Skip to main content

Lysophosphatidylcholine (lysolecithin) and its synthetic analogues. Immunemodulating and other biologic effects

This is a preview of subscription content, access via your institution.

Abbreviations

LPC:

2-lysophosphatidylcholine (lysolecithin)

3-PC:

3-sn-phosphatidylcholine (lecithin)

3-PE:

3-sn-phospliatidylethanolamine (kephalin)

PEC:

Peritoneal cell

DMEM:

Dulbecco's modified Eagle's medium

PBS:

Phospahte buffered saline

FA:

Fatty acids

FCA:

Freund's complete adjuvant

BGG:

Bovine gamma globulin

BSA:

Bovine serum albumin

PFC:

Plaque forming cell

SRBC:

Sheep red blood cells

Cy:

Cyclophosphamide

ALP:

Alkyl-lysophospholipids

DTH:

Delayed type hypersensitivity

References

  1. Andreesen, R., Modolell, M., Weltzien, H. U., Eibl, H., Common, H. H., Löhr, G. W., Munder, P. G.: Selective destruction of human leukemic cells by alkyl-lysophospholipids. Cancer Res.38, 3894 (1978)

    PubMed  Google Scholar 

  2. Andreesen, R., Modolell, M., Munder, P. G.: Alkyl-lysophospholipids as new antimetabolites selective for human leukemic cells. Proceedings of the XII. Int. Cancer Congress, Buenos Aires, Vol.3, p. 241, 1978

    Google Scholar 

  3. Arnold, B., Miller, J.F.A.P., Weltzien, H. U.: Lysolecithin analogs as adjuvants in delayed type hypersensitivity in mice. I. Characterization of the adjuvant effect. Eur. J. Immunol. (in press, 1979)

  4. Arnold, D., Weltzien, H. U.: Über die strukturabhängige hämolytische Aktivität einiger Cholin-Phosphatide. Z. Naturforsch. [C]23 b, 675 (1968)

    Google Scholar 

  5. Arnold, B., Reuther, R., Weltzien, H. U.: Distribution and metabolism of synthetic alkyl-analogs of lysophosphatidylcholine in mice. Biochim. Biophys. Acta530, 47 (1978)

    PubMed  Google Scholar 

  6. Aunis, D., Pescheloche, M., Zwiller, J., Mandel, P.: Effect of lysolecithin on adenylate cyclase and guanylate cyclase activities in bovine adrenal medullary plasma membranes. J. Neurochem.31, 355 (1978)

    PubMed  Google Scholar 

  7. Barton, M. A., Diener, E.: Anew perspective on B cell triggering: Control of the immune response by organizational changes in the lipid bilayer. Transplant. Rev.23, 5 (1975)

    PubMed  Google Scholar 

  8. Bausert, W.: Der Einfluß von synthetischen Lysolecithin-Analoga auf das Wachstum experimenteller Tumoren der Maus. Thesis, University of Freiburg i. Br. 1978

  9. Berdel, W.: Metastasierung des 3-Lewis Lungenkarzinoms (3-LL) unter dem Einfluß von Lysophospholipiden und Lysophospholipidaktivierten Makrophagen. Thesis, University of Freiburg i. Br. 1979

  10. Berdel, W., Bausert, W., Weltzien, H, U., Modolell, M., M under, P. G.: Metastatic growth of 3-Lewis lung carcinoma treated with alkyl-lysophospholipids and lysophospholipid activated macrophages. J. Natl. Cancer Inst. (in press 1979)

  11. Bell, D. P.: Lipoprotein lipid exchange in biological system, In: Low density lipoproteins, Day, C. E., Levy, R. S., ed., pp, 111–126, New York: Plenum Press 1976

    Google Scholar 

  12. Bergenhem, B., Fahraeus, R.: Über spontane Hämolysinbildung im Blut unter besonderer Berücksichtigung der Physiology der Milz. Z. Ges. Exp. Med.97, 555 (1936)

    Google Scholar 

  13. Betz, O. M,: Untersuchungen zur Immunmodulation durch Lysophospholipide. Thesis, University of Freiburg i. Br. 1979

  14. Blattmann, R. B.: Untersuchungen in vitro zum Wirkungsmechanismus von Lysophosphatiden auf das Wachstum experimenteller Tumoren, Thesis, University of Freiburg i. Br. 1977

