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Article

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

1
Department of Chemistry, Faculty of Science, University Zagreb, Horvatovac 102, HR-10000 Zagreb, Croatia
2
Division of Molecular Medicine and Division of Molecular Biology, Ruđer Bošković Institute, Bijenička cesta 54, HR-10000 Zagreb, Croatia
3
Department of Nursing, University Center Varaždin, University North, Jurja Križanića 31b, HR-42000 Varaždin, Croatia
*
Author to whom correspondence should be addressed.
These authors contributed equally to this work.
Academic Editor: Vadim T. Ivanov
Molecules 2021, 26(21), 6352; https://doi.org/10.3390/molecules26216352
Received: 30 September 2021 / Revised: 16 October 2021 / Accepted: 18 October 2021 / Published: 21 October 2021
(This article belongs to the Special Issue Bioactive Peptides and Proteins)
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. View Full-Text
Keywords: mannose; desmuramyl peptide; adamantyl-triazole; immunostimulant activity mannose; desmuramyl peptide; adamantyl-triazole; immunostimulant activity
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MDPI and ACS Style

Peroković, V.P.; Car, Ž.; Draženović, J.; Stojković, R.; Milković, L.; Antica, M.; Škalamera, Đ.; Tomić, S.; Ribić, R. Design, Synthesis, and Biological Evaluation of Desmuramyl Dipeptides Modified by Adamantyl-1,2,3-triazole. Molecules 2021, 26, 6352. https://doi.org/10.3390/molecules26216352

AMA Style

Peroković VP, Car Ž, Draženović J, Stojković R, Milković L, Antica M, Škalamera Đ, Tomić S, Ribić R. Design, Synthesis, and Biological Evaluation of Desmuramyl Dipeptides Modified by Adamantyl-1,2,3-triazole. Molecules. 2021; 26(21):6352. https://doi.org/10.3390/molecules26216352

Chicago/Turabian Style

Peroković, Vesna Petrović, Željka Car, Josip Draženović, Ranko Stojković, Lidija Milković, Mariastefania Antica, Đani Škalamera, Srđanka Tomić, and Rosana Ribić. 2021. "Design, Synthesis, and Biological Evaluation of Desmuramyl Dipeptides Modified by Adamantyl-1,2,3-triazole" Molecules 26, no. 21: 6352. https://doi.org/10.3390/molecules26216352

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