Enhanced DNA-Directed Effects of FdUMP[10] Compared to 5FU

Nucleosides, Nucleotides and Nucleic Acids

Volumn 23, Issue 1-2, 2004, Pages 401-410

  Gmeiner, William H ^a   Trump, Eric ^b   Wei, Cui ^a  

^a WAKE FOREST SCHOOL OF MEDICINE   (United States)

^b EMPORIA STATE UNIVERSITY   (United States)

Author keywords

5FU; Cancer chemotherapy; Fluoropyrimidine; Thymidylate synthase

Indexed keywords

5' O (4,4' DIMETHOXYTRITYL) 5 FLUORO 2' DEOXYURIDINE 3' O (CYANOETHYL N,N DIISOPROPYL PHOSPHORAMIDITE); FLUOROPYRIMIDINE DERIVATIVE; FLUOROURACIL; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CELL CYCLE S PHASE; CELL DEATH; CELL PROLIFERATION; CELL STRAIN HT29; CONCENTRATION RESPONSE; CONTROLLED STUDY; DNA DAMAGE; DRUG ACTIVITY; DRUG CONJUGATION; DRUG EFFICACY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; HUMAN; HUMAN CELL; MITOSIS INHIBITION; TUMOR CELL;

COLONIC NEOPLASMS; DNA; FLUORODEOXYURIDYLATE; FLUOROURACIL; HT29 CELLS; HUMANS;

EID: 1542469481     PISSN: 15257770     EISSN: None     Source Type: Journal    
DOI: 10.1081/NCN-120028336     Document Type: Article

References (30)