  15. Brash, J. L., Lyman, D. J.: The adsorption of proteins and lipids to non-biological surfaces, In: The chemistry of biosurfaces. Hair, M. L., ed., pp. 177–232, New York: Marcell Dekker Inc. 1971

    Google Scholar 

  16. Burdzy, K., Munder, P. G., Fischer, H., Westphal, O.,: Steigerung der Phagocytose von Peritonealmakrophagen durch Lysolecithin. Z. Naturforsch, [C]19b, 1118 (1964)

    Google Scholar 

  17. Cotran, R. S., Majno, G.: A light and electron microscopic analysis of vascular injury. Ann. N, Y. Acad. Sci.116, 750 (1964)

    Google Scholar 

  18. Dresser, D. W.: Adjuvanticity of vitamin A, Nature217, 527 (1966)

    Google Scholar 

  19. Dresser, D. W.: Effectiveness of lipid and lipidophilic substances as adjuvants, Nature191, 1169 (1961)

    PubMed  Google Scholar 

  20. Elsbach, P., van den Berg, J. W. O., van den Bosch, H., van Deenen, L. L. M.: Metabolism of phospholipids by polymorphonuclear leukocytes. Biochim. Biophys. Acta106, 338 (1965)

    PubMed  Google Scholar 

  21. Ferber, E., Resch, K.: Structure and physiologic role of lipids in the lymphocyte membrane. In: The lymphocyte: Structure and function, Marchalonis, J., ed., pp. 593–620. New York: Marcell Dekker Inc. 1977

    Google Scholar 

  22. Fischer, H., Haupt, I.: Das cytolysierende Prinzip von Serumkomplement Z. Naturforsch.16b, 321 (1961)

    Google Scholar 

  23. Freudenberg, M. A,: Über den Einfluß von Lysolezithin und von synthetischen Lysolezithinanaloga auf die Stimulierung von Lymphozyten in Vitro, Thesis, Universität of Freiburg 1974

  24. Gillett, M. P. T., Besterman, E. M. M.: Plasma concentrations of lysolecithin and other phospholipids in the healthy population and in men suffering from atherosclerotic diseases. Atherosclerosis22, 111 (1975)

    PubMed  Google Scholar 

  25. Goerke, J., de Gier, J., Bonsen, P. P. M.: Silica gel stimulates the hydrolysis of lecithin by phospholipase A. Biochim. Biophys. Acta248, 245 (1971)

    PubMed  Google Scholar 

  26. Haley, J. E., Stefano, G. B., Catapane, E. J.: Correlation between acidic phospholipids and serotonin and between lysolecithin and dopamine in ganglia of the marine musselMytilus edulis. Experientia34, 210 (1977)

    Google Scholar 

  27. Hill, E. E., Lands, W. E. M.: Phospholipid metabolism, In: ‘Lipid metabolism’; Wakil, S. J., ed., pp. 185–277, London, New York: Academic Press 1970

    Google Scholar 

  28. Joist, J. H., Dolezel, G., Cucuianu, M. P., Nishizawa, E. E., Mustard, J. F.: Inhibition and potentiations of platelet function by lysolecithin. Blood49, 101 (1977)

    PubMed  Google Scholar 

  29. Kirschbaum, R. B., Bosmann, H. B.: Lysolecithin enhancement of glycoprotein: glycosyltransferase activity. FEBS Lett.34, 129 (1973)

    PubMed  Google Scholar 

  30. Klibansky, C., de Vries, A.: Quantitative study of erythrocyte-lysolecithin interaction. Biochim. Biophys. Acta70, 176 (1963)

    PubMed  Google Scholar 

  31. Klibansky, C., Smorodinsky, I., de Vries, A.: Action of lysolecithin on normal and leukemic human leukocytes. Med. Pharmacol. Exp.16, 297 (1967)

    Google Scholar 

  32. Lagrange, P. H., Mackaness, G. B., Miller, T. E.: Potentiation of T-cell-mediated immunity by selective suppression of antibody formation with cyclophosphamide. J. Exp. Med.139, 1529 (1974)

    PubMed  Google Scholar 

  33. Langer, W.: Untersuchungen zum Wirkungsmechanismus immunologischer Adjuvantien. Thesis, University of Freiburg i. Br. 1973

