SB-431542
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MedKoo CAT#: 401910

CAS#: 301836-41-9

Description: SB-431542 is a novel small molecule inhibitor of the type I TGF-beta receptor, on a panel of human malignant glioma cell lines. SB-431542 blocked the phosphorylation and nuclear translocation of the SMADs, intracellular mediators of TGF-beta signaling, with decreased TGF-beta-mediated transcription. Furthermore, SB-431542 inhibited the expression of two critical effectors of TGF-beta-vascular endothelial growth factor and plasminogen activator inhibitor-1.


Chemical Structure

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SB-431542
CAS# 301836-41-9

Theoretical Analysis

MedKoo Cat#: 401910
Name: SB-431542
CAS#: 301836-41-9
Chemical Formula: C22H16N4O3
Exact Mass: 384.12224
Molecular Weight: 384.39
Elemental Analysis: C, 68.74; H, 4.20; N, 14.58; O, 12.49

Price and Availability

Size Price Availability Quantity
25.0mg USD 150.0 Same day
50.0mg USD 250.0 Same day
100.0mg USD 450.0 Same day
200.0mg USD 750.0 Same day
500.0mg USD 1250.0 Same day
1.0g USD 1950.0 Same day
2.0g USD 2950.0 Same day
5.0g USD 4250.0 2 Weeks
10.0g USD 6450.0 2 Weeks
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Synonym: SB431542; SB-431542; SB 431542

IUPAC/Chemical Name: 4-(4-(benzo[d][1,3]dioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl)benzamide

InChi Key: FHYUGAJXYORMHI-UHFFFAOYSA-N

InChi Code: InChI=1S/C22H16N4O3/c23-21(27)13-4-6-14(7-5-13)22-25-19(20(26-22)16-3-1-2-10-24-16)15-8-9-17-18(11-15)29-12-28-17/h1-11H,12H2,(H2,23,27)(H,25,26)

SMILES Code: O=C(N)C1=CC=C(C2=NC(C3=CC=C(OCO4)C4=C3)=C(C5=NC=CC=C5)N2)C=C1

Appearance: white to off-white 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, not in water

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

Biological target: SB-431542 is an inhibitor of ALK5/TGF-β type I Receptor with an IC50 value of 94 nM.
In vitro activity: This study showed that the exposure of iPSCs and ESCs to SB431542 promotes the differentiation of these pluripotent stem cells to cells with characteristics that closely resemble those of hMSCs. In the absence of SB431542, undifferentiated iPSCs and ESCs cultured on Geltrex in complete E8 medium appeared as circular and flat colonies with a well-defined border. As expected, these cells lacked expression of the mesenchymal stem cell markers CD29 and CD44 and expressed high levels of the pluripotent stem cell markers Tra 1-60, Oct-4, SSEA-3, CD90, CD9, and HSP90β. Reference: Stem Cells Int. 2018; 2018: 7878201. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6051046/
In vivo activity: This study performed a fluorescent modified-TUNEL assay on injured muscle from PDGFRα-GFP reporter mice (N = 3/group) to assess for apoptotic cells. This study observed an increase in number of apoptotic cells in injured muscle of mice treated with SB431542 compared to vehicle (Fig 7C and 7D), with an FAP cell apoptotic index of 8.3 ± 1.4% in the injured muscle of mice treated with SB431542 compared to 3.0 ± 0.8% in the vehicle group (Fig 7E, p<0.05). There was no significant difference in apoptotic index of the sham-side muscle of both groups, with indices of 8.5 ± 2.1% and 10.9 ± 4.6% in the treatment and vehicle groups, respectively (Fig 7A and 7B). Reference: PLoS One. 2016; 11(5): e0155486. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4871364/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 51.81 134.78
Ethanol 8.0 62.46

