Design, synthesis and biological evaluation of immunostimulating mannosylated desmuramyl peptides

• Rosana Ribić,
• Ranko Stojković,
• Lidija Milković,
• Mariastefania Antica,
• Marko Cigler and
• Srđanka Tomić

Beilstein J. Org. Chem. 2019, 15, 1805–1814, doi:10.3762/bjoc.15.174

• 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). Keywords: adamantane; adjuvant activity; desmuramyl peptide; mannose; Introduction Dendritic cells capture and internalize invading pathogens. Pathogen-associated molecular patterns have been known for a long time to affect the immune system of

• TLR2 receptor, whereas MDP lacks TLR2-agonistic activity [10]. PGM and MDP have similar immunostimulating activity and they are reduced in comparison to the potent complete Freund’s adjuvant which is used as golden standard for adjuvant activity [11]. However, strong toxicity of complete Freund’s

Aminosugar-based immunomodulator lipid A: synthetic approaches

• Alla Zamyatina

Beilstein J. Org. Chem. 2018, 14, 25–53, doi:10.3762/bjoc.14.3

• requirements responsible for adjuvant activity, monophosphoryl lipid A and several analogues differing in the acylation pattern have been synthetically prepared [106][107]. The synthesis of MPLA equipped with shorter secondary acyl chains 58 was achieved via regioselective glycosylation of the primary hydroxy

• methyl glycoside 59 showed somewhat higher pro-inflammatory activity. Interestingly, attachment of varying 3-O-substitutions at position 3 of the reducing GlcN moiety in MPLA analogue 60 did not enhance the adjuvant activity [107]. Importantly, synthetic MPLA derivatives having variable acylation pattern

Triterpenoid saponins from the roots of Acanthophyllum gypsophiloides Regel

• Elena A. Khatuntseva,
• Vladimir M. Men’shov,
• Alexander S. Shashkov,
• Yury E. Tsvetkov,
• Rodion N. Stepanenko,
• Raymonda Ya. Vlasenko,
• Elvira E. Shults,
• Genrikh A. Tolstikov,
• Tatjana G. Tolstikova,
• Dimitri S. Baev,
• Vasiliy A. Kaledin,
• Nelli A. Popova,
• Valeriy P. Nikolin,
• Pavel P. Laktionov,
• Anna V. Cherepanova,
• Tatiana V. Kulakovskaya,
• Ekaterina V. Kulakovskaya and
• Nikolay E. Nifantiev

Beilstein J. Org. Chem. 2012, 8, 763–775, doi:10.3762/bjoc.8.87

• investigations into saponins, particularly concerning the study of the relationships between their structure, adjuvant activity and toxicity [5][7]. In this paper we report the isolation and structural assessment of two saponins from the roots of A. gypsophiloides Rgl. (Turkestan soap root) with the further

• . All experiments were performed in triplicate. Studies of adjuvant activity: Animals. Female Swiss mice (eight weeks old) of the C57B1/6J breed were purchased from the “Stolbovaya”, Russia, and rodent laboratory chow and tap water were provided ad libitum. Mice were maintained under a controlled