Camalexin | CAS# 135531-86-1 | Antiproliferative activity

MedKoo Cat#: 112126 | Name: Camalexin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Camalexin exhibits antiproliferative activity in vitro against various cancer cell lines.

Chemical Structure

Camalexin

CAS# 135531-86-1

Theoretical Analysis

MedKoo Cat#: 112126

Name: Camalexin

CAS#: 135531-86-1

Chemical Formula: C11H8N2S

Exact Mass: 200.0408

Molecular Weight: 200.26

Elemental Analysis: C, 65.98; H, 4.03; N, 13.99; S, 16.01

Price and Availability

Size	Price	Availability
10mg	USD 285.00	2 Weeks
25mg	USD 550.00	2 Weeks
50mg	USD 950.00	2 Weeks

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Related CAS #

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Synonym

Camalexin

IUPAC/Chemical Name

2-(1H-indol-3-yl)thiazole

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

SMILES Code

C12=C(C=CC=C2)NC=C1C3=NC=CS3

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

	Solvent	mg/mL	mM
Solubility
	DMF	14.0	69.91
	DMSO	33.0	164.79
	Ethanol	10.0	49.94

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 200.26 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Glawischnig E. Camalexin. Phytochemistry. 2007 Feb;68(4):401-6. doi: 10.1016/j.phytochem.2006.12.005. Epub 2007 Jan 10. PMID: 17217970. 2: Nguyen NH, Trotel-Aziz P, Clément C, Jeandet P, Baillieul F, Aziz A. Camalexin accumulation as a component of plant immunity during interactions with pathogens and beneficial microbes. Planta. 2022 May 5;255(6):116. doi: 10.1007/s00425-022-03907-1. PMID: 35511374. 3: Yamashita N, Taga C, Ozawa M, Kanno Y, Sanada N, Kizu R. Camalexin, an indole phytoalexin, inhibits cell proliferation, migration, and mammosphere formation in breast cancer cells via the aryl hydrocarbon receptor. J Nat Med. 2022 Jan;76(1):110-118. doi: 10.1007/s11418-021-01560-8. Epub 2021 Aug 31. PMID: 34463909. 4: Yang Y, Wang G, Wu W, Yao S, Han X, He D, He J, Zheng G, Zhao Y, Cai Z, Yu R. Camalexin Induces Apoptosis via the ROS-ER Stress-Mitochondrial Apoptosis Pathway in AML Cells. Oxid Med Cell Longev. 2018 Nov 14;2018:7426950. doi: 10.1155/2018/7426950. PMID: 30538806; PMCID: PMC6261074. 5: Rauhut T, Glawischnig E. Evolution of camalexin and structurally related indolic compounds. Phytochemistry. 2009 Oct-Nov;70(15-16):1638-44. doi: 10.1016/j.phytochem.2009.05.002. Epub 2009 Jun 10. PMID: 19523656. 6: Nguyen NH, Trotel-Aziz P, Villaume S, Rabenoelina F, Clément C, Baillieul F, Aziz A. Priming of camalexin accumulation in induced systemic resistance by beneficial bacteria against Botrytis cinerea and Pseudomonas syringae pv. tomato DC3000. J Exp Bot. 2022 Jun 2;73(11):3743-3757. doi: 10.1093/jxb/erac070. PMID: 35191984. 7: Mucha S, Heinzlmeir S, Kriechbaumer V, Strickland B, Kirchhelle C, Choudhary M, Kowalski N, Eichmann R, Hückelhoven R, Grill E, Kuster B, Glawischnig E. The Formation of a Camalexin Biosynthetic Metabolon. Plant Cell. 2019 Nov;31(11):2697-2710. doi: 10.1105/tpc.19.00403. Epub 2019 Sep 11. PMID: 31511315; PMCID: PMC6881122. 8: Liao A, Li L, Wang T, Lu A, Wang Z, Wang Q. Discovery of Phytoalexin Camalexin and Its Derivatives as Novel Antiviral and Antiphytopathogenic-Fungus Agents. J Agric Food Chem. 2022 Mar 2;70(8):2554-2563. doi: 10.1021/acs.jafc.1c07805. Epub 2022 Feb 18. Erratum in: J Agric Food Chem. 2022 Apr 27;70(16):5270. PMID: 35179026. 