Low folate conditions may enhance the interaction of trifluorothymidine with antifolates in colon cancer cells

Cancer Chemotherapy and Pharmacology

Volumn 57, Issue 2, 2006, Pages 171-179

  Temmink, Olaf H ^a   Hoogeland, Marco F M ^a   Fukushima, Masakazu ^b   Peters, Godefridus J ^a  

^a VU UNIVERSITY MEDICAL CENTER   (Netherlands)

^b TAIHO PHARMACEUTICAL CO LTD   (Japan)

Author keywords

Antifolates; Colon cancer; DNA damage; Thymidylate synthase; Trifluorothymidine

Indexed keywords

2 [5 [[(1,2 DIHYDRO 3 METHYL 1 OXOBENZO[F]QUINAZOLIN 9 YL)METHYL]AMINO] 1 OXO 2 ISOINDOLINYL]GLUTARIC ACID; FOLIC ACID; FOLIC ACID ANTAGONIST; GW1843; NOLATREXED; RALTITREXED; THYMIDINE TRIPHOSPHATE; THYMIDYLATE SYNTHASE; TRIFLURIDINE;

ARTICLE; COLON CANCER; CONTROLLED STUDY; CYTOTOXICITY; DNA DAMAGE; DRUG TARGETING; GROWTH INHIBITION; HUMAN; HUMAN CELL; IC 50; NUCLEOTIDE BINDING SITE; PRIORITY JOURNAL;

ANTIMETABOLITES; COLONIC NEOPLASMS; DNA DAMAGE; DRUG INTERACTIONS; FOLIC ACID; FOLIC ACID ANTAGONISTS; HOMEOSTASIS; HUMANS; INDOLES; QUINAZOLINES; THIOPHENES; TRIFLURIDINE; TUMOR CELLS, CULTURED;

EID: 28844476598     PISSN: 03445704     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00280-005-0033-4     Document Type: Article

References (52)

