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Bromoditerpenes from the red seaweed Sphaerococcus coronopifolius as potential cytotoxic agents and proteasome inhibitors and related mechanisms of action

2022Journal article Open access
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dc.contributor.authorAlves, Celso
dc.contributor.authorSilva, Joana
dc.contributor.authorPintéus, Susete
dc.contributor.authorGuedes, Romina A.
dc.contributor.authorGuedes, Rita C.
dc.contributor.authorAlvariño, Rebeca
dc.contributor.authorFreitas, Rafaela
dc.contributor.authorGoettert, Márcia I.
dc.contributor.authorGaspar, Helena
dc.contributor.authorAlfonso, Amparo
dc.contributor.authorAlpoím, Maria C.
dc.contributor.authorBotana, Luis M.
dc.contributor.authorPedrosa, Rui
dc.date.accessioned2023-07-27T13:53:05Z
dc.date.available2023-07-27T13:53:05Z
dc.date.issued2022
dc.descriptionThis work was funded by the Portuguese Foundation for Science and Technology (FCT) through the strategic projects granted to the MARE—Marine and Environmental Sciences Center (UIDP/04292/2020; UIDB/04292/2020), the BioISI—BioSystems and Integrative Sciences Institute (UIDP/Multi/04046/2020; UIDB/04046/2020), iMed. ULisboa (UIDB/04138/2020; UIDP/04138/2020), and the Associate Laboratory ARNET (LA/P/0069/2020). FCT also support this study through the POINT4PAC project (SAICTPAC/0019/2015-LISBOA- 01-0145-FEDER-016405) and through the PDTC/QEQ-MED/7042/2014 and CROSS-ATLANTIC project (PTDC/BIA-OUT/29250/2017), co-financed by COMPETE (PO-CI-01-0145-FEDER-029250). The Spanish part was funded by Conselleria de Cultura, Educacion e Ordenación Universitaria, Xunta de Galicia, GRC (ED431C 2021/01). This work was also supported by the FCT and CAPES cooperation agreement through the project MAr-Tics (FCT/DRI/CAPES 2019.00277.CBM). Rebeca Alvariño is supported by a fellowship from Xunta de Galicia (ED481B-2021-038), Spain.pt_PT
dc.description.abstractSeaweeds are a great source of compounds with cytotoxic properties with the potential to be used as anticancer agents. This study evaluated the cytotoxic and proteasome inhibitory activities of 12R-hydroxy-bromosphaerol, 12S-hydroxy-bromosphaerol, and bromosphaerol isolated from Sphaerococcus coronopifolius. The cytotoxicity was evaluated on malignant cell lines (A549, CACO-2, HCT-15, MCF-7, NCI-H226, PC-3, SH-SY5Y, and SK-MEL-28) using the MTT and LDH assays. The ability of compounds to stimulate the production of hydrogen peroxide (H2O2) and to induce mitochondrial dysfunction, the externalization of phosphatidylserine, Caspase-9 activity, and changes in nuclear morphology was also studied on MCF-7 cells. The ability to induce DNA damage was also studied on L929 fibroblasts. The proteasome inhibitory activity was estimated through molecular docking studies. The compounds exhibited IC50 values between 15.35 and 53.34 μM. 12Rhydroxy-bromosphaerol and 12S-hydroxy-bromosphaerol increased the H2O2 levels on MCF-7 cells, and bromosphaerol induced DNA damage on fibroblasts. All compounds promoted a depolarization of mitochondrial membrane potential, Caspase-9 activity, and nuclear condensation and fragmentation. The compounds have been shown to interact with the chymotrypsin-like catalytic site through molecular docking studies; however, only 12S-hydroxy-bromosphaerol evidenced interaction with ALA20 and SER169, key residues of the proteasome catalytic mechanism. Further studies should be outlined to deeply characterize and understand the potential of those bromoditerpenes for anticancer therapeutics.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationAlves, C.; Silva, J.; Pintéus, S.; Guedes, R.A.; Guedes, R.C.; Alvariño, R.; Freitas, R.; Goettert, M.I.; Gaspar, H.; Alfonso, A.; et al. Bromoditerpenes from the Red Seaweed Sphaerococcus coronopifolius as Potential Cytotoxic Agents and Proteasome Inhibitors and Related Mechanisms of Action. Mar. Drugs 2022, 20, 652. https://doi.org/10.3390/md20100652pt_PT
dc.identifier.doi10.3390/md20100652pt_PT
dc.identifier.issn1660-3397
dc.identifier.urihttp://hdl.handle.net/10400.8/8694
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherMDPIpt_PT
dc.relationMarine and Environmental Sciences Centre
dc.relationMarine and Environmental Sciences Centre
dc.relationBiosystems and Integrative Sciences Institute
dc.relationResearch Institute for Medicines
dc.relationResearch Institute for Medicines
dc.relation.publisherversionhttps://www.mdpi.com/1660-3397/20/10/652pt_PT
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/pt_PT
dc.subjectTerpenespt_PT
dc.subjectAlgaept_PT
dc.subjectMarine natural productspt_PT
dc.subjectApoptosispt_PT
dc.subjectMitochondrial dysfunctionpt_PT
dc.subjectOxidative stresspt_PT
dc.subjectAnticancerpt_PT
dc.subjectSphaerococcus coronopifoliuspt_PT
dc.titleBromoditerpenes from the red seaweed Sphaerococcus coronopifolius as potential cytotoxic agents and proteasome inhibitors and related mechanisms of actionpt_PT
dc.typejournal article
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oaire.awardTitleBiosystems and Integrative Sciences Institute
oaire.awardTitleResearch Institute for Medicines
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oaire.citation.titleMarine Drugspt_PT
oaire.citation.volume20pt_PT
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