Antiproliferation activity and the mechanism of action of 9-bromo-5- morpholino-tetrazolo[1,5-c]quinazoline-potentional anticancer drug

Neoplasma

Volumn 44, Issue 4, 1997, Pages 240-246

  Jantova S ^a   Ruzekova L ^b   Stankovsky S ^a   Spirkova K ^a  

^a SLOVAK UNIVERSITY OF TECHNOLOGY   (Slovakia)

^b INSTITUTE OF CHEMISTRY   (Slovakia)

Author keywords

Cell cycle; Cytotoxicity; DNA single strand breaks; Quinazoline derivatives; Unbalanced growth

Indexed keywords

9 BROMO 5 MORPHOLINO TETRAZOLO[1,5 C]QUINAZOLINE; ANTINEOPLASTIC AGENT; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CANCER INHIBITION; CYTOPATHOGENIC EFFECT; DNA STRAND BREAKAGE; DRUG POTENCY; HELA CELL; HUMAN; HUMAN CELL;

EID: 0030765158     PISSN: 00282685     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (44)

1. AHNSTROM, G., ERIXON, K.: Measurement of strand breaks by alkaline denaturation and hydroxylapapite chromatography. In: DNA Repair. Eds: Friedberg, E.C., Hanawalt, P.C., Dekker, M. A Laboratory Manual of Research Procedures, 18, 1981, 403-418.
2. BISHOP, J.A.M., JACKMAN, A.L., HUGHES, L.R., CALVERT, A.H.: Cross-resistance studies with quinazoline inhibitors of thymidylate synthase against two methotrexate (MTX)-resistant sublines of the L1210. Br. J. Cancer, 60, 1989, 499-506.
3. CHAURASIA, M.R., SHARMA, S.K.: Synthesis of some heterocyclic compounds with bridgeheadcd nitrogen atoms. Heterocycles, 14, 1980, 1759-1765.
4. CHERN, J.W., SHIAU, C.Y., LU, G.Y.: Studies on quinazolinones. 3. Novel and efficient route to the synthesis of conformationally restricted analogs of ketanserin and Sgb-1534 as antihypertensive agents. Bioorg. Med. Chem. Lett., 1, 1991, 571.
5. th NCI-EORTC Symposium on New Drugs in Cancer Therapy. Amsterdam, March 12-15, 1996, 29.
6. CURTIN, N.J., HARRIS, A.L., JAMES, O.F.W., BASSENDINE, M.F.: Inhibition of the growth of human hepatocellular carcinoma in vitro and in athymic mice by a quinazoline inhibitor of thymidylate synthase, CB 3717. Br. J. Cancer, 53, 1986, 361-368.
7. ELZOHRY, M.F., ELHAME, A., AHMED, N., OMAR, F.A., ABDALLA, M.A.: Synthesis and antibacterial activity of certain quinoline and quinazoline derivatives containing sulfide and sulfone moieties. J. Chem.Technol. Biotechnol., 53, 1992, 329-336.
8. FAAGHALY, A.M., CHAABAN, I., KHALIL, M.A., BEKHIT, A.A.: Nonsteroidal antiinflammatory agents. Synthesis of novel 2-pyrazolyl-4(3H)-quinazolinones. Arch. Pharmacol., 323, 1990, 833-836.
9. GABRIEL, S.: Über das Chinazolin. Ber. Deut. Chem. Ges., 36, 1903, 800-813.
10. GEORGOPOULOS, C., WELCH, W.J.: Role of the major heat shock proteins as molecular chaperones. Annu. Rev. Cell Biol., 9, 1993, 601-634.
11. GLADYS, I., RODRIGUEZ, M.: New chemotherapy agents in phase I/II trials in the United States of America. In: Abstracts of 6th International Congress on Anti-Cancer Treatment. Paris, February 6-9, 1996, 54.
12. GREISS, P.: Über die Einwirkung des Lyans auf Anthranisäure. Ber. Deut. Chem. Ges., 2, 1869, 415-418.
