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Funalenone

Item No. 23491

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3,4,7,9-tetrahydroxy-2-methoxy-6-methyl-1H-phenalen-1-one
CAS Number
259728-61-5
Molecular Formula
C15H12O6
Formula Weight
288.3
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: solubleDMSO: solubleMethanol: soluble
SMILES
O=C1C(OC)=C(O)C2=C(O)C=C(C)C3=C2C1=C(O)C=C3O
InChi Code
InChI=1S/C15H12O6/c1-5-3-6(16)10-12-9(5)7(17)4-8(18)11(12)14(20)15(21-2)13(10)19/h3-4,16-19H,1-2H3
InChi Key
QAPJKCNKHLDDAK-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $235

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    Product Description

    Funalenone is a phenalenone originally isolated from A. niger.1 It inhibits HIV-1 integrase (IC50 = 10 μM) and HIV-1 replication in human peripheral blood cells transformed by murine leukemia virus (HPB-M(a); IC50 = 1.7 μM) but is less cytotoxic to mammalian HPB-M(a) cells (IC50 = 87 μM).2 Funalenone selectively inhibits matrix metalloproteinase-1 (MMP-1; IC50 = 170 μM) over MMP-2 and MMP-9, which it inhibits by 18.3 and 38.2%, respectively, when used at a concentration of 400 μM.1 It also inhibits the bacterial cell wall synthesis enzymes MraY and MurG (IC50s = 25.5 μM in a membrane plate assay) and inhibits growth of S. aureus with a MIC value of 64 μg/mL.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Inokoshi, J., Shiomi, K., Masuma, R., et al. Funalenone, a novel collagenase inhibitor produced by Aspergillus niger. J. Antibiot. (Tokyo) 52(12), 1095-1100 (1999).

    2. Shiomi, K., Matsui, R., Isozaki, M., et al. Fungal phenalenones inhibit HIV-1 integrase. J. Antibiot. (Tokyo) 58(1), 65-68 (2005).

    3. Zawadzke, L.E., Wu, P., Cook, L.S., et al. Targeting the MraY and MurG bacterial enzymes for antimicrobial therapeutic intervention. Anal. Biochem. 314(2), 243-252 (2003).