6-SUBSTITUTED 5-FLUOROURACIL DERIVATIVES AS TRANSITION STATE ANALOGUE INHIBITORS OF THYMIDINE PHOSPHORYLASE

REFERENCES

• Friedkin , M. and Roberts , D. 1954 . The enzymatic synthesis of nucleosides. I. Thymidine phosphorylase in mammalian tissue . J. Biol. Chem. , 207 ( 1 ) : 245 – 256 .
   PubMed Web of Science ®Google Scholar
• Brown , N. S. , Jones , A. , Fujiyama , C. , Harris , A. L. and Bicknell , R. 2000 . Thymidine phosphorylase induces carcinoma cell oxidative stress and promotes secretion of angiogenic factors . Cancer Res. , 60 : 6298 – 6302 .
   PubMed Web of Science ®Google Scholar
• Langen , P. , Etzgold , G. , Barwolff , D. and Preussel , B. 1967 . Inhibition of thymidine phosphorylase by 6-aminothymine and derivatives of 6-aminouracil . Biochem. Pharmacol. , 76 ( 9 ) : 1833 – 1837 .
   Web of Science ®Google Scholar
• Focher , F. , Ubiali , D. , Pregnolato , M. , Zhi , C. , Gambino , J. , Wright , G. E. and Spadari , S. 2000 . Novel nonsubstrate inhibitors of human thymidine phosphorylase, a potential target for tumor-dependent angiogenesis . J. Med. Chem. , 43 : 2601 – 2607 .
   PubMed Web of Science ®Google Scholar
• Klein , R. S. , Lenzi , M. , Lim , T. H. , Hotchkiss , K. A. , Wilson , P. and Schwartz , E. L. 2001 . Novel 6-substituted uracil analogs as inhibitors of the angiogenic actions of thymidine phosphorylase . Biochem. Pharmacol. , 62 ( 9 ) : 1257 – 1263 .
   PubMed Web of Science ®Google Scholar
• Murray , P. E. , McNally , V. A. , Lockyer , S. D. , Williams , K. J. , Stratford , I. J. , Jaffar , M. and Freeman , S. 2002 . Synthesis and enzymatic evaluation of pyridinium-substituted uracil derivatives as novel inhibitors of thymidine phosphorylase . Bioorg. Med. Chem. , 70 : 525 – 530 .
   Web of Science ®Google Scholar
• Fukushima , M. , Suzuki , N. , Emura , T. , Yano , S. , Kazuno , H. , Tada , Y. , Yamada , Y. and Asao , T. 2000 . Structure and activity of specific inhibitors of thymidine phosphorylase to potentiate the function of antitumor 2′- deoxyribonucleosides . Biochem. Pharmacol. , 59 ( 10 ) : 1227 – 1236 .
   PubMed Web of Science ®Google Scholar
• Cole , C. , Reigan , P. , Gbaj , A. , Edwards , P. N. , Douglas , K. T. , Stratford , I. J. , Freeman , S. and Jaffar , M. 2003 . Potential tumor-selective nitroimidazolylmethyluracil prodrug derivatives: inhibitors of the angiogenic enzyme thymidine phoesphorylase . J. Med. Chem. , 46 : 207 – 209 .
   PubMed Web of Science ®Google Scholar
• Balzarini , J. , Gamboa , A. E. , Esnouf , R. , Liekens , S. , Neyts , J. , De Clercq , E. , Camaraza , M. J. and Perez-Perez , M. J. 1998 . 7-Deazaxanthine, a novel prototype inhibitor of thymidine phosphorylase . FEBS Lett. , 438 ( 1–2 ) : 91 – 95 .
   PubMed Web of Science ®Google Scholar
• Esteban-Gamboa , A. , Balzarini , J. , Esnouf , R. , De Clercq , E. , Camaraza , M. J. and Perez-Perez , M. J. 2000 . Design, synthesis, and enzymatic evaluation of multisubstrate analogue inhibitors of Escherichia coli thymidine phosphorylase . J. Med. Chem. , 43 ( 5 ) : 971 – 983 .
   PubMed Web of Science ®Google Scholar
• Price , M. L.P. , Guida , W. C. , Jackson , T. E. , Nydick , J. A. , Gladstone , P. L. , Juarez , J. C. , Donate , F. and Ternansky , R. J. 2003 . Design of novel N-(2,4-dioxo-1,2,3,4-tetrahydro-thieno[3,2-d]pyrimidin-7-yl)-guanidines as thymidine phosphorylase inhibitors, and flexible docking to a homology model . Bioorg. Med. Chem. Lett. , 73 : 107 – 110 .
   Web of Science ®Google Scholar
• Nakajima , Y. , Gotanda , T. , Uchimiya , H. , Furukawa , T. , Haraguchi , M. , Ikeda , R. , Sumizawa , T. , Yoshida , H. and Akiyama , S. 2004 . Cancer Res. , 64 : 1794 – 1801 .
   PubMed Web of Science ®Google Scholar
• Folkman , J. 1971 . Tumor angiogenesis: therapeutic implications . N. Engl. J. Med. , 285 : 1182 – 1186 .
   PubMed Web of Science ®Google Scholar
• Thorpe , P. E. 2004 . Vascular targeting agents as cancer therapeutics . Clin. Cancer Res. , 70 ( 2 ) : 415 – 427 .
   Web of Science ®Google Scholar
• Pugmire , M. J. , Cook , W. J. , Jasanoff , A. , Walter , M. R. and Ealick , S. E. 1998 . Structural and theoretical studies suggest domain movement produces an active conformation of thymidine phosphorylase . J. Mol. Biol. , 287 : 285 – 299 .
   Web of Science ®Google Scholar
• Schramm , V. L. 2003 . Transition state analogues for enzymes of nucleic acid metabolism . Nucleic Acids Res., Suppl. , : 107 – 108 .
   PubMedGoogle Scholar
• Birck , M. R. and Schramm , V. L. 2004 . Nucleophilic participation in the transition state for human thymidine phosphorylase . J. Am. Chem. Soc. , 126 : 2447 – 2453 .
   PubMed Web of Science ®Google Scholar
• Schwartz , M. 1971 . Thymidine phosphorylase from Escherichia coli: properties and kinetics . Methods Enzymol. , 51 : 442 – 445 .
   Google Scholar
• Norman , R. A. , Barry , S. T. , Bate , M. , Breed , J. , Colls , J. D. , Ernill , R. J. , Luke , R. W.A. , Minshull , C. A. , McAllister , M. S.B. , McCall , E. J. , McMiken , H. HJ. , Paterson , D. S. , Timms , D. , Tucker , J. A. and Pauptit , R. A. 2004 . Crystal structure of human thymidine phosphorylase in complex with a small molecule inhibitor . Structure , 12 : 75 – 84 .
   PubMed Web of Science ®Google Scholar