[N-acetylmuramyl-L-alanyl-D-isoglutamine glycosides. Effect of glycoside center configuration and aglycone nature on biological activity].
Hexyl, octyl, and cyclohexyl beta-glycosides and heptyl and cyclohexyl alpha-glycosides of muramyl dipeptide (MDP) were synthesized. Tests in vitro and in vivo revealed lower immunostimulating activities of MDP alpha-glycosides in comparison with the corresponding beta-glycosides and MDP itself. In the case of alkyl beta-glycosides, differences in hydrocarbon chain lengths (C4-C8) and in aglycone (aliphatic chain and aliphatic or aromatic ring) exerted no substantial effect on the immunostimulating activity.
Zemliakov
A E
AE
Vernadsky Tauriyan National University, ul. Yaltinskaya 4, Simferopol, 95007 Ukraine.
Tsikalov
V V
VV
Kaliuzhin
O V
OV
Kur'ianov
V O
VO
Chirva
V Ia
VIa
D000119:Acetylmuramyl-Alanyl-Isoglutamine / Q000737:chemistry* / Q000494:pharmacology; D000276:Adjuvants, Immunologic / Q000737:chemistry* / Q000494:pharmacology*; D000818:Animals; D001671:Biochemistry / Q000379:methods; D004317:Doxorubicin / Q000031:analogs & derivatives* / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry* / Q000494:pharmacology; D007375:Interleukin-1 / Q000378:metabolism; D007376:Interleukin-2 / Q000378:metabolism; D017737:Macrophages, Peritoneal / Q000187:drug effects / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008810:Mice, Inbred C57BL; D015394:Molecular Structure; D010538:Peritonitis / Q000188:drug therapy / Q000276:immunology; D012480:Salmonella Infections / Q000188:drug therapy / Q000276:immunology; D013154:Spleen / Q000166:cytology / Q000187:drug effects / Q000378:metabolism; D013329:Structure-Activity Relationship; D014409:Tumor Necrosis Factor-alpha / Q000378:metabolism
D000276:Adjuvants, Immunologic; D006027:Glycosides; D007375:Interleukin-1; D007376:Interleukin-2; D014409:Tumor Necrosis Factor-alpha; C074869:7-deoxy-13-dihydroadriamycinone; D000119:Acetylmuramyl-Alanyl-Isoglutamine; D004317:Doxorubicin