer B. Protective role of glutathione and glutathione transferases in mutagenesis and carcinogenesis. Mutation Res 1988;202:343–361.
  • Hayes JD, Pulford DJ. The glutathione S-transferase supergene family: regulation of GST and the contribution of the isoenzymes to cancer chemoprevention and drug resistance. Critical Rev Biochem Mol Biol 1995;30:445–600.
  • Boone CW, Kelloff GJ, Malone WE. Identification of candidate cancer chemopreventive agents and their evaluation in animal models and human clinical trials: A review. Cancer Res 1990;50:2–9.
  • Lippman SM, Benner SE, Hong WK. Cancer chemoprevention. J Clin Oncol 1994;12:851–873.
  • Ito N, Fukushima S, Tsuda H. Carcinogenicity and modification of the carcinogenic response by BHA, BHT and other antioxidants. CRC Critical Rev Toxicol 1985;15:109–150.
  • Gopalakrishnan M, Kanagarajan V, Thanusu J. Novel one-pot synthesis of 1,2,4-triazolidin-3-thiones comprising piperidine moiety. Green Chem Lett Rev 2008;1:241–246.
  • Gopalakrishnan M, Sureshkumar P, Kanagarajan V, Thanusu J, Govindaraju R.A simplified green chemistry approaches to organic synthesis in solid media. activated fly ash, an industrial waste (pollutant) as an efficient and novel catalyst for some selected organic reactions in solvent-free conditions under microwave irradiation. Arkivoc 2006;13:130–141.
  • Gopalakrishnan M, Sureshkumar P, Kanagarajan V, Thanusu J, Govindaraju R, Ezhilarasi MR. Microwave-promoted facile and rapid solvent-free procedure for the efficient synthesis of 3,4-dihydropyrimidin-2(1H)-ones and -thiones using ZrO2/SO42- as a reusable heterogeneous catalyst. Lett Org Chem 2006;3:484–488.
  • Gopalakrishnan M, Sureshkumar P, Kanagarajan V, Thanusu J. Aluminium metal powder (atomized) catalyzed Friedel-Crafts acylation in solvent-free conditions: A facile and rapid synthesis of aryl ketones under microwave irradiation. Catalysis Commun 2005;6:753–756.
  • Gopalakrishnan M, Sureshkumar P, Kanagarajan V, Thanusu J, Govindaraju R. Silica gel supported sodium hydrogen sulfate as an efficient and reusable heterogeneous catalyst for the synthesis of imines in solvent-free conditions under microwave irradiation. J Chem Res 2005;5:299–303.
  • Gopalakrishnan M, Sureshkumar P, Kanagarajan V, Thanusu J. Organic synthesis in solid media. Alumina supported sodium hydrogen sulfate as an effective and reusable catalyst for ‘one-pot’ synthesis of amides from ketones in dry media under microwave irradiation. Lett Org Chem 2005;2:444–446.
  • Gopalakrishnan M, Sureshkumar P, Kanagarajan V, Thanusu J. Design, ‘one-pot’ synthesis, characterization, antibacterial and antifungal activities of novel 6-aryl-1,2,4,5-tetrazinan-3-thiones in dry media. J Sulfur Chem. 2007;8:383–392.
  • Gopalakrishnan M, Sureshkumar P, Thanusu J, Kanagarajan V, Govindaraju R, Jayasri G. A convenient ‘one-pot’ synthesis and in vitro microbiological evaluation of novel 2,7-diaryl-[1,4]-diazepan-5-ones. J Enz Inhib Med Chem 2007;22:709–715.
  • Gopalakrishnan M, Thanusu J, Kanagarajan V. Heterogeneous NaHSO4.SiO2 catalyzed ‘one-pot’ synthesis and in vitro antibacterial and antifungal activities of pyridino-1,2,3-thiadiazoles. J Sulfur Chem 2008;29:179–185.
