A plant defense alkaloid
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Camalexin

Item No. 21971

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-(2-thiazolyl)-1H-indole
CAS Number
135531-86-1
Molecular Formula
C11H8N2S
Formula Weight
200.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 14 mg/mlDMSO: 33 mg/mlDMSO:PBS (pH 7.2) (1:40): 0.02 mg/mlEthanol: 10 mg/ml
λmax
217, 319 nm
SMILES
C1(C(C2=NC=CS2)=CN3)=C3C=CC=C1
InChi Code
InChI=1S/C11H8N2S/c1-2-4-10-8(3-1)9(7-13-10)11-12-5-6-14-11/h1-7,13H
InChi Key
IYODIJVWGPRBGQ-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $36

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    5 mg

    $86

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    10 mg

    $135

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    Product Description

    Camalexin is an alkaloid released by plants of the Brassicaceae family in response to pathogen infection.1 In addition to antimicrobial properties and a role in plant defense, camalexin exhibits antiproliferative activity in vitro against various cancer cell lines.2,3,4,5 Camalexin is active against HeLa, Jurkat, MDA-MB-231, and CEM cancer cell lines (IC50s = 50.0, 46.2, 77.7, and 67.6 μM, respectively), but it is also toxic to primary human umbilical vein endothelial cells (HUVEC; (IC50 = 74.0 μM).3 Camalexin induces apoptosis in Jurkat cells by increasing reactive oxygen species (ROS) levels and activating caspase-8 and caspase-9.2 In human prostate cancer cell lines, camalexin (25 μM) is more active against aggressive lines and increases ROS levels and apoptosis via cathepsin D relocation from lysosomes to the cytosol.5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ahuja, I., Kissen, R., and Bones, A.M. Phytoalexins in defense against pathogens. Trends Plant Sci. 17(2), 73-90 (2012).

    2. Mezencev, R., Updegrove, T., Kutschy, P., et al. Camalexin induces apoptosis in T-leukemia Jurkat cells by increased concentration of reactive oxygen species and activation of caspase-8 and caspase-9. J. Nat. Med. 65(3-4), 488-499 (2011).

    3. Pilatova, M., Ivanova, L., Kutschy, P., et al. In vitro toxicity of camalexin derivatives in human cancer and non-cancer cells. Toxicol. In Vitro 27(2), 939-944 (2013).

    4. Smith, B.A., Neal, C.L., Chetram, M., et al. The phytoalexin camalexin mediates cytotoxicity towards aggressive prostate cancer cells via reactive oxygen species. J. Nat. Med. 67(3), 607-618 (2013).

    5. Smith, B., Randle, D., Mezencev, R., et al. Camalexin-induced apoptosis in prostate cancer cells involves alterations of expression and activity of lysosomal protease cathepsin D. Molecules 19(4), 3988-4005 (2014).

    6. Festa, C., Renga, B., D'Amore, C., et al. Exploitation of cholane scaffold for the discovery of potent and selective farnesoid X receptor (FXR) and G-protein coupled bile acid receptor 1 (GP-BAR1) ligands. J. Med. Chem. 57(20), 8477-8495 (2014).