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Volumn 29, Issue 1, 2010, Pages 49-54

Synthesis and in vitro evaluation of 5-fluoro-6-[(2-iminopyrrolidin-1-YL) methyl]Uracil, TPI(F): An inhibitor of human thymidine phosphorylase (TP)

Author keywords

Human thymidine phosphorylase; TP; TPI; TPI(F); Transition state inhibitor analog

Indexed keywords

5 FLUORO 6 [(2 IMINOPYRROLIDIN 1 YL)METHYL]URACIL; RADIOPHARMACEUTICAL AGENT; THYMIDINE PHOSPHORYLASE; UNCLASSIFIED DRUG; URACIL DERIVATIVE; 5-FLUORO-6-((2-IMINOPYRROLIDIN-1-YL)METHYL)URACIL; ENZYME INHIBITOR; PYRROLIDINE DERIVATIVE; THYMIDINE; URACIL;

EID: 77949549501     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770903451603     Document Type: Article
Times cited : (8)

References (20)
  • 2
    • 0014508663 scopus 로고
    • Thymidine salvage pathway in normal and leukemic leukocytes with effects of ATP on enzyme control
    • Rabinowitz, Y.; Wilhite, B.A. Thymidine salvage pathway in normal and leukemic leukocytes with effects of ATP on enzyme control. Blood 1969, 33, 759-771.
    • (1969) Blood , vol.33 , pp. 759-771
    • Rabinowitz, Y.1    Wilhite, B.A.2
  • 3
    • 14644393663 scopus 로고    scopus 로고
    • Thymidine phosphorylase (platelet-derived endothelial-cell growth factor) in cancer biology and treatment
    • Toi, M.; Atiqur Rahman, M.; Bando, H.; Chow, L.W.C. Thymidine phosphorylase (platelet-derived endothelial-cell growth factor) in cancer biology and treatment. Lancet Oncol. 2005, 6, 158-166.
    • (2005) Lancet Oncol. , vol.6 , pp. 158-166
    • Toi, M.1    Atiqur Rahman, M.2    Bando, H.3    Chow, L.W.C.4
  • 4
    • 0032529047 scopus 로고    scopus 로고
    • Thymidine phosphorylase, 2-deoxy-D-ribose and angiogenesis
    • Brown, N.S.; Bicknell, R. Thymidine phosphorylase, 2-deoxy-D-ribose and angiogenesis. Biochem. J. 1998, 334, 1-8.
    • (1998) Biochem. J. , vol.334 , pp. 1-8
    • Brown, N.S.1    Bicknell, R.2
  • 5
    • 0037439694 scopus 로고    scopus 로고
    • Mechanisms by which tumor cells and monocytes expressing the angiogenic factor thymidine phosphorylase mediate human endothelial cell migration
    • Hotchkiss, K.A.; Ashton, A.W.; Klein, R.S.; Lenzi, M.L.; Zhu, G.H.; Schwartz, E.L. Mechanisms by which tumor cells and monocytes expressing the angiogenic factor thymidine phosphorylase mediate human endothelial cell migration. Cancer Res. 2003, 63, 527-533.
    • (2003) Cancer Res. , vol.63 , pp. 527-533
    • Hotchkiss, K.A.1    Ashton, A.W.2    Klein, R.S.3    Lenzi, M.L.4    Zhu, G.H.5    Schwartz, E.L.6
  • 7
    • 0037436280 scopus 로고    scopus 로고
    • Rapid disappearance of deoxyribose-1-phosphate in platelet derived endothelial cell growth factor/thymidine phosphorylase overexpressing cells
    • de Bruin, M.; Smid, K.; Laan, A.C.; Noordhuis, P.; Fukushima, M.; Hoekman, K.; Pinedo, H.M.; Peters, G.J. Rapid disappearance of deoxyribose-1-phosphate in platelet derived endothelial cell growth factor/thymidine phosphorylase overexpressing cells. Biochem. Biophys. Res. Comm. 2003, 301, 675-679.
