Skip to main content
SpringerLink
Log in

Cytostatic activity of syntheticO-alkylglycerolipids

  • Published:
Lipids

Abstract

A series of halogen-containing alkylglycerolipid analogs has been checked for their cytostatic activity both in vitro and in vivo. The compounds included alkyldeoxyhaloglycerols (I), alkyldeoxyhaloglycerophosphocholines (II), and alkyldeoxyhaloglycerophosphoric acids and alkyl esters (III). While compounds I and III were moderately active, compounds II were found to have a strong inhibitory effect on the proliferation of Ehrlich ascites tumor cells in vitro. Cell growth inhibition of 50% or more was found mainly in the late S- or G2-phase of the cell cycle as revealed by flow cytometry. Alkyl lysophospholipid analogs II and cholesterol form liposomes with high encapsulation efficiency and low permeability for entrapped substances. Compounds II were active against Lewis lung carcinoma in mice when applied in free form or as liposomes.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Abbreviations

ALP:

alkyl lysophospholipids

CF:

6-carboxyfluorescein

CH:

cholesterol

DG:

diacylglycerol

EAT cells:

Ehrlich ascites tumor cells

EPC:

egg phosphatidylcholine

HEPC:

hydrogenated egg phosphatidylcholine; ip, intraperitoneal(ly)

IP3 :

inositol-1,4,5-triphosphate

MLV:

multilamellar vesicles

PA:

phosphatidic acid

PI:

phosphatidylinositol

PIP:

phosphatidylinositol-4-phosphate

PIP2 :

phosphatidylinositol-4,5-diphosphate

PKC:

proteinkinase C

SUV:

small unilamellar vesicles

References

  1. Langen, P. (1975)Antimetabolites of Nucleic Acid Metabolism, Gordon and Bresch, New York, London and Paris

    Google Scholar 

  2. Ferber, E., Körner, E., Schmidt, B., Peskar, B.A., and Anders, C. (1980) inMembrane Fluidity: Biophysical Techniques and Cellular Regulation, Part IV: Phospholipid Changes Accompanying Physiological Events, (Kates, M., and Kuksis, A., eds.) pp. 239–263, The Human Press, Inc., Clifton, NJ.

    Google Scholar 

  3. Nishizuka, Y. (1984)Science 225, 1365–1370.

    Article  PubMed  CAS  Google Scholar 

  4. Munder, P.G., Modolell, M., Bausert, W., Oettgen, H.F., and Westphal, O. (1981) inAugmenting Agents in Cancer Therapy, (Hersh, E.M., ed.) pp. 441–467, Raven Press, New York.

    Google Scholar 

  5. Berdel, W.E. (1982)Blutt 44, 71–78.

    Article  CAS  Google Scholar 

  6. Kraft, R., Brachwitz, H., Etzold, G., Langen, P., and Zöpfl, H.J. (1979)J. Prakt. Chem. 321, 756–768.

    Article  CAS  Google Scholar 

  7. Brachwitz, H., Kraft, R., Langen, P., Etzold, G., and Schildt, J. (1979)J. Prakt, Chem. 321, 769–774.

    Article  CAS  Google Scholar 

  8. Brachwitz, H., Langen, P., Otto, A., and Schildt, J. (1979)J. Prakt. Chem. 321, 775–786.

    Article  CAS  Google Scholar 

  9. Brachwitz, H., Langen, P., Hintsche, R., and Schildt, J. (1982)Chem. Phys. Lipids 31, 33–52.

    Article  PubMed  CAS  Google Scholar 

  10. Brachwitz, H., Langen, P., and Schildt, J. (1984)Chem. Phys. Lipids 34, 355–362.

    Article  CAS  Google Scholar 

  11. Brachwitz, H., Franke, P., Hintsche, R., Langen, P., and Schildt, J. (1984)Chem. Phys. Lipids 36, 137–152.

    Article  CAS  Google Scholar 

  12. Langen, P., Brachwitz, H., and Schildt, J. (1979)Acta Biol. Med. Germ. 38, 965–974.

    PubMed  CAS  Google Scholar 

  13. Müller, E., Hegewald, H., Jaroszewicz, K., Kumme, G., Hoppe, H., and Frunder, H. (1986)Biochem. J. 235, 775–783.

    PubMed  Google Scholar 

  14. Uchida, T., and Filburn, C.R. (1984)J. Biol. Chem. 259, 12311–12314.

    PubMed  CAS  Google Scholar 

  15. Nuhn, P., Schenk, P., Richter, H., Arndt, D., Jandrig, J., and Winsel, K. (1985)Pharmazie 40, 705–709.

    PubMed  CAS  Google Scholar 

  16. Soodsma, J.F., Piantadosi, C., and Snyder, F. (1970)Cancer Res. 30, 309–311.

    PubMed  CAS  Google Scholar 

  17. Modolell, M., Andreesen, R., Pahlke, W., Brugger, U., and Munder, P.G. (1979)Cancer Res. 39, 4681–4686.

    PubMed  CAS  Google Scholar 

  18. Helfman, D.M., Barnes, K.C., Kindade, J.M., Vogler, W.R., Shoji, M., and Kuo, J.F. (1983)Cancer Res. 43, 2955–2961.

    PubMed  CAS  Google Scholar 

  19. Honma, Y., Kasukabe, T., Hozumi, M., Tsushima, S., and Nomura, H. (1981)Cancer Res. 41, 3211–3216.

    PubMed  CAS  Google Scholar 

  20. Langen, P., Brachwitz, H., Schildt, J., Waschke, S., and Guenther, W. (1981) DDR-Patent 0153116.

  21. Ostermann, G., Brachwitz, H., and Till, U. (1984)Biomed. Biochim. Acta 43, 349–355.

    PubMed  CAS  Google Scholar 

  22. de Chaffey de Courcelles, D., Raevens, P., and Van Belle, H. (1984)Biochem. Biophys. Res. Commun. 123, 589–594.

    Article  Google Scholar 

  23. Berger, M.R., and Schmähl, D. (1986)J. Cancer Res. Clin. Oncol. 111 Suppl., 47.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Central Institute of Molecular Biology, Academy of Sciences of the German Democratic Republic, Robert-Rössle-Strasse 10, DDR-115, Berlin-Buch, German Democratic Republic

    Hans Brachwitz & Peter Langen

  2. Central Institute of Cancer Research, Academy of Sciences of the German Democratic Republic, Robert-Rössle-Strasse 10, DDR-115, Berlin-Buch, German Democratic Republic

    Dieter Arndt & Iduna Fichtner

Authors
  1. Hans Brachwitz
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Peter Langen
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Dieter Arndt
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Iduna Fichtner
    View author publications

    You can also search for this author in PubMed Google Scholar

About this article

Cite this article

Brachwitz, H., Langen, P., Arndt, D. et al. Cytostatic activity of syntheticO-alkylglycerolipids. Lipids 22, 897–903 (1987). https://doi.org/10.1007/BF02535551

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02535551

Keywords

Search

Navigation