  34. Lebert, St,: Biochemische Untersuchungen zum Einfluß von SiO2-Modifikationen auf den Phospholipidstoffwechsel von Makrophagen. Thesis, University of Freiburg i. Br. 1975

  35. Lyn, Y. N., Wassef, M. K., Horowitz, M. I.: Effect of aspirin and salicylic acid on phospholipid metabolizing enzymes. Fed. Proc.37, 1832 (1978)

    Google Scholar 

  36. Marikovsky, Y., Brown, C. S., Weinstein, R. S., Wortis, H. H.: Effects of lysolecithin on the surface properties of human erythrocytes. Exp. Cell Res.98, 313 (1976)

    PubMed  Google Scholar 

  37. Metcalf, D.: Hemopoietic colonies. Recent Results Cancer Res.61, 1 (1977)

    Google Scholar 

  38. Middleton, E. Jr., Phillips, G. B.: Effect of lysolecithin on the smooth muscle stimulating activity of histamine, acetylcholine, 5-hydroxy-tryptamine, anaphylactic slow-reacting substance and bradykinin. Nature198, 758 (1963)

    PubMed  Google Scholar 

  39. Mitchison, N. A.: The immunogenic capacity of antigen taken up by peritoneal exudate cells. Immunology16, 1 (1969)

    PubMed  Google Scholar 

  40. Modolell, M., Andreesen, R., Pahlke. W., Brugger, U., M under, P. G.: Disturbance of phospholipid metabolism during the selective destruction of tumor cells induced by alkyl-lysophospholipids. Cancer Res. (in press, 1979)

  41. Modolell, M., Krause-Jauer, M., Munder, P. G.: Oxygen tension and pH as critical parameters for the cytotoxicity of macrophages. Proceedings of the XII. Int. Cancer Congress, Buenos Aires, Vol. 1, p. 163, 1978

    Google Scholar 

  42. Mookerja, S., Yung, J. W. M.: A study on the effect of lysolecithin and phospholipase A on membrane-bound galactosyltransferase. Can. J. Biochem.52, 1053 (1974)

    PubMed  Google Scholar 

  43. Mookerja, S., Yung, J. W. M.: Stimulation of galactosyltransferase in liver microsome by lysolecithin. Biochem. Biophys. Res. Commun.57, 815 (1974)

    PubMed  Google Scholar 

  44. Munder, P. G., Ferber, E., Fischer, H.: Lysophosphatide und Zellmembran. Untersuchungen über die Abhängigkeit der cytolytischen Wirkung des Lysolecithin von Membranenzymen. Z. Naturforsch. [C]206, 1048 (1965)

    Google Scholar 

  45. Munder, P. G., Modolell, M., Ferber, E., Fischer, H.: Phospholipoide in quarzgeschliäigten Makrophagen. Biochem. Z.344, 310 (1966)

    PubMed  Google Scholar 

  46. Munder, P. G., Modolell, M., Ferber, E., Fischer, H.: The relationship between macrophages and adjuvant activity. In: Mononuclear phagocytes, v. Furth, R., ed., pp. 445–460. Oxford: Blackwell Scientific Publications 1970

    Google Scholar 

  47. Munder, P. G., Modolell, M., Wallach, D. F. H.: Cell propagation on films of polymeric fluorocarbon as a means to regulate pericellular pH and pO2 in cultured monolayers. FEBS Lett.15, 191 (1971)

    PubMed  Google Scholar 

  48. Munder, P. G., Modolell, M., Reatz, W., Lockenbach, G. A.: Primary antibody formation in vitro by mouse cells in a complete homologous system. Eur. J. Immunol.3, 454 (1973)

    PubMed  Google Scholar 

  49. Munder, P. G., Modolell, M.: The influence of mycobacterium bovis and corynebacterium parvum on the phospholipid metabolism of macrophagges. Recent Results Cancer Res.47, 244 (1974)

    Google Scholar 

  50. Munder, P. G., Fischer, H., Weltzien, H. U., Oettgen, H. W., Westphal, O.: Lysolecithin analogs: a new class of immunopotentiators with antitumor activity. Proc. Am. Assoc. Cancer Res.17, 174 (1976)

