D- and N-Methyl Amino Acids for Modulating the Therapeutic Properties of Antimicrobial Peptides and Lipopeptides

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dc.citation.titleAntibiotics
dc.citation.volume12
dc.contributor.orcidhttps://orcid.org/0000-0003-4479-2356
dc.contributor.orcidhttps://orcid.org/0000-0002-8946-0462
dc.contributor.orcidhttps://orcid.org/0000-0002-7790-5532
dc.creatorHumpola, Maria Veronica
dc.creatorSpinelli, Roque
dc.creatorErben, Melina
dc.creatorPerdomo, Virginia Gabriela
dc.creatorTonarelli, Georgina Guadalupe
dc.creatorAlbericio, Fernando
dc.creatorSiano, Alvaro Sebastian
dc.date.accessioned2024-11-12T18:15:00Z
dc.date.available2024-11-12T18:15:00Z
dc.date.issued2023-04-27
dc.description.abstractHere we designed and synthesized analogs of two antimicrobial peptides, namely C10:0-A2, a lipopeptide, and TA4, a cationic α-helical amphipathic peptide, and used non-proteinogenic amino acids to improve their therapeutic properties. The physicochemical properties of these analogs were analyzed, including their retention time, hydrophobicity, and critical micelle concentration, as well as their antimicrobial activity against gram-positive and gram-negative bacteria and yeast. Our results showed that substitution with D- and N-methyl amino acids could be a useful strategy to modulate the therapeutic properties of antimicrobial peptides and lipopeptides, including enhancing stability against enzymatic degradation. The study provides insights into the design and optimization of antimicrobial peptides to achieve improved stability and therapeutic efficacy. TA4(dK), C10:0-A2(6-NMeLys), and C10:0-A2(9-NMeLys) were identified as the most promising molecules for further studies.
dc.description.filFil: Humpola, Maria Veronica. Universidad Nacional del Litoral. Facultad de Bioquímica y Ciencias Biológicas. Departamento de Química Orgánica. Laboratorio de Péptidos Bioactivos; Argentina.
dc.description.filFil: Spinelli, Roque. Universidad Nacional del Litoral. Facultad de Bioquímica y Ciencias Biológicas. Departamento de Química Orgánica. Laboratorio de Péptidos Bioactivos; Argentina.
dc.description.filFil: Spinelli, Roque. Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET); Argentina.
dc.description.filFil: Erben, Melina. Universidad Nacional del Litoral. Facultad de Bioquímica y Ciencias Biológicas. Departamento de Química Orgánica. Laboratorio de Péptidos Bioactivos; Argentina.
dc.description.filFil: Perdomo, Virginia Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET); Argentina.
dc.description.filFil: Perdomo, Virginia Gabriela. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Área Parasitología; Argentina.
dc.description.filFil: Tonarelli, Georgina Guadalupe. Universidad Nacional del Litoral. Facultad de Bioquímica y Ciencias Biológicas. Departamento de Química Orgánica. Laboratorio de Péptidos Bioactivos; Argentina.
dc.description.filFil: Albericio, Fernando. University of KwaZulu-Natal. School of Chemistry and Physics; South Africa.
dc.description.filFil: Albericio, Fernando. University of Barcelona. Networking Centre on Bioengineering, Biomaterials and Nanomedicine. Department of Organic Chemistry (CIBER-BBN); Spain.
dc.description.filFil: Siano, Alvaro Sebastian. Universidad Nacional del Litoral. Facultad de Bioquímica y Ciencias Biológicas. Departamento de Química Orgánica. Laboratorio de Péptidos Bioactivos; Argentina.
dc.description.filFil: Siano, Alvaro Sebastian. Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET); Argentina.
dc.description.sponsorshipAgencia Nacional de Promoción Científica y Tecnológica: PICT-2017-0035, ASACTEI: IO-2018-00152
dc.description.versionpeerreviewed
dc.format.extent1-15
dc.identifier.citationHúmpola, Maria Veronica; Spinelli, Roque; Erben, Melina; Perdomo, Virginia; Tonarelli, Georgina Guadalupe; et al.; D- and N-Methyl Amino Acids for Modulating the Therapeutic Properties of Antimicrobial Peptides and Lipopeptides; MDPI; Antibiotics; 12; 5; 4-2023; 821-837
dc.identifier.issn2079-6382
dc.identifier.urihttps://hdl.handle.net/2133/28108
dc.language.isoen
dc.publisherMDPI
dc.relation.publisherversionhttps://www.mdpi.com/2079-6382/12/5/821
dc.relation.publisherversionhttps://doi.org/10.3390/antibiotics12050821
dc.rightsopenAccess
dc.rights.holderHumpola, Maria Veronica
dc.rights.holderSpinelli, Roque
dc.rights.holderErben, Melina
dc.rights.holderPerdomo, Virginia Gabriela
dc.rights.holderTonarelli, Georgina Guadalupe
dc.rights.holderAlbericio, Fernando
dc.rights.holderSiano, Alvaro Sebastian
dc.rights.textAttribution 4.0 Internationalen
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.subjectAntimicrobial peptides
dc.subjectN-methyl amino acids
dc.subjectD-amino acids
dc.subjectEnzymatic stability
dc.subjectToxicity
dc.titleD- and N-Methyl Amino Acids for Modulating the Therapeutic Properties of Antimicrobial Peptides and Lipopeptides
dc.typearticulo
dc.type.collectionarticulo
dc.type.versionpublishedVersion

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