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Volumn 52, Issue 22, 2009, Pages 6958-6961

Synthesis, crystallization, and biological evaluation of an orally active prodrug of gemcitabine

Author keywords

[No Author keywords available]

Indexed keywords

2, 5' O ISOLEUCINE GEMCITABINE; ACICLOVIR; ANTINEOPLASTIC AGENT; CAPECITABINE; DEOXYCYTIDINE KINASE; FLUOROURACIL; GEMCITABINE; LY 2334737; UNCLASSIFIED DRUG; VALACICLOVIR; VALPROIC ACID;

EID: 70949086288     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm901181h     Document Type: Article
Times cited : (94)

References (22)
  • 3
    • 2942571455 scopus 로고    scopus 로고
    • Gemcitabine (Gemzar) in non-small cell lung cancer
    • (c) Manegold, C. Gemcitabine (Gemzar) in non-small cell lung cancer. Expert Rev. Anticancer Ther. 2004, 4, 345-360.
    • (2004) Expert Rev. Anticancer Ther. , vol.4 , pp. 345-360
    • Manegold, C.1
  • 4
    • 21244462774 scopus 로고    scopus 로고
    • Gemcitabine in metastatic breast cancer
    • (d) Heinemann, V. Gemcitabine in metastatic breast cancer. Expert Rev. Anticancer Ther. 2005, 5, 429-443.
    • (2005) Expert Rev. Anticancer Ther. , vol.5 , pp. 429-443
    • Heinemann, V.1
  • 5
    • 0026324313 scopus 로고
    • Action of 2′,2′-difluorodeoxycytidine on DNA synthesis
    • (a) Huang, P.; Chubb, S.; Hertel, L.; Grindey, G.; Plunkett, W. Action of 2′,2′-difluorodeoxycytidine on DNA synthesis. Cancer Res. 1991, 51, 6110-6117.
    • (1991) Cancer Res. , vol.51 , pp. 6110-6117
    • Huang, P.1    Chubb, S.2    Hertel, L.3    Grindey, G.4    Plunkett, W.5
  • 6
    • 0027180521 scopus 로고
    • 2′,2′-Difluorodeoxycytidine (gemcitabine) incorporation into RNA and DNA from tumour cell lines
    • (b) Ruiz van Haperen, V.; Vererman, G.; Vermorken, J.; Peters, G. 2′,2′-Difluorodeoxycytidine (gemcitabine) incorporation into RNA and DNA from tumour cell lines. Biochem. Pharmacol. 1993, 46, 762-766.
    • (1993) Biochem. Pharmacol. , vol.46 , pp. 762-766
    • Van Ruiz Haperen, V.1    Vererman, G.2    Vermorken, J.3    Peters, G.4
  • 7
    • 0026571795 scopus 로고
    • Cellular elimination of 2′,2′-difluorodeoxycytidine 5′-triphosphate: A mechanism of self-potentiation
    • (c) Heinemann, V.; Xu, Y.; Chubb, S.; Sen, A.; Hertel, L.; Grindey, G.; Plunkett, W. Cellular elimination of 2′,2′-difluorodeoxycytidine 5′-triphosphate: a mechanism of self-potentiation. Cancer Res. 1992, 52, 533-539.
    • (1992) Cancer Res. , vol.52 , pp. 533-539
    • Heinemann, V.1    Xu, Y.2    Chubb, S.3    Sen, A.4    Hertel, L.5    Grindey, G.6    Plunkett, W.7
  • 8
    • 0026465478 scopus 로고
    • Metabolism and disposition of gemcitabine, and oncolytic deoxycytidine analog, in mice, rats, and dogs
    • (a) Shipley, L.; Brown, T.; Cornpropst, J.; Hamilton, M.; Daniels, W.; Culp, H. Metabolism and disposition of gemcitabine, and oncolytic deoxycytidine analog, in mice, rats, and dogs. Drug Metab. Dispos. 1992, 20, 849-855.
    • (1992) Drug Metab. Dispos. , vol.20 , pp. 849-855
    • Shipley, L.1    Brown, T.2    Cornpropst, J.3    Hamilton, M.4    Daniels, W.5    Culp, H.6
  • 9
  • 10
    • 43549110055 scopus 로고    scopus 로고
    • Prolonged versus standard gemcitabine infusion: Translation of molecular pharmacology to new treatment strategy
    • (a) Veltkamp, S. A.; Beijnen, J. H.; Schellend, J. H. H. Prolonged versus standard gemcitabine infusion: translation of molecular pharmacology to new treatment strategy. Oncologist 2008, 13, 261-276.
    • (2008) Oncologist , vol.13 , pp. 261-276
    • Veltkamp, S.A.1    Beijnen, J.H.2    Schellend, J.H.H.3
  • 11
    • 0035424877 scopus 로고    scopus 로고
    • Phase II clinical investigation of gemcitabine in advanced soft tissue sarcomas and window evaluation of dose rate on gemcitabine triphosphate accumulation
    • (b) Patel, S. R.; Gandhi, V.; Jenkins, J.; Papadopolous, N.; Burgess, M. A.; Plager, C.; Plunkett, W.; Benjamin, R. S. Phase II clinical investigation of gemcitabine in advanced soft tissue sarcomas and window evaluation of dose rate on gemcitabine triphosphate accumulation. J Clin. Oncol. 2001, 19, 3483-3489.
