Novel 1,2,3-triazolium-based dicationic amphiphiles synthesized using click-chemistry approach for efficient plasmid delivery.

作者: Mallikarjun Gosangi , Hithavani Rapaka , Thasneem Yoosuf Mujahid , Srilakshmi V. Patri

DOI: 10.1039/C6MD00699J

关键词:

摘要: Herein, we report the synthesis, characterization and evaluation of transfection efficiencies a series dicationic amphiphiles designed to construct quaternary ammonium ion-based cationic lipids varying in chain length hydrophobic back bone connected individually through head group 1,2,3-triazolium cation consisting 2-hydroxy ethyl as substitution. Accordingly, three were synthesized by “click chemistry” approach formulated bilayered vesicles using DOPE co-lipid. The efficacies these novel lipid formulations measured correlated with results obtained from various physicochemical techniques. Importantly, observed gradient activity profile, where potential increased decreasing bone, highlights synergistic interplay alkyl coordination charge delocalization modulating potency 1,2,3-triazolium-based lipids.

参考文章(43)
Antonino Lauria, Riccardo Delisi, Francesco Mingoia, Alessio Terenzi, Annamaria Martorana, Giampaolo Barone, Anna Maria Almerico, 1,2,3‐Triazole in Heterocyclic Compounds, Endowed with Biological Activity, through 1,3‐Dipolar Cycloadditions European Journal of Organic Chemistry. ,vol. 2014, pp. 3289- 3306 ,(2014) , 10.1002/EJOC.201301695
Li-Ting Zheng, Wen-Jing Yi, Rong-Chuan Su, Qiang Liu, Zhi-Gang Zhao, Reducible Amino Acid Based Cationic Lipids as Highly Efficient and Serum-Tolerant Gene Vectors ChemPlusChem. ,vol. 81, pp. 125- 134 ,(2016) , 10.1002/CPLU.201500307
Ramishetti Srinivas, Sanjoy Samanta, Arabinda Chaudhuri, Cationic amphiphiles: promising carriers of genetic materials in gene therapy Chemical Society Reviews. ,vol. 38, pp. 3326- 3338 ,(2009) , 10.1039/B813869A
Christian W. Tornøe, Caspar Christensen, Morten Meldal, Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. Journal of Organic Chemistry. ,vol. 67, pp. 3057- 3064 ,(2002) , 10.1021/JO011148J
P. L. Felgner, T. R. Gadek, M. Holm, R. Roman, H. W. Chan, M. Wenz, J. P. Northrop, G. M. Ringold, M. Danielsen, Lipofection: a highly efficient, lipid-mediated DNA-transfection procedure Proceedings of the National Academy of Sciences of the United States of America. ,vol. 84, pp. 7413- 7417 ,(1987) , 10.1073/PNAS.84.21.7413
Koushik Mukherjee, Jayanta Bhattacharyya, Joyeeta Sen, Ramakrishna Sistla, Arabinda Chaudhuri, Covalent Grafting of Common Trihydroxymethylaminomethane in the Headgroup Region Imparts High Serum Compatibility and Mouse Lung Transfection Property to Cationic Amphiphile Journal of Medicinal Chemistry. ,vol. 51, pp. 1967- 1971 ,(2008) , 10.1021/JM070879U
DeFu Zhi, ShuBiao Zhang, Bing Wang, YiNan Zhao, BaoLing Yang, ShiJun Yu, Transfection efficiency of cationic lipids with different hydrophobic domains in gene delivery. Bioconjugate Chemistry. ,vol. 21, pp. 563- 577 ,(2010) , 10.1021/BC900393R
Bhavani Kedika, Srilakshmi V. Patri, Benzothiazole head group based cationic lipids: synthesis and application for gene delivery. European Journal of Medicinal Chemistry. ,vol. 74, pp. 703- 716 ,(2014) , 10.1016/J.EJMECH.2013.08.034
Santanu Bhattacharya, Avinash Bajaj, Advances in gene delivery through molecular design of cationic lipids Chemical Communications. pp. 4632- 4656 ,(2009) , 10.1039/B900666B