A Cdk1 inhibitor
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Butyrolactone I

Item No. 21765

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2R)-2,5-dihydro-4-hydroxy-2-[[4-hydroxy-3-(3-methyl-2-buten-1-yl)phenyl]methyl]-3-(4-hydroxyphenyl)-5-oxo-2-furancarboxylic acid, methyl ester
CAS Number
87414-49-1
Molecular Formula
C24H24O7
Formula Weight
424.5
Purity
≥90%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: solubleMethanol: soluble
SMILES
O=C1O[C@@](CC2=CC(C/C=C(C)/C)=C(O)C=C2)(C(OC)=O)C(C3=CC=C(O)C=C3)=C1O
InChi Code
InChI=1S/C24H24O7/c1-14(2)4-6-17-12-15(5-11-19(17)26)13-24(23(29)30-3)20(21(27)22(28)31-24)16-7-9-18(25)10-8-16/h4-5,7-12,25-27H,6,13H2,1-3H3/t24-/m1/s1
InChi Key
NGOLMNWQNHWEKU-XMMPIXPASA-N
Origin
Fungus/Aspergillus sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Butyrolactone I is a secondary metabolite from A. terreus that acts as an ATP-competitive inhibitor of cyclin-dependent kinase 1 (Cdk1; IC50 = 20 μg/ml in PC-14 cells).1 It induces dose-dependent G2/M arrest, inhibits DNA synthesis, and decreases Cdk1 protein expression in vitro.1 Butyrolactone I has antitumor effects in non-small cell lung, small cell lung, and prostate cancer cell lines (mean IC50 = 50 μg/ml).1,2 It inhibits in vitro Cdk1 phosphorylation of tau and in vivo phosphorylation of transcription factor E2F-1.3,4 Additionally, exogenous application of butyrolactone I to A. terreus cultures increases biogenesis of the secondary metabolites lovastatin (Item No. 10010338) and conidiation in a quorum-sensing manner.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nishio, K., Arioka, H., Kurokawa, H., et al. Antitumor effects of butyrolactone I, a selective cdc2 kinase inhibitor, on human lung cancer cell lines. Anticancer Res. 16(6B), 3387-3395 (1996).

    2. Suzuki, M., Hosaka, Y., Matsushima, H., et al. Butyrolactone I induces cyclin B1 and causes G2/M arrest and skipping of mitosis in human prostate cell lines. Cancer Lett. 138(1-2), 121-130 (1999).

    3. Hosoi, T., Uchiyama, M., Okumura, E., et al. Evidence for cdk5 as a major activity phosphorylating tau protein in porcine brain extract. J. Biochem. 117(4), 741-749 (1995).

    4. Kitagawa, M., Higashi, H., Suzuki-Takahashi, I., et al. Phosphorylation of E2F-1 by cyclin A-cdk2. Oncogene 10(2), 229-236 (1995).

    5. Palonen, E.K., Raina, S., Brandt, A., et al. Transcriptomic complexity of Aspergillus terreus velvet gene family under the influence of butyrolactone I. Microorganisms 14;5(1), (2017).