Sulfamide antifolates inhibiting thymidylate synthase: Synthesis, enzyme inhibition and cytotoxicity

Acta Biochimica Polonica

Volumn 49, Issue 2, 2002, Pages 407-420

  Pawełczak, Krzysztof ^a   Makowski, Maciej ^a   Kempny, Michał ^a   Dzik, Jolanta M ^b   Gołos, Barbara ^b   Rode, Wojciech ^b   Rzeszotarska, Barbara ^a  

^a UNIVERSITY OF OPOLE   (Poland)

^b NENCKI INSTITUTE OF EXPERIMENTAL BIOLOGY   (Poland)

Author keywords

Antifolate analogues; Antifolates; P aminobenzenesulfonic acid; Thymidylate synthase inhibitors

Indexed keywords

HYMENOLEPIS DIMINUTA;

ENZYME INHIBITOR; FOLIC ACID ANTAGONIST; SULFONAMIDE; THYMIDYLATE SYNTHASE;

ANIMAL; ARTICLE; CELL DIVISION; CHEMICAL STRUCTURE; DRUG ANTAGONISM; DRUG EFFECT; EHRLICH ASCITES TUMOR; ENZYMOLOGY; KINETICS; LIVER; METABOLISM; MOUSE; PATHOLOGY; RAT; SYNTHESIS;

ANIMALS; CARCINOMA, EHRLICH TUMOR; CELL DIVISION; ENZYME INHIBITORS; FOLIC ACID ANTAGONISTS; KINETICS; LIVER; MICE; MOLECULAR STRUCTURE; RATS; SULFONAMIDES; THYMIDYLATE SYNTHASE;

EID: 0040668350     PISSN: 0001527X     EISSN: None     Source Type: Journal    
DOI: 10.18388/abp.2002_3799     Document Type: Article

References (28)

