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Unravelling the structure of peroxides with antiparasitic activity: the relative impact of a trioxolane or a tetraoxane pharmacophore on the overall molecular structure

2022Journal article Restricted access
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dc.contributor.authorAmado, Patrícia
dc.contributor.authorJesus, A. J. Lopes
dc.contributor.authorPaixão, José A.
dc.contributor.authorFausto, Rui
dc.contributor.authorCristiano, Maria De Lurdes
dc.date.accessioned2022-12-19T15:23:02Z
dc.date.available2022-12-19T15:23:02Z
dc.date.issued2022
dc.description.abstractPlasmodium falciparum artemisinin-resistance boosted the quest for novel plasmodial "fast killers," uncovering antimalarial candidates OZ439 and E209, whose peroxide precursors are 1,2,4-trioxolane (1) and 1,2,4,5-tetraoxane (2), differing solely in the pharmacophore (trioxolane or tetraoxane). Combining X-ray crystallography and vibrational spectroscopy, along with Hirsh-feld surface analysis and calculations (CE-B3LYP/6-31G(d,p)) of pairwise interaction energies of intermolecular contacts existing in the crystal structure, may deepen the understanding of relative reactivity and properties of these endoperoxides classes. In the crystal, the tetraoxane ring in 2 and the trioxolane-adamantyl fragment in 1 are disordered, with molecules 1 and 2 existing as two distinct, stable conformations. Whereas the dominant C-H center dot center dot center dot O H-bonds in 1 connect an adamantyl C-H and O1 or O2 of the trioxolane ring, in 2 they involve the carbonyl oxygen, acting as a double acceptor from phenyl ring C-H groups. C-H center dot center dot center dot O and C-H center dot center dot center dot pi H-bonds define the molecular packing of 2, while C-H center dot center dot center dot H-C van der Waals interactions determine the packing of 1. The dispersive component dominates the interaction energies calculated for the most representative molecular pairs.pt_PT
dc.description.sponsorshipUI0313P/QUI/2020
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.doi10.1002/cplu.202200207pt_PT
dc.identifier.issn2192-6506
dc.identifier.urihttp://hdl.handle.net/10400.1/18662
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherWileypt_PT
dc.relationA Chemical Proteomics Approach to Defining the Mechanism of Artemisinin Action and Resistance in PfK13 Resistant parasites
dc.relationA Chemical Proteomics Approach to Defining the Mechanism of Artemisinin Action and Resistance in PfK13 Resistant parasites
dc.relationAlgarve Centre for Marine Sciences
dc.relationAlgarve Centre for Marine Sciences
dc.relationCenter for Physics of the University of Coimbra
dc.relationCenter for Physics of the University of Coimbra
dc.relationCentre for Marine and Environmental Research
dc.relationInstitute of Molecular Sciences
dc.subject1,2,4,5-tetraoxanespt_PT
dc.subject1,2,4-trioxolanespt_PT
dc.subjectHirshfeld surface analysispt_PT
dc.subjectPeroxidespt_PT
dc.subjectX-ray diffractionpt_PT
dc.titleUnravelling the structure of peroxides with antiparasitic activity: the relative impact of a trioxolane or a tetraoxane pharmacophore on the overall molecular structurept_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleA Chemical Proteomics Approach to Defining the Mechanism of Artemisinin Action and Resistance in PfK13 Resistant parasites
oaire.awardTitleA Chemical Proteomics Approach to Defining the Mechanism of Artemisinin Action and Resistance in PfK13 Resistant parasites
oaire.awardTitleAlgarve Centre for Marine Sciences
oaire.awardTitleAlgarve Centre for Marine Sciences
oaire.awardTitleCenter for Physics of the University of Coimbra
oaire.awardTitleCenter for Physics of the University of Coimbra
oaire.awardTitleCentre for Marine and Environmental Research
oaire.awardTitleInstitute of Molecular Sciences
oaire.awardURIinfo:eu-repo/grantAgreement/FCT//SFRH%2FBD%2F130407%2F2017/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT//COVID%2FBD%2F152392%2F2022/PT
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oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/LA%2FP%2F0056%2F2020/PT
oaire.citation.issue8pt_PT
oaire.citation.titleChemPlusChempt_PT
oaire.citation.volume87pt_PT
oaire.fundingStream6817 - DCRRNI ID
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person.familyNameMenalha Amado
person.familyNameCristiano
person.givenNamePatrícia Sofia
person.givenNameMaria de Lurdes
person.identifier.ciencia-id8617-A360-B70A
person.identifier.ciencia-idE411-6006-5A01
person.identifier.orcid0000-0002-7307-9210
person.identifier.orcid0000-0002-9447-2855
person.identifier.ridG-2345-2012
person.identifier.scopus-author-id9238724800
project.funder.identifierhttp://doi.org/10.13039/501100001871
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project.funder.nameFundação para a Ciência e a Tecnologia
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project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsrestrictedAccesspt_PT
rcaap.typearticlept_PT
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