Skip to main content
PMC home page
Infection and Immunity logoLink to Infection and Immunity
. 1979 Apr;24(1):83–89. doi: 10.1128/iai.24.1.83-89.1979

Adjuvant activity of 6-O-mycoloyl derivatives of N-acetylmuramyl-L-seryl-D-isoglutamine and related compounds in mice and guinea pigs.

M Uemiya, K Sugimura, T Kusama, I Saiki, M Yamawaki, I Azuma, Y Yamamura
PMCID: PMC414265  PMID: 313372

Abstract

Adjuvant and antitumor activities of synthetic-6-O-mycoloyl-N-acetylmuramyl-L-seryl-D-isoglutamine and 6-O-mycoloyl-N-acetylmuramyl-glycyl-D-isoglutamine were examined in comparison with those of 6-O-mycoloyl-N-acetylmuramyl-L-alanyl-D-isoglutamine. Synthetic 6-O-mycoloyl-N-acetylmuramyl-L-seryl-D-isoglutamine was active as an adjuvant for the induction of delayed-type hypersensitivity to m-[4-(4'-arsono-phenylazo)-phenyl]-N-acetyl-L-tyrosine in guinea pigs and for cell-mediated cytotoxicity in allogeneic mice. 6-O-mycoloyl-N-acetylmuramyl-glycyl-D-isoglutamine was inactive as an adjuvant for the induction of delayed-type hypersensitivity in guinea pigs; however, it was active for cell-mediated cytotoxicity in allogeneic mice. 6-O-mycoloyl-N-acetylmuramyl-L-seryl-D-isoglutamine and 6-O-mycoloyl-N-acetylmuramyl-glycyl-D-isoglutamine were not pyrogenic in rabbits. The antitumor activity of these 6-O-mycoloyl-N-acetylmuramyldipeptides was examined preliminarily by using transplantable syngeneic mouse tumors.

Full text

PDF
83

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Adam A., Ciorbaru R., Ellouz F., Petit J. F., Lederer E. Adjuvant activity of monomeric bacterial cell wall peptidoglycans. Biochem Biophys Res Commun. 1974 Feb 4;56(3):561–567. doi: 10.1016/0006-291x(74)90640-8. [DOI] [PubMed] [Google Scholar]
  2. Adam A., Devys M., Souvannavong V., Lefrancier P., Choay J., Lederer E. Correlation of structure and adjuvant activity of N-acetyl muramyl-L-alanyl-D-isoglutamine (MDP), its derivatives and analogues. Anti-adjuvant and competition properties of stereoisomers. Biochem Biophys Res Commun. 1976 Sep 7;72(1):339–346. doi: 10.1016/0006-291x(76)90999-2. [DOI] [PubMed] [Google Scholar]
  3. 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]
  4. 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]
  5. 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]
  6. Azuma I., Sugimura K., Yamawaki M., Uemiya M., Kusumoto S., Okada S., Shiba T., Yamamura Y. Adjuvant activity of synthetic 6-O-"mycoloyl"-N-acetylmuramyl-L-alanyl-D-isoglutamine and related compounds. Infect Immun. 1978 Jun;20(3):600–607. doi: 10.1128/iai.20.3.600-607.1978. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. 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]
  8. 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]
  9. 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]
  10. 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]
  11. 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]
  12. Kotani S., Watanabe Y., Kinoshita F., Morisaki I., Kato K. The effect of replacement of L-alanine residue by glycine, L-serine or D-alanine in an N-acetylmuramyl-L-alanyl-D-isoglutamine on immunoadjuvancies of molecules. Biken J. 1977 Jun;20(2):39–45. [PubMed] [Google Scholar]
  13. 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]
  14. 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]
  15. 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]
  16. 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]
  17. 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]

Articles from Infection and Immunity are provided here courtesy of American Society for Microbiology (ASM)

RESOURCES