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Chemical Compound Review

Manosamine     (2S,3R,4R,5R)-2-amino- 3,4,5,6-tetrahydroxy...

Synonyms: mannosamine, D-ManN, AG-D-85245, CHEBI:27503, AC1L3XMM, ...
 
 
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Disease relevance of D-ManN

 

High impact information on D-ManN

  • Moreover, complete inhibition of GPI biogenesis by mannosamine treatment did not impair the HBsAg apical secretion, discarding the possibility that HBsAg could be "hitchhiking" with a newly synthesized GPI-protein [6].
  • The leukemic T-cell lines, subgrouped according to the degree of mannosamine inhibition on nucleic acid biosyntheses, were: Subgroup 1, HPB-MLT cells; Subgroup 2, CCRF-HSB-2 and HPB-ALL cells; and Subgroup 3, MOLT-4 cells [7].
  • We observed heterogeneity of mannosamine susceptibility among those cell lines [7].
  • Thus, the primary target of the tumoricidal activity of mannosamine may also be the cellular membranes [7].
  • Morphological and pulse-chase studies with isolated pancreatic lobules revealed that after inhibition of GPI-anchor biosynthesis by mannosamine or the fungal metabolite YW 3548, granule formation was impaired leading to an accumulation of newly synthesized proteins in the Golgi apparatus and the rough endoplasmic reticulum [8].
 

Biological context of D-ManN

  • On the basis of these results, it is concluded that aminosugars, especially ManN, produce H2O2 to cause DNA damage, which mediates apoptosis resulting in tumor growth inhibition [9].
  • These results suggest that ManN-induced apoptosis is preceded by H2O2-mediated DNA damage [9].
  • They are, therefore, released with neuraminidases or by mild acid hydrolysis and then converted with neuraminic acid aldolase to their corresponding mannosamine derivatives, which are then PMP-labeled, separated, and quantitated as described above [10].
  • Mannosamine inhibits GPtdIns biosynthesis at a concentration of 5 mm, but neither an accumulation of aberrant intermediates nor significant inhibition of total protein biosynthesis was observed in the presence of this analogue [11].
  • These results suggest that the suppression of NK activity by amino sugars is due to the reduction of the ATP-based energy supply of the effector cells and that amino sugars, especially D-mannosamine, should be recognized as potent suppressors of natural cell-mediated immunity [12].
 

Anatomical context of D-ManN

  • Pre-incubation of cells in 10 mM D-mannosamine, an inhibitor of GPI incorporation into protein, resulted in a reduction of the incorporation of label into the three GPI-anchored proteins, nearly complete inhibition of differentiation and a reduction in the rate of digestive vacuole formation [13].
  • Aprotinin, a plasmin inhibitor, and mannosamine, which inhibits the synthesis of glycosylphosphatidylinositol (GPI), thereby preventing anchorage of GPI-linked proteins such as uPAR to the cell membrane, also decreased IGF-II- (P<0.05 for both) but not IGF-I-induced migration [14].
  • This effect of mannosamine appears to be due to its capacity to inhibit the synthesis of glycosylphosphatidylinositol (GPI)-linked proteins by chondrocytes since the GPI synthesis inhibitor 2-deoxyfluoroglucose (2-DFG) also inhibited the aggrecanase response to IL-1b and RA in rat cells [15].
  • Mannosamine inhibits aggrecanase-mediated changes in the physical properties and biochemical composition of articular cartilage [16].
  • In control rats, binding of epididymal spermatozoa to Vicia faba, a lectin specific for glucose and glucosamine, and mannose and mannosamine residues, decreased from the proximal caput to the distal corpus coincident with the increase in alpha-glucosidase activity on the epithelial brush border [17].
 

