1,1′-{[3,5-Bis(dodecyloxycarbonyl)-4-(naphthalen-2-yl)-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis{4-[(E)-2-(naphthalen-2-yl)vinyl]pyridin-1-ium}dibromide
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Date
2022-09
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Abstract
Synthesis of a double-charged cationic amphiphilic 1,4-dihydropyridine derivative with dodecyl ester groups at positions 3 and 5 of the 1,4-DHP ring was performed starting from Hantzsch type cyclization of dodecyl acetoacetate, 2-naphthaldehyde and ammonium acetate. Bromination of this compound followed by nucleophilic substitution of bromine with (E)-4-(2-(naphthalen-2-yl)vinyl)pyridine gave the desired cationic amphiphilic 1,1′-{[3,5-bis(dodecyloxycarbonyl)-4-(naph-thalen-2-yl)-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis{4-[(E)-2-(naphthalen-2-yl)vinyl]pyridin-1-ium}dibromide. The obtained target compound was fully characterized by IR, UV,1 H-NMR,13 C-NMR, HRMS and microanalysis. The characterization of the cationic 1,4-DHP nanoparticles in an aqueous solution was performed by DLS measurements. The obtained results showed that the compound formed nanoparticles with an average diameter of around 300 nm, a PDI value of around 490 and a zeta-potential of around 20 mV for freshly prepared samples. However, after one week of storage at room temperature, an aggregation of nanoparticles was detected.
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Funding Information: Funding: This research was funded by the EuroNanoMed3 project TENTACLES No ES RTD/2020/18. Publisher Copyright: © 2022 by the authors. Licensee MDPI, Basel, Switzerland.
Keywords
1,4-dihydropyridines, DLS, nanoparticles, self-assembling properties, styrylpyridinium dyes, synthetic lipids, 1.4 Chemical sciences, 1.6 Biological sciences, 1.1. Scientific article indexed in Web of Science and/or Scopus database, Biochemistry, Physical and Theoretical Chemistry, Organic Chemistry
Citation
Rucins, M, Kaukulis, M, Plotniece, A, Pajuste, K, Pikun, N & Sobolev, A 2022, '1,1 ′ -{[3,5-Bis(dodecyloxycarbonyl)-4-(naphthalen-2-yl)-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis{4-[(E)-2-(naphthalen-2-yl)vinyl]pyridin-1-ium}dibromide', MolBank, vol. 2022, no. 3, M1396. https://doi.org/10.3390/M1396