Multivalent catanionic GalCer analogs derived from first generation dendrimeric phosphonic acids

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 1, 2010, Pages 242-248

  Pérez Anes, Alexandra ^a,b,c   Stefaniu, Cristina ^c   Moog, Christine ^d   Majoral, Jean Pierre ^a,b   Blanzat, Muriel ^c   Turrin, Cédric Olivier ^a,b   Caminade, Anne Marie ^a,b   Rico Lattes, Isabelle ^c  

^a CNRS   (France)

^b UNIVERSITÉ DE TOULOUSE   (France)

^c Université Paul Sabatier   (France)

^d INSERM   (France)

Author keywords

Dendrimer; Galactosylceramide; Galcer

Indexed keywords

DENDRIMER; GALCER DERIVATIVE; HUMAN IMMUNODEFICIENCY VIRUS ANTIBODY; LACTITOL; N HEXADECYLAMINO LACTITOL DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; STOICHIOMETRY;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 72149119234     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.10.058     Document Type: Article

References (46)

1. Buhleier E., Wehner F., and Vögtle F. Synthesis 78 (1978) 155
2. Rolland O., Turrin C.-O., Caminade A.-M., and Majoral J.-P. New J. Chem. 33 (2009) 1809
3. Patri A.K., Kukowska-Latallo J.F., and Baker J.R. Adv. Drug Delivery Rev. 57 (2005) 2203
4. Blanzat M., Turrin C.O., Aubertin A.M., Couturier-Vidal C., Caminade A.M., Majoral J.P., Rico-Lattes I., and Lattes A. ChemBioChem 6 (2005) 2207
5. Najlah M., and D'Emanuele A. Curr. Opin. Drug Discovery Dev. 10 (2007) 756
6. Myc A., Douce T.B., Ahuja N., Kotlyar A., Kukowska-Latallo J., Thomas T.P., and Baker J.R. Anti-Cancer Drugs 19 (2008) 143
7. Rosa Borges A., and Schengrund C.L. Curr. Drug Targets Infect. Disord. 5 (2005) 247
8. Mammen M., Choi S.K., and Whitesides G.M. Angew. Chem., Int. Ed. 37 (1998) 2754-2794
9. Kitov P.I., and Bundle D.R. J. Am. Chem. Soc. 125 (2003) 16271
10. Dutta T., Garg M., and Jain N.K. Eur. J. Pharm. Sci. 34 (2008) 181
11. Dutta T., and Jain N.K. Biochim. Biophys. Acta, Gen. Subj. 1770 (2007) 681
12. Weber N., Ortega P., Clemente M.I., Shcharbin D., Bryszewska M., de la Mata F.J., Gomez R., and Munoz-Fernandez M.A. J. Controlled Release 132 (2008) 55
13. Berger E.A., Murphy P.M., and Farber J.M. Annu. Rev. Immunol. 17 (1999) 657
14. Kensinger R.D., Catalone B.J., Krebs F.C., Wigdahl B., and Schengrund C.L. Antimicrob. Agents Chemother. 48 (2004) 1614
15. Kensinger R.D., Yowler B.C., Benesi A.J., and Schengrund C.L. Bioconjugate Chem. 15 (2004) 349
16. Wang S.K., Liang P.H., Astronomo R.D., Hsu T.L., Hsieh S.L., Burton D.R., and Wong C.H. Proc. Natl. Acad. Sci. U.S.A. 105 (2008) 3690
17. Yahi N., Sabatier J.-M., Nickel P., Mabrouk K., Gonzalez-Scarano F., and Fantini J. J. Biol. Chem. 269 (1994) 24349
18. Alfsen A., and Bomsel M. J. Biol. Chem. 277 (2002) 25649
19. Faroux-Corlay B., Greiner J., Terreux R., Cabrol-Bass D., Aubertin A.M., Vierling P., and Fantini J. J. Med. Chem. 44 (2001) 2188
20. Rico-Lattes I., Blanzat M., Franceschi-Messant S., Perez E., and Lattes A. C.R. Chimie 8 (2005) 807
21. Rico-Lattes I., Garrigues J.C., Perez E., André-Barrès C., Madelaine-Dupuich C., Lattes A., Linas M.D., and Aubertin A.M. New J. Chem. 19 (1995) 341