1. Longley, D.B.; Harkin, D.P.; Johnston, P.G. 5-Fluorouracil: mechanisms of action and clinical strategies. Nat. Rev. Cancer 2003, 3, 330-338.
2. Grem, J.L. 5-Fluorouracil: forty-plus and still ticking. A review of its pre-clinical and clinical development. Invest. New Drugs 2000, 18, 299-313.
3. Santi, D.V.; McHenry, C.S.; Sommer, H. Mechanism of interaction of thymidylate synthase with 5-fluorodeoxyuridylate. Biochemistry 1974, 13, 471-480.
4. Houghton, J.A.; Tillman, D.M.; Harwood, F.G. Ratio of 2′-deoxyadenosine-′-triphosphate/thymidine-5′-triphosphate influences the commitment of human colon carcinoma cells to thymineless death. Clin. Cancer Res. 1995, 1, 723-730.
5. Houghton, J.A.; Harwood, F.G.; Tillman, D.M. Thymineless cell death in colon carcinoma cells is mediated via Fas signaling. Proc. Natl. Acad. Sci. U. S. A. 1997, 94, 8144-8149.
6. Edler, D.; Hallstrom, M.; Johnston, P.G.; Magnusson, I.; Ragnhammar, P.; Blomgren, H. Thymidylate synthase expression: an independent prognostic factor for local recurrence, distant metastasis, disease-free and overall survival in rectal cancer. Clin. Cancer Res. 2000, 6, 1378-1384.
7. Cao, S.; Baccanari, D.P.; Rustum, Y.M.; Davis, S.T.; Tansik, R.L.; Porter, D.J.T.; Spector, T. α-fluoro-β-alanine: effects on the antitumor activity and toxicity of 5-FU. Biochem. Pharmacol. 2000, 59, 953-960.
8. Pritchard, D.M.; Watson, A.J.M.; Potten, C.S.; Jackman, A.L.; Hickman, J.A. Inhibition by uridine but not thymine of p53-dependent intestinal apoptosis initiated by 5-fluorouracil: evidence for the involvement of RNA perturbation. Proc. Natl. Acad. Sci. U. S. A. 1997, 94, 1795-1799.
9. van Laar, J.A.M.; Rustum, Y.M.; ckland, S.P.; van Groeningen, C.J.; Peters, G.J. Comparison of 5-fluoro-2′-deoxyuridine with 5-fluorouracil and their role in the treatment of colorectal cancer. Eur. J. Cancer 1998, 34, 296-306.
10. Tew, K.D.; Houghton, P.J.; Houghton, J.A. Pre-Clinical and Clinical Modulation of Anticancer Drugs; CRC Press: Boca Raton, FL, 1993; 197-321.
11. Eng, C.; Kindler, H.L.; Schilsky, R.L. Oral fluoropyrimidine treatment of colorectal cancer. Clin. Colorectal Cancer 2001, 1, 95-103.
12. Pentheroudakis, G.; Twelves, C. Capecitabine (Xeloda): from the laboratory to the patient's home. Anticancer Res. 2002, 22, 3589-3596.
13. Gmeiner, W.H.; Sahasrabudhe, P.; Pon, R.T.; Sonntag, J.; Srinivasan, S.; Iversen, P.L. Preparation of oligomeric 2′-deoxy-5-fluorouridine of defined length and backbone composition: a novel pro-drug form of the potent anti-cancer drug 2′-deoxy-5-fluorouridylate. Nucl. Nuct. 1995, 14, 243-253.
14. Gmeiner, W.H. Delivery of traditional anticancer drugs as oligodeoxynucleotides. Cancer Watch 1995, 4, 120-121.
15. Liu, J.; Skradis, A.; Kolar, C.; Kolath, J.; Anderson, J.; Lawson, T.; Talmadge, J.; Gmeiner, W.H. Increased cytotoxicity and decreased in vivo toxicity of FdUMP[10] relative to 5-FU. Nucl. Nuct. 1999, 18, 1789-1802.
16. Liu, J.; Kolath, J.; Anderson, J.; Kolar, C.; Lawson, T.; Talmadge, J.; Gmeiner, W.H. Positive interaction between 5-FU and FdUMP[10] in the inhibition of human colorectal tumor cell proliferation. Antisense Nucleic Acid Drug Des. 1999, 9, 481-485.
17. Liu, J.; Kolar, C.; Lawson, T.A.; Gmeiner, W.H. Targeted drug delivery to chemoresistant cells: folic acid derivatization of FdUMP[10] enhances cytotoxicity toward human colorectal tumor cells. J. Org. Chem. 2001, 66, 5655-5663.
18. Liu, C.; Willingham, M.; Liu, J.; Gmeiner, W.H. Efficacy and safety of FdUMP[10] in treatment of HT-29 human colon cancer xenografts. Int. J. Oncol. 2002, 21, 303-308.
19. Chang, D.K.; Goel, A.; Ricciardiello, L.; Lee, D.H.; Chang, C.L.; Carethers, J.M.; Boland, C.R. Effect of H2O2 on cell cycle and survival in DNA mismatch repair-deficient and -proficient cell lines. Cancer Lett. 2003, 196, 243-251.
20. Gmeiner, W.H.; Sahasrubudhe, P.; Pon, R. Synthesis of 5′-O-(4,4′dimethoxytrityl)-2′-O-(tert-butyldimethylsilyl) -5-fluorouridine 3′-N,N-Diisopropyl(cyanoethyl)phosphoramidite and its use in the synthesis of RNA. J. Org. Chem. 1994, 59, 5779-5789.
21. Damha, M.J.; Giannaris, P.A.; Zabarylo, S.V. An improved procedure for derivatization of controlled-pore glass beads for solid-phase oligonucleotide synthesis. Nucl. Acids Res. 1990, 18, 3813-3821.
22. Petak, I.; Tillman, D.M.; Houghton, J.A. p53 dependence of Fas induction and acute apoptosis in response to 5-fluorouracil-leucovorin in human colon carcinoma cell lines. Clin. Cancer Res. 2000, 6, 4432-4441.
23. Ren, Q.; van Groeningen, J.V.; Hardcastle, A.; Aherne, G.W.; Geoffrey, F.; Allegra, C.J.; Johnston, P.G.; Grem, J.L. Determinants of cytotoxicity with prolonged exposure to fluorouracil in human colon cancer cells. Oncol. Res. 1997, 9, 77-88.
24. Peters, G.J.; van Triest, B.; Backus, H.H.; Kuiper, C.M.; van der Wilt, C.L.; Pinedo, H.M. Induction of thymidylate synthase as a 5-fluorouracil resistance mechanism. Eur. J. Cancer 2000, 36, 916-924.
25. Petak, I.; Tillman, D.M.; Harwood, F.G.; Mihalik, R.; Houghton, J.A. Fas-dependent and -independent mechanisms of cell death following DNA damage in human colon carcinoma cells. Cancer Res. 2000, 60, 2643-2650.
26. Peters, G.J.; Backus, H.H.J.; Freemantle, S.; van Triest, B.; Codacci-Pisanelli, G.; van der Wilt, C.L.; Smid, K.; Lunec, J.; Calvert, A.H.; Marsh, S.; McLeaod, H.L.; Bloemena, E.; Meijer, S.; Jansen, G.; van Groeningen, C.J.; Pinedo, H.M. Induction of thymidylate synthase as a 5-fluorouracil resistance mechanism. Biochim. Biophys. Acta 2002, 1587, 194-205.
27. Allegra, C.J.; Chabner, B.A.; Drake J.C.; Lutz, R.; Rodbard, D.; Jolivet, J. Enhanced inhibition of thymidylate synthase by methotrexate polyglutamates. J. Biol. Chem. 1985, 260, 9720-9726.
28. Chu, E.; Voeller, D.; Koeller, D.M.; Drake, J.C.; Takimoto, C.H.; Maley, G.F.; Maley, F.; Allegra, C.J. Identification of an RNA binding site for human thymidylate synthase. Proc. Natl. Acad. Sci. U. S. A. 1993, 90, 517-521.
29. Chu, E.; Allegra, C.J. The role of thymidylate synthase as an RNA binding protein. BioEssays 1996, 18, 191-198.
30. Yoshikawa, R.; Kusunoki, M.; Yanagi, H.; Noda, M.; Furuyama, J.I.; Yamamura, T.; Hashimoto-Tamaoki, T. Dual antitumor effects of 5-fluorouracil on the cell cycle in colorectal carcinoma cells: a novel target mechanism concept for pharmacokinetic modulating chemotherapy. Cancer Res. 2001, 61, 1029-1037.