1. Peters GJ, van der Wilt CL, Van Moorsel CJ, Kroep JR, Bergman AM, Ackland SP (2000) Basis for effective combination cancer chemotherapy with antimetabolites. Pharmacol Ther 87:227-253
2. Schmoll HJ, Buchele T, Grothe A, Dempke W (1999) Where do we stand with 5-fluorouracil? Semin Oncol 26:589-605
3. Pinedo HM, Peters GJ (1988) Fluorouracil: biochemistry and pharmacology. J Clin Oncol 6:1653-1664
4. Peters GJ, Backus HH, Freemantle S, van Triest B, Codacci-Pisanelli G, van der Wilt CL, Smid K, Lunec J, Calvert AH, Marsh S, McLeod HL, Bloemena E, Meijer S, Jansen G, Van Groeningen CJ, Pinedo HM (2002) Induction of thymidylate synthase as a 5-fluorouracil resistance mechanism. Biochim Biophys Acta 1587:194-205
5. van Triest B, Peters GJ (1999) Thymidylate synthase: a target for combination therapy and determinant of chemotherapeutic response in colorectal cancer. Oncology 57:179-194
6. Danenberg PV, Malli H, Swenson S (1999) Thymidylate synthase inhibitors. Semin Oncol 26:621-631
7. Carreras CW, Santi DV (1995) The catalytic mechanism and structure of thymidylate synthase. Annu Rev Biochem 64:721-762
8. Takemura Y, Jackman AL (1997) Folate-based thymidylate synthase inhibitors in cancer chemotherapy. Anticancer Drugs 8:3-16
9. Rustum YM, Harstrick A, Cao S, Vanhoefer U, Yin MB, Wilke H, Seeber S (1997) Thymidylate synthase inhibitors in cancer therapy: direct and indirect inhibitors. J Clin Oncol 15:389-400
10. Touroutoglou N, Pazdur R (1996) Thymidylate synthase inhibitors. Clin Cancer Res 2:227-243
11. Jackman AL, Calvert AH (1995) Folate-based thymidylate synthase inhibitors as anticancer drugs. Ann Oncol 6:871-881
12. Eckstein JW, Foster PG, Finer-Moore J, Wataya Y, Santi DV (1994) Mechanism-based inhibition of thymidylate synthase by 5-(trifluoromethyl)- 2′-deoxyuridine 5′-monophosphate. Biochemistry 33:15086-15094
13. Santi DV, Sakai TT (1971) Thymidylate synthetase. Model studies of inhibition by 5-trifluoromethyl-2′-deoxyuridylic acid. Biochemistry 10:3598-3607
14. Temmink OH, De Bruin M, Comijn EM, Fukushima M, Peters GJ (2005) Determinants of trifluorothymidine sensitivity and metabolism in colon and lung cancer cells. Anticancer Drugs 16:285-292
15. Tsuchiya H, Kuwata K, Nagayama S, Yamashita K, Kamiya H, Harashima H (2004) Pharmacokinetic modeling of species-dependent enhanced bioavailability of trifluorothymidine by thymidine phosphorylase inhibitor. Drug Metab Pharmacokinet 19:206-215
16. Emura T, Nakagawa F, Fujioka A, Ohshimo H, Yokogawa T, Okabe H, Kitazato K (2004) An optimal dosing schedule for a novel combination antimetabolite, TAS-102, based on its intracellular metabolism and its incorporation into DNA. Int J Mol Med 13:249-255
17. Thomas MB, Hoff PM, Carter S, Bland G, Lassere Y, Wolff R, Xiong H, Hayakawa T, Abbruzzese J (2002) A dose-finding, safety and pharmacokinetics study of TAS-102, an antitumor/antiangiogenic agent given orally on a once-daily schedule for five days every three weeks in patients with solid tumors. Proc Amer Assoc Cancer Res 43:554 (#2754)
18. Santi DV, Sakai TT (1972) Irreversible inhibition of thymidylate synthetase by 5-formyl-2′-deoxyuridylic acid. Biochem Biophys Res Commun 46:1320-1325
19. McGuire JJ (2003) Anticancer antifolates: current status and future directions. Curr Pharm Des 9:2593-2613
20. Webber S, Bartlett CA, Boritzki TJ, Hillard JA, Howland EF, Johnston AL, Kosa M, Margosiak SA, Morse CA, Shetty BV (1996) AG337, a novel lipophilic thymidylate synthase inhibitor: in vitro and in vivo preclinical studies. Cancer Chemother Pharmacol 37:509-517