22. Moulard M., Lortat-Jacob H., Mondor I., Roca G., Wyatt R., Sodroski J., Zhao L., Olson W., Kwong P.D., and Sattentau Q.J. J. Virol. 74 (2000) 1948
23. McCarthy T.D., Karellas P., Henderson S.A., Giannis M., O'Keefe D.F., Heery G., Paull J.R.A., Matthews B.R., and Holan G. Mol. Pharm. 2 (2005) 312
24. Weber J., Desai K., and Darbyshire J. Plos Med. 2 (2005) 392
25. McCarthy T., Karellas P., Henderson S., Giannis M., O'Keefe D., Matthews B., Braggs B., Paull J., Heery G., Krippner G., and Holan G. Antiviral Res. 62 (2004) A44
26. Blanzat M., Turrin C.O., Perez E., Rico-Lattes I., Caminade A.M., and Majoral J.P. Chem. Commun. (2002) 1864
27. Iampietro D.J., and Kaler E.W. Langmuir 15 (1999) 8590
28. Consola S., Blanzat M., Perez E., Garrigues J.C., Bordat P., and Rico-Lattes I. Chem. Eur. J. 13 (2007) 3039
29. Pasc-Banu A., Stan R., Blanzat M., Perez E., Rico-Lattes I., Lattes A., Labrot T., and Oda R. Colloids Surf., A 242 (2004) 195
30. Soussan E., Mille C., Blanzat M., Bordat P., and Rico-Lattes I. Langmuir 24 (2008) 2326
31. Caminade A.M., Maraval V., Laurent R., Turrin C.O., Sutra P., Leclaire J., Griffe L., Marchand P., Baudoin-Dehoux C., Rebout C., and Majoral J.P. C.R. Chimie 6 (2003) 791
32. Poupot M., Griffe L., Marchand P., Maraval A., Rolland O., Martinet L., L'Faqihi-Olive F.E., Turrin C.O., Caminade A.M., Fournié J.J., Majoral J.P., and Poupot R. FASEB J. 20 (2006) 2339
33. Marchand P., Griffe L., Poupot M., Turrin C.-O., Bacquet G., Fournié J.-J., Majoral J.-P., Poupot R., and Caminade A.-M. Bioorg. Med. Chem. Lett. 19 (2009) 3963
34. Blais J.C., Turrin C.O., Caminade A.M., and Majoral J.P. Anal. Chem. 72 (2000) 5097
35. Pérez-Anes A., Spataro G., Coppel Y., Blanzat M., Turrin C.-O., Moog C., Caminade A.-M., Rico-Lattes I., and Majoral J.-P. Org. Biomol. Chem. 7 (2009) 3491
36. Moog C., Wick A., Ber P.L., Kirn A., and Aubertin A.-M. Antiviral Res. 24 (1994) 275
37. Pauwels R., Balzarini J., Baba M., Snoeck R., Schols D., Herdewijn P., Desmyter J., and Clercq E.D. J. Virol. Methods 20 (1988) 309
38. Peytou V., Condom R., Patino N., Guedj R., Aubertin A.-M., Gelus N., Bailly C., Terreux R., and Cabrol-Bass D. J. Med. Chem. 42 (1999) 4042
39. Fletcher P.S., Wallace G.S., Mesquita P.M.M., and Shattock R.J. Retrovirology 3 (2006) 46
40. Macri R.V., Karlovská J., Doncel G.F., Du X., Maisuria B.B., Williams A.A., Sugandhi E.W., Falkinham III J.O., Esker A.R., and Gandour R.D. Bioorg. Med. Chem. 17 (2009) 3162
41. Fichorova R.N., Tucker L.D., and Anderson D.J. J. Infect. Dis. 184 (2001) 418
42. Rolland O., Griffe L., Poupot M., Maraval A., Ouali A., Coppel Y., Fournié J.J., Bacquet G., Turrin C.O., Caminade A.M., Majoral J.P., and Poupot R. Chem. Eur. J. 14 (2008) 4836
43. Perrin D.D., and Armarego W.L.F. Purification of Laboratory Chemicals. 3rd ed. (1988), Pergamon Press, Oxford
44. Launay N., Caminade A.M., Lahana R., and Majoral J.P. Angew. Chem., Int. Ed. Engl. 33 (1994) 1589
45. Launay N., Caminade A.M., and Majoral J.P. J. Organomet. Chem. 529 (1997) 51
46. Vivares D., Soussan E., Blanzat M., and Rico-Lattes I. Langmuir 24 (2008) 9260