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Original Articles

Syntheses of 1-[2-(Phosphonomethoxy)Alkyl]Thymine Monophosphates and an Evaluation of their Inhibitory Activity Toward Human Thymidine Phosphorylase

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Pages 159-171 | Received 03 Aug 2011, Accepted 05 Dec 2011, Published online: 22 Feb 2012

REFERENCES

  • Holý , A. 2003 . Phosphonomethoxyalkyl analogs of nucleotides . Curr. Pharm. Design. , 9 : 2567 – 2592 .
  • Holý , A. 2002 . Recent Advances in Nucleosides: Chemistry and Chemotherapy Synthesis and Biological Activity of Isopolar Acyclic Nucleotide Analogs , Edited by: Chu , C. K. 167 – 238 . Amsterdam : Elsevier . Synthesis and biological activity of isopolar acyclic nucleotide analogs, in
  • Esteban-Gamboa , A. , Balzarini , J. , Esnouf , R. , De Clercq , E. , Camarasa , M.-J. and Pérez-Pérez , M.-J. 2000 . Design, synthesis, and enzymatic evaluation of multisubstrate analogue inhibitors of Escherichia coli thymidine phosphorylase . J. Med. Chem. , 43 : 971 – 983 .
  • Balzarini , J. , Degréve , B. , Esteban-Gamboa , A. , Esnouf , R. , De Clercq , E. , Engelborghs , Y. , Camarasa , M.-J. and Pérez-Pérez , M.-J. 2000 . Kinetic analysis of novel multisubstrate analogue inhibitors of thymidine phosphorylase . FEBS Lett. , 483 : 181 – 185 .
  • Moghaddam , A. and Bicknell , R. 1992 . Expression of platelet-derived endothelial cell growth factor in Escherichia coli and confirmation of its thymidine phosphorylase activity . Biochemistry , 31 : 12141 – 12146 .
  • Furukawa , T. , Yoshimura , A. , Sumizawa , T. , Haraguchi , M. , Akiyama , S. , Fukui , K. , Ishizawa , M. and Yamada , Y. 1992 . Angiogenic factor . Nature , 356 : 668
  • Miyazono , K. , Okabe , T. , Urabe , A. , Takaku , F. and Heldin , Ch. 1987 . Purification and properties of an endothelial cell growth factor from human platelets . J. Biol. Chem. , 262 : 4098 – 4103 .
  • Usuki , K. , Sarasi , J. , Waltenberger , J. , Miyazono , K. , Pierce , G. , Thomason , A. and Heldin , C. H. 1992 . Platelet-derived endothelial cell growth factor has thymidine phosphorylase activity . Biochem. Biophys. Res. Commun. , 184 : 1311 – 1316 .
  • Friedkin , M. and Roberts , D. W. 1954 . The enzymatic synthesis of nucleosides I. Thymidine phosphorylase in mammalian tissue . J. Biol. Chem. , 207 : 245 – 256 .
  • Brown , N. S. and Bicknell , R. 1998 . Thymidine phosphorylase, 2-deoxy-ribose and angiogenesis . Biochem. J. , 334 : 1 – 8 .
  • Sengupta , S. , Sellers , L. A. , Matheson , H. B. and Fan , T.-P.D. 2003 . Thymidine phosphorylase induces angiogenesis in vivo and in vitro: an evaluation of possible mechanisms . Br. J. Pharmacol. , 139 : 219 – 231 .
  • Ishikawa , F. , Miyazono , K. , Hellman , U. , Drexler , H. , Wernstedt , C. , Hagiwara , K. , Usuki , K. , Takaku , F. , Risau , W. and Heldin , C. H. 1989 . Identification of angiogenic activity and the cloning and expression of platelet-derived endothelial cell growth factor . Nature , 338 : 557 – 562 .
  • Haraguchi , M. , Miyadera , K. , Uemura , K. , Sumizawa , T. , Furukawa , T. , Yamada , K. , Akiyama , S. and Yamada , Y. 1994 . Angiogenic activity of enzymes . Nature , 368 : 198
