An inhibitor of splicing factor SF3b
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Pladienolide B

Item No. 16538

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(4R,7R,8S,9E,11S,12S)-8-(acetyloxy)-4,7-dihydroxy-12-[(1E,3E,5S)-6-[(2R,3R)-3-[(1R,2S)-2-hydroxy-1-methylbutyl]-2-oxiranyl]-1,5-dimethyl-1,3-oxacyclododec-9-en-2-one
CAS Number
445493-23-2
Molecular Formula
C30H48O8
Formula Weight
536.7
Purity
≥95%
Formulation (Request formulation change)
A clear film
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
λmax
241 nm
SMILES
O[C@H]1CC(O[C@H](/C(C)=C/C=C/[C@@H](C)C[C@@H]2[C@]([C@H](C)[C@H](CC)O)([H])O2)[C@@H](C)/C=C/[C@H](OC(C)=O)[C@](C)(O)CC1)=O
InChi Code
InChI=1S/C30H48O8/c1-8-24(33)21(5)29-25(37-29)16-18(2)10-9-11-19(3)28-20(4)12-13-26(36-22(6)31)30(7,35)15-14-23(32)17-27(34)38-28/h9-13,18,20-21,23-26,28-29,32-33,35H,8,14-17H2,1-7H3/b10-9+,13-12+,19-11+/t18-,20+,21-,23-,24+,25-,26+,28-,29-,30-/m1/s1
InChi Key
SDOUORKJIJYJNW-QHOUZYGJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 µg

    $131

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    500 µg

    $459

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    Cayman Chemical
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    Product Description

    Spliceosomes mediate the processing of pre-mRNA into mature mRNA.1,2 Each spliceosome is a multiunit complex containing several proteins and RNA molecules that work in unison to repeatedly cleave and rejoin segments of mRNA.1,3 Pladienolide B is a macrocyclic lactone that selectively binds splicing factor 3b and inhibits mRNA splicing.4,5 Through this action, pladienolide B potently blocks the growth of proliferating cells with mean IC50 values of 1.6 nM for six gastric cancer cell lines.6,7 In xenograft tumors generated in mice using human cancer cells, pladienolide B blocks mRNA splicing and induces apoptosis, clearing tumors within two weeks after treatment.7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Naro, C., and Sette, C. Phosphorylation-mediated regulation of alternative splicing in cancer. Int. J. Cell Biol. 151839 (2013).

    2. Webb, T.R., Joyner, A.S., and Potter, P.M. The development and application of small molecule modulators of SF3b as therapeutic agents for cancer. Drug Discov. Today 18(1-2), 43-49 (2013).

    3. Yokoi, A., Kotake, Y., Takahashi, K., et al. Biological validation that SF3b is a target of the antitumor macrolide pladienolide. FEBS J. 278(24), 4870-4880 (2011).

    4. Kotake, Y., Sagane, K., Owa, T., et al. Splicing factor SF3b as a target of the antitumor natural product pladienolide. Nat. Chem. Biol. 3, 570-575 (2007).

    5. Effenberger, K.A., Anderson, D.D., Bray, W.M., et al. Coherence between cellular responses and in vitro splicing inhibition for the anti-tumor drug pladienolide B and its analogs. The Journal of Biological Chemisty 289, 1938-1947 (2014).

    6. Sato, M., Muguruma, N., Nakagawa, T., et al. High antitumor activity of pladienolide B and its derivative in gastric cancer. Cancer Sci. 105(1), 110-116 (2014).