Nmr and molecular dynamics study of four carbocyclic muramyl dipeptide analogues

Biopolymers ◽  
1993 ◽  
Vol 33 (7) ◽  
pp. 1149-1157 ◽  
Author(s):  
P. Pristov?ek ◽  
J. Kidri? ◽  
J. Mavri ◽  
D. Had?I
Keyword(s):  
Molecular Dynamics ◽  
Muramyl Dipeptide ◽  
Dipeptide Analogues

Muramyl-dipeptide analogues: Synthesis and biological activities

1988 ◽  
Vol 53 (11) ◽  
pp. 2897-2906 ◽  
Author(s):  
Jan Ježek ◽  
Milan Zaoral ◽  
Miloš Buděšínský ◽  
Jiří Günther ◽  
Jiří Rotta
Keyword(s):  
Biological Activities ◽  
Muramyl Dipeptide ◽  
Delayed Hypersensitivity ◽  
Test Compound ◽  
Active Compounds ◽  
Dipeptide Analogues ◽  
Pyrogenic Activity

In the search for immunoadjuvant active compounds without pyrogenic activity we prepared N-Ac-norMur-L-Abu-D-Gln-O-Bu (V), N-Ac-Mur-L-Abu-D-Gln-O-Bu (VII) and their respective α-benzylglycosides VI and VIII. All the prepared compounds are nonpyrogenic. In the delayed hypersensitivity test, compound V is inactive, VI is comparable to MDP, VII is more and VIII is less active than MDP.

scholarly journals Design, synthesis and biological evaluation of immunostimulating mannosylated desmuramyl peptides

2019 ◽  
Vol 15 ◽  
pp. 1805-1814 ◽  
Author(s):  
Rosana Ribić ◽  
Ranko Stojković ◽  
Lidija Milković ◽  
Mariastefania Antica ◽  
Marko Cigler ◽  
...  
Keyword(s):  
Muramyl Dipeptide ◽  
Biological Evaluation ◽  
Adjuvant Activity ◽  
Design Synthesis ◽  
C Terminus ◽  
Minimal Structure ◽  
Dipeptide Analogues ◽  
Peptide Derivatives ◽  
Mannose Receptors ◽  
Synthesis And Biological Evaluation

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).

Mannosylated adamantane-containing desmuramyl peptide recognition by NOD2 receptor: a molecular dynamics study

2021 ◽  
Author(s):  
Aleksandra Maršavelski ◽  
Marija Paurević ◽  
Rosana Ribic
Keyword(s):  
Molecular Dynamics ◽  
Muramyl Dipeptide ◽  
Nucleotide Binding ◽  
Peptide Recognition ◽  
Intracellular Receptor ◽  
Bacterial Peptidoglycan ◽  
Oligomerization Domain

Nucleotide-binding oligomerization domain 2 (NOD2) is an intracellular receptor that recognizes the bacterial peptidoglycan fragment, muramyl dipeptide (MDP). Our group has synthesized and biologically evaluated desmuramyl peptides containing adamantane and...

scholarly journals Advances in Desmuramyl Peptide Research

2019 ◽  
Vol 92 (2) ◽  
pp. 153-161 ◽  
Author(s):  
Rosana Ribić ◽  
Marija Paurević ◽  
Srđanka Tomić
Keyword(s):  
Structural Unit ◽  
Muramyl Dipeptide ◽  
Receptor Activation ◽  
Pharmacological Properties ◽  
Future Design ◽  
Immune Adjuvants ◽  
Dipeptide Analogues ◽  
Pathogen Recognition Receptor ◽  
Multiple Pathogen ◽  
Recognition Receptor

Immune adjuvants are added to vaccines in order to enhance the immune response to an antigen. Muramyl dipeptide, N-acetylmuramyl-L-alanyl-D-isoglutamine, is the smallest structural unit of peptidoglycans showing the immunostimulating activity. Muramyl dipeptide analogues without the hydrophilic N-acetylmuramyl moiety are called desmuramyl peptides. Here, we provide review of desmuramyl peptides which were synthesized in order to improve the pharmacological properties of parent muramyl dipeptide, including our results regarding adamantane containing derivatives. Approach for future design of novel immunostimulators based on multiple pathogen recognition receptor activation was also considered.

A conformational analysis of mouse Nalp3 domain structures by molecular dynamics simulations, and binding site analysis

2014 ◽  
Vol 10 (5) ◽  
pp. 1104-1116 ◽  
Author(s):  
Bikash R. Sahoo ◽  
Jitendra Maharana ◽  
Gopal K. Bhoi ◽  
Santosh K. Lenka ◽  
Mahesh C. Patra ◽  
...  
Keyword(s):  
Molecular Dynamics ◽  
Free Energy ◽  
Conformational Analysis ◽  
Molecular Dynamics Simulations ◽  
Binding Site ◽  
Muramyl Dipeptide ◽  
Free Energy Calculations ◽  
Site Analysis ◽  
Domain Structures ◽  
Dynamics Simulations

A binding site analysis of adenosine triphosphate, muramyl dipeptide and imidazoquinoline, with mouse Nalp3 domains and free energy calculations.

Induction of tumoricidal macrophages and production of cytokines by synthetic muramyl dipeptide analogues

Vaccine ◽  
1988 ◽  
Vol 6 (3) ◽  
pp. 238-244 ◽  
Author(s):  
Ikuo Salki ◽  
Shinji Saito ◽  
Chiharu Fujita ◽  
Hideharu Ishida ◽  
Joji Iida ◽  
...  
Keyword(s):  
Muramyl Dipeptide ◽  
Dipeptide Analogues

scholarly journals Design, synthesis and biological evaluation of immunostimulating mannosylated desmuramyl peptides

2019 ◽  
Author(s):  
Rosana Ribić ◽  
Ranko Stojković ◽  
Lidija Milković ◽  
Mariastefania Antica ◽  
Marko Cigler ◽  
...  
Keyword(s):  
Muramyl Dipeptide ◽  
Biological Evaluation ◽  
Adjuvant Activity ◽  
Design Synthesis ◽  
C Terminus ◽  
Minimal Structure ◽  
Dipeptide Analogues ◽  
Peptide Derivatives ◽  
Present Design ◽  
Synthesis And Biological Evaluation

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 design, synthesis and biological evaluation of novel mannosylated desmuramyl peptide derivatives. Mannose was coupled to dipeptide containing lipophilic adamantane on N- or C-terminus through 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 the compound 21 (Man-OCH2-D-(1-Ad)Gly-L-Ala-D-isoGln).

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