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Sceptrin . dihydrochloride

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AG-CN2-0440-C250250 µgCHF 120.00

Specifications / Handling

More Information
Product Details
Product Type Chemical
Properties
Formula

C22H24Br2N10O2 . 2HCl

MW 620.3 . 72.9
CAS 79703-25-6
Source/Host Chemicals Isolated from the sponge Agelas nakamurai.
Purity Chemicals ≥97% (HPLC)
Appearance Amorphous powder.
Solubility Soluble in DMSO or ethanol.
Identity Determined by 1H-NMR, 13C-NMR and MS.
InChi Key WCZVIHWVHOXPDO-QZWVQEDUSA-N
Smiles NC1N=CC(=N1)[C@H]1[C@H](CNC(=O)C2=CC(Br)=CN2)[C@@H](CNC(=O)C2=CC(Br)=CN2)[C@@H]1C1=NC(N)N=C1
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Keep cool and dry.
Protect from light.
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS Download PDF Download PDF
Product Specification Sheet
Datasheet Download PDF Download PDF

Scientific Background Information

Product Description
  • Antibiotic. Inhibits the growth of several Gram-positive and Gram-negative bacteria. Binds to MreB inducing disruption of the bacterial cell wall.
  • Competitive inhibitor of muscarinic acetylcholine receptors (mAChR).
  • Cell motility inhibitor by specifically blocking contractility of the cell. Direct binding with monomeric actin disrupts the polymerization of actin into microfilaments necessary for cellular mechanical processes.
Product-specific References
  1. Anti-muscarinic activity of a family of C11N5 compounds isolated from Agelas sponges: R. Rosa, et al.; Experientia 48, 885 (1992)
  2. A study on the mechanism of action of sceptrin, an antimicrobial agent isolated from the South Pacific sponge Agelas mauritiana: V.S. Bernan, et al.; J. Antimicrob. Chemother. 32, 539 (1993)
  3. Identification of the binding of sceptrin to MreB via a bidirectional affinity protocol: A.D. Rodriguez, et al.; JACS 130, 7256 (2008)
  4. Sceptrin, a marine natural compound, inhibits cell motility in a variety of cancer cell lines: A. Cipres, et al.; ACS Chem. Biol. 5, 195 (2010)
  5. Asymmetric syntheses of sceptrin and massadine and evidence for biosynthetic enantiodivergence: Z. Ma, et al.; Science 346, 219 (2014)
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