An AChE inhibitor
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Cyclopenin

Item No. 23145

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
rel-(-)-4-methyl-3'S-phenyl-spiro[3H-1,4-benzodiazepine-3,2'R-oxirane]-2,5(1H,4H)-dione
CAS Number
20007-87-8
Synonyms
  • (–)-Cyclopenin
  • NSC 114538
  • NSC 604989
Molecular Formula
C17H14N2O3
Formula Weight
294.3
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
λmax
213 nm
SMILES
O=C(C1=CC=CC=C1N2)N(C)[C@]3([C@@](O3)([H])C4=CC=CC=C4)C2=O
InChi Code
InChI=1S/C17H14N2O3/c1-19-15(20)12-9-5-6-10-13(12)18-16(21)17(19)14(22-17)11-7-3-2-4-8-11/h2-10,14H,1H3,(H,18,21)/t14-,17+/m1/s1
InChi Key
APLKWZASYUZSBL-PBHICJAKSA-N
Origin
Fungus/Penicillium sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Cyclopenin is an inhibitor of acetylcholinesterase (AChE; IC50 = 2.04 μM for human recombinant AChE) that is produced by Penicillium.1,2,3 It exhibits greater than 2,000-fold selectivity over recombinant equine butyrylcholinesterase with an IC50 value greater than 4,080 μM.4 Cyclopenin also has antibacterial activity against E. coli and M. pyogenes.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bracken, A., Pocker, A., and Raistrick, H. Studies in the biochemistry of microorganisms. 93. Cyclopenin, a nitrogen-containing metabolic product of Penicillium cyclopium westling. Biochem. J. 57(4), 587-595 (1954).

    2. Nover, L., and Luckner, M. On the biosynthesis of cyclopenin and cyclopenol, benzodiazepine alkaloids from Penicillium cyclopium westling. Eur. J. Biochem. 10(2), 268-273 (1969).

    3. Frisvad, J.C., Filtenborg, O., and Wicklow, D.T. Terverticillate penicillia isolated from underground seed caches and cheek pouches of banner-tailed kangaroo rats (Dipodomys spectabilis). Can. J. Bot. 65(4), 765-773 (1987).

    4. Kuno, F., Otoguro, K., Shiomi, K., et al. Arisugacins A and B, novel and selective acetylcholinesterase inhibitors from Penicillium sp. FO-4259. I. Screening, taxonomy, fermentation, isolation and biological activity. J. Antibiot. (Tokyo) 49(8), 742-747 (1996).