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Designing type V deep eutectic solvents with antimalarial pharmaceutical ingredients

2024Journal article Restricted access
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dc.contributor.authorTeixeira, Gabriel
dc.contributor.authorBrandão, Paula
dc.contributor.authorFerreira, Ana I.M.C. Lobo
dc.contributor.authorAbranches, Dinis O.
dc.contributor.authorSantos, L.uís M.N.B.F.
dc.contributor.authorFerreira, Olga
dc.contributor.authorCoutinho, João A.P.
dc.date.accessioned2024-10-16T08:34:33Z
dc.date.available2024-10-16T08:34:33Z
dc.date.issued2024
dc.description.abstractThis work studies the formation of deep eutectic solvents formed by one active pharmaceutical ingredient (quinine, pyrimethamine, or 2-phenylimidazopyridine) and a second component potentially acting as an excipient (betaine, choline chloride, tetramethylammonium chloride, thymol, menthol, gallic acid, vanillin, acetovanillone, 4-hydroxybenzaldehyde, syringaldehyde, propyl gallate, propylparaben, or butylated hydroxyanisole), aiming to address challenges regarding drug solubility, bioavailability, and permeability. A preliminary screening was carried out using the thermodynamic model COSMO-RS, narrowing down the search to three promising excipients (thymol, propyl gallate, and butylated hydroxyanisole). Nine solid–liquid equilibrium (SLE) phase diagrams were experimentally measured combining the three model drugs with the screened excipients, and using a combination of a visual melting method and differential scanning calorimetry. Negative deviations from thermodynamic ideality were observed in all nine systems. Furthermore, a total of four new cocrystals were found, with powder and single crystal X-ray diffraction techniques being employed to verify their unique diffraction patterns. In the thermodynamic modelling of the SLE diagrams, two COSMO-RS parametrizations (TZVP and TZVPD-FINE) were also applied, though neither consistently delivered a better description over the other.pt_PT
dc.description.sponsorshipThis work was developed within the scope of the project CICECO - Aveiro Institute of Materials, Portugal, UIDB/50011/2020, UIDP/ 50011/2020, and LA/P/0006/2020, CIQUP, Centro de Investigação em Química da Universidade do Porto, Portugal (UIDB/00081/ 2020); IMS, Institute of Molecular Sciences (LA/P/0056/2020), and CIMO, Portugal, UIDB/00690/2020 (DOI: 10.54499/UIDB/00690/2020) and UIDP/ 00690/2020 (DOI: 10.54499/UIDP/00690/2020); and SusTEC, Portugal, LA/P/0007/2020 (DOI: 10.54499/LA/P/0007/2020), financed by national funds through the Portuguese Foundation for Science and Technology FCT/MCTES (PIDDAC). AIMCLF is financed by national funds through the FCT-I.P., in the framework of the execution of the program contract provided in paragraphs 4, 5, and 6 of art. 23 of Law no. 57/2016 of 29 August, as amended by Law no. 57/2017 of 19 July. G.T. thanks FCT, Portugal for his Ph.D. grant (UI/BD/151114/2021).pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationTeixeira, Gabriel; Brandão, Paula; Ferreira, Ana I.M.C.Lobo; Abranches, Dinis O.; Santos, Luís M.N.B.F.; Ferreira, Olga; Coutinho, João A.P. (2024). Designing type V deep eutectic solvents with antimalarial pharmaceutical ingredients. European Journal of Pharmaceutics and Biopharmaceutics. ISSN 0939-6411. 203, p. 1-12pt_PT
dc.identifier.doi10.1016/j.ejpb.2024.114463pt_PT
dc.identifier.issn0939-6411
dc.identifier.urihttp://hdl.handle.net/10198/30425
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherElsevierpt_PT
dc.relationCICECO-Aveiro Institute of Materials
dc.relationCICECO-Aveiro Institute of Materials
dc.relationCICECO – Aveiro Institute of Materials
dc.relationChemistry Research Unit of University of Porto
dc.relationInstitute of Molecular Sciences
dc.relationMountain Research Center
dc.relationMountain Research Center
dc.relationAssociate Laboratory for Sustainability and Tecnology in Mountain Regions
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/pt_PT
dc.subjectActive pharmaceutical ingredientspt_PT
dc.subjectDeep eutectic solventspt_PT
dc.subjectXRDpt_PT
dc.subjectCOSMO-RSpt_PT
dc.subjectSolid–liquid equilibriapt_PT
dc.titleDesigning type V deep eutectic solvents with antimalarial pharmaceutical ingredientspt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleCICECO-Aveiro Institute of Materials
oaire.awardTitleCICECO-Aveiro Institute of Materials
oaire.awardTitleCICECO – Aveiro Institute of Materials
oaire.awardTitleChemistry Research Unit of University of Porto
oaire.awardTitleInstitute of Molecular Sciences
oaire.awardTitleMountain Research Center
oaire.awardTitleMountain Research Center
oaire.awardTitleAssociate Laboratory for Sustainability and Tecnology in Mountain Regions
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F50011%2F2020/PT
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oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F00690%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/LA%2FP%2F0007%2F2020/PT
oaire.citation.endPage12pt_PT
oaire.citation.startPage1pt_PT
oaire.citation.titleEuropean Journal of Pharmaceutics and Biopharmaceuticspt_PT
oaire.citation.volume203pt_PT
oaire.fundingStream6817 - DCRRNI ID
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oaire.fundingStream6817 - DCRRNI ID
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oaire.fundingStream6817 - DCRRNI ID
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person.familyNameFerreira
person.givenNameOlga
person.identifier.ciencia-id9F1D-C75A-4A54
person.identifier.orcid0000-0001-8414-3479
person.identifier.ridM-4567-2013
person.identifier.scopus-author-id57203083219
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project.funder.nameFundação para a Ciência e a Tecnologia
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rcaap.rightsrestrictedAccesspt_PT
rcaap.typearticlept_PT
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