Brassinin | CAS#105748-59-2 | indoleamine-2,3-dioxygenase inhibitor

MedKoo Cat#: 540050 | Name: Brassinin

Description:

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

Brassinin is an indoleamine-2,3-dioxygenase inhibitor found in cruciferous vegetables. It induces cell cycle arrest and apoptosis in prostate cancer cells and inhibits DMBA-induced skin tumor formation in vivo.

Chemical Structure

Brassinin

CAS#105748-59-2

Theoretical Analysis

MedKoo Cat#: 540050

Name: Brassinin

CAS#: 105748-59-2

Chemical Formula: C11H12N2S2

Exact Mass: 236.0442

Molecular Weight: 236.35

Elemental Analysis: C, 55.90; H, 5.12; N, 11.85; S, 27.13

Price and Availability

Size	Price	Availability
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 Weeks
200mg	USD 1,250.00	2 Weeks
500mg	USD 2,850.00	2 Weeks
1g	USD 3,850.00	2 Weeks
2g	USD 6,450.00	2 Weeks

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Synonym

Brassinine; CCG-208623; CCG208623; CCG 208623; HE-005916; HE005916; HE 005916; HE-292778; HE292778; HE292778; BSN

IUPAC/Chemical Name

methyl ((1H-indol-3-yl)methyl)carbamodithioate

InChi Key

QYKQWFZDEDFELK-UHFFFAOYSA-N

InChi Code

InChI=1S/C11H12N2S2/c1-15-11(14)13-7-8-6-12-10-5-3-2-4-9(8)10/h2-6,12H,7H2,1H3,(H,13,14)

SMILES Code

S=C(SC)NCC1=CNC2=C1C=CC=C2

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

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

An anticancer phytoalexin.

In vitro activity:

Brassinin reduced cell proliferation in a dose-dependent manner (Figure 1A,B). Specifically, 100 µM of brassinin reduced the proliferation of Huh7 cells to 39% and that of Heb3B cells to 49% (*** p < 0.001). In contrast, brassinin suppressed the viability of AML-12 cells (mouse normal liver cells) to about 86% compared with the vehicle, which implies that brassinin works specifically on HCC cells (Supplementary Figure S1A). Reference: Cells. 2021 Feb; 10(2): 332. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7915448/

In vivo activity:

BSN (brassinin) alone when given at 180 mg/kg very effective inhibited the growth of the tumor when compared with control. Paclitaxel alone was also significantly when compared with control. The combination of the two agents was more effective in reducing the tumor burden (Fig. 6B and C). The tumor weight (Fig. 6D) in the combination of BSN and paclitaxel group was significantly lower than BSN alone group or paclitaxel alone group. Furthermore, the BSN and paclitaxel did not affect the body weight of mice (Fig. 6E). Reference: Oncotarget. 2015 Mar 20;6(8):6386-405. https://pubmed.ncbi.nlm.nih.gov/25788267/

	Solvent	mg/mL	mM
Solubility
	DMSO	10.0	42.31
	DMF	10.0	42.31
	Ethanol	10.0	42.31

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 236.35 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

Formulation protocol:

1. Hong T, Ham J, Song J, Song G, Lim W. Brassinin Inhibits Proliferation in Human Liver Cancer Cells via Mitochondrial Dysfunction. Cells. 2021 Feb 5;10(2):332. doi: 10.3390/cells10020332. PMID: 33562611; PMCID: PMC7915448. 2. Yang MH, Lee JH, Ko JH, Jung SH, Sethi G, Ahn KS. Brassinin Represses Invasive Potential of Lung Carcinoma Cells through Deactivation of PI3K/Akt/mTOR Signaling Cascade. Molecules. 2019 Apr 22;24(8):1584. doi: 10.3390/molecules24081584. PMID: 31013639; PMCID: PMC6514890. 3. Lee JH, Kim C, Sethi G, Ahn KS. Brassinin inhibits STAT3 signaling pathway through modulation of PIAS-3 and SOCS-3 expression and sensitizes human lung cancer xenograft in nude mice to paclitaxel. Oncotarget. 2015 Mar 20;6(8):6386-405. doi: 10.18632/oncotarget.3443. PMID: 25788267; PMCID: PMC4467444.

