Effect of a new 1,3,4-thiadiazolium mesoionic compound (MI-D) on B16-F10 murine melanoma

Melanoma Research

Volumn 13, Issue 5, 2003, Pages 465-471

  Senff Ribeiro, Andrea ^a   Echevarria, Aurea ^b   Fernandes Silva, Edson ^b   Sanches Veiga, Silvio ^a   Oliveira, Maria Benigna Martinelli ^a  

^a FEDERAL UNIVERSITY OF PARANÁ   (Brazil)

^b FEDERAL RURAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

Antitumour effect; B16 F10 melanoma; MI D

Indexed keywords

4 PHENYL 5 (4 NITROCINNAMOYL) 1,3,4 THIADIAZOLIUM 2 PHENYLAMINE CHLORIDE; AMPHOLYTE; ANTINEOPLASTIC AGENT; DACARBAZINE; FOTEMUSTINE; THIADIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; BIOASSAY; CANCER INHIBITION; CELL LINE; CELL PROLIFERATION; CELL VIABILITY; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG MECHANISM; DRUG SCREENING; FEMALE; IN VITRO STUDY; IN VIVO STUDY; INOCULATION; MALE; MELANOMA; MELANOMA CELL; MOUSE; NONHUMAN; PRIORITY JOURNAL;

ANIMALS; CELL DIVISION; CELL LINE, TUMOR; CELL SURVIVAL; CINNAMATES; DOSE-RESPONSE RELATIONSHIP, DRUG; FEMALE; MALE; MELANOMA; MICE; MICE, INBRED C57BL; MODELS, CHEMICAL; THIAZOLES; TIME FACTORS;

EID: 0142120664     PISSN: 09608931     EISSN: None     Source Type: Journal    
DOI: 10.1097/00008390-200310000-00005     Document Type: Article

References (38)

