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Zemlyakov, A. E.; Tsikalov, V. V.; Kur'yanov, V. O.; Chirva, V. Ya.; Бовин, Н. В.

doi:10.1023/a:1012940803366

Cited by 6 publications

(7 citation statements)

References 5 publications

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“…The activity of β-2-(p-biphenyl)ethyl- 3.54ddd (10) 3.80ddd (10.5) 3.74ddd (10.5) 3.86ddd (10) 3.79ddd (10.5) H3 (J 3,4 ) 5.37dd (9.5) 5.32dd (9.5) 5.25dd (9.5) 5.26dd (9.5) 5.37dd (9.5) H4 (J 4,5 ) 4.98dd (9.5) 5.07dd (9.5) 5.05dd (9.5) 5.08dd (9.5) 5.08dd (9.5) H5 (J 5,6a ; J 5,6b ) 3.64ddd (2.5; 5) 3.70ddd ( Cl 3 * MDP (VIId) decreased with a decrease in the immunomodulator dose, whereas that of β-2,2-diphenylethyl-MDP (VIIc) dramatically increased. Previously, we synthesized [16] β-n-(1,1,3,3-tetramethylbutyl)phenyl MDP (VIIg), a glycopeptide with alkylphenyl aglycone also containing 14 carbon atoms; in general, it proved to be more active than glycosides (VIIc) and (VIId). β-2-(Adamant-1-yl)ethyl MDP (VIIb) demonstrated a moderate protective effect, whereas β-4-tertbutylcyclohexyl MDP (VIIa) exhibited the lowest immunostimulating activity among all the compounds.…”

Section: Resultsmentioning

confidence: 99%

“…The glycosides of N -acetylmuramyl-L -alanyl-Disoglutamine (muramyl dipeptide) with various ë 4 -ë 8 aglycones have been shown to exhibit amphiphilic properties and high immunostimulating activity in various tests in vitro and in vivo [1,2]. 2 In contrast, the glycosides with predominating lipophylic properties have not been studied methodically.…”

Section: Introductionmentioning

confidence: 99%

“…2 In contrast, the glycosides with predominating lipophylic properties have not been studied methodically. However, some experiments [3,4] indicated that β -hexadecyl MDP [5], β -(2,3-didodecyloxypropyl) MDP [6], and β -cholesteryl MDP [7] activate immune reactions more effectively than MDP itself.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Protective Activity of β-Glycosides of N-Acetylmuramyl-L-Alanyl-D-Isoglutamine with Alkylalicyclic and Arylaliphatic Aglycons

et al. 2005

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The following glycosides of N -acetylmuramyl-L -alanyl-D -isoglutamine (MDP) were synthesized: β -4-tert -butylcyclohexyl MDP, β -2-(adamant-1-yl)ethyl MDP, β -2,2-diphenylethyl MDP, and β -2-( p -biphenyl)ethyl MDP. The starting peracetylated β -N -acetylglucosaminides were prepared by the oxazoline method. They were converted into 4,6-O -isopropylidene-N -acetyl-D -muramic acids, which were coupled with L -Ala-D -Glu(NH 2 )OBn. The target glycopeptides were obtained after their deprotection. The stimulation of the antiinfection resistance of mice against Staphylococcus aureus by the MDP glycosides was studied.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and Protective Activity of β-Glycosides of N-Acetylmuramyl-L-Alanyl-D-Isoglutamine with Alkylalicyclic and Arylaliphatic Aglycons

et al. 2005

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“…1) [1]. Unmodifi ed MDP was synthesized [10] and served as the reference agent in all biological tests.…”

Section: Methodsmentioning

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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“…1). The methods of synthesis and chemical characteristics of substances were described previously [2]. Unmodified MDP was synthesized as described elsewhere [1] and served as the reference preparation.…”

Section: Methodsmentioning

confidence: 99%

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

et al. 2008

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We studied the capacity of anomeric pairs of alpha- and beta-dodecyl, alpha- and beta-(1-pentylhexyl), and alpha- and beta-cyclododecyl glycosides of N-acetylmuramyl-L-alanyl-D-isoglutamine (muramyl dipeptide) to stimulate the nonspecific resistance of mice to intraperitoneal infection of Staphylococcus aureus and Escherichia coli cultures. Intraperitoneal pretreatment with the test substances in a wide dose range increased survival of infected animals. No differences were found between the biological effects of alpha- and beta-dodecyl and alpha- and beta-(1-pentylhexyl) glycosides of muramyl dipeptide. An inverse relationship was found between stimulatory activity and dose of alpha- and beta-cyclododecyl glycosides of muramyl dipeptide during sepsis caused by Staphylococcus aureus.

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Cited by 6 publications

References 5 publications

Synthesis and Protective Activity of β-Glycosides of N-Acetylmuramyl-L-Alanyl-D-Isoglutamine with Alkylalicyclic and Arylaliphatic Aglycons

Synthesis and Protective Activity of β-Glycosides of N-Acetylmuramyl-L-Alanyl-D-Isoglutamine with Alkylalicyclic and Arylaliphatic Aglycons

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

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

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