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Chemical Compound Review

Nojirimycin     (3R,4S,5R,6R)-6- (hydroxymethyl)piperidine...

Synonyms: CHEMBL120638, SureCN140917, CHEBI:28945, LS-71459, BRN 5246306, ...
 
 
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Disease relevance of C06763

  • About 40 years have passed since the classical glycosidase inhibitor nojirimycin was discovered from the cultured broth of the Streptomyces species [1].
  • Inhibition of mouse tumor metastasis with nojirimycin-related compounds [2].
  • In this study, we found nojirimycin (NM) to be a substantially non-toxic carbohydrate synthesis inhibitor that inhibited the experimental metastasis of B16-F10 melanoma cells not only in vitro but also in vivo [3].
  • The antimetastatic activity of ten compounds structurally related to nojirimycin A was examined using a pulmonary metastatic model of mouse B16 melanoma [2].
  • The ex vivo treatment of rat hepatoma cKDH-8/11 cells with this new synthetic product of the antibiotic nojirimycin, ND-2001 (50 microg/ml), inhibited the experimentally induced lung metastases of the tumor cells significantly at an inhibition rate of 69.2% (one of 10 animals remained metastasis free) [4].
 

High impact information on C06763

  • Effects of the glucosidase inhibitors nojirimycin and deoxynojirimycin on the biosynthesis of membrane and secretory glycoproteins [5].
  • X-ray crystallographic binding studies to 2.4 A resolution with T state phosphorylase b crystals showed that nojirimycin tetrazole binds at the catalytic site and promotes the binding of phosphate through direct interactions [6].
  • The two enzymes were similar in following characteristics: their optimum activity is around pH 6.2; the enzymes are stable above pH 7; they are effectively inhibited by the beta-glycosidase inhibitors nojirimycin delta-gluconolactone and 1-amino-beta-D-glucoside [7].
  • Role of asparagine-linked carbohydrates in pulmonary metastasis of B16-F10 murine melanoma cells: implication through glycosylation inhibition by nojirimycin [3].
  • It also inhibited Molt-4 beta-glucocerebrosidase completely at 2 micrograms/ml when the enzyme was assayed with a synthetic labeled substrate, and the inhibitory activity was more than one hundred times higher than that of nojirimycin, castanospermine, or of deoxynojirimycin [8].
 

Chemical compound and disease context of C06763

References

  1. Glycosidase inhibitors: update and perspectives on practical use. Asano, N. Glycobiology (2003) [Pubmed]
  2. Inhibition of mouse tumor metastasis with nojirimycin-related compounds. Tsuruoka, T., Fukuyasu, H., Ishii, M., Usui, T., Shibahara, S., Inouye, S. J. Antibiot. (1996) [Pubmed]
  3. Role of asparagine-linked carbohydrates in pulmonary metastasis of B16-F10 murine melanoma cells: implication through glycosylation inhibition by nojirimycin. Tsukamoto, K., Uno, A., Kubota, Y., Shimada, S., Hori, Y., Imokawa, G. Melanoma Res. (1992) [Pubmed]
  4. A new anti-metastatic drug, ND-2001, inhibits lung metastases in rat hepatoma cells by suppressing haptotaxis of tumor cells toward laminin. Kuramitsu, Y., Hamada, J., Tsuruoka, T., Morikawa, K., Kobayashi, H., Hosokawa, M. Anticancer Drugs (1998) [Pubmed]
  5. Effects of the glucosidase inhibitors nojirimycin and deoxynojirimycin on the biosynthesis of membrane and secretory glycoproteins. Peyrieras, N., Bause, E., Legler, G., Vasilov, R., Claesson, L., Peterson, P., Ploegh, H. EMBO J. (1983) [Pubmed]
  6. Ternary complex crystal structures of glycogen phosphorylase with the transition state analogue nojirimycin tetrazole and phosphate in the T and R states. Mitchell, E.P., Withers, S.G., Ermert, P., Vasella, A.T., Garman, E.F., Oikonomakos, N.G., Johnson, L.N. Biochemistry (1996) [Pubmed]
  7. Characterization of beta-glucosidases with high specificity for the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) moench seedlings. Hösel, W., Tober, I., Eklund, S.H., Conn, E.E. Arch. Biochem. Biophys. (1987) [Pubmed]
  8. Biological activities of cyclophellitol. Atsumi, S., Iinuma, H., Nosaka, C., Umezawa, K. J. Antibiot. (1990) [Pubmed]
  9. Antibiotics produced by Streptomyces ficellus II. Feldamycin and nojirimycin. Argoudelis, A.D., Reusser, F., Mizsak, S.A., Baczynskyj, L. J. Antibiot. (1976) [Pubmed]
  10. Novel glycosidase inhibitors, nojirimycin B and D-mannonic-delta-lactam. Isolation, structure determination and biological property. Niwa, T., Tsuruoka, T., Goi, H., Kodama, Y., Itoh, J., Inouye, S., Yamada, Y., Niida, T., Nobe, M., Ogawa, Y. J. Antibiot. (1984) [Pubmed]
 
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