Sceptrin

Sceptrin is a bioactive marine isolate.[1] It has been isolated from the marine sponge Agelas conifera and appears to have affinity for the bacterial actin equivalent MreB.[2] As such, this compound possess antibiotic potential.

Sceptrin
Names
Systematic IUPAC name
N,N′-{[(1R,2R,3S,4S)-3,4-Bis(2-amino-1H-imidazol-5-yl)cyclobutane-1,2-diyl]bis(methylene)}bis(4-bromopyrrole-2-carboxamide)
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
  • InChI=1S/C22H24Br2N10O2/c23-9-1-13(27-3-9)19(35)29-5-11-12(6-30-20(36)14-2-10(24)4-28-14)18(16-8-32-22(26)34-16)17(11)15-7-31-21(25)33-15/h1-4,7-8,11-12,17-18,27-28H,5-6H2,(H,29,35)(H,30,36)(H3,25,31,33)(H3,26,32,34)/t11-,12-,17-,18-/m1/s1
    Key: YPZNLFZLPZWWAD-GWIYSAMLSA-N
  • InChI=1/C22H24Br2N10O2/c23-9-1-13(27-3-9)19(35)29-5-11-12(6-30-20(36)14-2-10(24)4-28-14)18(16-8-32-22(26)34-16)17(11)15-7-31-21(25)33-15/h1-4,7-8,11-12,17-18,27-28H,5-6H2,(H,29,35)(H,30,36)(H3,25,31,33)(H3,26,32,34)/t11-,12-,17-,18-/m1/s1
    Key: YPZNLFZLPZWWAD-GWIYSAMLBB
  • C1=C(NC=C1Br)C(=O)NC[C@@H]2[C@H]([C@@H]([C@H]2C3=CN=C(N3)N)C4=CN=C(N4)N)CNC(=O)C5=CC(=CN5)Br
Properties
C22H24Br2N10O2
Molar mass 620.310 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

References
  1. Cipres, A; O'Malley, DP; Li, K; Finlay, D; Baran, PS; Vuori, K (2010). "Sceptrin, a marine natural compound, inhibits cell motility in a variety of cancer cell lines". ACS Chemical Biology. 5 (2): 195–202. doi:10.1021/cb900240k. PMC 2825093. PMID 20030414.
  2. Rodriguez, AD; Lear, MJ; La Clair, JJ (2008). "Identification of the binding of sceptrin to MreB via a bidirectional affinity protocol". J Am Chem Soc. 130 (23): 7256–7258. doi:10.1021/ja7114019. PMID 18479102.
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