Comparison of Biological Activities of Chemically Synthesized Monosaccharide Analogues of Reducing and Nonreducing Sugar Moieties of Lipid A(Blological)

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The antitumor activity against ascites form of Ehrlich carcinoma, the lethal toxicity, and the mitogenicity of five chemically synthesized acylated 4-O-monophosphoryIglucosamine derivatives, as analogues of the nonreducing sugar moiety of lipid A, were compared with those of synthesized lipid X (2,3-diacyl-1-O-monophosphorylglucosamine) and lipid Y (2-acyloxyacyl-3-acyl-1-O-monophosphorylglucosamine), as analogues of the reducing sugar moiety. Although the antitumor activity of the 4-O-monophosphorylglucosamine derivatives was weaker than that of natural lipopolysaccharide, compound A-103 with di-3-tetradecanoyloxytetradecanoyl (C_<14>-O-C_<14>) at the C-2 and C-3 positions, and compound A-104 with di-3-dodecanoyIoxytetradecanoyl (C_<14>-O-C_<12>), showed activity, whereas compounds A-101 (di-3-hexadecanoyloxytetradecanoyl) and A-105 (C_<14>-O-C_<12> and C_<14>-O-C_<14>) were less effective. However, lipid X and A-102 (2,3-di-tetradecanoyl) did not possess antitumor activity. Four derivatives of 4-O-monophosphorylglueosamtne, but not A-102, exhibited lethal toxicity on intravenous injection of a high dose (50μg/mouse) into C57BL/6 mice loaded with galactosamine, and had little or no mitogenic activity toward splenocytes from C57BL/6 mice. On the other hand, lipid X and lipid Y did not show lethal toxicity and lipid X induced a significant inhibition of deoxyribonucleic acid (DNA) synthesis in a mitogenicity test. These findings suggest that the nonreducing sugar moiety of lipid A has more potent biological activities than the reducing sugar moiety.
1986-12-25

Comparison of Biological Activities of Chemically Synthesized Monosaccharide Analogues of Reducing and Nonreducing Sugar Moieties of Lipid A(Blological)

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