Synthesis and Evaluation of Self-Assembling Properties of 3-(3,5-Difluoro-3,5-bis((alkoxy)carbonyl)-2,6-dioxoheptan-4-yl)-1-methylpyridin-1-ium Iodides

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dc.contributor.authorPikun, Nadiia
dc.contributor.authorLacis, Davis
dc.contributor.authorSobolev, Arkadij
dc.contributor.authorRucins, Martins
dc.contributor.authorPlotniece, Mara
dc.contributor.authorPajuste, Karlis
dc.contributor.authorPlotniece, Aiva
dc.contributor.institutionDepartment of Pharmaceutical Chemistry
dc.date.accessioned2022-09-02T12:45:01Z
dc.date.available2022-09-02T12:45:01Z
dc.date.issued2022-09
dc.descriptionFunding Information: Funding: This research was funded by EuroNanoMed3 project NANO4GLIO No ES RTD/2020/9 and PostDocLatvia Project No 1.1.1.2/VIAA/3/19/587 (K.Pajuste). Publisher Copyright: © 2022 by the authors. Licensee MDPI, Basel, Switzerland.
dc.description.abstractA synthesis of 3-(3,5-difluoro-3,5-bis((alkoxy)carbonyl)-2,6-dioxoheptan-4-yl)-1-methylpyridin-1-ium iodides with ethyl or nonyl ester groups at positions 3 and 5 was performed. Treatment of the corresponding 2’,6’-dimethyl-1’,4’-dihydro-[3,4’-bipyridine]-3’,5’-dicarboxylates with Selectfluor® followed by quaternization of pyridine moiety in the obtained dialkyl 2,4-diacetyl-2,4-difluoro-3-(pyridin-3-yl)pentanedioates with methyl iodide gave the desired 3-(3,5-difluoro-3,5-bis((alkoxy)carbonyl)-2,6-dioxoheptan-4-yl)-1-methylpyridin-1-ium iodides. This type of compound would be useful as synthetic lipids for further development of the delivery systems. The obtained target compounds were fully characterized by1H NMR,19F NMR,13C NMR, HRMS, IR and UV data. The estimation of self-assembling properties and characterization of the nanoparticles obtained by ethanol solution injection in an aqueous media were performed by dynamic light scattering (DLS) measurements. DLS measurement data showed that 3-(3,5-difluoro-3,5-bis((nonyloxy)carbonyl)-2,6-dioxoheptan-4-yl)-1-methylpyridin-1-ium iodide created liposomes with the average diameter of 300–400 nm and polydispersity index (PDI) value around 0.30–0.40, while 3-(3,5-difluoro-3,5-bis((ethyloxy)carbonyl)-2,6-dioxoheptan-4-yl)-1-methylpyridin-1-ium iodide formed a heterogeneous sample with PDI value 1, which was not prospective for delivery system development.en
dc.description.statusPeer reviewed
dc.format.extent565972
dc.identifier.citationPikun, N, Lacis, D, Sobolev, A, Rucins, M, Plotniece, M, Pajuste, K & Plotniece, A 2022, 'Synthesis and Evaluation of Self-Assembling Properties of 3-(3,5-Difluoro-3,5-bis((alkoxy)carbonyl)-2,6-dioxoheptan-4-yl)-1-methylpyridin-1-ium Iodides', MolBank, vol. 2022, no. 3, M1402. https://doi.org/10.3390/M1402
dc.identifier.doi10.3390/M1402
dc.identifier.issn1422-8599
dc.identifier.urihttps://dspace.rsu.lv/jspui/handle/123456789/9512
dc.identifier.urlhttp://www.scopus.com/inward/record.url?scp=85133884282&partnerID=8YFLogxK
dc.language.isoeng
dc.relation.ispartofMolBank
dc.rightsinfo:eu-repo/semantics/openAccess
dc.subject2,4-diacetyl-2,4-difluoro-3-pyridinylpentanedioates
dc.subjectDLS
dc.subjectnanoparticles
dc.subjectpyridinium
dc.subjectSelectfluor®
dc.subjectself-assembling properties
dc.subjectsynthetic lipids
dc.subject1.4 Chemical sciences
dc.subject1.6 Biological sciences
dc.subject3.1 Basic medicine
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.titleSynthesis and Evaluation of Self-Assembling Properties of 3-(3,5-Difluoro-3,5-bis((alkoxy)carbonyl)-2,6-dioxoheptan-4-yl)-1-methylpyridin-1-ium Iodidesen
dc.type/dk/atira/pure/researchoutput/researchoutputtypes/contributiontojournal/article

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