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Synthesis and characterization of peptide-chitosan conjugates (PepChis) with lipid bilayer affinity and antibacterial activity

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dc.contributor.authorCosta Petrin, Thais H.
dc.contributor.authorFadel, Valmir
dc.contributor.authorMartins, Danubia B.
dc.contributor.authorDias, Susana
dc.contributor.authorCruz, Ana
dc.contributor.authorSergio, Luciana Marciano
dc.contributor.authorArcisio-Miranda, Manoel
dc.contributor.authorCastanho, Miguel A. R. B.
dc.contributor.authorCabrera, Marcia P. dos Santos
dc.date.accessioned2023-04-18T11:39:35Z
dc.date.available2023-04-18T11:39:35Z
dc.date.issued2019
dc.description© 2019 American Chemical Societypt_PT
dc.description.abstractAntimicrobial peptides appear among innovative biopolymers with potential therapeutic interest. Nevertheless, issues concerning efficiency, production costs, and toxicity persist. Herein, we show that conjugation of peptides with chitosans can represent an alternative in the search for these needs. To increase solubility, deacetylated and degraded chitosans were prepared. Then, they were functionalized via N-succinimidyl-S-acetylthiopropionate or via glutathione (GSH), an endogenous peptide linker. To the best of our knowledge, it is the first time that GSH is used as a thiolating agent for the conjugation of peptides. Next, thiolated chitosans were conjugated through a disulfide bond with designed shortchain peptides, one of them derived from the antimicrobial peptide Jelleine-I. Conjugates and respective reaction intermediates were characterized by absorciometry, attenuated total reflectance−Fourier transform infrared, and 1H NMR. Zeta potential measurements showed the cationic nature of these biomacromolecules and their preferential partitioning to Gram-positive bacterial-like model membranes. In vitro investigation using representative Gram-positive and -negative bacteria (Staphylococcus aureus and Escherichia coli, respectively) showed that the conjugation strategies lead to enhanced activity in relation to the unconjugated peptide and to the unconjugated chitosan. The obtained products showed selectivity toward S. aureus at low cytotoxicity as determined in NIH/3T3 cells. Overall, our study demonstrates that an appropriate choice of antimicrobial peptide and chitosan characteristics leads to increased antimicrobial activity of the conjugated product and represents a strategy to modulate the activity and selectivity of antimicrobials resorting to low-cost chemicals. The present proposal starts from less expensive raw materials (chitosan and short-chain peptide), is based on aqueous solvents, and minimizes the use of reactants with a higher environmental impact. The final biopolymer contains the backbone of chitosan, just 3−6% peptide derived from royal jelly and GSH, all of them considered safe for human use or as a physiological molecule.pt_PT
dc.description.sponsorshipThis work was supported by Fundação de Amparo à Pesquisa do Estado de São Paulo—FAPESP nos. 2012/24259-0, 2012/02065-0, 2014/08372-7, 2015/07548-7, 2016/13368-4, 2016/50178-8, FCT (Fundação para a Ciência e a Tecnologia, Portugal) grant PTDC/QEQ-MED/4412/2014, and European Commission, Marie S. Curie action RISE, H2020-MSCA-RISE-2014, grant 644167. DBM was a recipient of the CAPES scholarships, LMS is a recipient of the CNPq scholarship, and AC and SAD are recipients of scholarships PD/BD/136866/2018 and PD/BD/114425/2016 from FCT, respectively.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citation2019, 2743−2753pt_PT
dc.identifier.doi10.1021/acs.biomac.9b00501pt_PT
dc.identifier.eissn1526-4602
dc.identifier.issn1525-7797
dc.identifier.urihttp://hdl.handle.net/10451/57175
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherACS Publicationspt_PT
dc.relationTowards the development of innovative highly effective dual action anti-HIV peptides
dc.relationInnovative peptides against cancer and pathogenic bacteria, with advances in science, biopharmaceutical drug development, product market targeting, training , and communication.
dc.relationDevelopment of viral-derived peptides to fight bacterial bioflims and unraveling their mechanism of action
dc.relationTowards the development of antimicrobial peptides active against bacterial biofilms
dc.relation.publisherversionhttps://pubs.acs.org/journal/bomaf6pt_PT
dc.titleSynthesis and characterization of peptide-chitosan conjugates (PepChis) with lipid bilayer affinity and antibacterial activitypt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleTowards the development of innovative highly effective dual action anti-HIV peptides
oaire.awardTitleInnovative peptides against cancer and pathogenic bacteria, with advances in science, biopharmaceutical drug development, product market targeting, training , and communication.
oaire.awardTitleDevelopment of viral-derived peptides to fight bacterial bioflims and unraveling their mechanism of action
oaire.awardTitleTowards the development of antimicrobial peptides active against bacterial biofilms
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/3599-PPCDT/PTDC%2FQEQ-MED%2F4412%2F2014/PT
oaire.awardURIinfo:eu-repo/grantAgreement/EC/H2020/644167/EU
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/OE/PD%2FBD%2F136866%2F2018/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT//PD%2FBD%2F114425%2F2016/PT
oaire.citation.endPage2753pt_PT
oaire.citation.startPage2743pt_PT
oaire.citation.titleBiomacromoleculespt_PT
oaire.citation.volume20pt_PT
oaire.fundingStream3599-PPCDT
oaire.fundingStreamH2020
oaire.fundingStreamOE
person.familyNameDias
person.familyNameCastanho
person.givenNameSusana
person.givenNameMiguel
person.identifier.ciencia-idF61D-0A28-659A
person.identifier.orcid0000-0001-8910-5404
person.identifier.orcid0000-0001-7891-7562
person.identifier.scopus-author-id56605575600
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100008530
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.nameEuropean Commission
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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