Design, Synthesis, and Biological Evaluation of Desmuramyl Dipeptides Modified by Adamantyl-1,2,3-triazole

Muramyl dipeptide (MDP) is the smallest peptidoglycan fragment able to trigger the immune response. Structural modification of MDP can lead to the preparation of analogs with improved immunostimulant properties, including desmuramyl peptides (DMPs). The aim of this work was to prepare the desmuramyl...

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Autores principales:	Vesna Petrović Peroković, Željka Car, Josip Draženović, Ranko Stojković, Lidija Milković, Mariastefania Antica, Đani Škalamera, Srđanka Tomić, Rosana Ribić
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	mannose desmuramyl peptide adamantyl-triazole immunostimulant activity Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/9b803ac093d84ef5b36854a56efc2aa2
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spelling	oai:doaj.org-article:9b803ac093d84ef5b36854a56efc2aa22021-11-11T18:22:59ZDesign, Synthesis, and Biological Evaluation of Desmuramyl Dipeptides Modified by Adamantyl-1,2,3-triazole10.3390/molecules262163521420-3049https://doaj.org/article/9b803ac093d84ef5b36854a56efc2aa22021-10-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/21/6352https://doaj.org/toc/1420-3049Muramyl dipeptide (MDP) is the smallest peptidoglycan fragment able to trigger the immune response. Structural modification of MDP can lead to the preparation of analogs with improved immunostimulant properties, including desmuramyl peptides (DMPs). The aim of this work was to prepare the desmuramyl peptide (L-Ala-D-Glu)-containing adamantyl-triazole moiety and its mannosylated derivative in order to study their immunomodulatory activities in vivo. The adjuvant activity of the prepared compounds was evaluated in a murine model using ovalbumin as an antigen, and compared to the reference adjuvant ManAdDMP. The results showed that the introduction of the lipophilic adamantyl-triazole moiety at the C-terminus of L-Ala-D-Glu contributes to the immunostimulant activity of DMP, and that mannosylation of DMP modified with adamantyl-triazole causes the amplification of its immunostimulant activity.Vesna Petrović PerokovićŽeljka CarJosip DraženovićRanko StojkovićLidija MilkovićMariastefania AnticaĐani ŠkalameraSrđanka TomićRosana RibićMDPI AGarticlemannosedesmuramyl peptideadamantyl-triazoleimmunostimulant activityOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6352, p 6352 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	mannose desmuramyl peptide adamantyl-triazole immunostimulant activity Organic chemistry QD241-441
spellingShingle	mannose desmuramyl peptide adamantyl-triazole immunostimulant activity Organic chemistry QD241-441 Vesna Petrović Peroković Željka Car Josip Draženović Ranko Stojković Lidija Milković Mariastefania Antica Đani Škalamera Srđanka Tomić Rosana Ribić Design, Synthesis, and Biological Evaluation of Desmuramyl Dipeptides Modified by Adamantyl-1,2,3-triazole
description	Muramyl dipeptide (MDP) is the smallest peptidoglycan fragment able to trigger the immune response. Structural modification of MDP can lead to the preparation of analogs with improved immunostimulant properties, including desmuramyl peptides (DMPs). The aim of this work was to prepare the desmuramyl peptide (L-Ala-D-Glu)-containing adamantyl-triazole moiety and its mannosylated derivative in order to study their immunomodulatory activities in vivo. The adjuvant activity of the prepared compounds was evaluated in a murine model using ovalbumin as an antigen, and compared to the reference adjuvant ManAdDMP. The results showed that the introduction of the lipophilic adamantyl-triazole moiety at the C-terminus of L-Ala-D-Glu contributes to the immunostimulant activity of DMP, and that mannosylation of DMP modified with adamantyl-triazole causes the amplification of its immunostimulant activity.
format	article
author	Vesna Petrović Peroković Željka Car Josip Draženović Ranko Stojković Lidija Milković Mariastefania Antica Đani Škalamera Srđanka Tomić Rosana Ribić
author_facet	Vesna Petrović Peroković Željka Car Josip Draženović Ranko Stojković Lidija Milković Mariastefania Antica Đani Škalamera Srđanka Tomić Rosana Ribić
author_sort	Vesna Petrović Peroković
title	Design, Synthesis, and Biological Evaluation of Desmuramyl Dipeptides Modified by Adamantyl-1,2,3-triazole
title_short	Design, Synthesis, and Biological Evaluation of Desmuramyl Dipeptides Modified by Adamantyl-1,2,3-triazole
title_full	Design, Synthesis, and Biological Evaluation of Desmuramyl Dipeptides Modified by Adamantyl-1,2,3-triazole
title_fullStr	Design, Synthesis, and Biological Evaluation of Desmuramyl Dipeptides Modified by Adamantyl-1,2,3-triazole
title_full_unstemmed	Design, Synthesis, and Biological Evaluation of Desmuramyl Dipeptides Modified by Adamantyl-1,2,3-triazole
title_sort	design, synthesis, and biological evaluation of desmuramyl dipeptides modified by adamantyl-1,2,3-triazole
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/9b803ac093d84ef5b36854a56efc2aa2
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Design, Synthesis, and Biological Evaluation of Desmuramyl Dipeptides Modified by Adamantyl-1,2,3-triazole

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