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Design and Synthesis of Immunostimulating Mannosylated Muropeptide Analogs Containing 2-Aminoadamantane-2- carboxylic Acid


Ribić, Rosana; Paurević, Marija; Tomić, Srđanka
Design and Synthesis of Immunostimulating Mannosylated Muropeptide Analogs Containing 2-Aminoadamantane-2- carboxylic Acid // 2nd Molecules Medicinal Chemistry Symposium: Facing Novel Challenges in Drug Discovery
Španjolska, Barcelona, 2019. str. 196-196 (poster, međunarodna recenzija, sažetak, ostalo)


Naslov
Design and Synthesis of Immunostimulating Mannosylated Muropeptide Analogs Containing 2-Aminoadamantane-2- carboxylic Acid

Autori
Ribić, Rosana ; Paurević, Marija ; Tomić, Srđanka

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

Izvornik
2nd Molecules Medicinal Chemistry Symposium: Facing Novel Challenges in Drug Discovery / - , 2019, 196-196

Skup
2nd Molecules Medicinal Chemistry Symposium: Facing Novel Challenges in Drug Discovery

Mjesto i datum
Španjolska, Barcelona, 15-17.05.2019

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
Adamantane, desmuramyl peptides, mannose, immunostimulating activity

Sažetak
Peptidoglycan fragments of well defined structures, the best known of which are muramyl peptides, have been extensively studied as possible adjuvants for human and animal vaccines. Muramyl dipeptide (MDP, N-acetylmuramyl-L-alanyl-D-isoglutamine) is known as the smallest synthetic adjuvant molecule capable of replacing whole Mycobacteria in Freund’s adjuvant.1 Mannose receptors (MR), present on immunocompetent cells (such as macrophages and dendritic cells) are considered to be pattern- recognition receptors biding compounds with mannose, N-acetylglucosamine or fucose as their essential parts. Therefore, they are responsible for the binding, among others, of mannosylated antigens or relevant biologically active molecules containing mannose, thus affecting the immune reactions.2 Up to now our research in the field of potential adjuvants was directed towards desmuramyl peptides which contain adamantylglycine and mannosylated adamantylglycine moieties bound to the essential part of MDP, L-Ala-D-isoGln.3 Here we present synthesis and biological evaluation of novel mannosylated desmuramyl peptides containing glycolyl linker. Investigation of their immunostimulating activity was conducted in vivo in mouse model using ovalbumin as an antigen. Synthesized glycopeptides showed improved immunological activity than previously described mannosylated desmuramyl peptides with (R)- hydroxyisobutyl linker.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
HRZZ-IP-2014-09-7899 - Sinteza, strukturna analiza i biološka evaluacija peptidomimetika i glikonjugata (Srđanka Tomić-Pisarović, )

Ustanove
Prirodoslovno-matematički fakultet, Zagreb,
Sveučilište J. J. Strossmayera u Osijeku,
Sveučilište Sjever, Koprivnica