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

Petrović Peroković, Vesna; Car, Željka; Draženović, Josip; Stojković, Ranko; Milković, Lidija; Antica, Mariastefania; Škalamera, Đani; Tomić, Srđanka; Ribić, Rosana (2021) Design, Synthesis, and Biological Evaluation of Desmuramyl Dipeptides Modified by Adamantyl-1,2,3-triazole. Molecules, 26 (21). ISSN 1420-3049

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Abstract

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.

Item Type: Article
Uncontrolled Keywords: mannose ; desmuramyl peptide ; adamantyl-triazole ; immunostimulant activity
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Molecular Biology
Division of Molecular Medicine
Projects:
Project titleProject leaderProject codeProject type
Sinteza, strukturna analiza i biološka evaluacija peptidomimetika i glikonjugataTomić-Pisarović, SrđankaIP-2014-09-7899HRZZ
Obnova timusa za preciznu medicinu u liječenju tumora i leukemijaAntica, MariastefaniaIP-2020-02-2431HRZZ
Depositing User: Sofija Konjević
Date Deposited: 12 Nov 2021 14:47
URI: http://fulir.irb.hr/id/eprint/6675
DOI: 10.3390/molecules26216352

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