1. Ollis WD, Ramsden CA. Meso-ionic compounds. Adv Heterocycl Chem 1976; 19:1-121.
2. Newton CG, Ramsden CA. Meso-ionic heterocycles. Tetrahedron 1982; 38:2965-3011.
3. Cheng KK, Echevarria A, Gallembeck S, Maciel MAM, Miller J, Rumjanek VM, et al. Mesoionic compounds 3. Structure of the hydrochloride of 5-(4-methoxyphenyl)-1,3,4-thiadiazolium-2-phenylamine. Acta Crystallogr 1992; 48:1471.
4. Kier LB, Roche EB. Medicinal chemistry of the mesoionic compounds. J Pharm Sci 1967; 56:148-169.
5. Moustafa MAA, Eisa HM. Synthesis and antimicrobial activity of 3-(substituted phenyl)-sydnones. Arch Pharm 1991; 325:397-401.
6. Corell T, Pedersen SB, Lissau B, Moilanen E, Mëtsa-Ketelä T, Kankaanranta H, et al. Pharmacology of mesoionic oxatriazole derivatives in blood, cardiovascular and respiratory systems. Pol J Pharmacol 1994; 46:553-566.
7. Satyanarayana K, Rao MNA. Synthesis and antiinflamatory, analgesic and antipyretic testing of 4-[1-oxo-(3-substituted aryl)-2-propenyl]-3-phenylsydnones and of 3-[4-[3-(substituted aryl)-1-oxo-2-propenyl] phenyl] sydnones. J Pharm Sci 1995; 84:263-266.
8. Rehse K, Ciborski T, Müller B. Platelet aggregation inhibiting and anticoagulant effects of oligoamines. XXVII: Inhibition of leucocyte adherence to endothelium by oligoamine RE 1492C and the NO-donor RE 2047. Arch Pharm 1995; 328:125-126.
9. Badachikar SV, Tikare RK, Puranik GS. Synthesis, reactions and biological activity of 3-[p-(N-methyl/ethyl-N-phenylcarbamoyl)]phenylsydnones. Indian J Chem 1986; 25B:1079-1080.
10. Montanari CA, Beezer AE, Sandall JPB, Montanari, MLC, Miller J, Giesbrecht AM. On the interaction of some mesoionic compounds with Saccharomyces cerevisiae by biological microcalorimetry. Rev Microbiol 1992; 23:274-278.
11. Kankaanranta H, Rydell E, Peterson AS, Holm P, Moilanen E, Corell T, et al. Nitric oxide-donating properties of mesoionic 3-aryl substituted oxatriazole-5-imine derivatives. Br J Pharmacol 1996; 117:401-406.
12. Shinzato TO, Grynberg N, Gomes RM, Echevarria A, Miller J. Antitumor activity of new mesoionic compounds against three murine tumors. Med Sci Res 1989; 17:865-866.
13. Grynberg N, Gomes R, Shinzato T, Echevarria A, Miller J. Some new aryl sydnones: effects on murine tumors. Anticancer Res 1992; 12:1025-1028.
14. Grynberg N, Santos AC, Echevarria A. Synthesis and in vivo antitumor activity of new heterocyclic derivatives of 1,3,4-thiadiazolium-2-aminide class. Anticancer Drugs 1997; 8:88-91.
15. Majid PA, DeFeyter PJF, Van der Wall EE, Wardeh R, Ross JP. Molsidomine in the treatment of patients with angina pectoris. N Engl J Med 1980; 302:1-6.
16. Rudolph W, Derschinger J. Clinical comparison of nitrates and sydnonimines. Eur Heart J 1991; 12:33-41.
17. Rehse K, Konig P. New NO donors with antithrombotic and vasodilating activities. XII. Mesoionic oxatriazoles and related monocyclic nitrosohydrazine derivatives. Arch Pharm 1995; 328:137-142.
18. Hogg N, Darley-Usmar VM, Wilson MT, Moncada S. Production of hydroxyl radicals from simultaneous generation of superoxide and nitric oxide. Biochem J 1992; 281:419-424.
19. Cadena SMSC, Carnieri, EGS, Echevarria A, Oliveira MBM. Effect of MI-D, a new mesoionic compound, on energy-linked functions of rat liver mitochondria. FEBS Lett 1998; 440:46-50.
20. Cadena SMSC, Carnieri EGS, Echevarria A, Oliveira MBM. Interference of MI-D, a new mesoionic compound, on artificial and native membranes. Cell Biochem Funct 2002; 20:31-37.
21. Vicente JR, Ortega VV, Jordana MC. The effects of different antineoplastic agents and of pretreatment by modulators on three melanoma lines. Cancer 1998; 82:495-502.
22. Ries LAG, Eisner MP, Kosary CL, Hankey BF, Miller BA, Clegg L, et al. (editors). SEER Cancer Statistics Review, 1975-2000. http://seer.cancer.gov/csr/1975_2000/. Bethesda: National Cancer Institute; 2002.
23. Huncharek M, Caubet JF, McGarry R. Single agent DTIC versus combination chemotherapy with or without immunotherapy in metastatic melanoma: a meta-analysis of 3273 patients from 20 randomized trials. Melanoma Res 2001; 11:75-81.
24. Boaziz C. Activity of a new nitrosurea - fotemustin. Pathol Biol (Paris)1992, 40:(9 pt 2):964-968.
25. Phillips HJ. Dye exclusion tests for cell viability. In: Kruse JR, Patterson JRMK (editors): Tissue Culture, Methods and Applications. New York: Academic Press; 1973, pp. 406-408.
26. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983; 65:55-63.
27. Blaschek W, Käsbauer J, Kraus J, Franz G. Phythium aphanidermatum: culture, cell-wall composition, and isolation and structure of antitumor storage and solubilised cell-wall (1→3), (1→6)-β-D-glucans. Carbohydr Res 1992; 231:293-307.
28. Ren DL, Wang JZ, Noda H, Amano H, Ogawa S. The effects of an algal polysaccharide from Gloiopeltis tenax on transplantable tumors and immune activities in mice. Planta Med 1995; 61:120-125.
29. Slapak CA, Kufe DW. Principles of cancer therapy. In: Isselbacher KJ, Braunwald E, Wilson JD, Martin JB, Fauci AS, Kasper DL (editors): Harrison's Principles of Internal Medicine. New York: McGraw-Hill; 1994, pp. 1826-1839.
30. Hayes MT, Bartley J, Parsons PG, Eaglesham GK, Prakash AS. Mechanism of action of fotemustine, a new chloroethylnitrosourea anticancer agent: evidence for the formation of two DNA-reactive intermediates contributing to cytotoxicity. Biochemistry 1997; 36:10646-10654.
31. Wack C, Becker JC, Bröcker EB, Lutz WK, Fischer WH. Chemoimmunotherapy for melanoma with dacarbazine and 2,4-dinitrochlorobenzene: results from a murine tumor model. Melanoma Res 2001; 11:247-253.
32. Colombo P, Gunnarsson K, Iatroupoulos M, Brughera M. Toxicological testing of cytotoxic drugs. Int J Oncol 2001; 19:1021-1028.
33. Martin DS, Bertino JR, Koutcher JA. ATP depletion + pyrimidine depletion can markedly enhance cancer therapy: fresh insight for a new approach. Cancer Res 2000; 60:6776-6783.
34. Wadhwa R, Sugihara T, Yoshida A, Nomura H, Reddel RR, Simpson R, et al. Selective toxicity of MKT-077 to cancer cells is mediated by its binding to the hsp70 family protein mot-2 and reactivation of p53 function. Cancer Res 2000; 60:6818-6821.
35. Skulachev VP. Uncoupling: new approaches to an old problem of bioenergetics. Biochim Biophys Acta 1998; 1363:100-124.
36. Newell KJ, Tannock IF. Reduction of intracellular pH as a possible mechanism for killing cells in acidic regions of solid tumors: effects of carbonylcyanide-3-chlorophenylhydrazone. Cancer Res 1989; 49:4477-4482.
37. Keller BJ, Marsman DS, Popp JA, Thurman RG. Several nongenotoxic carcinogens uncouple mitochondrial oxidative phosphorylation. Biochim Biophys Acta 1992; 1102:237-244.
38. Susin SA, Zamzami N, Kroemer G. Mitochondria as regulators of apoptosis: doubt no more. Biochim Biophys Acta 1998; 1366:151-165.