    Google Scholar 

  51. Munder, P. G., Weltzien, H. U., Modolell, M.: Lysolecithin analogs: anew class of immunopotentiators. In: Immunopathology, VIIth Int. Symposium, Miescher, P. A., ed., pp. 411–424. Basel: Schwabe and Co. 1976

    Google Scholar 

  52. Munder, P. G., Jansen, A., Andreesen, R., Modolell, M.: Synthetic lysophosphatides as inducers of macrophages cytotoxicity. Proceedings of the XII. Int. Cancer Congress. Buenos Aires. Vol. 1, p. 166, 1978

    Google Scholar 

  53. Nakano, K., Muramatsi, S.: Studies on the role of macrophages in the antibody response of mice: stimulation of T cell dependent antibody responses by tolerogenic soluble antigen trapped by macrophages. J. Reticuloenothel. Soc.19, 347 (1976)

    Google Scholar 

  54. Old, L. J., Boyse, E. A., Clarke, D. A., Carswell, E.: Antigenic properties of chemically induced tumors. Ann. N. Y. Acad. Sci.101, 80 (1962)

    Google Scholar 

  55. O'Doherty, P. J. A., Smith, N. B., Kuksis, A.: Stimulation of CDP-choline biosynthesis by enantiomeric lysophosphatidylcholines in rat intestinal mucosa. Arch. Biochm.180, 10 (1977)

    Google Scholar 

  56. Perkins, E. H.: Digestion of antigen by peritoneal macrophages. In: Mononuclear phagocytes, v. Furth, R., ed., pp. 562–578. Oxford: Blackwell Scientific Publications 1970

    Google Scholar 

  57. Pernis, B., Paronetto, F.: Adjuvant effect of silica (trydimite) on antibody production. Proc. Soc. Exp. Biol.110, 390 (1962)

    Google Scholar 

  58. Poole, A. R., Howell, J. I., Lucy, J. A.: Lysolecithin and cell fusion. Nature227, 810 (1970)

    PubMed  Google Scholar 

  59. Portman, P. W., Alexander, M.: Influence of lysophosphatidylcholine on the metabolism of plasma lipoproteins. Biochim. Biophys. Acta450, 322 (1976)

    PubMed  Google Scholar 

  60. Rakhit, S.: On the structure of the renin inhibitor from hog kidney. Can. J. Biochem.49, 1012 (1971)

    PubMed  Google Scholar 

  61. Rampone, A. J., Long, L. R.: The effect of phosphatidylcholine and lysophosphatidylcholine on the absorption and mucosal metabolism of oleic acid and cholesterol in vitro. Biochim. Biophys. Acta486, 500 (1977)

    PubMed  Google Scholar 

  62. Shier, W. T., Trotter, J. T., III.: Stimulation of liver microsomal sialyltransferase activity by lysolecithin. FEBS Lett.62, 165 (1976)

    PubMed  Google Scholar 

  63. Shier, W. T., Baldwin, J. H., Nilsen-Hamilton, M., Hamilton, R. T., Thanassi, N. M.: Regulation of guanylate and adenylate cyclase activities by lysolecithin. Proc. Natl. Acad. Sci. U.S.A.,73, 1583 (1976)

    Google Scholar 

  64. Shier, W. T.: Inhibition of prostaglandin synthesis by lysolecithin. Biochim. Biophys. Res. Commun.78, 1168 (1977)

    Google Scholar 

  65. Sjödahl, R., Tagesson, C.: Formation and inhibition of lysolecithin in human gallbladder bile. Acta Chir. Scand.142, 395 (1976)

    PubMed  Google Scholar 

  66. Snyder, F.: Ether-linked lipids and fatty alcohol precursors in neoplasma. In: Ether lipids, chemistry and biology, Snader, F., ed., pp. 273–296. New York: Academic Press 1972

    Google Scholar 

  67. Snyder, F., Malone, B., Piantadosi, C.: Tetrahydropteridine-dependent cleavage enzyme for O-alkyl-lipids: substrate specificity. Biochim. Biophys. Acta316, 259 (1973)

    PubMed  Google Scholar 

  68. Soodsma, J. F., Piantadosi, C., Snyder, F.: The biocleavage of alkyl-glyceryl ethers in Morris hepatomas and other transplantable neoplasms. Cancer Res.30, 309 (1970)