In vitro protocol:

In vivo protocol:

1. Lee JH, Kim C, Sethi G, Ahn KS. Brassinin inhibits STAT3 signaling pathway through modulation of PIAS-3 and SOCS-3 expression and sensitizes human lung cancer xenograft in nude mice to paclitaxel. Oncotarget. 2015 Mar 20;6(8):6386-405. doi: 10.18632/oncotarget.3443. PMID: 25788267; PMCID: PMC4467444.

1: Cho Y, Ohm RA, Devappa R, Lee HB, Grigoriev IV, Kim BY, Ahn JS. Transcriptional responses of the Bdtf1-deletion mutant to the phytoalexin brassinin in the necrotrophic fungus Alternaria brassicicola. Molecules. 2014 Jul 24;19(8):10717-32. doi: 10.3390/molecules190810717. PubMed PMID: 25061722. 2: Srivastava A, Cho IK, Cho Y. The Bdtf1 gene in Alternaria brassicicola is important in detoxifying brassinin and maintaining virulence on Brassica species. Mol Plant Microbe Interact. 2013 Dec;26(12):1429-40. doi: 10.1094/MPMI-07-13-0186-R. PubMed PMID: 23945003. 3: Pedras MS, Minic Z, Abdoli A. The phytoalexin camalexin induces fundamental changes in the proteome of Alternaria brassicicola different from those caused by brassinin. Fungal Biol. 2014 Jan;118(1):83-93. doi: 10.1016/j.funbio.2013.11.005. Epub 2013 Dec 1. PubMed PMID: 24433679. 4: Pedras MS, Minic Z. Differential protein expression in response to the phytoalexin brassinin allows the identification of molecular targets in the phytopathogenic fungus Alternaria brassicicola. Mol Plant Pathol. 2012 Jun;13(5):483-93. doi: 10.1111/j.1364-3703.2011.00765.x. Epub 2011 Nov 24. PubMed PMID: 22111639. 5: Izutani Y, Yogosawa S, Sowa Y, Sakai T. Brassinin induces G1 phase arrest through increase of p21 and p27 by inhibition of the phosphatidylinositol 3-kinase signaling pathway in human colon cancer cells. Int J Oncol. 2012 Mar;40(3):816-24. doi: 10.3892/ijo.2011.1246. Epub 2011 Oct 27. Erratum in: Int J Oncol. 2016 Mar;48(3):1305. PubMed PMID: 22307336. 6: Pedras MS, Minic Z, Sarma-Mamillapalle VK. Brassinin oxidase mediated transformation of the phytoalexin brassinin: structure of the elusive co-product, deuterium isotope effect and stereoselectivity. Bioorg Med Chem. 2011 Feb 15;19(4):1390-9. doi: 10.1016/j.bmc.2011.01.011. Epub 2011 Jan 13. PubMed PMID: 21292494. 7: Quiroga D, Becerra LD, Sadat-Bernal J, Vargas N, Coy-Barrera E. Synthesis and Antifungal Activity against Fusarium oxysporum of Some Brassinin Analogs Derived from l-tryptophan: A DFT/B3LYP Study on the Reaction Mechanism. Molecules. 2016 Oct 11;21(10). pii: E1349. PubMed PMID: 27727186. 8: Pedras MS, Minic Z, Hossain S. Discovery of inhibitors and substrates of brassinin hydrolase: Probing selectivity with dithiocarbamate bioisosteres. Bioorg Med Chem. 2012 Jan 1;20(1):225-33. doi: 10.1016/j.bmc.2011.11.009. Epub 2011 Nov 12. PubMed PMID: 22137599. 9: Kim SM, Oh EY, Lee JH, Nam D, Lee SG, Lee J, Kim SH, Shim BS, Ahn KS. Brassinin Combined with Capsaicin Enhances Apoptotic and Anti-metastatic Effects in PC-3 Human Prostate Cancer Cells. Phytother Res. 2015 Nov;29(11):1828-36. doi: 10.1002/ptr.5478. Epub 2015 Oct 1. PubMed PMID: 26426257. 