A new nanomedicine based on didanosine glycerolipidic prodrug enhances the long term accumulation of drug in a HIV sanctuary

International Journal of Pharmaceutics

Volumn 414, Issue 1-2, 2011, Pages 285-297

  Skanji, Rym ^a   Andrieux, Karine ^a   Lalanne, Muriel ^a   Caron, Joachim ^b   Bourgaux, Claudie ^a   Degrouard, Jéril ^b   Brisset, Franois ^b   Gueutin, Claire ^a   Chacun, Hélne ^a   Dereuddre Bosquet, Nathalie ^c   Paci, Angelo ^a   Vassal, Gilles ^a   Bauduin, Laurent ^d   Garcia Argote, Sébastien ^e   Rousseau, Bernard ^e   Clayette, Pascal ^c   Desmaële, Didier ^b   Couvreur, Patrick ^a  

^a UNIVERSITÉ PARIS SACLAY   (France)

^b CNRS   (France)

^c INSTITUT DE RADIOPROTECTION ET DE SÛRETÉ NUCLÉAIRE   (France)

^d DIF   (France)

^e CEA SACLAY   (France)

Author keywords

Antiviral activity; Didanosine; In vivo experiments; Liposomes; Prodrug

Indexed keywords

DIDANOSINE; LIPOSOME; PRODRUG; SOLVENT; TRITIUM;

ANIMAL EXPERIMENT; ANTIVIRAL ACTIVITY; ARTICLE; BIOMIMETICS; CONTROLLED STUDY; CRYOELECTRON MICROSCOPY; CYTOTOXICITY; DIFFERENTIAL SCANNING CALORIMETRY; DRUG DOSAGE FORM COMPARISON; DRUG FORMULATION; DRUG SOLUBILITY; EMULSION; ENCAPSULATION; EVAPORATION; FREEZE DRYING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; IN VIVO STUDY; ISOTOPE LABELING; NANOMEDICINE; NONHUMAN; PRIORITY JOURNAL; RAT; SCANNING ELECTRON MICROSCOPY; TEMPERATURE; TISSUE DISTRIBUTION; TRANSMISSION ELECTRON MICROSCOPY; X RAY DIFFRACTION;

1,2-DIPALMITOYLPHOSPHATIDYLCHOLINE; ADMINISTRATION, ORAL; ANIMALS; ANTI-HIV AGENTS; DIDANOSINE; DRUG CARRIERS; DRUG COMPOUNDING; DRUG DELIVERY SYSTEMS; FREEZE DRYING; HIV; HIV INFECTIONS; HUMANS; LEUKOCYTES, MONONUCLEAR; LIPOSOMES; NANOSTRUCTURES; PARTICLE SIZE; PRODRUGS; RATS; RATS, WISTAR; TIME FACTORS;

EID: 79959754349     PISSN: 03785173     EISSN: 18733476     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2011.05.005     Document Type: Article

References (30)