9: Koprivova A, Schwier M, Volz V, Kopriva S. Shoot-root interaction in control of camalexin exudation in Arabidopsis. J Exp Bot. 2023 Apr 18;74(8):2667-2679. doi: 10.1093/jxb/erad031. PMID: 36651631. 10: Lemarié S, Robert-Seilaniantz A, Lariagon C, Lemoine J, Marnet N, Levrel A, Jubault M, Manzanares-Dauleux MJ, Gravot A. Camalexin contributes to the partial resistance of Arabidopsis thaliana to the biotrophic soilborne protist Plasmodiophora brassicae. Front Plant Sci. 2015 Jul 21;6:539. doi: 10.3389/fpls.2015.00539. PMID: 26257750; PMCID: PMC4508518. 11: Almasry M, Jemaà M, Mischitelli M, Lang F, Faggio C. Camalexin-Induced Cell Membrane Scrambling and Cell Shrinkage in Human Erythrocytes. Cell Physiol Biochem. 2017;41(2):731-741. doi: 10.1159/000458733. Epub 2017 Feb 13. PMID: 28222420. 12: Zhang N, Lariviere A, Tonsor SJ, Traw MB. Constitutive camalexin production and environmental stress response variation in Arabidopsis populations from the Iberian Peninsula. Plant Sci. 2014 Aug;225:77-85. doi: 10.1016/j.plantsci.2014.05.020. Epub 2014 Jun 11. PMID: 25017162. 13: Savatin DV, Bisceglia NG, Gravino M, Fabbri C, Pontiggia D, Mattei B. Camalexin Quantification in Arabidopsis thaliana Leaves Infected with Botrytis cinerea. Bio Protoc. 2015 Jan 20;5(2):e1379. doi: 10.21769/BioProtoc.1379. PMID: 29085857; PMCID: PMC5660616. 14: Yang L, Zhang Y, Guan R, Li S, Xu X, Zhang S, Xu J. Co-regulation of indole glucosinolates and camalexin biosynthesis by CPK5/CPK6 and MPK3/MPK6 signaling pathways. J Integr Plant Biol. 2020 Nov;62(11):1780-1796. doi: 10.1111/jipb.12973. Epub 2020 Jun 26. PMID: 32449805; PMCID: PMC7687085. 15: Møldrup ME, Salomonsen B, Geu-Flores F, Olsen CE, Halkier BA. De novo genetic engineering of the camalexin biosynthetic pathway. J Biotechnol. 2013 Sep 10;167(3):296-301. doi: 10.1016/j.jbiotec.2013.06.013. Epub 2013 Jul 3. PMID: 23830903. 16: Zook M, Leege L, Jacobson D, Hammerschmidt R. Camalexin accumulation in Arabis lyrata. Phytochemistry. 1998 Dec;49(8):2287-9. doi: 10.1016/s0031-9422(98)00373-2. PMID: 9887527. 17: Zook M, Hammerschmidt R. Origin of the thiazole ring of camalexin, a phytoalexin from Arabidopsis thaliana. Plant Physiol. 1997 Feb;113(2):463-8. doi: 10.1104/pp.113.2.463. PMID: 9046593; PMCID: PMC158161. 18: Liao A, Li L, Wang T, Lu A, Wang Z, Wang Q. Correction to Discovery of Phytoalexin Camalexin and Its Derivatives as Novel Antiviral and Antiphytopathogenic-Fungus Agents. J Agric Food Chem. 2022 Apr 27;70(16):5270. doi: 10.1021/acs.jafc.2c01561. Epub 2022 Apr 14. Erratum for: J Agric Food Chem. 2022 Mar 2;70(8):2554-2563. PMID: 35420031. 19: Su T, Li Y, Yang H, Ren D. Reply: complexity in camalexin biosynthesis. Plant Cell. 2013 Feb;25(2):367-70. doi: 10.1105/tpc.113.109975. Epub 2013 Feb 28. PMID: 23449502; PMCID: PMC3608765. 20: Smith B, Randle D, Mezencev R, Thomas L, Hinton C, Odero-Marah V. Camalexin- induced apoptosis in prostate cancer cells involves alterations of expression and activity of lysosomal protease cathepsin D. Molecules. 2014 Apr 2;19(4):3988-4005. doi: 10.3390/molecules19043988. PMID: 24699144; PMCID: PMC4376535.