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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dc.contributor.authorRucins, Martins
dc.contributor.authorKaukulis, Martins
dc.contributor.authorPlotniece, Aiva
dc.contributor.authorPajuste, Karlis
dc.contributor.authorPikun, Nadiia
dc.contributor.authorSobolev, Arkadij
dc.date.accessioned2022-09-02T10:25:01Z
dc.date.available2022-09-02T10:25:01Z
dc.date.issued2022-09
dc.descriptionFunding 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.
dc.description.abstractSynthesis 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.en
dc.description.statusPeer reviewed
dc.format.extent488154
dc.identifier.citationRucins, 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
dc.identifier.doi10.3390/M1396
dc.identifier.issn1422-8599
dc.identifier.urihttps://dspace.rsu.lv/jspui/handle/123456789/9511
dc.identifier.urlhttp://www.scopus.com/inward/record.url?scp=85133329504&partnerID=8YFLogxK
dc.language.isoeng
dc.relation.ispartofMolBank
dc.rightsinfo:eu-repo/semantics/openAccess
dc.subject1,4-dihydropyridines
dc.subjectDLS
dc.subjectnanoparticles
dc.subjectself-assembling properties
dc.subjectstyrylpyridinium dyes
dc.subjectsynthetic lipids
dc.subject1.4 Chemical sciences
dc.subject1.6 Biological sciences
dc.subject1.1. Scientific article indexed in Web of Science and/or Scopus database
dc.subjectBiochemistry
dc.subjectPhysical and Theoretical Chemistry
dc.subjectOrganic Chemistry
dc.title1,1′-{[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}dibromideen
dc.type/dk/atira/pure/researchoutput/researchoutputtypes/contributiontojournal/article

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