Biotinylated cyclen-contained cationic lipids as non-viral gene delivery vectors

Chemical Biology and Drug Design

Volumn 82, Issue 4, 2013, Pages 376-383

  Liu, Qiang ^a   Yi, Wen Jing ^a,b   Zhang, Yi Mei ^a   Zhang, Ji ^a   Guo, Liandi ^b   Yu, Xiao Qi ^a  

^a Sichuan University   (China)

^b SICHUAN UNIVERSITY   (China)

Author keywords

Biotin; Cationic lipid; Cyclen; Gene delivery; Non viral vector

Indexed keywords

1,4,7,10 TETRAAZACYCLODODECANE; ALPHA TOCOPHEROL; BIOTIN; CARBAMIC ACID; CHOLESTEROL; CYCLODECANE DERIVATIVE; DIOLEOYLPHOSPHATIDYLETHANOLAMINE; DIOSGENIN; ETHIDIUM BROMIDE; LIPID; LIPOFECTAMINE; LIPOPLEX; NANOPARTICLE; PLASMID DNA; UNCLASSIFIED DRUG;

ARTICLE; BIOTINYLATION; CELL STRAIN HEK293; CELL VIABILITY; CONTROLLED STUDY; CYTOTOXICITY; DNA BINDING; GENE VECTOR; GENETIC TRANSFECTION; HUMAN; HUMAN CELL; IN VITRO GENE TRANSFER; NONVIRAL GENE DELIVERY SYSTEM; PARTICLE SIZE; PRIORITY JOURNAL; ZETA POTENTIAL;

BIOTIN; CATIONIC LIPID; CYCLEN; GENE DELIVERY; NON-VIRAL VECTOR;

BIOTIN; CATIONS; CELL LINE, TUMOR; GENETIC VECTORS; HETEROCYCLIC COMPOUNDS; HUMANS; LIPIDS; MAGNETIC RESONANCE SPECTROSCOPY; PLASMIDS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 84884817740     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/cbdd.12159     Document Type: Article

References (25)