13. HORÁKOVÁ, K., KALAFUT, F., NAVAROVÁ, J., PATERSON, A. R. P.: Delayed expression of 6-mercaptopurine cytotoxicity toward HeLa cells. Neoplasma, 21, 1974, 555-560.
14. HORÁKOVA, K., LUKÁĆOVÁ, D., KOZÁNKOVÁ, Z., DŹURBA, A., ZIEGELHOFFER, A., JANTOVÁ, S. : The mechanism of cytolytic and cytostatic activity of benfluron. Neoplasma, 35, 1988, 177-183.
15. HORAKOVA, K., JANTOVA, S., STREḊANSKY, M., NOVOTNÁ, L.: Ethyl 4-isothiocyanatobutanoate - antiproliferative activity in vitro and in vivo. Anticancer Drugs, 4, 1993, 369-375.
16. HUGHES, L.R., JACKMAN, A.L., OLDFIELD, J., SMITH, R.C., BURROWS, K.D., MARSHAM, P.R., BISHOP, J.A.M., JONES, T.R., O'CONNOR, B.M., CALVERT, A.H.:Quinazoline antifolate thymidylate synthase inhibitors: alkyl, substituted alkyl and aryl substituants in the C2 position. J. Med. Chem., 33, 1990, 3060-3067.
17. JACKMAN, A.L.,TAYLOR, G.A., GIBSON, W., KIMBELL, R., BROWN, M., CALVERT, A.H., JUDSON, I.R., HUGHES, L.R.: ICI D1694, a quinazoline antifolate thymidylate synthase inhibitor that is a potent of L 1210 tumor cell growth in vitro and in vivo: A new agent for clinical study. Cancer Res., 51, 1991, 5579-5586.
18. th NCI-EORTS Symposium on New Drugs in Cancer Therapy. Amsterdam, March 12-15, 1996, 90.
19. JANTOVÁ, S., HORÁKOVÁ, K., HIANIKOVÁ, L., FLOCH, L.: Study of biological effect of 2-isothiocyanate carboxylic acids. III. The effect L-α-ethylester of 2-isothiocyanate propane acid on proliferation and metabolism on HeLa cells. Biologia, 44, 1989, 647-655.
20. JANTOVÁ. S., HORÁKOVÁ, K.: 9-Hydroxybenfluron induced inhibition of proliferation and metabolism in HeLa cells. Cell Biochem. Funct., 11, 1993, 131-135.
21. JANTOVÁ, S., HORÁKOVÁ, K., NOVOTOVA, M., UHRIK, B.: Mechanism of cytostatic and cytolytic activity of 9-hydroxybenfluron in HMB-2 human melanom cells. Biologia. 50, 1995, 615-622.
22. JANTOVÁ, S., RUŽEKOVÁ, L., ŠPIRKOVÁ, K., STANKOVSKÝ, Š.: Cytotoxic effect of substituted tetrazolo[1,5-c]quinazolincs on HeLa cells. Biológia. (In press.)
23. KORNET, M.J.: Synthesis and anticonvulsant activity of 3-alkyl-3,4-dihydro-2(1H)-quinazolinones. J. Heterocyclic Chem., 29, 1992, 103-105.
24. LOWRY, O.H., ROSEBROUGH, N.J., FARR, A.L., RANDALL, R.J.: Protein measurement with the folin phenol reagent. J. Biol. Chem., 143, 1951, 265-275.
25. MALAMAS, M.S . MILLEN, J.: Quinazolineacetic acids and related analogues as aldose reductase inhibitors. J. Med. Chem., 34, 1991, 1492-1503.
26. MARSHAM., P.R.: Quinazoline inhibitors of thymidylate synthasepotent new anticancer agents. J. Heterocyclic Chem., 31, 1994, 603-613.
27. NAITHANI, P.K., PALIT, G., SRIVASTAVA, V.K., SHANKER, K.: 2,3-disubstituted quinazolinones and their antiparkinsonian activity. Ind. J. Chem., Sect.B, Org. Chem. Incl. Med. Chem., 28, 1989, 745-750.
28. PANADERO, A., YIN, M.B., VOIGT, W., RUSTUM, Y.M.: Contrasting patterns of DNA fragmentation induced by thymidylate synthase inhibitors, ZD1694 and AG 331. Oncol. Res., 7(2), 1995, 73-81.
