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

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

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
19th Tetrahedron Symposium / - , 2018, 30-30

Skup
19th Tetrahedron Symposium

Mjesto i datum
Riva del Garda, Italija, 26.06.2018. - 29.06.2018

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
desmuramyl peptides ; mannose ; immunostimulating activity

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Temeljne medicinske znanosti

POVEZANOST RADA