Associations of D-ManN with other chemical compounds

 

Gene context of D-ManN

  • Mannosamine treatment, which down-regulates cell-surface uPAR, decreased MEF-2 migration by 40% without significantly affecting MEF-1 migration [22].
  • Recent studies have demonstrated that the hexosamines glucosamine (GlcN) and mannosamine (ManN) can inhibit aggrecanase-mediated cleavage of aggrecan in IL-1-treated cartilage cultures [16].
  • The inhibition of glycosylphosphatidylinositol anchor biosynthesis by mannosamine has been described previously in the procyclic forms of Trypanosoma brucei and in mammalian cells (Lisanti, M. P., Field, M. C., Caras, I. W. J., Menon, A. K., and Rodriguez-Boulan, E. (1991) EMBO J. 10, 1969-1977) [23].
  • The biosynthesis of lipoarabinomannan (LAM), a key mycobacterial lipoglycan that has been implicated in numerous immunoregulatory functions, was examined utilizing D-mannosamine (ManN) as a tool to identify mannosyltransferase genes involved in LAM synthesis [4].
  • THe beta-galactoside-binding lectin binds to glucosamine, mannosamine and galactosamine in addition to beta-galactoside, as determined by the inhibition of haemagglutination [24].
 

Analytical, diagnostic and therapeutic context of D-ManN

References

  1. Biochemical engineering of surface alpha 2-8 polysialic acid for immunotargeting tumor cells. Liu, T., Guo, Z., Yang, Q., Sad, S., Jennings, H.J. J. Biol. Chem. (2000) [Pubmed]
  2. Structure of linkage region between ribitol teichoic acid and peptidoglycan in cell walls of Staphylococcus aureus H. Kojima, N., Araki, Y., Ito, E. J. Biol. Chem. (1983) [Pubmed]
  3. Bioengineering of surface GD3 ganglioside for immunotargeting human melanoma cells. Zou, W., Borrelli, S., Gilbert, M., Liu, T., Pon, R.A., Jennings, H.J. J. Biol. Chem. (2004) [Pubmed]
  4. The pimB gene of Mycobacterium tuberculosis encodes a mannosyltransferase involved in lipoarabinomannan biosynthesis. Schaeffer, M.L., Khoo, K.H., Besra, G.S., Chatterjee, D., Brennan, P.J., Belisle, J.T., Inamine, J.M. J. Biol. Chem. (1999) [Pubmed]
  5. Synthesis and high-throughput screening of N-acetyl-beta-hexosaminidase inhibitor libraries targeting osteoarthritis. Liu, J., Numa, M.M., Liu, H., Huang, S.J., Sears, P., Shikhman, A.R., Wong, C.H. J. Org. Chem. (2004) [Pubmed]
  6. Apical sorting of hepatitis B surface antigen (HBsAg) is independent of N-glycosylation and glycosylphosphatidylinositol-anchored protein segregation. Marzolo, M.P., Bull, P., González, A. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  7. Antitumor activity of D-mannosamine in vitro: different sensitivities among human leukemia cell lines possessing T-cell properties. Onoda, T., Morikawa, S., Harada, T., Suzuki, Y., Inoue, K., Nishigami, K. Cancer Res. (1982) [Pubmed]
  8. Regulated apical secretion of zymogens in rat pancreas. Involvement of the glycosylphosphatidylinositol-anchored glycoprotein GP-2, the lectin ZG16p, and cholesterol-glycosphingolipid-enriched microdomains. Schmidt, K., Schrader, M., Kern, H.F., Kleene, R. J. Biol. Chem. (2001) [Pubmed]
  9. Involvement of oxidative DNA damage and apoptosis in antitumor actions of aminosugars. Hiraku, Y., Kawanishi, S. Free Radic. Res. (1999) [Pubmed]
  10. Monosaccharide composition analysis of oligosaccharides and glycoproteins by high-performance liquid chromatography. Fu, D., O'Neill, R.A. Anal. Biochem. (1995) [Pubmed]