29. PEET, N.P., BAUGH, L.E., LEWIS, J.E., MATHEWS, E.H., OLBDRDING, E.L., SHAH, D.N., SUNDER, S.: Chemistry and antiallergic activity of 3-(1H-tetrazol-5-yl)-4(H)-quinazolinone sodium salt (MDL-427). Abstract Pap. Am. Chem. Soc., 192, 1986, 13.
30. PENDARGAST, W., DICKERSON, S.H., DEV, I.K., FERONE, R., DUCH, D.S., SMITH, G.K.: Benzo(F)quinazoline inhibitors of thymidylate synthase-metylenamino-linked aroylglutamate derivatives. J. Med. Chem., 37, 1994, 838-844.
31. POMARNACKA, E., ANGIELSKI, S., HOPPE, A.: Derivatives of 4-chloro-5-sulfanoyl-benzoic acid. 8. Synthesis and diuretic activity of pyrazolc [3,2-b]-quinazoline and 1-benzoylpyrazole derivatives. Acta Polon. Pharm., 41, 1984, 141-151.
32. RENAULT, S.G., RENAULT, J., SERVOLLCS, P.G., BARON, M., PAOLETTI, C., GROS, S., BISSERY, M.C., LAVELLE, F., ATASSI, G. : Hcterocyclic quinoncs. 17. A new in vivo active antineoplastic drug: 6,7-bis(1-aziridinyl)-4-((3-(N,N-dimethylamino)propyl)amino)-5,8- quinazolinedione. J.Med.Chem. 34, 1991, 38-46.
33. th NCIEORTC Symposium on New Drug in Cancer Therapy. Amsterdam, March 12-15, 1996, 85.
34. SLAMEǸOVÁ, D., BOHUŠOVÁ T., ORAVEC, C.: Inhibitory effect of theophylline on repair of potentially lethal MMS-inducod damage to NA in V79 cells. Mutation Res., 242, 1990, 127-134.
35. th NCI-EORTC Symposium on New Drug in Cancer Therapy. Amsterdam, March 12-15, 1996, 105.
36. STANKOVSKẎ, Š., ŠPIRKOVÁ, K.: Amidinoyl isothiocyanates in the synthesis of condensed heterocycles: Tetrazolo-azidoazomethine tautomerism in substituted tetrazolo[1,5-c]quinazolines. Monatsh. Chemie, 122, 1991, 849-852.
37. SUSSE, M., JOHNE, S.: Chinazolinderivate mit phytoeffektorischen oder bioziden Eigenschaften. Z. Chem., 21, 1981, 431-442.
38. TAYLOR, G.A., JACKMAN, A.L., BALMANNO, K., CALVERT, A.H.: Thymidylate synthase activity in L1210 cells following in vitro or in vivo exposure to quinazoline antifolates. Br. J. Cancer, 56, 1987, 195.
39. TERASIMA, T., TOLMACH, L.J.: Growth and nucleic acid synthesis in synchronously dividing populations of HeLa cells. Exp. Cell Res., 30, 1969, 344.
40. TIDD, D.M., KIM, S.C., HORAKOVA, K., MORIWAKI, A., PATERSON, A.R.P. : A delayed cytotoxic reaction for 6-mercaptopurine. Cancer Res., 32, 1972, 317-321.
41. th NCI-EORTC Symposium on New Drugs in Cancer Therapy, No. 276, Amsterdam, March 12-15, 1996.
42. WISELOGE, F.W.: Survey of Antimalaric Drugs 1941-1945. Eds: Brothers. Michigan, Ann Arbor 1946.
43. YAMAGISHI, M., YAMADA, Y., OZAKI, K., ASAO, M., SHIMIZU, R., SUZUKI, M., MATSUMOTO, M., MATSUOKA, Y., MATSUMOTO, K.: Biological activities and quantitative structure-activity relationships of spiro[imidazolidine-4,4-(1H)-quinazoline]-2,2,5(H)-triones as aidose reductase inhibitors. J. Med. Chem., 35, 1992, 2085-2094.
44. YIN, M.B., GUIMARAES, M.A., ZHANG, Z.G., ARREDONDO, M.A., RUSTUM, Z.M. : Time-dependence of DNA lesions and growth-inhibition by ICI D1694 a new quinazoline antifolate thymidylate synthase inhibitor. Cancer Res., 52, 1992, 5900-5905.