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Syntheses and anti microbial activities of alkyl lyso phospho lipids



Syntheses and anti microbial activities of alkyl lyso phospho lipids



Chemical & Pharmaceutical Bulletin (Tokyo) 30(9): 3260-3270



Alkyl analogs (27) of lysophospholipid were synthesized and their structure-antimicrobial activity relationships were examined. These analogs differed in the structures of the long-chain alkyl moiety at position 1 and the .beta.-N-substituted aminoethylphosphoryl moiety at position 3 and in the presence or absence of the 2-methoxy group of the glycerol moiety. Many of the alkyl lysophospholipids possess antimicrobial activities much more potent than those of naturally occurring lysolecithin and lecithin against Tetrahymena pyriformis W and a variety of fungi, including human pathogens. The maximal activity was observed with 2-methyl-1-tetradecylglycero-3-phosphocholines; 1-alkyl-2-methylglycero-3-phosphocholines with longer and shorter alkyl chains tended to have lower antimicrobial activity. Alkyl lysophospholipids with pyridinioethyl instead of the choline group showed a potent antifungal activity comparable to alkyl glycerophosphocholines with the corresponding alkyl group, but a lower antiprotozoal activity. The tetradecyl congeners in these 2 classes of compounds showed potent inhibitory activity against Trichophyton spp., comparable to that of clotrimazole. Alkyl lysophospholipids with an ethanolamine moiety in the polar head group showed decreased activity. Changing the molecular backbone from glycerol to 1,3-propanediol had little effect upon the activity and the resulting 1-alkyl-2-deoxyglycerol-3-phosphocholines displayed antimicrobial properties similar to those of 1-alkyl-2-methylglycero-3-phosphocholines.

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Accession: 006559393

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PMID: 7172334



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