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Chemical Compound Review

NSC-622170     N-[[(2S,4R)-2,3-bis(2-amino- 3H-imidazol-4...

Synonyms: NSC622170, AC1L7G6I
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Disease relevance of N-[[(1S,3R)-2,3-bis(2-amino-3H-imidazol-4-yl)-4-[[(4-bromo1H-pyrrole-2-carbonyl)amino]methyl]cyclobutyl]methyl]-4-bromo-1H-pyrrole-2-carboxamide

  • In our studies, sceptrin demonstrated a bacteriostatic rather than bactericidal effect on exponentially growing Escherichia coli cells at the MIC [1].
 

High impact information on N-[[(1S,3R)-2,3-bis(2-amino-3H-imidazol-4-yl)-4-[[(4-bromo1H-pyrrole-2-carbonyl)amino]methyl]cyclobutyl]methyl]-4-bromo-1H-pyrrole-2-carboxamide

  • Subsequent studies of the release of potassium ions from E. coli and the lysis of red blood cells suggested that sceptrin disrupts the cell membranes of both prokaryotic and eukaryotic cells [1].
  • At concentrations higher than the MIC, sceptrin was bactericidal, inhibited the incorporation of all radiolabelled precursors, and induced the formation of unusual spheroplasts [1].
  • Two new dimeric bromopyrrole alkaloids, nakamuric acid (1) and its corresponding methyl ester (2), have been isolated from the Indopacific sponge Agelas nakamurai along with the known metabolites sceptrin (3), debromosceptrin (4), and ageliferin (5) [2].

References

  1. A study on the mechanism of action of sceptrin, an antimicrobial agent isolated from the South Pacific sponge Agelas mauritiana. Bernan, V.S., Roll, D.M., Ireland, C.M., Greenstein, M., Maiese, W.M., Steinberg, D.A. J. Antimicrob. Chemother. (1993) [Pubmed]
  2. New bromopyrrole alkaloids from the Indopacific sponge Agelas nakamurai. Eder, C., Proksch, P., Wray, V., van Soest, R.W., Ferdinandus, E., Pattisina, L.A., Sudarsono, S. J. Nat. Prod. (1999) [Pubmed]
 
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