| Identification | Back Directory | [Name]
camalexin | [CAS]
135531-86-1 | [Synonyms]
camalexin
Camalexine
Camalexin >=98% (HPLC)
3-(Thiazol-2-yl)-1H-indole
1H-Indole, 3-(2-thiazolyl)-
3-(1,3-Thiazol-2-yl)-1H-indole, camalexin | [Molecular Formula]
C11H8N2S | [MDL Number]
MFCD18451889 | [MOL File]
135531-86-1.mol | [Molecular Weight]
200.26 |
| Chemical Properties | Back Directory | [Boiling point ]
424.8±47.0 °C(Predicted) | [density ]
1.336±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: soluble20mg/mL, clear | [form ]
powder | [pka]
15.49±0.30(Predicted) | [color ]
white to light brown |
| Hazard Information | Back Directory | [Description]
Camalexin is an alkaloid released by plants of the Brassicaceae family in response to pathogen infection. In addition to antimicrobial properties and a role in plant defense, camalexin exhibits antiproliferative activity in vitro against various cancer cell lines. 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). Camalexin induces apoptosis in Jurkat cells by increasing reactive oxygen species (ROS) levels and activating caspase-8 and caspase-9. 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. | [Uses]
Camalexin has been used in quantification and tolerance assays in Arabidopsis thaliana leaves. | [Definition]
ChEBI: An indole phytoalexin that is indole substituted at position 3 by a 1,3-thiazol-2-yl group. | [Synthesis Reference(s)]
Tetrahedron, 51, p. 773, 1995 DOI: 10.1016/0040-4020(94)00987-6 | [Biochem/physiol Actions]
Camalexin is a phytoalexin isolated from cruciferous plants that exhibits antibacterial, antifungal, antiproliferative and cancer chemopreventive activities. Apparently, camalexin increases the ROS levels and is more effective in aggressive prostate cancer cells that express high ROS levels. In Arabidopsis thaliana, camalexin and salicylic acid confer resistance to Phytophthora capsici. | [References]
[1] ISHITA AHUJA Atle M B Ralph Kissen. Phytoalexins in defense against pathogens.[J]. Trends in Plant Science, 2012, 17 2: 73-90. DOI: 10.1016/j.tplants.2011.11.002
[2] ROMAN MEZENCEV. Camalexin induces apoptosis in T-leukemia Jurkat cells by increased concentration of reactive oxygen species and activation of caspase-8 and caspase-9[J]. Journal of Natural Medicines, 2011, 65 3-4. DOI: 10.1007/s11418-011-0526-x
[3] MARTINA PILATOVA . In vitro toxicity of camalexin derivatives in human cancer and non-cancer cells[J]. Toxicology in Vitro, 2013, 27 2: Pages 939-944. DOI: 10.1016/j.tiv.2013.01.006
[4] BASIL A. SMITH. The phytoalexin camalexin mediates cytotoxicity towards aggressive prostate cancer cells via reactive oxygen species[J]. Journal of Natural Medicines, 2012, 67 3: 607-618. DOI: 10.1007/s11418-012-0722-3
[5] BASIL SMITH. Camalexin-induced apoptosis in prostate cancer cells involves alterations of expression and activity of lysosomal protease cathepsin D.[J]. Molecules, 2014, 19 4: 3988-4005. DOI: 10.3390/molecules19043988
[6] CARMEN FESTA. 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]. Journal of Medicinal Chemistry, 2014, 57 20: 8477-8495. DOI: 10.1021/jm501273r |
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