    • (2003) Biochem. Biophys. Res. Comm. , vol.301 , pp. 675-679
    • De Bruin, M.1    Smid, K.2    Laan, A.C.3    Noordhuis, P.4    Fukushima, M.5    Hoekman, K.6    Pinedo, H.M.7    Peters, G.J.8
  • 8
    • 59649097114 scopus 로고    scopus 로고
    • Proteomics identifies thymidine phosphorylase as a key regulator of the angiogenic potential of colony-forming units of endothelial progenitor cell cultures
    • Pula, G.; Mayr, U.; Evans, C.; Prokopi, M.; Vara, D.S.; Yin, X.; Astroulakis, Z.; Xiao, Q.; Hill, J.; Xu, Q.; Mayr, M. Proteomics identifies thymidine phosphorylase as a key regulator of the angiogenic potential of colony-forming units of endothelial progenitor cell cultures. Circ. Res. 2009, 104, 32-40.
    • (2009) Circ. Res. , vol.104 , pp. 32-40
    • Pula, G.1    Mayr, U.2    Evans, C.3    Prokopi, M.4    Vara, D.S.5    Yin, X.6    Astroulakis, Z.7    Xiao, Q.8    Hill, J.9    Xu, Q.10    Mayr, M.11
  • 9
    • 34250766826 scopus 로고    scopus 로고
    • Evaluation of 5-deoxy-5-[F-18]fluorothymidine ([F-18]DFT) as a tracer of intracellular thymidine phosphorylase activity
    • Grierson, J.R.; Brokenbrough, J.S.; Rasey, J.S.; Wiens, L.W.; Schwartz, J.L.; Jordan, R.; Vesselle, H. Evaluation of 5-deoxy-5-[F-18]fluorothymidine ([F-18]DFT) as a tracer of intracellular thymidine phosphorylase activity. Nucl. Med. Biol. 2007, 34, 471-478.
    • (2007) Nucl. Med. Biol. , vol.34 , pp. 471-478
    • Grierson, J.R.1    Brokenbrough, J.S.2    Rasey, J.S.3    Wiens, L.W.4    Schwartz, J.L.5    Jordan, R.6    Vesselle, H.7
  • 10
    • 0034657004 scopus 로고    scopus 로고
    • Structure and activity of specific inhibitors of thymidine phosphorylase to potentiate the function of antitumor 2-deoxyribonucleosides
    • Fukushima, M.; Suzuki, N.; Emura, T.; Yano, S.; Kazuno, H.; Tada, Y.; Yamada, Y.; Asao, T. Structure and activity of specific inhibitors of thymidine phosphorylase to potentiate the function of antitumor 2-deoxyribonucleosides. Biochem. Pharmacol. 2000, 59, 1227-1236.
    • (2000) Biochem. Pharmacol. , vol.59 , pp. 1227-1236
    • Fukushima, M.1    Suzuki, N.2    Emura, T.3    Yano, S.4    Kazuno, H.5    Tada, Y.6    Yamada, Y.7    Asao, T.8
  • 11
    • 33747355468 scopus 로고    scopus 로고
    • Synthesis radiolabeling, and in vivo evaluation of an 18F-labeled isatin analog for imaging caspase-3 activation in apoptosis
    • Zhou, D.; Chu, W.; Rothfuss, J.; Zeng, C.; Xu, J.; Jones, L.; Welch, M.J.; Mach, R.H. Synthesis, radiolabeling, and in vivo evaluation of an 18F-labeled isatin analog for imaging caspase-3 activation in apoptosis. Bioorg. Med. Chem. Lett. 2006, 16, 5041-5046.
    • (2006) Bioorg. Med. Chem. Lett. , vol.16 , pp. 5041-5046
    • Zhou, D.1    Chu, W.2    Rothfuss, J.3    Zeng, C.4    Xu, J.5    Jones, L.6    Welch, M.J.7    MacH, R.H.8
  • 12
    • 66749110952 scopus 로고    scopus 로고
    • [F-18]- and [C-11]-Labeled N-benzyl-isatin sulfonamide analogues as PET tracers for apoptosis: Synthesis, radiolabeling mechanism, and in vivo imaging study of apoptosis in fas-treated mice using [C-11] WC-98