1. Mintzer M.A., Simanek E.E. (2009) Nonviral vectors for gene delivery. Chem Rev;109:259-302.
2. Guo X., Huang L. (2012) Recent advances in nonviral vectors for gene delivery. Acc Chem Res;45:971-979.
3. Bhattacharya S., Bajaj A. (2009) Advances in gene delivery through molecular design of cationic lipids. Chem Commun;45:4632-4656.
4. Zhi D., Zhang S., Wang B., Zhao Y., Yang B., Yu S. (2010) Transfection efficiency of cationic lipids with different hydrophobic domains in gene delivery. Bioconjug Chem;21:563-577.
5. Huang Q.D., Ren J., Ou W.J., Fu Y., Cai M.Q., Zhang J., Zhu W., Yu X.Q. (2012) Cationic lipids containing cyclen and ammonium moieties as gene delivery vectors. Chem Biol Drug Des;79:879-887.
6. Radchatawedchakoon W., Krajarng A., Niyomtham N., Watanapokasin R., Yingyongnarongkul B.E. (2011) High transfection efficiency of cationic lipids with asymmetric acyl-cholesteryl hydrophobic tails. Chem Eur J;17:3287-3295.
7. Mukthavara R., Joyeeta S., Marepally S., Koushik M., Bojja S., Arabinda C. (2007) Dramatic influence of the orientation of linker between hydrophilic and hydrophobic lipid moiety in liposomal gene delivery. J Am Chem Soc;129:11408-11420.
8. Izalt R.M., Pawlak K., Bradshaw J.S. (1991) Thermodynamic and kinetic data for macrocycle interaction with cations and anions. Chem Rev;91:1721-2085.
9. Liu J.L., Ma Q.P., Huang Q.D., Yang W.H., Zhang J., Wang J.Y., Zhu W., Yu X.Q. (2011) Cationic lipids containing protonated cyclen and different hydrophobic groups linked by uracil-PNA monomer: synthesis and application for gene delivery. Eur J Med Chem;46:4133-4141.
10. Huang Q.D., Ou W.J., Chen H., Feng Z.H., Wang J.Y., Zhang J., Zhu W., Yu X.Q. (2011) Novel cationic lipids possessing protonated cyclen and imidazolium salt for gene delivery. Eur J Pharm Biopharm;78:326-335.
11. Huang Q.D., Ren J., Chen H., Ou W.J., Zhang J., Fu Y., Zhu W., Yu X.Q. (2012) Cyclen-based cationic lipids containing carbamate linkages as efficient gene delivery vectors with low toxicity. Chempluschem;77:584-591.
12. Huang Q.D., Zhong G.X., Zhang Y., Ren J., Fu Y., Zhang J., Zhu W., Yu X.-Q. (2011) Cyclen-based cationic lipids for highly efficient gene delivery towards tumor cells. PLoS ONE;6:e23134.
13. Sakahara H., Saga T. (1999) Avidin-biotin system for delivery of diagnostic agents. Adv Drug Deliv Rev;37:89-101.
14. Zhang Q., Chen S., Zhuo R.X., Zhang X.Z., Cheng S.X. (2010) Self-assembled terplexes for targeted gene delivery with improved transfection. Bioconjug Chem;21:2086-2092.
15. Medvedeva D.A., Maslov M.A., Serikov R.N., Morozova N.G., Serebrenikova G.A., Sheglov D.V., Latyshev A.V., Vlassov V.V., Zenkova M.A. (2009) Novel cholesterol-based cationic lipids for gene delivery. J Med Chem;52:6558-6568.
16. Zhi D.F., Zhang S.B., Qureshi F., Zhao Y.N., Cui S.H., Wang B., Chen H.Y., Wang Y.H., Zhao D.F. (2012) Synthesis and biological activity of carbamate-linked cationic lipids for gene delivery in vitro. Bioorg Med Chem Lett;22:3837-3841.
17. Islam R.U., Hean J., van Otterlo W.A., de Koning C.B., Arbuthnot P. (2009) Efficient nucleic acid transduction with lipoplexes containing novel piperazine and polyamine-conjugated cholesterol derivatives. Bioorg Med Chem Lett;19:100-103.
18. Koynova R., Wang L., MacDonald R.C. (2006) An intracellular lamellar-nonlamellar phase transition rationalizes the superior performance of some cationic lipid transfection agents. PNAS;103:14373-14378.
19. Metwally A.A., Reelfs O., Pourzand C., Blagbrough I.S. (2012) Efficient silencing of EGFP reporter gene with siRNA delivered by asymmetrical N4, N9-diacyl spermines. Mol Pharm;9:1862-1876.
20. Blagbrough I.S., Metwally A.A., Ghonaim H.M. (2012) Asymmetrical N4, N9-diacyl spermines: SAR studies of nonviral lipopolyamine vectors for efficient siRNA delivery with silencing of EGFP reporter gene. Mol Pharm;9:1853-1861.
21. Breipohl G., Will D.W., Peyman A., Uhlmann E. (1997) Novel synthetic routes to PNA monomers and PNA-DNA linker molecules. Tetrahedron;53:14671-14686.
22. Jeon J.W., Son S.J., Yoo C.E., Hong I.S., Song J.B., Suh J.H. (2002) Protein-cleaving catalyst selective for protein substrate. Org Lett;4:4155-4158.
23. Sheng R.L., Luo T., Zhu Y.D., Li H., Sun J.J., Chen S.D., Sun W.Y., Cao A.M. (2011) The intracellular plasmid DNA localization of cationic reducible cholesterol-disulfide lipids. Biomaterials;32:3507-3519.
24. Kedika B., Patri S.V. (2011) Design, synthesis, and in vitro transfection biology of novel tocopherol based monocationic lipids: a structure-activity investigation. J Med Chem;54:548-561.
25. Kedika B., Patri S.V. (2012) Synthesis and gene transfer activities of novel serum compatible reducible tocopherol-based cationic lipids. Mol Pharm;9:1146-1162.