    PubMed  Google Scholar 

  69. Stein, Y., Stein, O.: Metabolism of labelled lysolecithin, lysopliosphatidylethanolamin and lecithin in the rat. Biochim. Biophys. Acta116, 95 (1966)

    PubMed  Google Scholar 

  70. Strannegård, Ö., Roupe, G.: Adjuvant effect of lysolecithin analogues on the development of contact sensitivity in mice. Int. Arch. Allergy Appl. Immunol.51, 198 (1976)

    PubMed  Google Scholar 

  71. Tagesson, C., Norrby, S., Sjddahl, R.: The prerequisites for local lysolecithin formation in the human gallbladder, II. Studies on the positional specificity of the phospholipase A activity. Scand. J. Gastroenterol.13, 417 (1978)

    PubMed  Google Scholar 

  72. Tarnowski, G. S., Mountain, J. M., Stock, C. C., Mender, P. G. Weltzien, H. U., Westphal, O.: Effect of lysolecithin and analogs on mouse ascites tumors. Cancer Res.38, 339 (1978)

    PubMed  Google Scholar 

  73. Turcotte, J. G., Boyd, R. E., Quinn, J. G., Smeby, R. R.: Isolation and renin-inhibitory activity of phosphoglyceride from shark kidney. J. Med. Chem.16, 166 (1973)

    PubMed  Google Scholar 

  74. Weltzien, H. U., Arnold, B., Westphal, O.:14C-markierte Lysolecithin-Analoga. Liebigs Ann. Chem. p. 1439 (1973)

  75. Weltzien, H. U.: Effects of lysolecithin and synthetic analogs on concanavalin A induced agglutination of chicken, human and bovine erythrocytes. Exp. Cell Res.92, 111 (1975)

    PubMed  Google Scholar 

  76. Weltzien, H. U., Arnold, B., Reuther, G.: Quantiative studies on lysolecithin-mediated hemolysis. Use of ether-deoxy lysolecithin analogs with varying aliphatic chain lengths. Biochim. Biophys. Acta466, 411 (1977)

    PubMed  Google Scholar 

  77. Westphal, O., Westphal, U., Andreesen, R., Munder, P. G.: Anti-tumor effects of bacterial endotoxin (lipopolysaccharides, lipid A) and synthetic lysolecithin analogues. ln: Proceedings of the study week on The role of nonspecific immunity in the prevention and treatment of cancer. (Vatican City, Oct. 17–21. 1977) Pontificia Academia Scientiarum: in press 1979

  78. Westphal, O., Fischer, H., Mender, P. G.: Adjuvanticity of lysolecithin and synthetic analogues. 8th Int. Congress Biochemistry, Interlaken;Sxtiss, Abstract No. 129, Rochester: Staples Printers 1970

  79. White, D. A.: The phospholipid composition of mammalian tissues. In: Form and function of phospholipids, Ansell, G. B., Hawthrne J. N., Dawson, R. M. C., eds., pp. 441–482. Amsterdam: Elsevier Scientific Publishing Company 1973

    Google Scholar 

  80. Wilkinson, P. J., Cater, D. B.: An electron-microscope study of the effects of lysolecithin on BPS ascites-tumour cells and phagocytes of mice compared with the effects of a specific anti-tumor serum plus complement. J. Pathol.97, 219 (1969)

    PubMed  Google Scholar 

  81. Wood, R.: Tumor lipids: structural and metabolism studies of Ehrlich ascites cells. In: Tumor lipids, biochemistry and metabolism, Wood, R., ed., pp. 139–182. Champaign: American Oil Chemists Soc. Press 1973

    Google Scholar 

  82. Zwiller, J., Ciesielski-Treska, J., Mandel, P.: Effect of lysolecithin on guanylate and adenylate cyclase activities in neuroblastoma cells in culture. FEBS Lett.69, 286 (1976)

    PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Munder, P.G., Modolell, M., Andreesen, R. et al. Lysophosphatidylcholine (lysolecithin) and its synthetic analogues. Immunemodulating and other biologic effects. Springer Semin Immunopathol 2, 187–203 (1979). https://doi.org/10.1007/BF01891668

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01891668

Keywords

  • Internal Medicine
  • Biologic Effect
  • Synthetic Analogue