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Synthesis and immunomodulating tumor control properties of albumin covalently connected to trehalose

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Summary

Proteins conjugated to a trehalose derivative are described. These include human serum albumin and bovine serum albumin covalently attached through appropriate molecular linkages to the 6- and 6,6′-positions of trehalose. The immunomodulating tumor control activities of these conjugated proteins has been assayed in several test systems.

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References

  1. Asselineau J (1966) The bacterial lipids, pp 269–284. Holden—Day, San Francisco

    Google Scholar 

  2. Bekierkunst A (1975) Immunotherapy and vaccination against cancer with non-living BCG and cord factor (trehalose-6,6′-dimycolate). Int J Cancer 16:442

    Google Scholar 

  3. Bekierkunst A (1976) Immunotherapy of cancer with non-living mycobacteria and cord factor (trehalose-6,6′-dimycolate) in aqueous media. J Natl Cancer Inst 57:963

    Google Scholar 

  4. Bekierkunst A, Levij IS, Yarkoni E, Vilkas E, Lederer E (1971) Supression of urethan-induced lung adenomas in mice treated with trehalose-6,6-dimycolate (cord factor) and living bacillus Calmette-Guérin. Science 174:1240

    Google Scholar 

  5. Bekierkunst A, Wang L, Toubiana R, Lederer E (1974) Immunotherapy of cancer with non-living BCG and fractions derived from mycobacteria: Role of cord factor (trehalose-6,6′-dimycolate) in tumor regression. Infect Immun 10:1044

    Google Scholar 

  6. Braun W, Plescia OJ, Raskova J, Webb D (1971) Basic proteins and synthetic polynucleotides as modifiers of immunogenicity of syngeneic tumor cells. In: Weiss DW (ed) Immunological parameters of host-tumor relationships. Academic Press, New York, p 72

    Google Scholar 

  7. Gensler WJ, Alam I (1977) Trehalose covalently conjugated to bovine serum albumin. J Org Chem 42:130

    Google Scholar 

  8. Granger DL, Ribi E, Azuma I, Brehmer W, Parker R, Strain SM, Smith RF (1975) Cancer immunotherapy with non-living mycobacterial components. In: Crispin RG (ed) Neoplasm immunity: Theory and application. ITR Publishers, Chicago, p 43

    Google Scholar 

  9. Gray GR, Ribi E, Granger D, Parker R, Azuma I, Yamamoto K (1975) Immunotherapy of cancer: Tumor suppression and regression by cell walls of Mycobacterium phlei attached to oil droplets. J Natl Cancer Inst 55:727

    Google Scholar 

  10. Hadd HE, Caspi E (1972) Improved preparative dry-column chromatography. Analysis of resolution by puncture sampling. J Chromatogr 71:353

    Google Scholar 

  11. Juy D, Chedid L (1975) Comparison between macrophage activation and enhancement of nonspecific resistance to tumors by mycobacterial immunoadjuvants. Proc Natl Acad Sci USA 72:4105

    Google Scholar 

  12. Kato M (1972) Antibody formation to trehalose-6,6′-dimycolate (cord factor) of mycobacterium tuberculosis. Infect Immun 5:203

    Google Scholar 

  13. Kato M (1973) Effect of anti-cord factor antibody on experimental tuberculosis in mice. Infect Immun 7:14

    Google Scholar 

  14. Kelly MT, McLaughlin CA, Ribi EE (1978) Eradication of microscopic lymph node metastases of the guinea pig line-10 tumor after intradermal injection of endotoxin plus mycobacterial components. Cancer Immunol Immunother 4:29

    Google Scholar 

  15. Leclerc C, Lamensans A, Chedid L, Drapier J-C, Petit J-F, Wietzerbin J, Lederer E (1976) Nonspecific immunoprevention of L1210 leukemia by cord factor (6–6′ dimycolate of trehalose) administered in a metabolizable oil. Cancer Immunol Immunother 1:227

    Google Scholar 

  16. Lederer E (1976) Cord factor and related trehalose esters. Chem Phys Lipids 16:91

    Google Scholar 

  17. Lederer E (1977) Natural and synthetic immunostimulants related to the mycobacterial cell wall. In: Medicinal chemistry V. Elsevier Scientific Publishing Company, Amsterdam, p 264

    Google Scholar 

  18. Loev B, Goodman MM (1967) Dry-column chromatography: A preparative chromatographic technique with the resolution of thin-layer chromatography. Chem Ind (London) 2026

  19. Loev B, Snader KM (1965) “Dry-column” chromatography. A preparative chromatographic technique with the resolvability of thin-layer chromatography. Chem Ind (London) 15:5

