Cationic nucleoside lipids derived from universal bases: A rational approach for siRNA transfection

Bioconjugate Chemistry

Volumn 21, Issue 6, 2010, Pages 1062-1069

  Ceballos, Claire ^a   Khiati, Salim ^b   Prata, Carla A H ^c   Zhang, Xiao Xiang ^c   Giorgio, Suzanne ^a   Marsal, Philippe ^a   Grinstaff, Mark W ^c   Barthélémy, Philippe ^b   Camplo, Michel ^a  

^a AIX MARSEILLE UNIVERSITÉ   (France)

^b UNIVERSITÉ DE BORDEAUX   (France)

^c BOSTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; CHEMICAL ANALYSIS; ELECTROPHORESIS; LIPIDS; SOLUTIONS; STEREOSELECTIVITY;

5-NITROINDOLE; AMPHIPHILIC MOLECULES; BINDING AFFINITIES; CATIONICS; D RIBOSE; D-RIBOSE; ETHIDIUM BROMIDE; NITROIMIDAZOLES; SELF-ASSEMBLE; SUPRAMOLECULAR ORGANIZATIONS;

BIOMOLECULES;

2',3' DIOLEYL 5' O (ALPHA,BETA) DEXTRO RIBOFURANOSYL 5 NITROINDOLE; 2',3' DIOLEYL 5' O ALPHA DEXTRO RIBOFURANOSYL 4 NITROIMIDAZOLE; NUCLEOSIDE DERIVATIVE; SMALL INTERFERING RNA; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG SYNTHESIS; GENETIC TRANSFECTION; MOLECULAR MODEL; NONHUMAN; PHYSICOCHEMICAL MODEL; STEREOCHEMISTRY;

EID: 77953630514     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc100005k     Document Type: Article

References (18)

1. Chabaud, P., Camplo, M., Payet, D., Serin, G., Moreau, L., Barthélémy, P., and Grinstaff, M. (2006) Cationic nucleoside lipids derived for gene delivery Bioconjugate Chem. 17, 466-472
2. Gissot, A., Camplo, M., Grinstaff, M. W., and Barthélémy, P. (2008) Nucleoside based amphiphiles: A Successful Marriage of nucleic acids with lipids Org. Biomol. Chem. Rev. 6, 1324-1333
3. Moreau, L., Camplo, M., Wathier, M., Taib, N., Laguerre, M., Bestel, I., Grinstaff, M. W., and Barthélémy, P. (2008) Real time imaging of supramolecular assembly formation via programmed nucleolipid recognition J. Am. Chem. Soc. 130, 14454-14455
4. Barthélémy, P. (2009) Nucleoside-based lipids at work: From supramolecular assemblies to biological applications C. R. Chim. 12, 171-179
5. Ceballos, C., Prata, C. H., Giorgio, S., Payet, D., Barthé lémy, P., Grinstaff, M. W., and Camplo, M. (2009) Cationic nucleoside lipids possessing a 3-nitropyrrole universal base for siRNA delivery Bioconjugate Chem. 20, 193-196
6. Loakes, D. (2001) The applications of universal DNA base analogues Nucleic Acids Res. 29, 2437-2447
7. Loakes, D., Hill, F., Brown, D. M., and Salisbury, S. A. (1997) Stability and structure of DNA oligonucleotides containing non-specific base analogues J. Mol. Biol. 270, 426-435
8. Lee, C. T., Wang, W. T., and Parr, R. G. (1988) Development of the the colle-salvettu correlation-energy formula into a functional of the electron density Phys. Rev. B 37, 785-789
9. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Montgomery, Jr., J. A., Vreven, T., Kudin, K. N., Burant, J. C., Millam, J. M., Iyengar, S. S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G. A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J. E., Hratchian, H. P., Cross, J. B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Ayala, P. Y., Morokuma, K., Voth, G. A., Salvador, P., Dannenberg, J. J., Zakrzewski, V. G., Dapprich, S., Daniels, A. D., Strain, M. C., Farkas, O., Malick, D. K., Rabuck, A. D., Raghavachari, K., Foresman, J. B., Ortiz, J. V., Cui, Q., Baboul, A. G., Clifford, S., Cioslowski, J., Stefanov, B. B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R. L., Fox, D. J., Keith, T., Al-Laham, M. A., Peng, C. Y., Nanayakkara, A., Challacombe, M., Gill, P. M. W., Johnson, B., Chen, W., Wong, M. W., Gonzalez, C., and Pople, J. A. (2004) Gaussian 03, rev C.02, Gaussian, Inc., Wallingford, CT.
10. Cossi, M., Scalmani, G., Rega, N., and Barone, V. (2002) New developments in the polarizable continuum model for quantum mechanical and classical calculations on molecules in solution J. Chem. Phys. 117, 43-54
11. Stewart, A. O. and Williams, R. M. (1985) C-glycosidation of pyridyl thioglycosides J. Am. Chem. Soc. 107, 4289-4296
12. Harusawa, S., Imazu, T., Takashima, S., Araki, L., Ohishi, H., Kurihara, T., Sakamoto, Y., Yamamoto, Y., and Yamatodani, A. J. (1999) Synthesis of 4(5)-[5-(aminomethyl)tetrahydrofuran-2-yl- or 5-(aminomethyl)-2,5-dihydrofuran- 2-yl]imidazoles by efficient use of a PHSe group: Application to novel histamine H3-ligands J. Org. Chem. 64, 8608-8615
13. Imbach, J. L., Barascut, J. L., Kam, B. L., Rayner, B., Tamby, C., and Tapiero, C. (1973) Synthesis of nucleosides. III. New criterion determination of the anomer configuration of ribosidic nucleosides J. Heterocycl. Chem. 10 (6) 1069-70
14. Bakthavachalam, V., Lin, L. G., Cherian, X. M., and Czarnik, A. W. (1987) Synthesis, stereochemistry, intramolecular cyclization, and rates of hydrolysis of adenosine 2′,3′-acetals Carbohydr. Res. 170, 124-135
15. Clark, V. M., Todd, A. R., and Zussman, J. (1951) Nucleotides. Part VIII cycloNucleoside salts. A novel rearrangement of some toluene-p- sulphonylnucleosides J. Chem. Soc. 2952-2958
16. Geall, A. J. and Blasgbrough, I. S. (2000) Rapid and sensitive ethidium bromide fluorescence quenching assay of polyamine conjugate-DNA interactions for the analysis of lipoplex formation in gene therapy J. Pharm. Biomed. Anal. 22, 849-859
17. Karmali, P. P. and Chaudhuri, A. (2006) Cationic liposomes as non-viral carriers of gene medicines: resolved issues, open questions, and future promises Med. Chem. Res. 27 (5) 696-722
18. Alberle, A. M., Bennet, M. J., Malone, R. W., and Nantz, M. H. (1996) The counterion influence of cationic lipid-mediated transfection of plasmid DNA Biochim. Biophys. Acta 1299, 281-283