  • Matsushita , S. , Nitanda , T. , Furukawa , T. , Sumizawa , T. , Tani , A. , Nishimoto , K. , Akiba , S. , Miyadera , K. , Fukushima , M. , Yamada , Y. , Yoshida , H. , Kanzaki , T. and Akiyama , S. 1999 . The effect of a thymidine phosphorylase inhibitor on angiogenesis and apoptosis in tumors . Cancer Res. , 59 : 1911 – 1916 .
  • Focher , F. and Spadari , S. 2001 . Thymidine phosphorylase: a two-face Janus in anticancer chemotherapy . Curr. Cancer Drug Targets , 1 : 141 – 153 .
  • Fukushima , M. , Suzuki , N. , Emura , T. , Yano , Y. , 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 : 1227 – 1236 .
  • 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 : 1257 – 1263 .
  • Yano , S. , Kazuno , H. , Suzuki , N. , Emura , T. , Wierzba , K. , Yamashita , J. , Tada , Y. , Yamada , Y. , Fukushima , M. and Asao , T. 2004 . Synthesis and evaluation of 6-methylene-bridged uracil derivatives. Part 1: discovery of novel orally active inhibitors of human thymidine phosphorylase . Bioorg. Med. Chem. , 12 : 3431 – 3441 .
  • Yano , S. , Kazuno , H. , Sato , T. , Suzuki , N. , Emura , T. , Wierzba , K. , Yamashita , J. Y. , Tada , Y. , Yamada , Y. , Fukushima , M. and Asao , T. 2004 . Synthesis and evaluation of 6-methylene-bridged uracil derivatives. Part 2: optimization of inhibitors of human thymidine phosphorylase and their selectivity with uridine phosphorylase . Bioorg. Med. Chem. , 16 : 3443 – 3450 .
  • Nencka , R. , Votruba , I. , Hřebabecký , H. , Tloušt’ová , E. , Horská , K. , Masojídková , M. and Holý , A. 2006 . Design and synthesis of novel 5,6-disubstituted uracil derivatives as potent inhibitors of thymidine phosphorylase . Bioorg. Med. Chem. Lett. , 16 : 1335 – 1337 .
  • Nencka , R. , Votruba , I. , Hřebabecký , H. , Jansa , P. , Tloušt’ová , E. , Horská , K. , Masojídková , M. and Holý , A. 2007 . Discovery of 5-substituted-6-chlorouracils as efficient inhibitors of human thymidine phosphorylase . J. Med. Chem. , 50 : 6016 – 6023 .
  • Pugmire , M. J. and Ealick , S. E. 1998 . The crystal structure of pyrimidine nucleoside phosphorylase in a closed conformation . Structure , 6 : 1467 – 1479 .
  • Norman , R. A. , Barry , S. T. , Bate , M. , Breed , J. , Colls , J. G. , Ernill , R. J. , Luke , R. W.A. , Minshull , C. A. , McAlister , M. S.B. , McCall , E. J. , McMiken , H. H.J. , 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 .
  • Pomeisl , K. , Holý , A. , Pohl , R. and Horská , K. 2009 . Use of Pd-catalyzed Suzuki–Miyaura coupling reaction in the rapid synthesis of 5-aryl-6-(phosphonomethoxy)uracils and evaluation of their inhibitory effect towards human thymidine phosphorylase . Tetrahedron , 65 : 8486 – 8492 .
  • Pomeisl , K. , Holý , A. and Pohl , R. 2007 . Pd-catalyzed Suzuki–Miyaura coupling reactions in the synthesis of 5-aryl-1-[2-(phosphonomethoxy)ethyl]uracils as potential multisubstrate inhibitors of thymidine phosphorylase . Tetrahedron Lett. , 48 : 3065 – 3067 .
  • Votruba , I. , Pomeisl , K. , Tloušt’ová , E. , Holý , A. and Otová , B. 2005 . Inhibition of thymidine phosphorylase (PD-ECGF) from SD-lymphoma by phosphonomethoxyalkyl thymines . Biochem. Pharmacol. , 69 : 1517 – 1521 .