    • Zhou D.; Chu, W.; Chen, D.L.; Wang, Q.; Reichert, E.E.; Rothfuss, J.; D'Avignon, A.; Welch, M.J.; Mach, R.H. [F-18]- and [C-11]-Labeled N-benzyl-isatin sulfonamide analogues as PET tracers for Apoptosis: synthesis, radiolabeling mechanism, and in vivo imaging study of apoptosis in Fas-treated mice using [C-11]WC-98. Org. Biomol. Chem. 2009, 7, 1337-1348.
    • (2009) Org. Biomol. Chem. , vol.7 , pp. 1337-1348
    • Zhou, D.1    Chu, W.2    Chen, D.L.3    Wang, Q.4    Reichert, E.E.5    Rothfuss, J.6    D'Avignon, A.7    Welch, M.J.8    MacH, R.H.9
  • 13
    • 26644453745 scopus 로고    scopus 로고
    • 6-Substituted 5-fluorouracil derivatives as transition state analogue inhibitors of thymidine phosphorylase
    • Kalman, T.I.; Lai, L. 6-Substituted 5-fluorouracil derivatives as transition state analogue inhibitors of thymidine phosphorylase. Nucleosides Nucleotides Nucleic Acids 2005, 24, 367-373.
    • (2005) Nucleosides Nucleotides Nucleic Acids , vol.24 , pp. 367-373
    • Kalman, T.I.1    Lai, L.2
  • 15
    • 2942608177 scopus 로고    scopus 로고
    • Synthesis and evaluation of 6-methylene-bridged uracil derivatives. Part 2: Optimization of inhibitors of human thymidine phosphorylase and their selectivity with uridine phosphorylase
    • Yano, S.; Kazuno, H.; Sato, T.; Suzuki, N.; Emura, T.; Wierzba, K.; Yamashita, J.-I.; Tada, Y.; Yamada, Y.; Fukushima, M.; Asao, T. 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. 2004, 12, 3443-3450.
    • (2004) Bioorg. Med. Chem. , vol.12 , pp. 3443-3450
    • Yano, S.1    Kazuno, H.2    Sato, T.3    Suzuki, N.4    Emura, T.5    Wierzba, K.6    Yamashita, J.-I.7    Tada, Y.8    Yamada, Y.9    Fukushima, M.10    Asao, T.11
  • 16
    • 0000153567 scopus 로고
    • The preparation and reactions of fluorinecontaining acetoacetic esters
    • McBee, E.T.; Pierce, O.R.; Kilbourne, H.W.; Wilson, E.R. The preparation and reactions of fluorinecontaining acetoacetic esters. J. Am. Chem. Soc. 1953, 75, 3152-3153.
    • (1953) J. Am. Chem. Soc. , vol.75 , pp. 3152-3153
    • McBee, E.T.1    Pierce, O.R.2    Kilbourne, H.W.3    Wilson, E.R.4
  • 18
    • 0011273279 scopus 로고
    • Synthesis and reactions of cyclic amidines
    • Moriconi, E.J.; Cevasco, A.A. Synthesis and reactions of cyclic amidines. J. Org. Chem. 1968, 33, 2109-2111.
    • (1968) J. Org. Chem. , vol.33 , pp. 2109-2111
    • Moriconi, E.J.1    Cevasco, A.A.2
  • 20
    • 0037028218 scopus 로고    scopus 로고
    • The Sp1 transcription factor contributes to the tumor necrosis factor-induced expression of the angiogenic factor thymidine phosphorylase in human colon carcinoma cells
    • Zhu, G.H.; Lenzi, M.; Schwartz, E.L. The Sp1 transcription factor contributes to the tumor necrosis factor-induced expression of the angiogenic factor thymidine phosphorylase in human colon carcinoma cells. Oncogene 2002, 21, 8477-8485
    • (2002) Oncogene , vol.21 , pp. 8477-8485
    • Zhu, G.H.1    Lenzi, M.2    Schwartz, E.L.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.