10: Pedras MS, Minic Z, Sarma-Mamillapalle VK. Substrate specificity and inhibition of brassinin hydrolases, detoxifying enzymes from the plant pathogens Leptosphaeria maculans and Alternaria brassicicola. FEBS J. 2009 Dec;276(24):7412-28. doi: 10.1111/j.1742-4658.2009.07457.x. PubMed PMID: 19922473. 11: Lee JH, Kim C, Sethi G, Ahn KS. Brassinin inhibits STAT3 signaling pathway through modulation of PIAS-3 and SOCS-3 expression and sensitizes human lung cancer xenograft in nude mice to paclitaxel. Oncotarget. 2015 Mar 20;6(8):6386-405. PubMed PMID: 25788267; PubMed Central PMCID: PMC4467444. 12: Pedras MS, Minic Z, Sarma-Mamillapalle VK. Synthetic inhibitors of the fungal detoxifying enzyme brassinin oxidase based on the phytoalexin camalexin scaffold. J Agric Food Chem. 2009 Mar 25;57(6):2429-35. doi: 10.1021/jf803666s. PubMed PMID: 19243099. 13: Chripkova M, Drutovic D, Pilatova M, Mikes J, Budovska M, Vaskova J, Broggini M, Mirossay L, Mojzis J. Brassinin and its derivatives as potential anticancer agents. Toxicol In Vitro. 2014 Aug;28(5):909-15. doi: 10.1016/j.tiv.2014.04.002. Epub 2014 Apr 18. PubMed PMID: 24747292. 14: Kim SM, Park JH, Kim KD, Nam D, Shim BS, Kim SH, Ahn KS, Choi SH, Ahn KS. Brassinin induces apoptosis in PC-3 human prostate cancer cells through the suppression of PI3K/Akt/mTOR/S6K1 signaling cascades. Phytother Res. 2014 Mar;28(3):423-31. doi: 10.1002/ptr.5010. Epub 2013 May 20. PubMed PMID: 23686889. 15: Pedras MS, Minic Z, Jha M. Brassinin oxidase, a fungal detoxifying enzyme to overcome a plant defense -- purification, characterization and inhibition. FEBS J. 2008 Jul;275(14):3691-705. doi: 10.1111/j.1742-4658.2008.06513.x. PubMed PMID: 18549452. 16: Pedras MS, Hossain M. Design, synthesis, and evaluation of potential inhibitors of brassinin glucosyltransferase, a phytoalexin detoxifying enzyme from Sclerotinia sclerotiorum. Bioorg Med Chem. 2007 Sep 1;15(17):5981-96. Epub 2007 Jun 7. PubMed PMID: 17590338. 17: Pedras MS, Gadagi RS, Jha M, Sarma-Mamillapalle VK. Detoxification of the phytoalexin brassinin by isolates of Leptosphaeria maculans pathogenic on brown mustard involves an inducible hydrolase. Phytochemistry. 2007 Jun;68(11):1572-8. Epub 2007 Apr 30. PubMed PMID: 17467751. 18: Pedras MS, Jha M, Minic Z, Okeola OG. Isosteric probes provide structural requirements essential for detoxification of the phytoalexin brassinin by the fungal pathogen Leptosphaeria maculans. Bioorg Med Chem. 2007 Sep 15;15(18):6054-61. Epub 2007 Jun 26. PubMed PMID: 17616463. 19: Pedras MS, Jha M. Toward the control of Leptosphaeria maculans: design, syntheses, biological activity, and metabolism of potential detoxification inhibitors of the crucifer phytoalexin brassinin. Bioorg Med Chem. 2006 Jul 15;14(14):4958-79. Epub 2006 Apr 17. PubMed PMID: 16616505. 20: Kello M, Drutovic D, Chripkova M, Pilatova M, Budovska M, Kulikova L, Urdzik P, Mojzis J. ROS-dependent antiproliferative effect of brassinin derivative homobrassinin in human colorectal cancer Caco2 cells. Molecules. 2014 Jul 25;19(8):10877-97. doi: 10.3390/molecules190810877. PubMed PMID: 25068784.