Synthesis and transfection properties of a series of lipidic neamine derivatives

Bioconjugate Chemistry

Volumn 20, Issue 11, 2009, Pages 2032-2046

  Le Gall, Tony ^a   Baussanne, Isabelle ^b   Halder, Somnath ^b   Carmoy, Nathalie ^a   Montier, Tristan ^a   Lehn, Pierre ^a   Décout, Jean Luc ^b  

^a UNIVERSITÉ DE BRETAGNE OCCIDENTALE   (France)

^b UNIV GRENOBLE ALPES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTICS; CELL CULTURE; GENES; MAMMALS; MOLECULAR BIOLOGY;

AMINOGLYCOSIDES; BUILDING BLOCKES; CATIONIC LIPIDS; GENE DELIVERY; HEAD GROUPS; LIPOPHILICITY; NATURAL ANTIBIOTICS; NONVIRAL VECTORS; PROPERTY; SYNTHESISED;

GENE TRANSFER;

ALKYL GROUP; AMINOGLYCOSIDE ANTIBIOTIC AGENT; FRAMYCETIN; LIPID; NEAMINE; PLASMID DNA;

ALKYLATION; ANIMAL EXPERIMENT; ARTICLE; CHEMICAL REACTION; COMPLEX FORMATION; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; FEMALE; GENETIC TRANSFECTION; HUMAN; HUMAN TISSUE; LIPOPHILICITY; MOUSE; NONHUMAN; NONVIRAL GENE DELIVERY SYSTEM; PARTICLE SIZE; PROTON TRANSPORT; REPORTER GENE; STRUCTURE ACTIVITY RELATION;

MAMMALIA;

EID: 71249123144     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc900062z     Document Type: Article

References (34)

