Design, synthesis and biological evaluation of immunostimulating mannosylated desmuramyl peptides (CROSBI ID 269196)
Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija
Podaci o odgovornosti
Ribić, Rosana ; Stojković, Ranko ; Milković, Lidija ; Antica, Mariastefania ; Cigler, Marko ; Tomić, Srđanka
engleski
Design, synthesis and biological evaluation of immunostimulating mannosylated desmuramyl peptides
Muramyl dipeptide is the minimal structure of peptidoglycan with adjuvant properties. Replacement of the N-acetylmuramyl moiety and increase of lipophilicity are important approaches in the preparation of muramyl dipeptide analogues with improved pharmacological properties. Mannose receptors present on immunocompetent cells are pattern-recognition receptors and by mannose ligands binding they affect the immune system. Here we present the design, synthesis and biological evaluation of novel mannosylated desmuramyl peptide derivatives. Mannose was coupled to dipeptides containing a lipophilic adamantane on N- or C- terminus through a glycolyl or hydroxyisobutyryl linker. Adjuvant activities of synthesized compounds were investigated in the mouse model using ovalbumin as an antigen. Their activities were compared to the previously described mannosylated adamantane-containing desmuramyl peptide and peptidoglycan monomer. Tested compounds exhibited adjuvant activity and the strongest enhancement of IgG production was stimulated by compound 21 (Man-OCH2-ᴅ-(1-Ad)Gly-ʟ-Ala-ᴅ-isoGln).
adamantane ; adjuvant activity ; desmuramyl peptide ; mannose
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Podaci o izdanju
15
2019.
1805-1814
objavljeno
1860-5397
1860-5397
10.3762/bjoc.15.174
Povezanost rada
Kemija, Temeljne medicinske znanosti