Synthesis and Characterization of Novel Amphiphilic N-Benzyl 1,4-Dihydropyridine Derivatives–Evaluation of Lipid Monolayer and Self-Assembling Properties
Materials 2023
Anna Krapivina, Davis Lacis, Martins Rucins, Māra Plotniece, Kārlis Pajuste, Arkadij Sobolev, Aiva Plotniece

Liposomes and other nanoparticles have been widely studied as innovative nanomaterials because of their unique properties. Pyridinium salts, on the basis of 1,4-dihydropyridine (1,4-DHP) core, have gained significant attention due to their self-assembling properties and DNA delivery activity. This study aimed to synthesize and characterize original N-benzyl substituted 1,4-dihydropyridines and evaluate the influence on structure modifications on compound physicochemical and self-assembling properties. Studies of monolayers composed of 1,4-DHP amphiphiles revealed that the mean molecular areas values were dependent on the compound structure. Therefore, the introduction of N-benzyl substituent to the 1,4-DHP ring enlarged the mean molecular area by almost half. All nanoparticle samples obtained by ethanol injection method possessed positive surface charge and average diameter of 395–2570 nm. The structure of the cationic head-group affects the size of the formed nanoparticles. The diameter of lipoplexes formed by 1,4-DHP amphiphiles and mRNA at nitrogen/phosphate (N/P) charge ratios of 1, 2, and 5 were in the range of 139–2959 nm and were related to the structure of compound and N/P charge ratio. The preliminary results indicated that more prospective combination are the lipoplexes formed by pyridinium moieties containing Nunsubstituted 1,4-DHP amphiphile 1 and pyridinium or substituted pyridinium moieties containing N-benzyl 1,4-DHP amphiphiles 5a–c at N/P charge ratio of 5, which would be good candidates for potential application in gene therapy.


Keywords
N-benzyl 1,4-dihydropyridines; pyridinium amphiphiles; langmuir monolayer; mean molecular area; self-assembling; nanoparticles; lipoplexes; DLS
DOI
10.3390/ma16124206
Hyperlink
https://www.mdpi.com/1996-1944/16/12/4206

Krapivina, A., Lacis, D., Rucins, M., Plotniece, M., Pajuste, K., Sobolev, A., Plotniece, A. The Primary Irradiation Damage of Hydrogen-Accumulated Nickel: An Atomistic Study. Materials, 2023, Vol. 16, No. 12, pp.4206-4222. e-ISSN 1996-1944. Available from: doi:10.3390/ma16124296

Publication language
English (en)
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