1. Magnet, S., and Blanchard, J. S. (2005) Molecular insights into aminoglycoside action and resistance. Chem. Rev. 105, 477-498.
2. Mei, H. Y., Galan, A. A., Halim, N. S., Mack, D. P., Moreland, D. W., Sanders, K. B., Truong, H. N., and Czarnik, A. W. (1995) Inhibition of an HIV-1 Tat-derived peptide binding to TAR RNA by aminoglycoside antibiotics. Bioorg. Med. Chem. Lett. 5, 2755-2760.
3. Ennifar, E., Paillart, J. C., Marquet, R., Ehresmann, B., Ehresmann, C., Dumas, P., and Walter, P. (2003) HIV-1 RNA dimerization initiation site is structurally similar to the ribosomal A site and binds aminoglycoside antibiotics. J. Biol. Chem. 278, 2723-2730. (Pubitemid 36801353)
4. Wilschanski, M., Yahav, Y., Yaacov, Y., Blau, H., Bentur, L., Rivlin, J., Aviram, M., Bdolah-Abram, T., Bebok, Z., Shushi, L., Kerem, B., and Kerem, E. (2003) Gentamicin-induced correction of CFTR function in patients with cystic fibrosis and CFTR stop mutations. N. Engl. J. Med. 349, 1433-1441. (Pubitemid 37211058)
5. Bedwell, D. M., Kaenjak, A., Benos, D. J., Bebok, Z., Bubien, J. K., Hong, J., Tousson, A., Clancy, J. P., and Sorscher, E. J. (1997) Suppression of a CFTR premature stop mutation in a bronchial epithelial cell line. Nat. Med. 3, 1280-1284.
6. Stephenson, J. (2001) Antibiotics show promise as therapy for genetic disorders. JAMA 285, 2067-2068.
7. Luft, F. C. (2002) Gentamicin as gene therapy. J. Mol. Med. 80, 543-544.
8. Aissaoui, A., Oudrhiri, N., Petit, L., Hauchecorne, M., Kan, E., Sainlos, M., Julia, S., Navarro, J., Vigneron, J. P., Lehn, J. M., and Lehn, P. (2002) Progress in gene delivery by cationic lipids: guanidinium-cholesterol-based systems as an example. Curr. Drug Targets 3, 1-16. (Pubitemid 34296301)
9. Belmont, P., Aissaoui, A., Hauchecorne, M., Oudrhiri, N., Petit, L., Vigneron, J. P., Lehn, J. M., and Lehn, P. (2002) Aminoglycoside- derived cationic lipids as efficient vectors for gene transfection in vitro and in vivo. J. Gene Med. 4, 517-526. (Pubitemid 40268378)
10. Sainlos, M., Belmont, P., Vigneron, J. P., Lehn, P., and Lehn, J. M. (2003) Aminoglycoside-derived cationic lipids for gene transfection: synthesis of kanamycin A derivatives. Eur. J. Org. Chem. 2764-2774.
11. Martin, B., Sainlos, M., Aissaoui, A., Oudrhiri, N., Hauchecorne, M., Vigneron, J. P., Lehn, J. M., and Lehn, P. (2005) The design of cationic lipids for gene delivery. Curr. Pharm. Des. 11, 375-394. (Pubitemid 40277864)
12. Sainlos, M., Hauchecorne, M., Oudrhiri, N., Zertal-Zidani, S., Aissaoui, A., Vigneron, J. P., Lehn, J. M., and Lehn, P. (2005) Kanamycin A-derived cationic lipids as vectors for gene transfection. ChemBioChem 6, 1023-1033. (Pubitemid 40825343)
13. Desigaux, L., Sainlos, M., Lambert, O., Chèvre, R., Letrou- Bonneval, E., Vigneron, J. P., Lehn, P., Lehn, J. M., and Pitard, B. (2007) Self-assembled lamellar complexes of siRNA with lipidic aminoglycoside derivatives promote efficient siRNA delivery and interference. Proc. Natl. Acad. Sci. U.S.A. 104, 16534-16539.
14. Gao, X., and Huang, L. (1995) Cationic liposome-mediated gene transfer. Gene Ther. 2, 710-722.
15. Horobin, R. W., and Weissig, V. (2005) A QSAR-modeling perspective on cationic transfection lipids. 1. Predicting efficiency and understanding mechanisms. J. Gene Med. 7, 1023-1034.
16. Gruneich, J. A., and Diamond, S. L. (2007) Synthesis and structure-activity relationships of a series of increasingly hydrophobic cationic steroid lipofection reagents. J. Gene Med. 9, 381-391.
17. Riguet, E., Désiré, J., Bailly, C., and Décout, J. L. (2004) A route for preparing new neamine derivatives targeting HIV-1 TAR RNA. Tetrahedron 60, 8053-8064. (Pubitemid 39094322)
18. Riguet, E., Tripathi, S., Chaubey, B., Désiré, J., Pandey, V. N., and Décout, J. L. (2004) A peptide nucleic acid-neamine conjugate that targets and cleaves HIV-1 TAR RNA inhibits viral replication. J. Med. Chem. 47, 4806-4809. (Pubitemid 39238253)
