+ Site Statistics
+ Search Articles
+ Subscribe to Site Feeds
EurekaMag Most Shared ContentMost Shared
EurekaMag PDF Full Text ContentPDF Full Text
+ PDF Full Text
Request PDF Full TextRequest PDF Full Text
+ Follow Us
Follow on FacebookFollow on Facebook
Follow on TwitterFollow on Twitter
Follow on LinkedInFollow on LinkedIn

+ Translate

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.

(PDF 0-2 workdays service: $29.90)

Accession: 006559393

Download citation: RISBibTeXText

PMID: 7172334

Related references

Metastatic growth of lewis 3ll lung carcinoma in mice treated with alkyl lyso phospho lipids and lyso phospho lipid induced peritoneal macrophages. Anticancer Research 1(6): 397-402, 1981

Failure to detect mutagenic effects of anti tumor alkyl lyso phospho lipids. Cancer Letters 12(3): 217-222, 1981

The effect of alkyl lyso phospho lipids on synthesis of phospho lipids in cultured leukemic cells. Experimental Hematology (Charlottesville) 11(SUPPL 14): 43, 1983

Studies on the correlation between the cyto toxic effect of alkyl lyso phospho lipids on rat brain tumor cells and their low content of alkyl cleavage enzyme. Onkologie 6(5): 262, 1983

Human macrophage activation by alkyl lyso phospho lipids. Immunobiology 156(3): 255, 1979

The mechanism of action of alkyl lyso phospho lipids on 2 cell lines hl 60 and k 562. Medical & Pediatric Oncology 9(1): 97, 1981

Permeability properties of liposomes prepared from di acyl phospho lipids di alkoxy phospho lipids di alkyl phospho lipids acylalkoxy phospho lipids with and without cholesterol. Papahadjopoulos, Demetrios (Ed ) Annals Of The New York Academy Of Sciences, Vol 308 Liposomes And Their Uses in Biology And Medicine Conference New York, N Y , Usa, Sept 14-16, 1977 V+462p Illus The New York Academy Of Sciences: New York, N Y , Usa Isbn 0-89072-063-0 441, 1978

Various parameters influencing leukemic cell destruction by alkyl lyso phospho lipids. Anticancer Research 2(1-2): 95-100, 1982

Selective destruction of human leukemic cells by alkyl lyso phospho lipids. Cancer Research 38(11 PART 1): 3894-3899, 1978

The effects of alkyl lyso phospho lipids on the human leukemic cell cultures hl 60 and k 562. Proceedings of the American Association for Cancer Research & American Society of Clinical Oncology 22: 237, 1981

Response of acute myelo monocytic leukemia to alkyl lyso phospho lipids. Blut 44(3): 177-186, 1982

Alkyl lyso phospho lipids in the treatment of autochthonous rat colonic adeno carcinomas. Journal Of Cancer Research & Clinical Oncologyuppl: S45, 1984

Halo lipids 5. synthesis nmr spectra and cytostatic properties of halo analogs of alkyl lyso phospho lipids. Chemistry and Physics of Lipids 31(1): 33-52, 1982

Influence of various synthetic alkyl lyso phospho lipids on tumor cells erythrocytes and platelets. Journal de Pharmacologie (Paris) 14(SUPPL 1): 50, 1983

Alkyl lyso phospho lipids inhibit growth of hyper nephroid carcinomas in vitro. Journal of Cancer Research & Clinical Oncology 101(3): 325-330, 1981