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Synthesis of mannoconjugates of glycolyl desmuramyl peptides and evaluation of their immunostimulatory activity (CROSBI ID 681034)

Prilog sa skupa u zborniku | sažetak izlaganja sa skupa | međunarodna recenzija

Ribić, Rosana ; Tir, Nora ; Škalamera, Đani ; Paurević, Marija ; Tomić, Srđanka Synthesis of mannoconjugates of glycolyl desmuramyl peptides and evaluation of their immunostimulatory activity // 19th Tetrahedron Symposium. 2018. str. 30-30

Podaci o odgovornosti

Ribić, Rosana ; Tir, Nora ; Škalamera, Đani ; Paurević, Marija ; Tomić, Srđanka

engleski

Synthesis of mannoconjugates of glycolyl desmuramyl peptides and evaluation of their immunostimulatory activity

Muramyl dipeptide (MDP, MurNAc-L-Ala-D-isoGln) is an immunostimulative peptide. It is the minimal structure of bacterial cell wall peptidoglycan with immunostimulatory (adjuvant) activity.[1] However, one of the major side-effects of MDP is pyrogenicity. Therefore, numerous MDP derivatives were synthesized with the aim to avoid unwanted side-effects, and many of them have a wide variety of therapeutical potentials ; clinical uses are known as well.[2] A very important parameter in the improvement of pharmacological properties of MDP is lipophilicity, e.g. it eliminates drawbacks caused by poor macrophage penetration and rapid elimination. In our previous work, we have prepared desmuramyl peptides modified at the N- terminus with the lipophilic adamantyl group as well as their mannosylated derivatives where mannose was connected to the peptide core over a lactyl linker. These compounds showed significant immunostimulating activity in experiments in vivo. [3, 4] Mannose was introduced in order to facilitate the targeting of immune cells by surface mannose receptors. In continuation of this research, we have designed novel mannosylated desmuramyl peptides in which mannose was connected to desmuramyl peptide over O-glycosyl linker and with lipophilic adamantane introduced at the peptide N- terminus. Immunomodulating properties of synthesized peptides will be evaluated in the mice model using ovalbumin as an antigen and compared with previously prepared derivatives.

desmuramyl peptides ; mannose ; immunostimulating activity

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Podaci o prilogu

30-30.

2018.

objavljeno

Podaci o matičnoj publikaciji

19th Tetrahedron Symposium

Podaci o skupu

19th Tetrahedron Symposium

poster

26.06.2018-29.06.2018

Riva del Garda, Italija

Povezanost rada

Kemija, Temeljne medicinske znanosti