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Camalexin

Cat No.:V40609 Purity: ≥98%
Camalexin is a naturally occuring indole-based phytoalexin isolated from Camelina sativa and Arabidopsis (Cruciferae) with antibacterial, antifungal, antiproliferative and anticancer activities.
Camalexin
Camalexin Chemical Structure CAS No.: 135531-86-1
Product category: Reactive Oxygen Species
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Camalexin is a naturally occuring indole-based phytoalexin isolated from Camelina sativa and Arabidopsis (Cruciferae) with antibacterial, antifungal, antiproliferative and anticancer activities. Camalexin can induce reactive oxygen species (ROS) production. Camalexin has been used in quantification and tolerance assays in Arabidopsis thaliana leaves.
Camalexin (CAS#: 135531-86-1) is a phytoalexin isolated from cruciferous plants including Camelina sativa and Arabidopsis thaliana. It exhibits antibacterial, antifungal, antiproliferative, and cancer chemopreventive activities. Camalexin induces reactive oxygen species (ROS) production and has been used in quantification and tolerance assays in Arabidopsis thaliana leaves. Its molecular formula is C11H8N2S with a molecular weight of 200.26 g/mol.
Biological Activity I Assay Protocols (From Reference)
Targets
Camalexin does not have a single well-defined pharmacological target; it exhibits pleiotropic effects through multiple mechanisms. It induces reactive oxygen species (ROS) production, which contributes to its antimicrobial and antiproliferative activities. Camalexin has been shown to be more effective in aggressive prostate cancer cells that express high ROS levels. In Arabidopsis thaliana, camalexin and salicylic acid confer resistance to Phytophthora capsici. The compound's targets include bacterial and fungal pathogens as well as cancer cells.
ln Vitro
Human breast cancer cell lines have antiproliferative activity in response to camalexin [2]. In oomycetes, the first steps toward the synthesis of Camalexin and the production of reactive oxygen species (ROS) are Phytophthora and Pythium Nep1-like proteins (necrosis and ethylene-inducing peptide 1-like proteins). ROS seem to have a ubiquitous role in the synthesis of camalexin. Camalexin synthesis and chemical stimulation of ROS (e.g., by applying acifluorfen) happen at the same time. An esa1 mutant with delayed Camalexin induction was found in a screen for enhanced susceptibility to Alternaria brassicae. The amounts of produced Camalexin are decreased, especially in reaction to ROS inducers. The fact that esa1 mutants are unable to produce Camalexin in response to Leptosphaeria maculans confirms the crucial role that ESA1 plays. Ups1, a different mutant that dramatically lowers Camalexin accumulation, was identified due to decreased tryptophan biosynthesis enzyme expression [2].
In vitro, Camalexin exhibits antiproliferative activity against human breast cancer cell lines and other cancer cells. It induces reactive oxygen species (ROS) production, which is believed to contribute to its cytotoxic effects. Camalexin shows antibacterial and antifungal activities. In oomycetes Phytophthora and Pythium, Nep1-like proteins trigger camalexin synthesis and ROS formation. The compound's activity is typically evaluated using cell viability and antimicrobial susceptibility assays.
ln Vivo
In vivo, Camalexin has been studied for its role in plant defense against pathogens. In Arabidopsis thaliana, camalexin and salicylic acid confer resistance to Phytophthora capsici. The compound's ability to induce ROS production and inhibit pathogen growth contributes to its in vivo efficacy in plants. As a phytoalexin, camalexin is produced by plants in response to pathogen attack. Its in vivo effects in mammalian systems are less well-characterized, though its antiproliferative activity suggests potential anticancer applications.
Enzyme Assay
Cell-free assays for Camalexin involve studying its antimicrobial activity and its ability to induce ROS production. Antimicrobial activity can be assessed using standard broth microdilution methods to determine minimum inhibitory concentrations (MICs) against bacterial and fungal pathogens. ROS production can be measured using cell-free systems with fluorescent probes such as DCFH-DA. The compound's chemical purity (≥98%) and identity are confirmed by HPLC and NMR analysis. Camalexin is soluble in DMSO (20 mg/mL).
Cell Assay
In vitro cellular assays for Camalexin typically involve treating cancer cell lines with various concentrations of the compound. Cells are incubated with camalexin for defined periods (24-72 hours). Cell viability is assessed using MTT, CellTiter-Glo, or other standard assays. ROS production is measured using fluorescent probes such as DCFH-DA. Apoptosis is evaluated using Annexin V/PI staining and caspase activity assays. Antimicrobial activity is assessed using broth microdilution methods. Dose-response curves are generated to determine IC50 values.
Animal Protocol
In vivo animal studies for Camalexin are limited, as the compound is primarily studied as a plant phytoalexin. In plant models, camalexin has been used in quantification and tolerance assays in Arabidopsis thaliana leaves. In mammalian models, the compound's anticancer activity has been investigated in xenograft models. However, specific dosing regimens and experimental protocols are not extensively documented in the available literature. Standard protocols for evaluating anticancer agents would typically be employed.
ADME/Pharmacokinetics
Pharmacokinetic properties of Camalexin include a molecular weight of 200.26 g/mol and molecular formula C11H8N2S. The compound has a purity of ≥98% (HPLC) and is soluble in DMSO (20 mg/mL). It is stored as a powder at 2-8°C. As a small molecule, it is expected to have moderate oral bioavailability and tissue penetration. Detailed ADME parameters such as half-life, Cmax, and AUC are not extensively reported in the available literature. The compound is typically handled as a solid and stored at appropriate conditions.
Toxicity/Toxicokinetics
The toxicity profile of Camalexin has been characterized for research use. The compound is classified with hazard warnings including Acute Tox. 4 Oral, Eye Irrit. 2, Skin Irrit. 2, and STOT SE 3 (respiratory system). Standard safety precautions should be followed when handling this compound, including the use of personal protective equipment. The compound is intended for research use only and not for therapeutic applications in humans.
References

