Synthesis and Immunological Evaluation of Mannosylated Desmuramyl Dipeptides Modified by Lipophilic Triazole Substituents

Petrović Peroković, Vesna; Car, Željka; Bušljeta, Mia; Mihelec, Danijela; Paurević, Marija; Ivanković, Siniša; Stojković, Ranko; Ribić, Rosana (2022) Synthesis and Immunological Evaluation of Mannosylated Desmuramyl Dipeptides Modified by Lipophilic Triazole Substituents. International journal of molecular sciences, 23 . ISSN 1422-0067

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Official URL: https://www.mdpi.com/1422-0067/23/15/8628

Abstract

Muramyl dipeptide (N-acetylmuramyl-L-alanyl-D-isoglutamine, MDP) is the smallest pep- tidoglycan fragment able to trigger an immune response by activating the NOD2 receptor. Structural modification of MDP can lead to analogues with improved immunostimulating properties. The aim of this work was to prepare mannosylated desmuramyl peptides (ManDMP) containing lipophilic triazole substituents to study their immunomodulating activities in vivo. The adjuvant activity of the prepared compounds was evaluated in the mouse model using ovalbumin as an antigen and compared to the MDP and referent adjuvant ManDMPTAd. The obtained results confirm that the α-position of D-isoGln is the best position for the attachment of lipophilic substituents, especially adamantylethyl triazole. Compound 6c exhibited the strongest adjuvant activity, comparable to the MDP and better than referent ManDMPTAd.

Item Type:

Article

Uncontrolled Keywords:

mannose ; desmuramyl peptide ; triazole ; immunostimulating activit

Subjects:

NATURAL SCIENCES > Chemistry

Divisions:

Division of Molecular Medicine

Projects: