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Chemical Compound Review

Neamine     (2R,3S,4R,5R,6S)-5-amino-2- (aminomethyl)-6...

Synonyms: Negamicin, Neamin, Nebramycin X, Dekamycin V, Neomycin A, ...
 
 
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Disease relevance of Neomycin A

 

High impact information on Neomycin A

  • Immunohistochemical staining showed that both angiogenesis and cancer cell proliferation are inhibited by neamine [6].
  • Neomycin, paromomycin, ribostamycin and neamine bind in the major groove of the A-site RNA in a unique binding pocket formed by non-canonical base pairs and a bulged nucleotide [7].
  • Alteration of ribosomal protein S17 by mutation linked to neamine resistance in Escherichia coli. I. General properties of neaA mutants [8].
  • Aminoglycoside antibiotics that bind to the aminoacyl-tRNA site (A site) of the ribosome are composed of a common neamine core in which a glycopyranosyl ring is attached to position 4 of a 2-deoxystreptamine moiety [9].
  • Quench-flow pre-steady-state kinetic analyses of the reactions of Gram-negative APH(3') types Ia and IIa with kanamycin A, neamine, and their respective difluorinated analogues 4'-deoxy-4',4'-difluorokanamycin A and 4'-deoxy-4',4'-difluoroneamine were carried out, in conjunction with measurements of thio effect and viscosity studies [10].
 

Chemical compound and disease context of Neomycin A

  • Three different changes within a conserved region of the 16S gene, equivalent to E. coli bases 1191-1193, confer varying levels of spectinomycin resistance, while resistance to neamine and kanamycin results from mutations in the 16S gene at bases equivalent to E. coli 1408 and 1409 [11].
 

Biological context of Neomycin A

  • Genetic and biochemical analyses indicate that the neamine-resistant phenotype is the result of two distinct mutations [12].
  • It is concluded that the added neamine is incorporated into antibiotic intact, without initial hydrolysis, and that the probable first step in the subunit assembly of neomycin is the formation of neamine [3].
  • Regioselective glycosylation of neamine core: a facile entry to kanamycin B related analogues [13].
  • The use of neamine as a molecular template: inactivation of bacterial antibiotic resistance enzyme aminoglycoside 3'-phosphotransferase type IIa [14].
  • In the search for antiviral agents targeting multiple binding sites for aminoglycosides in RNA, we report here the synthesis of new neamine dimers and a trimer in which the neamine cores are connected by different linking chains attached at the 4'- and/or 5-positions [15].
 

Anatomical context of Neomycin A

 

Associations of Neomycin A with other chemical compounds

 

Gene context of Neomycin A

  • The neamine part of the aminoglycoside antibiotic neomycin B was conjugated to a 16 mer peptide nucleic acid (PNA) targeting HIV-1 TAR RNA [2].
  • Chemical modification of neamine. Part III [17].
 

Analytical, diagnostic and therapeutic context of Neomycin A

References

  1. Alteration of ribosomal protein S17 by mutation linked to neamine resistance in Escherichia coli. II. Localization of the amino acid replacement in protein S17 from a meaA mutant. Yaguchi, M., Wittmann, H.G., Cabezón, T., DeWilde, M., Villarroel, R., Herzog, A., Bollen, A. J. Mol. Biol. (1976) [Pubmed]
  2. A peptide nucleic acid-neamine conjugate that targets and cleaves HIV-1 TAR RNA inhibits viral replication. Riguet, E., Tripathi, S., Chaubey, B., Désiré, J., Pandey, V.N., Décout, J.L. J. Med. Chem. (2004) [Pubmed]
  3. The role of the pseudo-disaccharide neamine as an intermediate in the biosynthesis of neomycin. Pearce, C.J., Barnett, J.E., Anthony, C., Akhtar, M., Gero, S.D. Biochem. J. (1976) [Pubmed]
  4. Aminoglycosides. V. Synthesis of glucopyranoside derivatives of neamine modified in the 2-deoxystreptamine ring. Pfeiffer, F.R., Ku, T.W., Peterson, D.C. J. Antibiot. (1981) [Pubmed]
  5. Selectively guanidinylated derivatives of neamine. Syntheses and inhibition of anthrax lethal factor protease. Jiao, G.S., Simo, O., Nagata, M., O'malley, S., Hemscheidt, T., Cregar, L., Millis, S.Z., Goldman, M.E., Tang, C. Bioorg. Med. Chem. Lett. (2006) [Pubmed]
  6. Neamine inhibits xenografic human tumor growth and angiogenesis in athymic mice. Hirukawa, S., Olson, K.A., Tsuji, T., Hu, G.F. Clin. Cancer Res. (2005) [Pubmed]
  7. Binding of neomycin-class aminoglycoside antibiotics to the A-site of 16 S rRNA. Fourmy, D., Recht, M.I., Puglisi, J.D. J. Mol. Biol. (1998) [Pubmed]
  8. Alteration of ribosomal protein S17 by mutation linked to neamine resistance in Escherichia coli. I. General properties of neaA mutants. Bollen, A., Cabezón, T., de Wilde, M., Villarroel, R., Herzog, A. J. Mol. Biol. (1975) [Pubmed]
  9. Binding of Neomycin-Class Aminoglycoside Antibiotics to Mutant Ribosomes with Alterations in the A Site of 16S rRNA. Hobbie, S.N., Pfister, P., Bruell, C., Sander, P., François, B., Westhof, E., Böttger, E.C. Antimicrob. Agents Chemother. (2006) [Pubmed]
  10. Fluorinated aminoglycosides and their mechanistic implication for aminoglycoside 3'-phosphotransferases from Gram-negative bacteria. Kim, C., Haddad, J., Vakulenko, S.B., Meroueh, S.O., Wu, Y., Yan, H., Mobashery, S. Biochemistry (2004) [Pubmed]
  11. Antibiotic resistance mutations in the chloroplast 16S and 23S rRNA genes of Chlamydomonas reinhardtii: correlation of genetic and physical maps of the chloroplast genome. Harris, E.H., Burkhart, B.D., Gillham, N.W., Boynton, J.E. Genetics (1989) [Pubmed]
  12. Resistance to the aminoglycoside antibiotic neamine in Escherichia coli. A new mutant whose NeaR phenotype results from the cumulative effects of two distinct mutations. Delcuve, G., Cabezón, T., Herzog, A., Cannon, M., Bollen, A. Biochem. J. (1978) [Pubmed]
  13. Regioselective glycosylation of neamine core: a facile entry to kanamycin B related analogues. Chou, C.H., Wu, C.S., Chen, C.H., Lu, L.D., Kulkarni, S.S., Wong, C.H., Hung, S.C. Org. Lett. (2004) [Pubmed]
  14. The use of neamine as a molecular template: inactivation of bacterial antibiotic resistance enzyme aminoglycoside 3'-phosphotransferase type IIa. Roestamadji, J., Mobashery, S. Bioorg. Med. Chem. Lett. (1998) [Pubmed]
  15. Neamine dimers targeting the HIV-1 TAR RNA. Riguet, E., Désiré, J., Boden, O., Ludwig, V., Göbel, M., Bailly, C., Décout, J.L. Bioorg. Med. Chem. Lett. (2005) [Pubmed]
  16. Sensitization potentials and immunologic specificities of neomycins. Chung, C.W., Carson, T.R. J. Invest. Dermatol. (1975) [Pubmed]
  17. Chemical modification of neamine. Part III. Suami, T., Nishiyama, S., Ishikawa, Y., Katsura, S. Carbohydr. Res. (1977) [Pubmed]
  18. Normal-phase high-performance liquid chromatographic determination of neomycin sulfate derivatized with 1-fluoro-2,4-dinitrobenzene. Tsuji, K., Goetz, J.F., vanMeter, W., Gusciora, K.A. J. Chromatogr. (1979) [Pubmed]
 
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