19. Chaubey, B., Tripathi, S., Désiré, J., Baussanne, I., Décout, J. L., and Pandey, V. N. (2007) Mechanism of RNA cleavage catalyzed by sequence specific polyamide nucleic acid-neamine conjugate. Oligonucleotides 17, 302-313. (Pubitemid 47463362)
20. Viswanadhan, V. N., Ghose, A. K., Revankar, G. R., and Robins, R. K. (1989) Atomic physicochemical parameters for three dimensional structure directed quantitative structure-activity relationships. 4. Additional parameters for hydrophobic and dispersive interactions and their application for an automated superposition of certain naturally occurring nucleoside antibiotics. J. Chem. Inf. Comput. Sci. 29, 163-172.
21. Cozens, A. L., Yezzi, M. J., Kunzelmann, K., Ohrui, T., Chin, L., Eng, K., Finkbeiner, W. E., Widdicombe, J. H., and Gruenert, D. C. (1994) CFTR expression and chloride secretion in polarized immortal human bronchial epithelial cells. Am. J. Respir. Cell Mol. Biol. 10, 38-47.
22. Ruponen, M., Yla-Herttuala, S., and Urtti, A. (1999) Interactions of polymeric and liposomal gene delivery systems with extracellular glycosaminoglycans: physicochemical and transfection studies. Biochim. Biophys. Acta 1415, 331-341. (Pubitemid 29065298)
23. Felgner, P. L., Gadek, T. R., Holm, M., Roman, R., Chan, H. W., Wenz, M., Northrop, J. P., Ringold, G. M., and Danielsen, M. (1987) Lipofection: a highly efficient, lipid-mediated DNA-transfection procedure. Proc. Natl. Acad. Sci. U.S.A. 84, 7413-7417.
24. Blaauw, M., Linskens, M. H., and van Haastert, P. J. (2000) Efficient control of gene expression by a tetracycline-dependent transactivator in single Dictyostelium discoideum cells. Gene 252, 71-82. (Pubitemid 30618814)
25. Delépine, P., Guillaume, C., Floch, V., Loisel, S., Yaouanc, J., Clément, J., Des Abbayes, H., and Férec, C. (2000) Cationic phosphonolipids as nonviral vectors: in vitro and in vivo applications. J. Pharm. Sci. 89, 629-638.
26. Picquet, E., Le Ny, K., Delépine, P., Montier, T., Yaouanc, J. J., Cartier, D., des Abbayes, H., Férec, C., and Clément, J. C. (2005) Cationic lipophosphoramidates and lipophosphoguanidines are very efficient for in vivo DNA delivery. Bioconjugate Chem. 16, 1051-1053.
27. Vigneron, J. P., Oudrhiri, N., Fauquet, M., Vergely, L., Bradley, J. C., Basseville, M., Lehn, P., and Lehn, J. M. (1996) Guanidinium-cholesterol cationic lipids: efficient vectors for the transfection of eukaryotic cells. Proc. Natl. Acad. Sci. U.S.A. 93, 9682-9686. (Pubitemid 26296669)
28. Koynova, R., Tarahovsky, Y. S., Wang, L., and MacDonald, R. C. (2007) Lipoplex formulation of superior efficacy exhibits high surface activity and fusogenicity, and readily releases DNA. Biochim. Biophys. Acta 1768, 375-386. (Pubitemid 46136190)
29. Koynova, R., Wang, L., and MacDonald, R. C. (2007) Synergy in lipofection by cationic lipid mixtures: superior activity at the gel-liquid crystalline phase transition. J. Phys. Chem. B 111, 7786-7795. (Pubitemid 47169690)
30. Dodds, E., Dunckley, M. G., Naujoks, K., Michaelis, U., and Dickson, G. (1998) Lipofection of cultured mouse muscle cells: a direct comparison of Lipofectamine and DOSPER. Gene Ther. 5, 542-551. (Pubitemid 28200648)
31. Ghosh, Y. K., Visweswariah, S. S., and Bhattacharya, S. (2000) Nature of linkage between the cationic headgroup and cholesteryl skeleton controls gene transfection efficiency. FEBS Lett. 473, 341-344.
32. Faneca, H., Simoes, S., and de Lima, M. C. (2002) Evaluation of lipid-based reagents to mediate intracellular gene delivery. Biochim. Biophys. Acta 1567, 23-33. (Pubitemid 35454043)
33. Lampela, P., Raisanen, J., Mannisto, P. T., Yla-Herttuala, S., and Raasmaja, A. (2002) The use of low-molecular-weight PEIs as gene carriers in the monkey fibroblastoma and rabbit smooth muscle cell cultures. J. Gene Med. 4, 205-214. (Pubitemid 40277170)
34. Lampela, P., Soininen, P., Urtti, A., Mannisto, P. T., and Raasmaja, A. (2004) Synergism in gene delivery by small PEIs and three different nonviral vectors. Int. J. Pharm. 270, 175-184. (Pubitemid 38077098)