Biological activity of anomeric pairs of lipophilic glycosides of N-acetylmuramyl-L-alanyl-D-isoglutamine

Kalyuzhin, O. V.; Zemlyakov, A. E.; Kalina, N. G.; Mulik, E. L.; Kuzovlev, F. N.; Makarova, Olga

doi:10.1007/s10517-008-0157-8

Cited by 5 publications

(5 citation statements)

References 8 publications

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“…Lipophilic 1- O -acyl and 1- S -acyl groups do change MDP adjuvant activity 100 . A recent synthetic approach of O -glycoside is described in Scheme 9 101–105 . It was reported that as the aglycone carbon number increased (R= 6 d< 6 a< 6 b< 6 c), the ability of MDP derivatives to stimulate NK cytotoxic activity also increased.…”

Section: Synthetic Approach Of Mdp Analogsmentioning

confidence: 99%

Muramyl Dipeptide and its Derivatives: Peptide Adjuvant in Immunological Disorders and Cancer Therapy

Ogawa

Liu²,

Kobayashi³

2011

CBC

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Muramyl dipeptide (MDP) is a synthetic immunoreactive peptide consisting of N-acetyl muramic acid attached to a short amino acid chain of L-Ala-D-isoGln. It was first identified in bacterial cell wall peptidoglycan as an active component in Freund’s complete adjuvant. In the cell, MDP is detected by NOD2, a cytoplasmic receptor belonging to the human innate immune system. NOD2 mutations are frequently observed in patients with Crohn’s disease, an autoimmune disorder, suggesting the significance of the MDP-NOD2 pathway in activating immunity. For this reason, structural modifications of MDP and its derivatives have been extensively studied in an attempt to increase adjuvant activity and boost the immune response effectively for clinical use in the treatment of cancer and other diseases. This review summarizes the synthetic chemistry of MDP and its derivatives and discusses their pharmacological action and stereoselective synthesis.

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Section: Synthetic Approach Of Mdp Analogsmentioning

confidence: 99%

Muramyl Dipeptide and its Derivatives: Peptide Adjuvant in Immunological Disorders and Cancer Therapy

Ogawa

Liu²,

Kobayashi³

2011

CBC

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“…Mutarotation of carbohydrate anomers is a fundamental phenomenon in chemistry − and of particular importance in synthesis when stereochemically pure products are targeted. The different anomers frequently possess distinct biological activities, − but similar physicochemical properties that can hamper the isolation of each stereoisomer. Although mutarotation has been studied for many decades, it still remains difficult to predict.…”

Section: Introductionmentioning

confidence: 99%

pH-Dependent Mutarotation of 1-Thioaldoses in Water. Unexpected Behavior of (2S)-d-Aldopyranoses

Caraballo

Deng²,

Amorim³

et al. 2010

J. Org. Chem.

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The pH-dependent mutarotation of 1-thioaldopyranoses in aqueous media has been investigated. Anomerization readily occurred at lower and neutral pH for all aldopyranoses studied, whereas mainly for (2S)-D-aldopyranoses at higher pH. 1-Thio-D-mannopyranose and 1-thio-D-altropyranose showed very strong pH dependence where the anomeric equilibrium ratios changed dramatically from a preference for the β-anomer at lower pH to the α-anomer at higher pH.

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“…The effect of glycopeptides on the resistance to bacterial infection was studied on outbred albino mice aging 20-25 days and weighing 12-14 g (Stolbovaya nursery) [4]. MDP glycosides in a fi nal volume of 0.5 ml were injected intraperitoneally to animals with sepsis induced by S. aureus strain Wood 46 (do ses 0.15, 1.5, and 15 mg/kg) or Escherichia coli strain 264 (doses 3.75, 75 μg/kg, and 1.5 mg/kg).…”

Section: Methodsmentioning

confidence: 99%

“…We previously attempted to attach a cyclic structure to the glycoside site of MDP. Biological activity of glycopeptide (β-cyclohexyl glycoside of MDP and β-adamantyl glycoside of MDP) increased [5,6,7], remained unchanged, or even decreased under these conditions (α-and β-cyclododecyl glycosides of MDP) [4].Here we evaluated the capacity of new cycloalkyl glycosides of MDP to increase the resistance of mice to infections with gram-positive and gram-negative bacteria and to stimulate the production of cytokines by human mononuclear cells. …”

mentioning

confidence: 99%

Effect of Cycloalkyl Glycosides of Muramyl Dipeptide on Antibacterial Resistance of Mice and Cytokine Production by Human Mononuclear Cells

et al. 2009

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Beta-cyclohexylmethyl-, beta-cyclohexylethyl-, and beta-4-tert-butyl-cyclohexyl glycosides of muramyl dipeptide were shown to increase the resistance of mice to intraperitoneal infection with cultures of Staphylococcus aureus and Escherichia coli. These compounds increased the production of cytokines by mononuclear cells from healthy donors. Beta-cyclohexylethyl glycoside of muramyl dipeptide was more potent than muramyl dipeptide and other derivatives in increasing in vivo antibacterial resistance and in vitro production of interleukin-1beta, interleukin-6, tumor necrosis factor-alpha, and interferon-gamma;. This glycopeptide had a strong stimulatory effect on the production of interleukin-4 and tended to stimulate the synthesis of interferon-alpha. Beta-cyclohexylmethyl glycoside of muramyl dipeptide was most potent in stimulating the production of interleukin-4. Biological activity of beta-4-tert-butyl-cyclohexyl glycoside of muramyl dipeptide was lower than that of other glycosides of muramyl dipeptide.

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Biological activity of anomeric pairs of lipophilic glycosides of N-acetylmuramyl-L-alanyl-D-isoglutamine

Cited by 5 publications

References 8 publications

Muramyl Dipeptide and its Derivatives: Peptide Adjuvant in Immunological Disorders and Cancer Therapy

Muramyl Dipeptide and its Derivatives: Peptide Adjuvant in Immunological Disorders and Cancer Therapy

pH-Dependent Mutarotation of 1-Thioaldoses in Water. Unexpected Behavior of (2S)-d-Aldopyranoses

Effect of Cycloalkyl Glycosides of Muramyl Dipeptide on Antibacterial Resistance of Mice and Cytokine Production by Human Mononuclear Cells

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