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. 1981 Sep;33(3):834–839. doi: 10.1128/iai.33.3.834-839.1981

Adjuvant activity of carbohydrate analogs of N-acetylmuramyl-L-alanyl-D-isoglutamine on the induction of delayed-type hypersensitivity to azobenzenearsonate-N-acetyl-L-tyrosine in guinea pigs.

I Azuma, H Okumura, I Saiki, M Kiso, A Hasegawa, Y Tanio, Y Yamamura
PMCID: PMC350787  PMID: 7287186

Abstract

The adjuvant activity of 29 kinds of carbohydrate analogs of N-acetylmuramyl-L-alanyl-D-isoglutamine on the induction of delayed-type hypersensitivity to azobenzenearsonate-N-acetyl-L-tyrosine was examined in guinea pigs. It was found that the D-manno- and D-galacto-type muramyldipeptides were as active as the D-gluco-type muramyldipeptide (MDP). The structural requirement of the carbohydrate moiety of analogs of N-acetylmuramyl-L-alanyl-D-isoglutamine is discussed.

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Selected References

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

  1. 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]
  2. Audibert F., Chedid L., Lefrancier P., Choay J., Lederer E. Relationship between chemical structure and adjuvant activity of some synthetic analogues of N-acetyl-muramyl-L-alanyl-D-isoglutamine (MDP). Ann Immunol (Paris) 1977 Apr-Jun;128C(3):653–661. [PubMed] [Google Scholar]
  3. Azuma I., Kamisango K. I., Saiki I., Tanio Y., Kobayashi S., Yamamura Y. Adjuvant activity of N-acetyl muramyl dipeptides for the induction of delayed-type hypersensitivity to azobenzenearsonate-N-acetyl-L-tyrosine in guinea pigs. Infect Immun. 1980 Sep;29(3):1193–1196. doi: 10.1128/iai.29.3.1193-1196.1980. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Azuma I., Okumura H., Saiki I., Tanio Y., Kiso M., Hasegawa A., Yamamura Y. Adjuvant activity of 6-amino-6-deoxy-muramyldipeptides and their acylamino derivatives on the induction of delayed hypersensitivity to azobenzenearsonate-N-acetyl-L-tyrosine in guinea pigs. Infect Immun. 1981 Jun;32(3):1305–1308. doi: 10.1128/iai.32.3.1305-1308.1981. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. 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]
  6. Chedid L., Audibert F., Johnson A. G. Biological activities of muramyl dipeptide, a synthetic glycopeptide analogous to bacterial immunoregulating agents. Prog Allergy. 1978;25:63–105. [PubMed] [Google Scholar]
  7. Damais C., Parant M., Chedid L., Lefrancier P., Choay J. In vitro spleen cell responsiveness to various analogs of MDP (N-acetylmuramyl-L-alanyl-D-isoglutamine), a synthetic immunoadjuvant, in MDP high-responder mice. Cell Immunol. 1978 Jan;35(1):173–179. doi: 10.1016/0008-8749(78)90137-5. [DOI] [PubMed] [Google Scholar]
  8. 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]
  9. Hasegawa A., Okumura H., Kiso M., Azuma I., Yamamura Y. Synthesis of N-acetyl-6-amino- and -6-(acylamino)-6-deoxymuramoyl dipeptides, and their immunoadjuvant activities. Carbohydr Res. 1980 Feb;79(1):C20–C23. doi: 10.1016/s0008-6215(00)85146-0. [DOI] [PubMed] [Google Scholar]
  10. Kiso M., Kaneda Y., Okumura H., Hasegawa A., Azuma I., Yamamura Y. Synthesis and immunoadjuvant activities of muramoyl-L-alanyl-D-isoglutamine and some carbohydrate analogs. Carbohydr Res. 1980 Feb;79(1):C17–C19. doi: 10.1016/s0008-6215(00)85145-9. [DOI] [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. Lederer E. Synthetic immunostimulants derived from the bacterial cell wall. J Med Chem. 1980 Aug;23(8):819–825. doi: 10.1021/jm00182a001. [DOI] [PubMed] [Google Scholar]
  13. Saiki I., Tanio Y., Yamawaki M., Uemiya M., Kobayashi S., Fukuda T., Yukimasa H., Yamamura Y., Azuma I. Adjuvant activities of quinonyl-N-acetyl muramyl dipeptides in mice and guinea pigs. Infect Immun. 1981 Jan;31(1):114–121. doi: 10.1128/iai.31.1.114-121.1981. [DOI] [PMC free article] [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. Uemiya M., Sugimura K., Kusama T., Saiki I., Yamawaki M., Azuma I., Yamamura Y. Adjuvant activity of 6-O-mycoloyl derivatives of N-acetylmuramyl-L-seryl-D-isoglutamine and related compounds in mice and guinea pigs. Infect Immun. 1979 Apr;24(1):83–89. doi: 10.1128/iai.24.1.83-89.1979. [DOI] [PMC free article] [PubMed] [Google Scholar]
  16. 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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