An alkaloid
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Penicinoline

Item No. 29932

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,4-dihydro-4-oxo-2-(1H-pyrrol-2-yl)-3-quinolinecarboxylic acid
CAS Number
1214268-60-6
Molecular Formula
C14H10N2O3
Formula Weight
254.2
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Methanol: Slightly soluble: 0.1-1 mg/ml
SMILES
O=C1C(C(O)=O)=C(C2=CC=CN2)NC3=CC=CC=C31
InChi Code
InChI=1S/C14H10N2O3/c17-13-8-4-1-2-5-9(8)16-12(11(13)14(18)19)10-6-3-7-15-10/h1-7,15H,(H,16,17)(H,18,19)
InChi Key
DWKAQISLZUQZNU-UHFFFAOYSA-N
Origin
Fungus/Penicillium sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $164

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    5 mg

    $615

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    Cayman Chemical
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    Product Description

    Penicinoline is an alkaloid that has been found in Penicillium and has antimalarial, insecticidal, and anticancer activities.1,2 It is active against chloroquine-sensitive and -resistant strains of P. falciparum (IC50 = 25 µM for both).1 Penicinoline (1,000 ppm) is also active against the aphid A. gossypii.2 It inhibits proliferation of 95-D and HepG2 cancer cells (IC50s = 0.57 and 6.5 µg/ml, respectively) but not HeLa, KB, KBv200, or Hep-2 cells (IC50s = >100 µg/ml).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Naveen, B., Ommi, N.B., Mudiraj, A., et al. Total synthesis of penicinoline E, marinamide, methyl marinamide and their antimalarial activity. ChemistrySelect 2(11), 3256-3261 (2017).

    2. Shao, C.-L., Wang, C.-Y., Gu, Y.-C., et al. Penicinoline, a new pyrrolyl 4-quinolinone alkaloid with an unprecedented ring system from an endophytic fungus Penicillium sp. Bioorg. Med. Chem. Lett. 20(11), 3284-3286 (2010).