21. Rafi I, Taylor GA, Calvete JA, Boddy AV, Balmanno K, Bailey N, Lind M, Calvert AH, Webber S, Jackson RC (1995) Clinical pharmacokinetic and pharmacodynamic studies with the nonclassical antifolate thymidylate synthase inhibitor 3,4-dihydro-2-amino-6-methyl-4-oxo-5-(4-pyridylthio)-quinazolone dihydrochloride (AG337) given by 24-hour continuous intravenous infusion. Clin Cancer Res 1:1275-1284
22. Jackman AL, Taylor GA, Gibson W, Kimbell R, Brown M, Calvert AH, Judson IR, Hughes LR (1991) ICI D1694, a quinazoline antifolate thymidylate synthase inhibitor that is a potent inhibitor of L1210 tumor cell growth in vitro and in vivo: a new agent for clinical study. Cancer Res 51:5579-5586
23. Schwartz G, Johnson TR, Goetz A, Burris H, Smetzer L, Lampkin T, Sailstad J, Hohneker JA, Von Hoff DD, Rowinsky EK (2001) A phase I and pharmacokinetic study of 1843U89, a noncompetitive inhibitor of thymidylate synthase, in patients with advanced solid malignancies. Clin Cancer Res 7:1901-1911
24. Hanlon MH, Ferone R (1996) In vitro uptake, anabolism, and cellular retention of 1843U89 and other benzoquinazoline inhibitors of thymidylate synthase. Cancer Res 56:3301-3306
25. Westerhof GR, Schornagel JH, Kathmann I, Jackman AL, Rosowsky A, Forsch RA, Hynes JB, Boyle FT, Peters GJ, Pinedo HM (1995) Carrier- and receptor-mediated transport of folate antagonists targeting folate-dependent enzymes: correlates of molecular-structure and biological activity. Mol Pharmacol 48:459-471
26. van der Wilt CL, Kuiper CM, Peters GJ (1999) Combination studies of antifolates with 5-fluorouracil in colon cancer cell lines. Oncol Res 11:383-391
27. Caponigro F, Avallone A, Budillon A, Comella P, Comella G (2001) Raltitrexed/5-fluorouracil-based combination chemotherapy regimens in anticancer therapy. Anticancer Drugs 12:489-497
28. Webley SD, Welsh SJ, Jackman AL, Aherne GW (2001) The ability to accumulate deoxyuridine triphosphate and cellular response to thymidylate synthase (TS) inhibition. Br J Cancer 85:446-452
29. Aherne GW, Hardcastle A, Raynaud F, Jackman AL (1996) Immunoreactive dUMP and TTP pools as an index of thymidylate synthase inhibition; effect of tomudex (ZD1694) and a nonpolyglutamated quinazoline antifolate (CB30900) in L1210 mouse leukaemia cells. Biochem Pharmacol 51:1293-1301
30. Emura T, Suzuki N, Yamaguchi M, Ohshimo H, Fukushima M (2004) A novel combination antimetabolite, TAS-102, exhibits antitumor activity in FU-resistant human cancer cells through a mechanism involving FTD incorporation in DNA. Int J Oncol 25:571-578
31. Peters GJ, van Triest B, Backus HH, Kuiper CM, van der Wilt CL, Pinedo HM (2000) Molecular downstream events and induction of thymidylate synthase in mutant and wild-type p53 colon cancer cell lines after treatment with 5-fluorouracil and the thymidylate synthase inhibitor raltitrexed. Eur J Cancer 36:916-924
32. McGinn CJ, Pestalozzi BC, Drake JC, Glennon MC, Kunugi K, Otterson G, Allegra CJ, Johnston PG, Kinsella TJ (2000) Cell cycle regulation of the G0/G1 transition in 5-fluorouracil-sensitive and -resistant human colon cancer cell lines. Cancer J 6:234-242
33. van Triest B, Pinedo HM, van Hensbergen Y, Smid K, Telleman F, Schoenmakers PS, van der Wilt CL, van Laar JA, Noordhuis P, Jansen G, Peters GJ (1999) Thymidylate synthase level as the main predictive parameter for sensitivity to 5-fluorouracil, but not for folate-based thymidylate synthase inhibitors, in 13 nonselected colon cancer cell lines. Clin Cancer Res 5:643-654
34. van der Wilt CL, Smid K, Aherne GW, Noordhuis P, Peters GJ (1997) Biochemical mechanisms of interferon modulation of 5-fluorouracil activity in colon cancer cells. Eur J Cancer 33:471-478
35. Xu JM, Song ST, Tang ZM, Liu XQ, Jiang ZF, Zhou L, Li YB, Huang Y (1998) Evaluation of in vitro chemosensitivity of antitumor drugs using the MTT assay in fresh human breast cancer. Breast Cancer Res Treat 49:251-259
