Bioreversible protection of nucleoside diphosphates

Angewandte Chemie - International Edition

Volumn 47, Issue 45, 2008, Pages 8719-8722

  Jessen, Henning Jacob ^a   Schulz, Tilmann ^a   Balzarini, Jan ^b   Meier, Chris ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Antiviral agents; Drug delivery; Medicinal chemistry; Nucleotides; Prodrugs

Indexed keywords

CYTOLOGY; DRUG DELIVERY; NUCLEIC ACIDS; NUCLEOTIDES;

ANTIVIRAL AGENTS; BIOREVERSIBLE; DIPHOSPHATE; MEDICINAL CHEMISTRY; NUCLEOSIDE DIPHOSPHATES; PRODRUG; PRODRUGS;

CELL MEMBRANES;

CELL EXTRACT; ESTERASE; NUCLEOSIDE; PRODRUG; PYROPHOSPHATE;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN IMMUNODEFICIENCY VIRUS; HYDROLYSIS; METABOLISM;

ANIMALS; CELL EXTRACTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIPHOSPHATES; ESTERASES; HIV; HYDROLYSIS; MOLECULAR STRUCTURE; NUCLEOSIDES; PRODRUGS;

EID: 55249108486     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200803100     Document Type: Article

References (24)

1. a) J. Balzarini, P. Herdewijn, E. De Clercq, J. Biol. Chem. 1989, 264, 6127-6133;
2. b) J. Balzarini, Pharm. World Sci. 1994, 16, 113-126.
3. a) C. Meier, T. Knispel, E. De Clercq, J. Balzarini, J. Med. Chem. 1999, 42, 1604-1614;
4. b) C. Meier, A. Lomp, A. Meerbach, P. Wutzler, J. Med. Chem. 2002, 45, 5157-5172;
5. c) D. Cahard, C. McGuigan, J. Balzarini, Mini-Rev. Med. Chem. 2004, 4, 371-381, and references therein.
6. a) X. Tan, C. K. Chu, F. D. Boudinot, Adv. Drug Delivery Rev. 1999, 39, 117-151;
7. b) C. Meier, Eur. J. Org. Chem. 2006, 1081-1102;
8. c) C. R. Wagner, V. V. Iyer, E. J. McIntee, Med. Res. Rev. 2000, 20, 417-451;
9. d) R. J. Jones, N. Bischofsberger, Antiviral Res. 1995, 27, 1-17, and references therein.
10. a) A. Lavie, I. Schlichting, I. R. Vetter, M. Konrad, J. Reinstein, R. S. Goody, Nat. Med. 1997, 3, 922-924;
11. b) A. Lavie, I. R. Vetter, M. Konrad, R. S. Goody, J. Reinstein, I. Schlichting, Nat. Struct. Biol. 1997, 4, 601-604.
12. a) J. P. Sommadossi, R. Carlisle, Z. Zhou, Mol. Pharmacol. 1989, 36, 9-14;
13. b) J. A. Harrington, J. E. Reardon, T. Spector, Antimicrob. Agents Chemother. 1993, 37, 918-920;
14. c) J. P. Yan, D. D. Ilsley, C. Frohlick, R. Street, E. T. Hall, R. D. Kuchta, P. Melanco, J. Biol. Chem. 1995, 270, 22 836-22 841.
15. a) K. Y. Hostetler, L. M. Stuhmiller, H. B. M. Lenting, H. van den Bosch, D. D. Richman, J. Biol. Chem. 1990, 265, 6112-6117;
16. b) G. M. T. van Wijk, K. Y. Hostetler, H. van den Bosch, Biochim. Biophys. Acta Lipids Lipid Metab. 1991, 1084, 307-310.
17. a) A. Kreimeyer, J. Ughetto-Monfrin, A. Namane, T. Huynh-Dinh, Tetrahedron Lett. 1996, 37, 8739-8742;
18. b) D. Bonnaff J, B. Dupraz, J. Ughetto-Monfrin, A. Namane, T. Huynh-Dinh, Tetrahedron Lett. 1995, 36, 531-534;
19. c) A. Kreimeyer, F. André, C. Gouyette, T. Huynh-Dinh, Angew. Chem. 1998, 110, 3013-3016;
20. Angew. Chem. Int. Ed. 1998, 37, 2853-2855.
21. D. Bonnaffé, B. Dupraz, J. Ughetto-Monfrin, A. Namane, Y. Henin, T. Huynh-Dinh, J. Org. Chem. 1996, 61, 895-902.
22. The bis(AB) approach was used to mask nucleoside monophosphates, but was not pursued further: a) A. Routledge, I. Walker, S. Freeman, A. Hay, N. Mahmood, Nucleosides Nucleotides 1995, 14, 1545-1558;
23. b) S. Freeman, K. C. Ross, Prog. Med. Chem. 1997, 34, 111-147;
24. c) C. Meier, U. Muus, J. Renze, L. Naesens, E. De Clercq, J. Balzarini, Antiviral Chem. Chemother. 2002, 13, 101-114.