title: N-[trans-2-[[2'-(acetylamino)cyclohexyl]oxy]acetyl]-L-alanyl-D-glutamic acid: a novel immunologically active carbocyclic muramyl dipeptide analogue.
abstract: A novel non-pyrogenic carbocyclic muramyl dipeptide (MDP) analogue, N-¿trans-2-[[2'-(acetylamino)cyclohexyl]oxy]acetyl¿-L-alanyl-D-glutamic acid, was obtained by replacement of the N-acetylmuramic acid part and the D-isoglutamine residue of the MDP molecule by a trans-2-[[2'-(acetylamino)cyclohexyl]oxy]acetyl moiety and D-glutamic acid, respectively. The title compound was selected as a promising candidate for further evaluation among several related analogues on the basis of an immunorestoration test in mice. This novel nor-MDP analogue protects mice against the immunosuppressive effect of cyclophosphamide and increases the nonspecific resistance of mice against fungal infection. It is an immunomodulator which enhances the maturation of lymphocytes B to plasma cells and increases the activity of lymphocytes B and lymphocytes T as well as that of macrophages but does not alter the number of these cells.
authors.affiliation: Faculty of Pharmacy, University of Ljubljana, Slovenia.
authors.forename: D
authors.initials: D
authors.lastname: Kikelj
authors.forename: S
authors.initials: S
authors.lastname: Pecar
authors.forename: V
authors.initials: V
authors.lastname: Kotnik
authors.forename: A
authors.initials: A
authors.lastname: Stalc
authors.forename: B
authors.initials: B
authors.lastname: Wraber-Herzog
authors.forename: S
authors.initials: S
authors.lastname: Simcic
authors.forename: A
authors.initials: A
authors.lastname: Ihan
authors.forename: L
authors.initials: L
authors.lastname: Klamfer
authors.forename: L
authors.initials: L
authors.lastname: Povsic
authors.forename: R
authors.initials: R
authors.lastname: Grahek
authors.forename: E
authors.initials: E
authors.lastname: Suhadolc
authors.forename: M
authors.initials: M
authors.lastname: Hocevar
authors.forename: H
authors.initials: H
authors.lastname: Hönig
authors.forename: R
authors.initials: R
authors.lastname: Rogi-Kohlenprath
mesh_terms: D000119:Acetylmuramyl-Alanyl-Isoglutamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000276:Adjuvants, Immunologic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D001402:B-Lymphocytes / Q000166:cytology / Q000187:drug effects / Q000276:immunology*; D003520:Cyclophosphamide / Q000633:toxicity; D005260:Female; D007108:Immune Tolerance / Q000187:drug effects; D007166:Immunosuppressive Agents / Q000633:toxicity; D007202:Indicators and Reagents; D008213:Lymphocyte Activation / Q000187:drug effects; D008264:Macrophages / Q000187:drug effects / Q000276:immunology*; D051379:Mice; D008815:Mice, Inbred Strains; D008958:Models, Molecular; D015394:Molecular Structure; D010950:Plasma Cells / Q000187:drug effects / Q000276:immunology*; D013154:Spleen / Q000276:immunology; D013237:Stereoisomerism; D013601:T-Lymphocytes / Q000187:drug effects / Q000276:immunology*
chemical_list: D000276:Adjuvants, Immunologic; D007166:Immunosuppressive Agents; D007202:Indicators and Reagents; C110783:N-trans-2-((2-(acetylamino)cyclohexyl)acetyl)-alanyl-glutamic acid; D000119:Acetylmuramyl-Alanyl-Isoglutamine; D003520:Cyclophosphamide