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Synthesis and immunostimulating properties of lipophilic ester and ether muramyl peptide derivatives.

Abstract : Macrophages can become cytotoxic toward tumor cells when activated by immunomodulators. Three different muramyl peptides were synthesized: one hydrolyzable lipophilic ester derivative (MTP-Chol) and two nonhydrolyzable lipophilic ether derivatives (MTP-octadecane and MTP-heptadecafluorooctadecane). Activation of the RAW 264.7 cell line was studied by measuring nitrite production as an indication of NO-synthase activity. The lipophilic ester derivative, incorporated within nanocapsules, was as active as free muramyl dipeptide, whereas the lipophilic ether derivatives were unable to activate macrophages. MTP-octadecane in micellar form was not capable of inducing macrophage cytotoxicity either. These results indicate that lipophilic muramyl peptides need to be hydrolyzed to yield a hydrosoluble metabolite in order to activate macrophages.Macrophages can become cytotoxic toward tumor cells when activated by immunomodulators. Three different muramyl peptides were synthesized: one hydrolyzable lipophilic ester derivative (MTP-Chol) and two nonhydrolyzable lipophilic ether derivatives (MTP-octadecane and MTP-heptadecafluorooctadecane). Activation of the RAW 264.7 cell line was studied by measuring nitrite production as an indication of NO-synthase activity. The lipophilic ester derivative, incorporated within nanocapsules, was as active as free muramyl dipeptide, whereas the lipophilic ether derivatives were unable to activate macrophages. MTP-octadecane in micellar form was not capable of inducing macrophage cytotoxicity either. These results indicate that lipophilic muramyl peptides need to be hydrolyzed to yield a hydrosoluble metabolite in order to activate macrophages.
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https://hal.archives-ouvertes.fr/hal-00313184
Contributor : Gilbert Deleage <>
Submitted on : Wednesday, August 27, 2008 - 9:44:40 AM
Last modification on : Tuesday, November 10, 2020 - 2:04:02 PM

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G. Merhi, Aw Coleman, Jp Devissaguet, Gm Barratt. Synthesis and immunostimulating properties of lipophilic ester and ether muramyl peptide derivatives.. Journal of Medicinal Chemistry, American Chemical Society, 1996, 39, pp.4483-4488. ⟨hal-00313184⟩

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