  11. Inhibition of glycosyl-phosphatidylinositol biosynthesis in Plasmodium falciparum by C-2 substituted mannose analogues. Santos de Macedo, C., Gerold, P., Jung, N., Azzouz, N., Kimmel, J., Schwarz, R.T. Eur. J. Biochem. (2001) [Pubmed]
  12. Suppression of human natural killer cell activity by amino sugars. Yagita, M., Nakajima, M., Saksela, E. Cell. Immunol. (1989) [Pubmed]
  13. Cytodifferentiation in Tetrahymena vorax is linked to glycosyl-phosphatidylinositol-anchored protein assembly. Yang, X., Ryals, P.E. Biochem. J. (1994) [Pubmed]
  14. Urokinase type plasminogen activator receptor is involved in insulin-like growth factor-induced migration of rhabdomyosarcoma cells in vitro. Gallicchio, M.A., Kaun, C., Wojta, J., Binder, B., Bach, L.A. J. Cell. Physiol. (2003) [Pubmed]
  15. Chondrocyte-mediated catabolism of aggrecan: evidence for a glycosylphosphatidylinositol-linked protein in the aggrecanase response to interleukin-1 or retinoic acid. Sandy, J.D., Thompson, V., Verscharen, C., Gamett, D. Arch. Biochem. Biophys. (1999) [Pubmed]
  16. Mannosamine inhibits aggrecanase-mediated changes in the physical properties and biochemical composition of articular cartilage. Patwari, P., Kurz, B., Sandy, J.D., Grodzinsky, A.J. Arch. Biochem. Biophys. (2000) [Pubmed]
  17. Study of the role of epididymal alpha-glucosidase in the fertility of male rats by the administration of the enzyme inhibitor castanospermine. Yeung, C.H., Cooper, T.G. J. Reprod. Fertil. (1994) [Pubmed]
  18. Inhibition of glycosylphosphatidylinositol biosynthesis in Leishmania mexicana by mannosamine. Field, M.C., Medina-Acosta, E., Cross, G.A. J. Biol. Chem. (1993) [Pubmed]
  19. Transformation of cells by rous sarcoma virus: cytoplasmic vacuolization. Bader, A.V., Bader, J.P. J. Cell. Physiol. (1976) [Pubmed]
  20. Distinctive anti-influenza properties of recombinant collectin 43. Hartshorn, K.L., Holmskov, U., Hansen, S., Zhang, P., Meschi, J., Mogues, T., White, M.R., Crouch, E.C. Biochem. J. (2002) [Pubmed]
  21. Purification, biochemical properties and active sites of N-acetyl-beta-D-hexosaminidases from human seminal plasma. Kapur, D.K., Gupta, G.S. Biochem. J. (1986) [Pubmed]
  22. Embryonic fibroblasts that are genetically deficient in low density lipoprotein receptor-related protein demonstrate increased activity of the urokinase receptor system and accelerated migration on vitronectin. Weaver, A.M., Hussaini, I.M., Mazar, A., Henkin, J., Gonias, S.L. J. Biol. Chem. (1997) [Pubmed]
  23. The mechanism of inhibition of glycosylphosphatidylinositol anchor biosynthesis in Trypanosoma brucei by mannosamine. Ralton, J.E., Milne, K.G., Güther, M.L., Field, R.A., Ferguson, M.A. J. Biol. Chem. (1993) [Pubmed]
  24. Mitogenicity and binding properties of beta-galactoside-binding lectin from chick-embryo kidney. Pitts, M.J., Yang, D.C. Biochem. J. (1981) [Pubmed]
  25. Formation of unusual mannosamine-containing lipid-linked oligosaccharides in Madin-Darby canine kidney cell cultures. Pan, Y.T., De Gespari, R., Warren, C.D., Elbein, A.D. J. Biol. Chem. (1992) [Pubmed]
  26. Purification and characterization of rat epididymal-fluid alpha-D-mannosidase: similarities to sperm plasma-membrane alpha-D-mannosidase. Tulsiani, D.R., Skudlarek, M.D., Nagdas, S.K., Orgebin-Crist, M.C. Biochem. J. (1993) [Pubmed]
  27. The binding of tissue-specific adhesive molecules to the cell surface. A molecular basis for specificity. Balsamo, J., Lilien, J. Biochemistry (1975) [Pubmed]
 
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