36. Keepers YP, Pizao PE, Peters GJ, Ark-Otte J, Winograd B, Pinedo HM (1991) Comparison of the sulforhodamine B protein and tetrazolium (MTT) assays for in vitro chemosensitivity testing. Eur J Cancer 27:897-900
37. Chou TC, Talalay P (1984) Quantitative analysis of dose-effect relationships: the combined effects of multiple drugs or enzyme inhibitors. Adv Enzyme Regul 22:27-55
38. Xu JM, Azzariti A, Colucci G, Paradiso A (2003) The effect of gefitinib (Iressa, ZD1839) in combination with oxaliplatin is schedule-dependent in colon cancer cell lines. Cancer Chemother Pharmacol 52:442-448
39. Yalowich JC, Kalman TI (1985) Rapid determination of thymidylate synthase activity and its inhibition in intact L1210 leukemia cells in vitro. Biochem Pharmacol 34:2319-2324
40. Rots MG, Pieters R, Kaspers GJ, van Zantwijk CH, Noordhuis P, Mauritz R, Veerman AJ, Jansen G, Peters GJ (1999) Differential methotrexate resistance in childhood T- versus common/preB-acute lymphoblastic leukemia can be measured by an in situ thymidylate synthase inhibition assay, but not by the MTT assay. Blood 93:1067-1074
41. Birnboim HC, Jevcak JJ (1981) Fluorometric method for rapid detection of DNA strand breaks in human white blood cells produced by low doses of radiation. Cancer Res 41:1889-1892
42. Sigmond J, Backus HH, Wouters D, Temmink OH, Jansen G, Peters GJ (2003) Induction of resistance to the multitargeted antifolate Pemetrexed (ALIMTA) in WiDr human colon cancer cells is associated with thymidylate synthase overexpression. Biochem Pharmacol 66:431-438
43. van der Wilt CL, Smid K, Peters GJ (2002) Effects of antifolates on the binding of 5-fluoro-2′-deoxyuridine monophosphate to thymidylate synthase. Biochem Pharmacol 64:669-675
44. Backus HH, Pinedo HM, Wouters D, Padron JM, Molders N, van Der Wilt CL, van Groeningen CJ, Jansen G, Peters GJ (2000) Folate depletion increases sensitivity of solid tumor cell lines to 5-fluorouracil and antifolates. Int J Cancer 87:771-778
45. Peters GJ, Smitskamp-Wilms E, Smid K, Pinedo HM, Jansen G (1999) Determinants of activity of the antifolate thymidylate synthase inhibitors Tomudex (ZD1694) and GW1843U89 against mono- and multilayered colon cancer cell lines under folate-restricted conditions. Cancer Res 59:5529-5535
46. Radparvar S, Houghton PJ, Houghton JA (1988) Characteristics of thymidylate synthase purified from a human colon adenocarcinoma. Arch Biochem Biophys 260:342-350
47. Temmink OH, Comijn EM, Fukushima M, Peters GJ (2004) Intracellular thymidylate synthase inhibition by trifluorothymidine in FM3A cells. Nucleosides, Nucleotides and Nucleic Acids 23:1491-1494
48. Duch DS, Banks S, Dev IK, Dickerson SH, Ferone R, Heath LS, Humphreys J, Knick V, Pendergast W, Singer S (1993) Biochemical and cellular pharmacology of 1843U89, a novel benzoquinazoline inhibitor of thymidylate synthase. Cancer Res 53:810-818
49. Weichsel A, Montfort WR, Ciesla J, Maley F (1995) Promotion of purine nucleotide binding to thymidylate synthase by a potent folate analogue inhibitor, 1843U89. Proc Natl Acad Sci USA 92:3493-3497
50. Longo GS, Izzo J, Chang YM, Tong WP, Zielinski Z, Gorlick R, Chou TC, Bertino JR (1998) Pretreatment of colon carcinoma cells with Tomudex enhances 5-fluorouracil cytotoxicity. Clin Cancer Res 4:469-473
51. Desjardins J, Emerson DL, Colagiovanni DB, Abbott E, Brown EN, Drolet DW (2004) Pharmacokinetics, safety, and efficacy of a liposome encapsulated thymidylate synthase inhibitor, OSI-7904L [(S)-2-[5-[(1,2-dihydro-3-methyl-1-ox- obenzo[f]quinazolin-9-yl)methyl]amino-1-oxo-2-isoindolynl]-glutaric acid] in mice. J Pharmacol Exp Ther 309:894-902
52. Hazarika M, White RM, Johnson JR, Pazdur R (2004) FDA drug approval summaries: pemetrexed (Alimta). Oncologist 9:482-488