    Google Scholar 

  20. Meyer TJ, Ribi EE, Azuma I, Zbar R (1974) Biologically active components from mycobacterial cell walls. II. Suppression and regression of strain-2 guinea pig hepatoma. J Natl Cancer Inst 52:103

    Google Scholar 

  21. Ohara T, Shimmyo Y, Sekikawa I, Morikawa K, Sumikawa E (1957) Studies on the cord factor with special reference to its immunological properties. Jpn J Tuberc 5:128

    Google Scholar 

  22. Old LJ, Boyse EA, Clarke DA, Carswell EA (1962) Antigenic properties of chemically induced tumors. Ann NY Acad Sci 101:80

    Google Scholar 

  23. Rapp HJ, Yarkoni E, Ruco L, Hunter JT (1978) Immunotherapy of a guinea pig hepatoma with vaccines containing mycobacterial fractions. Cancer Immunol Immunother 3:179

    Google Scholar 

  24. Ribi EE, Meyer TJ, Azuma I, Zbar B (1973) Mycobacterial cell wall components in tumor suppression and regression. Natl Cancer Inst Monogr 39:115

    Google Scholar 

  25. Spiro RG (1966) Analysis of sugars found in glycoproteins. Methods Enzymol 8:4

    Google Scholar 

  26. Tarnowski GS (1975) Approaches to the immunotherapy of experimental tumors. In: Mizuno D et al (eds) Host defense against cancer and its potentiation. Proceedings of the Fifth International Symposium of the Princess Takamatsu Cancer Research Fund. University Park Press, Baltimore, p 389

    Google Scholar 

  27. Toubiana R, Ribi E, McLaughlin C, Strain SM (1977) The effect of synthetic and naturally occurring trehalose fatty acid esters in tumor regression. Cancer Immunol Immunother 2:189

    Google Scholar 

  28. Yarkoni E, Bekierkunst A, Asselineau J, Toubiana R, Toubiana MJ, Lederer E (1973) Suppression of growth of Ehrlich ascites tumor cells in mice pretreated with synthetic analogs of trehalose-6,6′-dimycolate (cord factor). J Natl Cancer Inst 51:717

    Google Scholar 

  29. Yarkoni E, Wang L, Bekierkunst A (1974) Supression of growth of Ehrlich ascites tumor cells in mice by trehalose-6,6′-dimycolate (cord factor) and BCG. Infect Immun 9:977

    Google Scholar 

  30. Yarkoni E, Wang L, Bekierkunst A (1977) Stimulation of macrophages by cord factor and by heat-killed and living BCG. Infect Immun 16:1

    Google Scholar 

  31. Yarkoni E, Rapp HJ, Polonsky J, Lederer E (1978) Immunotherapy with an intralesionally administered synthetic cord factor analogue. Int J Cancer 22:564

    Google Scholar 

  32. Zbar B, Bernstein I, Tanada T, Rapp HJ (1970) Tumor immunity produced by the intradermal inoculation of living tumor cells and living Mycobacterium bovis (strain BCG). Science 170:1217

    Google Scholar 

  33. Zbar B, Rapp HJ, Ribi EE (1972) Tumor suppression by cell walls of Mycobacterium bovis attached to oil droplets. J Natl Cancer Inst 48:831

    Google Scholar 

  34. Zbar B, Ribi E, Rapp HJ (1973) An experimental model for immunotherapy of cancer. Natl Cancer Inst Monogr 39:3

    Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Boston University, Charles River Campus, 02215, Boston, Massachusetts, USA

    Walter J. Gensler, Vijay Kumar Chhatwal, Iftekhar Alam & Edwin Constantino

  2. Sloan-Kettering Institute for Cancer Research, Donald S. Walker Laboratory, 145 Boston Post Road, 10580, Rye, New York, USA

    George S. Tarnowski

  3. Cancer Research Campaign Laboratories, The University of Nottingham, NG 7 2 RD, University Park, Nottingham, England

    M. V. Pimm & R. W. Baldwin

Authors
  1. Walter J. Gensler
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  2. Vijay Kumar Chhatwal
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  3. Iftekhar Alam
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  4. Edwin Constantino
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  5. George S. Tarnowski
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  6. M. V. Pimm
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  7. R. W. Baldwin
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Gensler, W.J., Chhatwal, V.K., Alam, I. et al. Synthesis and immunomodulating tumor control properties of albumin covalently connected to trehalose. Cancer Immunol Immunother 9, 101–109 (1980). https://doi.org/10.1007/BF00199536

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  • DOI: https://doi.org/10.1007/BF00199536

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