  • Pomeisl , K. , Pohl , R. , Holý , A. and Votruba , I. 2006 . Syntheses of base and side-chain modified pyrimidine 1-[2-(phosphonomethoxy)propyl] derivatives as potent inhibitors of thymidine phosphorylase (PD-ECGF) from SD-lymphoma . Collect. Czech. Chem. Commun. , 71 : 595 – 624 .
  • Pomeisl , K. , Pohl , R. , Holý , A. and Votruba , I. 2005 . Simple transformation of thymine 1-[3-hydroxy-2-(phosphonomethoxy)propyl] derivatives to their 1-[3-fluoro-2-(phoshonomethoxy)propyl] counterparts . Collect. Czech. Chem. Commun. , 70 : 1465 – 1481 .
  • Pomeisl , K. , Holý , A. , Votruba , I. and Pohl , R. 2008 . Syntheses of N3-substituted thymine acyclic nucleoside phosphonates and a comparison of their inhibitory effect towards thymidine phosphorylase . Bioorg. Med. Chem. Lett. , 18 : 1364 – 1367 .
  • Allan , A. L. , Gladstone , P. L. , Price , M. L.P. , Hopkins , S. A. , Juarez , J. C. , Doñate , F. , Ternansky , R. J. , Shaw , D. E. , Ganem , B. G. , Li , Y. , Wang , W. and Ealick , S. 2006 . Synthesis and evaluation of multisubstrate bicyclic pyrimidine nucleoside inhibitors of human thymidine phosphorylase . J. Med. Chem. , 49 : 7807 – 7815 .
  • De Clerq , E. 2002 . Strategies in the design of antiviral drugs . Nature Rev. , 1 : 13 – 25 .
  • Jessen , H. S. , Schulz , T. , Balzarini , J. and Meier , C. 2008 . Bioreversible protection of nucleoside diphosphates . Angew. Chem. , 47 : 8719 – 8722 .
  • Otmar , M. , Masojídková , M. , Votruba , I. and Holý , A. 2001 . An alternative synthesis of HPMPC and HPMPA diphosphoryl derivatives . Collect. Czech. Chem. Commun. , 66 : 500 – 506 .
  • Hoard , D. E. and Ott , D. G. 1965 . Conversion of mono and oligodeoxyribonucleotides . J. Am. Chem. Soc. , 87 : 1785 – 1788 .
  • Mařák , D. , Otmar , M. , Votruba , I. , Dračínský , M. and Krečmerová , M. 2011 . 8-Aza-7,9-dideazaxanthine acyclic nucleoside phosphonate inhibitors of thymidine phosphorylase . Bioorg. Med. Chem. Lett. , 21 : 652 – 654 .
  • Allan , A. L. , Gladstone , P. L. , Price , M. L.P. , Hopkins , S. A. , Juarez , J. C. , Doñate , F. , Ternansky , R. J. , Shaw , D. E. , Ganem , B. , Li , Y. , Wang , W. and Ealick , S. E. 2006 . Synthesis and evaluation of multisubstrate bicyclic pyrimidine nucleoside inhibitors of human thymidine phosphorylase . J. Med. Chem. , 49 : 7807 – 7815 .
  • Doláková , P. , Dračinský , M. , Fanfrlík , J. and Holý , A. 2009 . Synthesis of analogues of acyclic nucleoside diphosphates containing a (phosphonomethyl)phosphanyl moiety and studies of their phosphorylation . Eur. J. Org. Chem. , 7 : 1082 – 1092 .
  • Wishart , D. S. , Bigam , C. G. , Yao , J. , Abildgaard , F. , Dyson , H. J. , Oldfield , E. , Markley , J. L. and Sykes , B. D. 1995 . 1H, 13C and 15N chemical shift referencing in biomolecular NMR . J. Biomol. NMR , 6 : 135 – 140 .
  • Copeland , R. A. 2000 . Enzymes: A Practical Introduction to Structure, Mechanism, and Data Analysis , 2nd edition , Edited by: Copeland , R. A. 352 – 354 . New York : Wiley-VCH . Random ordered bi bi reactions, in

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