    • (2001) J Clin. Oncol. , vol.19 , pp. 3483-3489
    • Patel, S.R.1    Gandhi, V.2    Jenkins, J.3    Papadopolous, N.4    Burgess, M.A.5    Plager, C.6    Plunkett, W.7    Benjamin, R.S.8
  • 12
    • 0026101039 scopus 로고
    • Saturation of 2′,2′-difluorodeoxycytidine 5′-triphosphate accumulation by mononuclear cells during a phase I trial of gemcitabine
    • (c) Grunewald, R.; Abbruzzese, J. L.; Tarassoff, P.; Plunkett, W. Saturation of 2′,2′-difluorodeoxycytidine 5′-triphosphate accumulation by mononuclear cells during a phase I trial of gemcitabine. Cancer Chemother. Pharmacol. 1991, 27, 258-262.
    • (1991) Cancer Chemother. Pharmacol. , vol.27 , pp. 258-262
    • Grunewald, R.1    Abbruzzese, J.L.2    Tarassoff, P.3    Plunkett, W.4
  • 13
    • 0025089191 scopus 로고
    • Pharmacologically directed design of the dose rate and schedule of 2',2'-difluorodeoxycytidine (gemcitabine) administration in leukemia
    • (d) Grunewald, R.; Kantarjian, H.; Keating, M.; Abbruzzese, J.; Tarassoff, P.; Plunkett, W. Pharmacologically directed design of the dose rate and schedule of 2′,2′-difluorodeoxycytidine (gemcitabine) administration in leukemia. Cancer Res. 1990, 50, 6823-6826. (Pubitemid 20361074)
    • (1990) Cancer Research , vol.50 , Issue.21 , pp. 6823-6826
    • Grunewald, R.1    Kantarjian, H.2    Keating, M.J.3    Abbruzzese, J.4    Tarassoff, P.5    Plunkett, W.6
  • 14
    • 0242665443 scopus 로고    scopus 로고
    • Phase II Trial of a 24-Hour Infusion of Gemcitabine in Previously Untreated Patients with Advanced Pancreatic Adenocarcinoma
    • DOI 10.1081/CNV-120023767
    • (e) Eckel, F.; Schmelz, R.; Erdmann, J.; Mayr, M.; Lersch, C. Phase II trial of a 24-h infusion of gemcitabine in previously untreated patients with advanced pancreatic adenocarcinoma. Cancer Invest. 2003, 21, 690-694. (Pubitemid 37377323)
    • (2003) Cancer Investigation , vol.21 , Issue.5 , pp. 690-694
    • Eckel, F.1    Schmelz, R.2    Erdmann, J.3    Mayr, M.4    Lersch, C.5
  • 17
    • 2342481809 scopus 로고    scopus 로고
    • Lessons learned frommarketed and investigational prodrugs
    • (a) Ettmayer, P.; Amidon, G. L.; Clement, B.; Testa, B. Lessons learned frommarketed and investigational prodrugs. J. Med. Chem. 2004, 47, 2393-2404.
    • (2004) J. Med. Chem. , vol.47 , pp. 2393-2404
    • Ettmayer, P.1    Amidon, G.L.2    Clement, B.3    Testa, B.4
  • 19
    • 23844467048 scopus 로고    scopus 로고
    • Amino acid ester prodrugs of the anticancer agent gemcitabine: Synthesis, bioconversion, metabolic bioevasion, and hPEPT-1 mediated transport
    • Song, X.; Lorenzi, P. L.; Landowski, C. P.; Balvinder, S. V.; Hilfdinger, J. M.; Amidon, G. L. Amino acid ester prodrugs of the anticancer agent gemcitabine: synthesis, bioconversion, metabolic bioevasion, and hPEPT-1 mediated transport. Mol. Pharmaceutics 2004, 2, 157-167.
    • (2004) Mol. Pharmaceutics , vol.2 , pp. 157-167
    • Song, X.1    Lorenzi, P.L.2    Landowski, C.P.3    Balvinder, S.V.4    Hilfdinger, J.M.5    Amidon, G.L.6
  • 21
    • 0033615679 scopus 로고    scopus 로고
    • Selective protection of 2′,2′-difluorodeoxycytidine (gemcitabine)
    • Guo, Z.-w.; Gallo, J. M. Selective protection of 2′,2′- difluorodeoxycytidine (gemcitabine). J. Org. Chem. 1999, 64, 8319-8322.
    • (1999) J. Org. Chem. , vol.64 , pp. 8319-8322
    • Guo, Z.-W.1    Gallo, J.M.2
  • 22
    • 0029998770 scopus 로고    scopus 로고
    • Base stacking and hydrogen bonding in protonated cytosine dimer: The role of molecular ion-dipole and induction interactions
    • Šponer, J.; Leszczynski, J.; Vetterl, V.; Hobza, P. Base stacking and hydrogen bonding in protonated cytosine dimer: the role of molecular ion-dipole and induction interactions. J. Biomol. Struct. Dyn. 1996, 13, 695-706.
    • (1996) J. Biomol. Struct. Dyn. , vol.13 , pp. 695-706
    • Šponer, J.1    Leszczynski, J.2    Vetterl, V.3    Hobza, P.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.