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. 1978 Jun;20(3):600–607. doi: 10.1128/iai.20.3.600-607.1978

Adjuvant activity of synthetic 6-O-"mycoloyl"-N-acetylmuramyl-L-alanyl-D-isoglutamine and related compounds.

I Azuma, K Sugimura, M Yamawaki, M Uemiya, S Kusumoto, S Okada, T Shiba, Y Yamamura
PMCID: PMC421900  PMID: 97234

Abstract

Adjuvant and antitumor activities of synthetic 6-O-"mycoloyl"-N-acetylmuramyl-L-alanyl-D-isoglutamine were examined. All the synthetic 6-O-corynomycoloyl-, 6-O-mocardomycoloyl-, and 6-O-mycoloyl-N-acetylmuramyl-L-alanyl-D-isoglutamine were active as adjuvants for cell-mediated immune responses. However, 6-O-mycoloyl-N-acetylmuramyl-L-alanyl-D-isoglutamine was less active as an adjuvant on circulating antibody formation. It was shown that pyrogenic activity of N-acetylmuramyldipeptide was reduced by 6-O-acylation with mycolic acid, but not with nocardomycolic or corynomycolic acid. Tumor-suppression activity was observed by the synthetic 6-O-mycoloyl-N-acetylmuramyl-L-alanyl-D-isoglutamine by using transplantable tumor in syngenic mice.

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Selected References

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  1. Alkan S. S., Williams E. B., Nitecki D. E., Goodman J. W. Antigen recognition and the immune response. Humoral and cellular immune responses to small mono- and bifunctional antigen molecules. J Exp Med. 1972 Jun 1;135(6):1228–1246. doi: 10.1084/jem.135.6.1228. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Azuma I., Kanetsuna F., Taniyama T., Yamamura Y., Hori M. Adjuvant activity of mycobacterial fractions. I. Purification and in vivo adjuvant activity of cell wall skeletons of Mycobacterium bovis BCG, Nocardia asteroides 131 and Corynebacterium diphtheriae PW8. Biken J. 1975 Mar;18(1):1–13. [PubMed] [Google Scholar]
  3. Azuma I., Ribi E. E., Meyer T. J., Zbar B. Biologically active components from mycobacterial cell walls. I. Isolation and composition of cell wall skeleton and component P3. J Natl Cancer Inst. 1974 Jan;52(1):95–101. doi: 10.1093/jnci/52.1.95. [DOI] [PubMed] [Google Scholar]
  4. Azuma I., Sugimura K., Taniyama T., Yamawaki M., Yamamura Y. Adjuvant activity of mycobacterial fractions: adjuvant activity of synthetic N-acetylmuramyl-dipeptide and the related compounds. Infect Immun. 1976 Jul;14(1):18–27. doi: 10.1128/iai.14.1.18-27.1976. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Azuma I., Taniyama T., Yamawaki M., Sugimura K., Yamamura Y. Adjuvant and antitumor activities of Nocardia cell-wall skeletons. Gan. 1976 Oct;67(5):733–736. [PubMed] [Google Scholar]
  6. Brunner K. T., Mauel J., Rudolf H., Chapuis B. Studies of allograft immunity in mice. I. Induction, development and in vitro assay of cellular immunity. Immunology. 1970 Apr;18(4):501–515. [PMC free article] [PubMed] [Google Scholar]
  7. Ellouz F., Adam A., Ciorbaru R., Lederer E. Minimal structural requirements for adjuvant activity of bacterial peptidoglycan derivatives. Biochem Biophys Res Commun. 1974 Aug 19;59(4):1317–1325. doi: 10.1016/0006-291x(74)90458-6. [DOI] [PubMed] [Google Scholar]
  8. Jerne N. K., Nordin A. A. Plaque Formation in Agar by Single Antibody-Producing Cells. Science. 1963 Apr 26;140(3565):405–405. doi: 10.1126/science.140.3565.405. [DOI] [PubMed] [Google Scholar]
  9. Juy D., Chedid L. Comparison between macrophage activation and enhancement of nonspecific resistance to tumors by mycobacterial immunoadjuvants. Proc Natl Acad Sci U S A. 1975 Oct;72(10):4105–4109. doi: 10.1073/pnas.72.10.4105. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Katz D. H., Paul W. E., Goidl E. A., Benacerraf B. Carrier function in anti-hapten immune responses. I. Enhancement of primary and secondary anti-hapten antibody responses by carrier preimmunization. J Exp Med. 1970 Aug 1;132(2):261–282. doi: 10.1084/jem.132.2.261. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. Kotani S., Watanabe Y., Kinoshita F., Shimono T., Morisaki I. Immunoadjuvant activities of synthetic N-acetyl-muramyl-peptides or -amino acids. Biken J. 1975 Jun;18(2):105–111. [PubMed] [Google Scholar]
  12. Kotani S., Watanabe Y., Shimono T., Harada K., Shiba T. Correlation between the immunoadjuvant activities and pyrogenicities of synthetic N-acetylmuramyl-peptides or -amino acids. Biken J. 1976 Mar;19(1):9–13. [PubMed] [Google Scholar]
  13. Marbrook J. Primary immune response in cultures of spleen cells. Lancet. 1967 Dec 16;2(7529):1279–1281. doi: 10.1016/s0140-6736(67)90393-5. [DOI] [PubMed] [Google Scholar]
  14. TABACHNICK M., SOBOTKA H. Azoproteins. I. Spectrophotometric studies of amino acid azo derivatives. J Biol Chem. 1959 Jul;234(7):1726–1730. [PubMed] [Google Scholar]
  15. Yamamura Y., Azuma I., Sugimura K., Yamawaki M., Uemiya M. Adjuvant activity of 6-O-mycoloyl-N-acetylmuramuyl-L-alanyl-D-isoglutamine. Gan. 1976 Dec;67(6):867–877. [PubMed] [Google Scholar]

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