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Hemi-synthesis of novel (S)-carvone hydrazone from Carum carvi L. essential oils: structural and crystal characterization, targeted bioassays and molecular docking on human protein kinase (CK2) and Epidermal Growth factor Kinase (EGFK)

2021Journal article Open access
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dc.contributor.authorTedjini, Rima
dc.contributor.authorZiani, Borhane E.C.
dc.contributor.authorCasimiro, Teresa
dc.contributor.authorViveiros, Raquel
dc.contributor.authorCalhelha, Ricardo C.
dc.contributor.authorBarros, Lillian
dc.contributor.authorBoukenna, Leila
dc.contributor.authorHamdi, Abderrezak
dc.contributor.authorChebout, Redouane
dc.contributor.authorBachari, Khaldoun
dc.contributor.authorTalhi, Oualid
dc.contributor.authorSilva, Artur
dc.date.accessioned2021-08-31T10:29:36Z
dc.date.available2021-08-31T10:29:36Z
dc.date.issued2021
dc.description.abstractPolyfunctional N,O,O,N-type ligands such as the oxalyl dihydrazide (ODH) may induce formation of mono- , di-, and polynuclear complexes with natural monoterpene ketones, involving ligand bridging and Oxo- bridging. In this context, a novel chiral dihydrazone is designed through hemi-synthesis process by re- acting oxalyldihydrazide (ODH) with ( s )-carvone, the major compound of caraway’s seeds essential oil. The C = N imine bi-condensation is performed without prior isolation of the natural ( s )-carvone and the resulting ( s )-carvone dihydrazone (s-CHD) is structurally characterized by Single-crystal X-ray diffrac- tion, 2D-NMR spectroscopy and chiral LCMS analysis to confirm the formation of a single pure enan- tiomer. In -vitro cell-based assays were conducted on normal fibroblast (L929) using a presBlue (PB) flu- orescence quantification method of cell-viability and by sulforhodamine B calorimetric cytotoxicity as- says to determine the anti-proliferative effect on four human tumoral lines (NCI-H460, Hela, HepG2 and MCF-7) and normal PLP2. Anti-inflammatory assays were determined through NO production by Maurine LPS-stimulated macrophages (RAW 264.7). The ( s )-CHD has no effect on normal cells viability ( > 88%) and PLP2 (GI50 = 326 ug/mL), while a moderate ( ∼55%) to significant ( ∼63%) antigrowth potential was recorded against HepG2, Hela and MCF-7 tumor cell lines, where RAW 264.7 was feebly sensitive. A molecular docking was performed using Autodock vina software on the protein kinase CK2 and Epi- dermal Growth factor Kinase proteins EGFK and the dock scores allowed to identify significant bind- ing affinities (lower G and Ki values) and potential hydrophilic/hydrophobic interactions with ( s )-CHD comparing to the clinical ellipticine as potential ligands. Molecular docking suggests that ( s )-CHD pos- sesses high affinity towards the kinase domain receptors CK2 and EGFR, being able to bind to the ATP region.pt_PT
dc.description.sponsorshipThanks are due to the Research Center Scientific and Technical in Analyzes Physico-Chimiques CRAPC Algerian Directorate for research DGRSDT for the financial support. The authors thanks Fundação para a Ciência e a Tecnologia (FC&T, Lisbon) for financial support through projects PTDC/MEC–ONC/29327/2017 and PTDC/EQU-EQU/32473/2017. We are thankful to NOVA University of Lisbon (FCT/UNL) for the financial support from Erasmus + EU international credit mobility 2017–2019. the laboratory for Green Chemistry LAQV-REQUIMTE FCT/MCTES (UID/QUI/50006/2019) is co-financed by the ERDF and the chemistry department for providing the instruments support.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationTedjini, Rima; Ziani, Borhane E.C.; Casimiro, Teresa; Viveiros, Raquel; Calhelha, Ricardo C.; Barros, Lillian; Boukenna, Leila; Hamdi, Abderrezak; Chebout, Redouane; Bachari, Khaldoun; Talhi, Oualid; Silva, Artur M.S. (2021). Hemi-synthesis of novel (S)-carvone hydrazone from Carum carvi L. essential oils: Structural and crystal characterization, targeted bioassays and molecular docking on human protein kinase (CK2) and Epidermal Growth factor Kinase (EGFK). Journal of Molecular Structure. ISSN 0022-2860. 1246, p. 1-13pt_PT
dc.identifier.doi10.1016/j.molstruc.2021.131220pt_PT
dc.identifier.issn0022-2860
dc.identifier.urihttp://hdl.handle.net/10198/23843
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.relationDendrimer-based Report-Eradication Antineoplasic Machines
dc.relationGreen strategy on the development of plastic antibodies for bio-recognition
dc.relationAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/pt_PT
dc.subject(s)-carvone hydrazonept_PT
dc.subjectHemi-synthesispt_PT
dc.subject2D NMRpt_PT
dc.subjectSingle-crystal X-raypt_PT
dc.subjectChiral HPLCpt_PT
dc.subjectCytotoxicitypt_PT
dc.subjectDockingpt_PT
dc.titleHemi-synthesis of novel (S)-carvone hydrazone from Carum carvi L. essential oils: structural and crystal characterization, targeted bioassays and molecular docking on human protein kinase (CK2) and Epidermal Growth factor Kinase (EGFK)pt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleDendrimer-based Report-Eradication Antineoplasic Machines
oaire.awardTitleGreen strategy on the development of plastic antibodies for bio-recognition
oaire.awardTitleAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/3599-PPCDT/PTDC%2FMEC-ONC%2F29327%2F2017/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/3599-PPCDT/PTDC%2FEQU-EQU%2F32473%2F2017/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UID%2FQUI%2F50006%2F2019/PT
oaire.citation.startPage131220pt_PT
oaire.citation.titleJournal of Molecular Structurept_PT
oaire.citation.volume1246pt_PT
oaire.fundingStream3599-PPCDT
oaire.fundingStream3599-PPCDT
oaire.fundingStream6817 - DCRRNI ID
person.familyNameCalhelha
person.familyNameBarros
person.givenNameRicardo C.
person.givenNameLillian
person.identifier469085
person.identifier.ciencia-idF313-E3CE-554E
person.identifier.ciencia-id9616-35CB-D001
person.identifier.orcid0000-0002-6801-4578
person.identifier.orcid0000-0002-9050-5189
person.identifier.ridJ-2172-2014
person.identifier.ridJ-3600-2013
person.identifier.scopus-author-id6507978333
person.identifier.scopus-author-id35236343600
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
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.rightsopenAccesspt_PT
rcaap.typearticlept_PT
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