Sceptrin dihydrochloride An antibiotic which inhibits cell motility

Sceptrin dihydrochloride (CAS 79703-25-6)

Sceptrin dihydrochloride | CAS 79703-25-6 is rated 5.0 out of 5 by 1.
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Synonym: N,N'-{[(1R,2R,3S,4S)-3,4-Bis(2-amino-1H-imidazol-4-yl)cyclobutane-1,2-diyl]bis(methylene)}bis(4-bromo-1H-pyrrole-2-carboxamide) dihydrochloride
Application: An antibiotic which inhibits cell motility
CAS Number: 79703-25-6
Purity: ≥97%
Molecular Weight: 693.23
Molecular Formula: C22H24Br2N10O22HCl
* Refer to Certificate of Analysis for lot specific data (including water content).
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Sceptrin dihydrochloride is a marine sponge bromopyrrole alkaloid natural product. Sceptrin has been shown to strongly inhibit cell motility by specifically blocking contractility of the cell. This observation has been correlated to a direct binding between sceptrin and monomeric actin, which disrupts the polymerization of actin into microfilaments necessary for cellular mechanical processes. Sceptrin Inhibits the growth of several Gram-positive and Gram-negative bacteria, and competitively inhibits muscarinic acetylcholine receptors (mAChR).


References

1. Rosa, R., et al. 1992. Experientia. 48: 885-887. PMID: 1397186
2. Bernan, V.S., et al. 1993. J. Antimicrob. Chemother. 32: 539-550. PMID: 8288495
3. Eder, C., et al. 1999. J. Nat. Prod. 62: 1295-1297. PMID: 10514317
4. O'Malley, D.P., et al. 2007. J. Am. Chem. Soc. 129: 4762-4775. PMID: 17375928
5. Cipres, A., et al. 2010. ACS Chem. Biol. 5: 195-202. PMID: 20030414

Appearance :
Amorphous powder
Physical State :
Solid
Derived From :
Agelas nakamurai
Solubility :
Soluble in DMSO, and 100% ethanol.
Storage :
Store at -20° C
Refractive Index :
n20D ~1.74 (Predicted)
IC50 :
Protein phosphatase 2A: IC50 = 50 µM (COS7 cells)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
PubChem CID :
157393
MDL Number :
MFCD03095571
SMILES :
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.Cl.Cl

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Certificate of Analysis

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Rated 5 out of 5 by from Sceptrin dihydrochloride is reported as an Sceptrin dihydrochloride is reported as an antibiotic and a muscarinic acetylcholine receptor inhibitor in many articles. -SCBT Publication Review
Date published: 2015-06-29
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