N-Acyl-phosphoramidates as potential novel form of gemcitabine prodrugs

Bioorganic and Medicinal Chemistry

Volumn 22, Issue 7, 2014, Pages 2133-2140

  Baraniak, Janina ^a   Pietkiewicz, Aleksandra ^a   Kaczmarek, Renata ^a   Radzikowska, Ewa ^a   Kulik, Katarzyna ^a   Krolewska, Karolina ^a   Cieslak, Marcin ^a   Krakowiak, Agnieszka ^a   Nawrot, Barbara ^a  

^a CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

Author keywords

Anticancer therapy; Cytotoxicity; DNA polymerase inhibitor; Gemcitabine; Prodrug

Indexed keywords

2',2' DIFLUORO 2' DEOXYCYTIDINE 5' O [N (3 CARBONYLPYRIDINE)]PHOSPHORAMIDATE; 2',2' DIFLUORO 2' DEOXYCYTIDINE 5' O [N (3 CARBONYLPYRIDINE)]THIOPHOSPHORAMIDATE; 2',2' DIFLUORO 2' DEOXYCYTIDINE 5' O [N (4 CARBONYLPYRIDINE)]PHOSPHORAMIDATE; 2',2' DIFLUORO 2' DEOXYCYTIDINE 5' O [N (4 CARBONYLPYRIDINE)]THIOPHOSPHORAMIDATE; 2',2' DIFLUORO 2' DEOXYCYTIDINE 5' O [N (ACETYL)]PHOSPHORAMIDATE; 2',2' DIFLUORO 2' DEOXYCYTIDINE 5' O [N (ACETYL)]THIOPHOSPHORAMIDATE; 2',2' DIFLUORO 2' DEOXYCYTIDINE 5' O [N (ALPHA N ACETYLPHENYLALANYL)]PHOSPHORAMIDATE; 2',2' DIFLUORO 2' DEOXYCYTIDINE 5' O [N (ALPHA N ACETYLPHENYLALANYL)]THIOPHOSPHORAMIDATE; 2',2' DIFLUORO 2' DEOXYCYTIDINE 5' O [N (ALPHA N ACETYLPROLYL)]PHOSPHORAMIDATE; 2',2' DIFLUORO 2' DEOXYCYTIDINE 5' O [N (ALPHA N ACETYLPROLYL)]THIOPHOSPHORAMIDATE; 2',2' DIFLUORO 2' DEOXYCYTIDINE 5' O [N (BENZOYL)]PHOSPHORAMIDATE; 2',2' DIFLUORO 2' DEOXYCYTIDINE 5' O [N (BENZOYL)]THIOPHOSPHORAMIDATE; CYTIDINE DERIVATIVE; DNA DIRECTED DNA POLYMERASE ALPHA; DNA DIRECTED DNA POLYMERASE BETA; GEMCITABINE; GEMCITABINE N ACYL PHOSPHORAMIDATE DERIVATIVE; PHOSPHORAMIDIC ACID DERIVATIVE; UNCLASSIFIED DRUG; AMIDE; DEOXYCYTIDINE; ENZYME INHIBITOR; PHOSPHORAMIDIC ACID; PHOSPHORIC ACID; PRODRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; HUMAN; HUMAN CELL; IC 50; NONHUMAN; ANALOGS AND DERIVATIVES; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; ENZYMOLOGY; HELA CELL LINE; K562 CELL LINE; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

BACTERIA (MICROORGANISMS);

AMIDES; DEOXYCYTIDINE; DNA POLYMERASE I; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; ESCHERICHIA COLI; HELA CELLS; HUMANS; K562 CELLS; MOLECULAR STRUCTURE; PHOSPHORIC ACIDS; PRODRUGS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84897462128     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2014.02.034     Document Type: Article

References (24)

1. E. Moysan, G. Basttiat, and J.-P. Benoit Mol. Pharm. 10 2013 430
2. A.M. Bergman, H.M. Pinedo, and G.J. Peters Drug Resist. Updat. 5 2002 19
3. D. Cahard, C. McGuigan, and J. Balzarini Mini-Rev. Med. Chem. 4 2004 371
4. McGuigan, C. Chemical compounds. 2005, WO 2005/012327 A2.
5. D.P. Drontle, and C.R. Wagner Mini-Rev. Med. Chem. 4 2004 409
6. P. Bieganowski, P.N. Garrison, S.C. Hodawadekar, G. Faye, L.D. Barnes, and C. Brenner J. Biol. Chem. 277 2002 10852
7. A. Krakowiak, R. Kaczmarek, J. Baraniak, M. Wieczorek, and W.J. Stec Chem. Comm. 2007 2163
8. C.R. Wagner, V.V. Iyer, and E.J. McIntee Med. Res. Rev. 20 2000 417
9. J. Zemlicka Biochim. Biophys. Acta 1587 2002 276
10. W. Weidong, J. Sigmond, G.J. Peters, and R.F. Borch J. Med. Chem. 50 2007 3743
11. R.L. Alexander, B.T. Greene, S.V. Torti, and G.L. Kucera Cancer Chemother. Pharmacol. 56 2005 15
12. J. Baraniak, R. Kaczmarek, E. Wasilewska, D. Korczyński, and W.J. Stec Tetrahedron Lett. 45 2004 4269
13. W.J. Stec, A. Grajkowski, M. Koziolkiewicz, and B. Uznanski Nucleic Acids Res. 19 1991 5883
14. M. Akada, T. Crnogorac-Jurcevic, S. Lattimore, P. Mahon, R. Lopes, M. Sunamura, S. Matsuno, and N.R. Lemoine Clin. Cancer Res. 11 2005 3094
15. A. Van den Broeck, L. Gremeaux, B. Topal, and H. Vankelecom BMC Cancer 12 2012 354 10.1186/1471-2407-12-354
16. M. Maszewska, J. Leclaire, M. Cieslak, B. Nawrot, A. Okruszek, A.M. Caminade, and J.P. Majoral Oligonucleotides 13 2003 193
17. A.F. Gardner, and W.E. Jack Nucleic Acids Res. 27 1999 2545 2555
18. A.F. Gardner, and W.E. Jack Nucleic Acids Res. 30 2002 605
19. P. Perlíková, L. Eberlin, P. Ménová, V. Raindlová, L. Slavětínská, E. Tloušť ová, G. Bahador, Y.J. Lee, and M. Hocek ChemMedChem 8 2013 832
20. O. Adelfinskaya, M. Terrazas, M. Froeyen, P. Marlière, K. Nauwelaerts, and P. Herdewijn Nucleic Acids Res. 35 2007 5060
21. I.V. Martynov, Y.L. Kruglyak, G.A. Leibovskaya, Z.I. Khromova, and O.G.Zh. Strukov Obshch. Khim. 39 1969 996
22. G. Zon, and W.J. Stec Oligonucleotides and Analogues - A Practical Approach 1991 IRL Press Oxford pp. 87
23. E.A. Jaffe, R.L. Nachman, C.G. Becker, and C.R. Minick J. Clin. Invest. 52 1973 2745
24. J. Gilmour, N. Liang, and J.M. Lowenstein Biochem. J. 326 1997 471