  • Shklar G. Experimental oral pathology in the Syrian hamster. Progress in Expt Tumour Res 1972;16:518–538.
  • Ohkawa H, Ohisi N, Yagi K. 1979. Assay for lipid peroxides in animal tissues by thiobarbituric acid reaction. Analyt Biochem 1979;95:351–358.
  • Oberley LW, Spitz DR. In: ed. Methods in Enzymology. New York: Academic Press, 1984:457.
  • Sinha AK. Colorimetric assay of Catalase. Anal Biochem 1972;47:389.
  • Beutler E, Kelley BM. The effect of sodium nitrate on RBC glutathione. Experimentia 1963;29:96–97.
  • Rotruck JT, Pope AL, Ganther HE, Swanson AB, Hafeman DG, Hoekstra WG. Selenium: Biochemical roles as a component of glutathione peroxidase. Science 1973;179:588–590.
  • Habig WH, Pabst MJ, Jakoby WB. Glutathione S-transferases, the first enzymatic step in mercapturic acid formation. J Biol Chem 1974;249:7130–7139.
  • Lowry OH, Rosebrough NJ, Farr AL, Randall RJ. Protein measurement with Folins phenol reagent. J Biol Chem 1951;193:265–275.
  • Das UN. A radical approach to cancer. Med Sci Monit 2002;8:79.
  • Subapriya R, Bhuvaneswari V, Ramesh V, Nagini S. Ethanolic Neem (Azadirachta indica) leaf extract induces apoptosis in the hamster buccal pouch carcinogenesis model by modulation of Bcl-2, Bim, caspase 8 and caspase 3. Cell Biochem Func 2005;23:229–234.
  • Kohno Y, Patel V, Kim Y, Tsuji T, Chin BR, Sun M, Bruce Donoff R, Kent R, Wong D, Todd R. Oncogene - P12CDK2-AP1 mediates DNA damage responses induced by DMBA. Oral Oncol 2002;38:274–280.
  • Ghalia AHB, Fouad IM. Glutathione and its metabolizing enzymes in patients with different benign and malignant diseases. Clin Biochem 2000;33:657.
  • Slater TF, Benedetto C, Burton GW, Cheeseman KH, Ingold KU, Nodes JT. Lipid peroxidation in animal tumours: A disturbance in the control of cell division. In: Thaler-Dao H, Paoletti R, Crastes de Paulet A, eds. Icosanoids and Cancer. New York: Raven Press, 1984:21–29.
  • Chandra Mohan KVP, Nagini S. Combination chemoprevention by tomato and garlic in the hamster buccal pouch carcinogenesis model. Nutr Res 2003;23:1403–1406.
  • Moghadasian MH, Freeman HJ, Godin DV. Endogenous antioxidant status in neoplastic and adjacent tissues in 1,2-dimethylhydrazine-induced colon cancer in rats: Effects of olsalazine. Carcinogenesis 1996;17:983–987.
  • Lam EWN, Zwacka R, Seftor EA, Nieva DRC, Davidson BL, Engelhardt JF, Hendrix MJC, Oberley LW. Effects of antioxidant enzyme overexpression on the invasive phenotype of hamster cheek pouch carcinoma cells. Free Radic Biol 1999;27:572–579.
  • Cheng SC, Prakash AS, Pigott MA, Hilton BD, Lee H, Harvey RG, Dipple A. A metabolite of the carcinogen 7,12-dimethylbenz[a]anthracene that inititate carcinogenesis by causing mutation. Carcinogenesis 1988;9:1721–1723.
  • Sinhababu AK, Thakker DR, Prodrugs of anticancer agents. Adv Drug Delivery Rev 1996;19:241–273.
  • Prestera T, Zhang Y, Spencer SR, Wilezak C, Talalay P. The electrophile counterattack response: protection against neoplasia and toxicity. Adv Enzyme Regul 1993;33:281–296.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.