1. Bavetsias V, Jackman AL. (1998) Nonpolyglutamatable antifolates as inhibitors of thymidylate synthase (TS) and potential antitumour agents. Curr Med Chem.; 5: 265-88.
2. 10-substitutions. In Human cancer, its characterisation and treatment. Davis W, Harrap KR, Stathopoulos G. eds, pp 272-83. Excerpta Medica, Amsterdam.
3. Carreras CW, Santi DV. (1995). The catalytic mechanism and structure of thymidylate synthase. Annu Rev Biochem.; 64: 721-62.
4. Dzik JM, Bretner M, Kulikowski T, Gołos B, Jarmuła A, Poznański J, Rode W, Shugar D. (1996) Synthesis and interactions with thymidylate synthase of 2,4-dithio-analogues of dUMP and 5-fluoro-dUMP. Biochim Biophys Acta.; 1293: 1-8.
5. Elslager EF, Colbry NL, Davoll J, Hutt MP, Johnson JL, Werbel LM. (1984) Folate antagonists. 22. Antimalarial and antibacterial effects of 2,4-diamino-6-quinazolinesulfonamides. J Med Chem.; 27: 1740-3.
6. Georgopapadakou NH, Walsh TJ. (1996) Antifungal agents: chemotherapeutic targets and immunologic strategies. Antimicrob Agents Chemother.; 40: 279-91.
7. Greenstein JP, Winitz M. (1961) In Chemistry of Amino Acids. Vol. 2, p 934. Wiley, New York.
8. Harrap KR. (1995) Initiatives with platinum-and quinazoline-based antitumor molecules. Fourteenth Bruce F. Cain memorial award lecture. Cancer Res.; 55: 2761-8.
9. Heidelberger C, Danenberg PV, Moran RG. (1983) Fluorinated pyrimidines and their nucleosides. Adu Enzymol; 54: 57-119.
10. Hughes LR, Jackman AL, Oldfield J, Smith RC, Burrows KD, Marsham PR, Bishop JAM, Jones TR, O'Connor BM, Calvert AH. (1990) Quinazoline antifolate thymidylate synthase inhibitors: alkyl, substituted alkyl, and aryl substituents in the C2 position. J Med Chem.; 33: 3060-7.
11. Jackman AL, Farrugia DC, Gibson W, Kimbell R, Harrap KR, Stephens TC, Azab M, Boyle FT. (1995) ZD1694 (Tomudex): a new thymidylate synthase inhibitor with activity in colorectal cancer. Eur J Cancer.; 31A: 1277-82.
12. 10-propargyl-5,8-dideaza folic acid (ICI 188583). Biochem Pharmacol.; 42: 1885-95.
13. Jastreboff M, Kȩdzierska B, Rode W. (1983) Properties of thymidylate synthase from Ehrlich ascites carcinoma cells. Biochem Pharmacol.; 28: 1251-3.
14. Jones TR, Smithers MJ, Betteridge RF, Taylor AM, Jackman AL, Calvert AH, Davies LC, Harrap KR. (1986) Quinazoline antifolates inhibiting thymidylate synthase: variation of the amino acid. J Med Chem.; 29: 1114-8.
15. Jones TR, Thornton TJ, Flinn A, Jackman AL, Newell DR, Calvert AH. (1989) Quinazoline antifolates inhibiting thymidylate synthase: 2-desamino derivatives with enhanced solubility and potency. J Med Chem.; 32: 847-52.
16. Jones TR, Varney MD, Webber SE, Lewis KK, Marzoni GP, Palmer CL, Kathardekar V, Welsh KM, Webber S, Matthews DA, Appelt K, Smith WW, Janson CA, Villafranca JE, Bacquet RJ, Howland EF, Bartlett CA, Morse CA. (1996) Structure-based design of lipophilic quinazoline inhibitors of thymidylate synthase. J Med Chem.; 39: 904-17.
17. α-[4-[N-[(3,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl]-N- propargylamino]phenylacetyl]-L-glutamic acid. Acta Biochim Polon.; 49: 197-203.
18. Marsham PR, Jackman AL, Barker AJ, Boyle FT, Pegg SJ, Wardleworth JM, Kimbell R, O'Connor BM, Calvert AH, Hughes LR. (1995) Quinazoline antifolate thymidylate synthase inhibitors: replacement of glutamic acid in the C2-methyl series. J Med Chem.; 38: 994-1004.
19. Marsham PR, Jackman AL, Oldfield J, Hughes LR, Thornton TJ, Bisset GMF, O'Connor BM, Bishop JAM, Calvert AH. (1990) Quinazoline antifolate thymidylate synthase inhibitors: benzoyl ring modifications in the C2-methyl series. J Med Chem.; 33: 3072-8.
20. Pendergast W, Dickerson SH, Johnson JV, Dev IK, Ferone R, Duch DS, Smith GK. (1993) Benzoquinazoline inhibitors of thymidylate synthase: enzyme inhibitory activity and cytotoxicity of some sulfonamidobenzoyl-glutamate and related derivatives. J Med Chem.; 36: 3464-71.
21. Rathod PK. (1997) Antimalarial agents directed at thymidylate synthase. J Pharm Pharmacol; 49 (Suppl. 2): 704-11.
22. Rode W, Kulikowski T, Kȩdzierska B, Jastreboff M, Shugar D. (1984) Inhibition of mammalian tumour thymidylate synthetase by 5-alkylated 2′-deoxyuridine 5′-phosphates. Biochem Pharmacol.; 33: 2699-705.
23. 4-hydroxy-5-fluoro-dCMP, and related analogues. Biochemistry.; 29: 10835-42.
24. Roeske R. (1963) Preparation of t-butyl esters of free amino acids. J Org Chem.; 28: 1251-3.
25. Rosowsky A. (1992) Development of new antifolate analogs as anticancer agents. Am J Pharmceut Education.; 56: 453-63.
26. Synold TW, Willits EM, Barredo JC. (1996) Role of folylpolyglutamate synthetase (FPGS) in antifolate chemotherapy; a biochemical and clinical update. Leukemia Lymphoma.; 21: 9-15.
27. Takemura Y, Jackman AL. (1997) Folate-based thymidylate synthase inhibitors in cancer chemotherapy. Anti-Cancer Drugs.; 8: 3-16.
28. Varney MD, Marzoni GP, Palmer CL, Deal JG, Webber S, Welsh KM, Bacquet RJ, Barlett CA, Morse CA, Booth CLJ, Herrmann SM, Howland EF, Ward RW, White J. (1992) Crystal structure-based design and synthesis of benzo[cd]indole-containing inhibitors of thymidylate synthase. J Med Chem.; 35: 663-76.