[1]. Synthesis of camalexin and related phytoalexins. Tetrahedron. Volume 48, Issue 14, 1992, Pages 2919-2924.

[2]. Glawischnig E. Camalexin. Phytochemistry. 2007 Feb;68(4):401-6.

[3]. Antiproliferative and cancer chemopreventive activity of phytoalexins: focus on indole phytoalexins from crucifers. Neoplasma. 2003;50(4):239-45.

Additional Infomation
Camalexin acid is an indole phytoalexin with a structure in which the indole ring at the 3-position is replaced by a 1,3-thiazolyl-2-yl group. It is a metabolite. Camalexin acid belongs to the indole phytoalexin class and is also a member of the 1,3-thiazolyl class of compounds. It has been reported that Camalexin acid exists in Arabidopsis thaliana, other Arabidopsis species, and Capsella bursa-pastoris, and relevant data are available for reference.
Camalexin is a phytoalexin isolated from cruciferous plants that exhibits antibacterial, antifungal, antiproliferative, and cancer chemopreventive activities. It induces reactive oxygen species (ROS) production and is more effective in aggressive prostate cancer cells that express high ROS levels. In Arabidopsis thaliana, camalexin confers resistance to Phytophthora capsici. Camalexin is a research tool for studying plant defense, antimicrobial activity, and cancer biology. It has not entered clinical trials and is strictly for research purposes.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C11H8N2S
Molecular Weight
200.25962
Exact Mass
200.041
CAS #
135531-86-1
PubChem CID
636970
Appearance
White to yellow solid powder
Melting Point
134 - 137 °C
LogP
3.291
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
1
Heavy Atom Count
14
Complexity
210
Defined Atom Stereocenter Count
0
InChi Key
IYODIJVWGPRBGQ-UHFFFAOYSA-N
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
Chemical Name
2-(1H-indol-3-yl)-1,3-thiazole
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~125 mg/mL (~624.19 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (10.39 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (10.39 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (10.39 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.9935 mL 24.9675 mL 49.9351 mL
5 mM 0.9987 mL 4.9935 mL 9.9870 mL
10 mM 0.4994 mL 2.4968 mL 4.9935 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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