Brassinin
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MedKoo CAT#: 540050

CAS#: 105748-59-2

Description: 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

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Brassinin
CAS# 105748-59-2
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 540050
Name: Brassinin
CAS#: 105748-59-2
Chemical Formula: C11H12N2S2
Exact Mass: 236.04
Molecular Weight: 236.350
Elemental Analysis: C, 55.90; H, 5.12; N, 11.85; S, 27.13

Price and Availability

Size Price Availability Quantity
100mg USD 550 2 Weeks
200mg USD 950 2 Weeks
500mg USD 1650 2 Weeks
1g USD 2650 2 Weeks
2g USD 4850 2 Weeks
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Synonym: Brassinine; CCG-208623; CCG208623; CCG 208623; HE-005916; HE005916; HE 005916; HE-292778; HE292778; HE292778

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:
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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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 10.0 42.31
DMF 10.0 42.31
Ethanol 10.0 42.31

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.

Recalculate based on batch purity %
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: 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.
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.

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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.