1. A.D. Bangham, H.W. Hill, and N.G.A. Miller Preparation and use of liposomes as models of biological membranes Methods Membr. Biol. 1 1974 1 68
2. F. Barre-Sinoussi, J.C. Chermann, F. Rey, M.T. Nugeyre, S. Chamaret, J. Gruest, C. Dauguet, C. Axler-Blin, F. Vezinet-Brun, C. Rouzioux, W. Rozenbaum, and L. Montagnier Isolation of a T-lymphotropic retrovirus from a patient at risk for acquired immune deficiency syndrome (AIDS) Science 220 1983 868 871 (Pubitemid 13080157)
3. S.L. Bramer, J.L. Au, and M.G. Wientjes Gastrointestinal and hepatic first-pass elimination of 2′,3′-dideoxyinosine in rats J. Pharmacol. Exp. Ther. 265 1993 731 738 (Pubitemid 23315580)
4. J.B. Brubach, V. Jannin, B. Mahler, C. Bourgaux, P. Lesieur, P. Roy, and M. Ollivon Structural and thermal characterization of glyceryl behenate by X-ray diffraction coupled to differential calorimetry and infrared spectroscopy Int. J. Pharm. 336 2007 248 256 (Pubitemid 46670648)
5. M.C. Carey, D.M. Small, and C.M. Bliss Lipid digestion and absorption Annu. Rev. Physiol. 45 1983 651 677
6. B. Carion-Taravella, S. Lesieur, J. Chopineau, P. Lesieur, and M. Ollivon Phase behavior of mixed aqueous dispersions of dipalmitoylphosphatidylcholine and dodecyl glycosides: a differential scanning calorimetry and X-ray diffraction investigation Langmuir 18 2002 325 335 (Pubitemid 35384141)
7. L.M. Crowe, J.H. Crowe, A. Rudolph, C. Womersley, and L. Appel Preservation of freeze-dried liposomes by trehalose Arch. Biochem. Biophys. 242 1985 240 247 (Pubitemid 16224092)
8. J. das Neves, M.M. Amiji, M.F. Bahia, and B. Sarmento Nanotechnology-based systems for the treatment and prevention of HIV/AIDS Adv. Drug Deliv. Rev. 62 2010 458 477
9. G.C. Ferreira, and J.S. Patton Inhibition of lipolysis by hydrocarbons and fatty alcohols J. Lipid Res. 31 1990 889 897 (Pubitemid 20175015)
10. L. Forte, K. Andrieux, G. Keller, C. Gabielle-Madelmont, S. Lesieur, M. Paternostre, M. Ollivon, C. Bourgaux, and P. Lesieur Sodium taurocholate-induced lamellar-micellar phase transitions of DPPC; determined by DSC and X-ray diffraction recording J. Therm. Anal. 51 1998 773 782
11. C. Gomez-Gaete, N. Tsapis, M. Besnard, A. Bochot, and E. Fattal Encapsulation of dexamethasone into biodegradable polymeric nanoparticles Int. J. Pharm. 331 2007 153 159 (Pubitemid 46216675)
12. C. Grabielle-Madelmont, and R. Perron Calorimetric studies on phospholipid/water systems: I. Dipalmitoylphosphatidylcholine (DPPC)/water system J. Colloid Interface Sci. 95 1983 471 482
13. P.R. Harrigan, T.D. Madden, and P.R. Cullis Protection of liposomes during dehydration or freezing Chem. Phys. Lipids 52 1990 139 149 (Pubitemid 20056132)
14. C. Huang Studies on phosphatidylcholine vesicles. Formation and physical characteristics Biochemistry 8 1969 344 352
15. G. Kärber Beitrag zur kollektiven Behandlung pharmakologischer Reihenversuche Arch. Exp. Path. Pharmak. 162 1931 956 959
16. M. Lalanne, A. Paci, K. Andrieux, N. Dereuddre-Bosquet, P. Clayette, A. Deroussent, M. Re, G. Vassal, P. Couvreur, and D. Desmaele Synthesis and biological evaluation of two glycerolipidic prodrugs of didanosine for direct lymphatic delivery against HIV Bioorg. Med. Chem. Lett. 17 2007 2237 2240 (Pubitemid 46505264)
17. M. Lalanne, H. Khoury, A. Deroussent, P. Couvreur, G. Vassal, A. Paci, and K. Andrieux Metabolism evaluation of biomimetic prodrugs by in vitro models and mass spectrometry Int. J. Pharm. 379 2009 235 243
18. S. Lesieur, C. Grabielle-Madelmont, M. Paternostre, and M. Ollivon Study of size distribution and stability of liposomes by high performance gel exclusion chromatography Chem. Phys. Lipids 64 1993 57 82 (Pubitemid 23290866)
19. K.K. Manouilov, Z.S. Xu, F.D. Boudinot, R.F. Schinazi, and C.K. Chu Lymphatic targeting of anti-HIV nucleosides: distribution of 2%,3%-dideoxyinosine after intravenous and oral administration of dipalmitoylphosphatidyl prodrug in mice Antivir. Res. 34 1997 91 99 (Pubitemid 27220185)
20. E. Mayhew, R. Lazo, W.J. Vail, J. King, and A.M. Green Characterization of liposomes prepared using a microemulsifier Biochim. Biophys. Acta 775 1984 169 174
21. C.M. O'Driscoll Lipid-based formulations for intestinal lymphatic delivery Eur. J. Pharm. Sci. 15 2002 405 415 (Pubitemid 34567104)
22. F. Olson, C.A. Hunt, F.C. Szoka, W.J. Vail, and D. Papahadjopoulos Preparation of liposomes of defined size distribution by extrusion through polycarbonate membranes Biochim. Biophys. Acta 557 1979 9 23 (Pubitemid 10245657)
23. G.F. Ray, W.D. Mason, and M.Z. Badr Pharmacokinetics of the anti-AIDS drug 2′,3′-dideoxyinosine in the rat Drug Metab. Dispos. 18 1990 654 658 (Pubitemid 20348855)
24. L. Saunders, J. Perrin, and D. Gammack Ultrasonic irradiation of some phospholipid sols J. Pharm. Pharmacol. 14 1962 567 572
25. B. Sjostrom, and B. Bergenstahl Preparation of submicron drug particles in lecithin-stabilized o/w emulsions. I. Model studies of the precipitation of cholesteryl acetate Int. J. Pharm. 88 1992 53 62 (Pubitemid 23000408)
26. O. Shaaya, A. Magora, T. Sheskin, N. Kumar, and A.J. Domb Anhydride prodrugs for nonsteroidal anti-inflammatory drugs Pharm. Res. 20 2003 205 211 (Pubitemid 36269727)
27. D. Small The physical chemistry of lipids D.J. Hanahan, Handbook of Lipid Research 4 1986 Plenum Press New York, USA 475 517
28. F. Szoka, and D. Papahadjopoulos Comparative properties and methods of preparation of lipid vesicles (liposomes) Ann. Rev. Biophys. Bioeng. 9 1980 467 508
29. J. Wang, D. Wu, and W.C. Shen Structure-activity relationship of reversibly lipidized peptides: studies of fatty acid-desmopressin conjugates Pharm. Res. 19 2002 609 614 (Pubitemid 34553667)
30. M.B. Yatvin, W. Li, M.J. Meredith, and M.A. Shenoy Improved uptake and retention of lipophilic prodrug to improve treatment of HIV Adv. Drug Deliv. Rev. 39 1999 165 182 (Pubitemid 29430235)