Synthesis and anti-HIV activity of prodrugs derived from saquinavir and indinavir

Antiviral Chemistry and Chemotherapy

Volumn 11, Issue 2, 2000, Pages 97-110

  Farèse Di Giorgio, Audrey ^a   Rouquayrol, Marielle ^a   Greiner, Jacques ^a   Aubertin, Anne Marie ^b   Vierling, Pierre ^a   Guedj, Roger ^a  

^a UNIVERSITÉ CÔTE D'AZUR   (France)

^b INSERM   (France)

Author keywords

HIV; Indinavir; Prodrugs; Protease inhibitors; Saquinavir

Indexed keywords

ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; INDINAVIR; MACROGOL 20000; PRODRUG; SAQUINAVIR;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG HALF LIFE; DRUG HYDROLYSIS; DRUG POTENCY; DRUG STABILITY; DRUG SYNTHESIS; NONHUMAN; PRIORITY JOURNAL; REACTION ANALYSIS; VIRUS INHIBITION;

ANTI-HIV AGENTS; BIOLOGICAL AVAILABILITY; CELL LINE; DRUG EVALUATION, PRECLINICAL; HIV-1; HUMANS; INDINAVIR; INHIBITORY CONCENTRATION 50; PRODRUGS; SAQUINAVIR; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0343238888     PISSN: 09563202     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (21)

1. Alexander J, Bindra D, Dorsey B & Repta A (1994) Prodrugs of an inhibitor of HIV protease. Chem. Abstr. 121:231363.
2. Beauchamp LM & Krenitsky TA (1993) Acyclovir prodrugs: the road to valacilovir. Drugs of the Future 18:619-628.
3. Bilello JA, Bilello PA, Stellrecht K, Leonard J, Norbeck DW, Kempf DJ, Robins T & Drusano GL (1996) Human serum alpha 1 acid glycoprotein reduces uptake, intracellular concentration, and antiviral activity of A-80987, an inhibitor of the human immunodeficiency virus type 1 protease. Antimicrobial Agents and Chemotherapy 40:1491-1497.
4. Bold G, Faessler A & Lang M (1994) Preparation of antiretroviral amino acid derivatives. Chem. Abstr 121:231363.
5. Chun TW, Stuyver L, Mizell SB, Ehler LA, Mican JAM, Baseler M, Lloyd AL, Nowak MA & Fauci AS. (1997) Presence of an inducible HIV-1 latent reservoir during highly active antiretroviral therapy. Proceedings of the National Academy of Sciences, USA 94:3193-3197.
6. Denissen JF, Grabowski BA, Johnson MK, Buko AM, Kempf DJ, Thomas SB & Surber BW (1997) Metabolism and disposition of the HIV-1 protease inhibitor ritonavir (ABT-538) in rats, dogs, and humans. Drug Metabolism and Disposition 25:481-501.
7. Dormont J, Brun-Vézinet F, Yéni P & Aboulker J-P (1996) Les antirétroviraux. Médecine Thérapeutique 2:127-137.
8. Flexner C (1998) HIV protease inhibitors. New England Journal of Medicine 338:1281-1292.
9. Génu-Dellac C, Gosselin G, Puech F, Henry JC, Aubertin A-M, Aubert G, Kim A & Imbach J-L (1991) Systematic synthesis and antiviral evaluation of L-arabinofuranosyl and 2′-deoxy-L-erythropentofuranosyl nucleosides of the five naturally occurring acid bases. Nucleosides andNucleotides 10:1345-1376.
10. Göhring W, Gokhale S, Hilpert H, Roessler F, Schlageter M & Vogt P (1996) Synthesis of the HIV-proteinase inhibitor saquinavir: a challenger for process research. Chimia 50:532-537.
11. Kempf DJ, Marsh KC, Kumar G, Rodrigues AD, Denissen JF, McDonald E, Kukulka MJ, Hsu A, Granneman GR, Baroldi PA, Sun E, Pizzuti D, Plattner JJ, Norbeck DW & Leonard JM (1997) Pharmacokinetic enhancement of inhibitors of the human immunodeficiency virus type 1 protease by coadministration with ritonavir. Antimicrobial Agents and Chemotherapy 41:654-660.
12. Kim RB, Fromm MF, Wandel C, Leake B, Wood AJ, Roden DM & Wilkinson GR (1998) The drug transporter P-glycoprotein limits oral absorption and brain entry of HIV-1 protease inhibitors. Journal of Clinical Investigation 101:289-294.
13. Leroux JC, Cozens RM, Roesel JL, Galli B, Doelker E & Gurny R (1996) pH-sensitive nanoparticles: an effective means to improve the oral delivery of HIV-1 protease inhibitors to dogs. Pharmaceutical Research 13:485-487.
14. McDonald CK & Kuritzkes DR (1997) Human immunodeficiency virus type 1 protease inhibitors. Archives of Internal Medicine 157:951-959.
15. Moog C, Wick A, Le Ber P, Kim A & Aubertin A-M (1994) Bicyclic imidazo derivatives, a new class of highly selective inhibitors for the human immunodeficiency virus type 1. Antiviral Research 24:275-288.
16. Oldendorf WH (1973) Stereospecificity of blood-brain barrier permeability to amino acids. American Journal of Physiology 224:967-969.
17. Pardridge WM (1995) Transport of small molecules through the blood-brain barrier: biology and methodology. Advanced Drug Delivery Reviews 15:5-36.
18. Pauwels R, Balzarini J, Baba M, Snoeck D, Herdewijn P, Desmyter J & De Clercq E (1988) Rapid and automated tetrazolium-based colorimetric assay for the detectior of anti-HIV compounds. Journal of Virological Methods 20:309-321.
19. Pialoux G, Fournier S, Moulignier A, Poveda JD, Clavel F & Dupont B (1997) Central nervous system as a sanctuary for HIV-1 infection despite treatment with zidovudine, lamivudine and indinavir. AIDS 11:1302-1303.
20. Pretzer E, Flasher D & Düzgünes N (1997) Inhibition of human immunodeficiency virus type-1 replication in macrophages and H9 cells by free or liposome-encapsulated L-689,502, an inhibitor of the viral protease. Antiviral Research 34:1-15.
21. Walker I, Nicholls D, Irwin WJ & Freeman S (1994) Drug delivery via active transport at the blood-brain barrier: affinity of a prodrug of phosphonoformate for the large amino acid transporter. International Journal of Pharmacology 104:157-167.