Preparing Stock Solutions

The following data is based on the product molecular weight 384.39 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. Leyendecker Junior A. TGF-β Inhibitor SB431542 Promotes the Differentiation of Induced Pluripotent Stem Cells and Embryonic Stem Cells into Mesenchymal-Like Cells. Stem Cells Int. 2018 Jul 2;2018:7878201. doi: 10.1155/2018/7878201. PMID: 30057627; PMCID: PMC6051046. 2. Liao K, Yong CW, Hua K. SB431542 inhibited cigarette smoke extract induced invasiveness of A549 cells via the TGF-β1/Smad2/MMP3 pathway. Oncol Lett. 2018 Jun;15(6):9681-9686. doi: 10.3892/ol.2018.8556. Epub 2018 Apr 23. PMID: 29963124; PMCID: PMC6020173. 3. Xu J, Liu J, Gan Y, Dai K, Zhao J, Huang M, Huang Y, Zhuang Y, Zhang X. High-Dose TGF-β1 Impairs Mesenchymal Stem Cell-Mediated Bone Regeneration via Bmp2 Inhibition. J Bone Miner Res. 2020 Jan;35(1):167-180. doi: 10.1002/jbmr.3871. Epub 2019 Oct 22. PMID: 31487395. 4. Davies MR, Liu X, Lee L, Laron D, Ning AY, Kim HT, Feeley BT. TGF-β Small Molecule Inhibitor SB431542 Reduces Rotator Cuff Muscle Fibrosis and Fatty Infiltration By Promoting Fibro/Adipogenic Progenitor Apoptosis. PLoS One. 2016 May 17;11(5):e0155486. doi: 10.1371/journal.pone.0155486. PMID: 27186977; PMCID: PMC4871364.
In vitro protocol: 1. Leyendecker Junior A. TGF-β Inhibitor SB431542 Promotes the Differentiation of Induced Pluripotent Stem Cells and Embryonic Stem Cells into Mesenchymal-Like Cells. Stem Cells Int. 2018 Jul 2;2018:7878201. doi: 10.1155/2018/7878201. PMID: 30057627; PMCID: PMC6051046. 2. Liao K, Yong CW, Hua K. SB431542 inhibited cigarette smoke extract induced invasiveness of A549 cells via the TGF-β1/Smad2/MMP3 pathway. Oncol Lett. 2018 Jun;15(6):9681-9686. doi: 10.3892/ol.2018.8556. Epub 2018 Apr 23. PMID: 29963124; PMCID: PMC6020173.
In vivo protocol: 1. Xu J, Liu J, Gan Y, Dai K, Zhao J, Huang M, Huang Y, Zhuang Y, Zhang X. High-Dose TGF-β1 Impairs Mesenchymal Stem Cell-Mediated Bone Regeneration via Bmp2 Inhibition. J Bone Miner Res. 2020 Jan;35(1):167-180. doi: 10.1002/jbmr.3871. Epub 2019 Oct 22. PMID: 31487395. 2. Davies MR, Liu X, Lee L, Laron D, Ning AY, Kim HT, Feeley BT. TGF-β Small Molecule Inhibitor SB431542 Reduces Rotator Cuff Muscle Fibrosis and Fatty Infiltration By Promoting Fibro/Adipogenic Progenitor Apoptosis. PLoS One. 2016 May 17;11(5):e0155486. doi: 10.1371/journal.pone.0155486. PMID: 27186977; PMCID: PMC4871364.

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1: Tanaka H, Shinto O, Yashiro M, Yamazoe S, Iwauchi T, Muguruma K, Kubo N, Ohira M, Hirakawa K. Transforming growth factor β signaling inhibitor, SB-431542, induces maturation of dendritic cells and enhances anti-tumor activity. Oncol Rep. 2010 Dec;24(6):1637-43. PubMed PMID: 21042762.

2: Mahmood A, Harkness L, Schrøder HD, Abdallah BM, Kassem M. Enhanced differentiation of human embryonic stem cells to mesenchymal progenitors by inhibition of TGF-beta/activin/nodal signaling using SB-431542. J Bone Miner Res. 2010 Jun;25(6):1216-33. PubMed PMID: 20200949.

3: Xiao YQ, Liu K, Shen JF, Xu GT, Ye W. SB-431542 inhibition of scar formation after filtration surgery and its potential mechanism. Invest Ophthalmol Vis Sci. 2009 Apr;50(4):1698-706. Epub 2008 Dec 20. PubMed PMID: 19098325.

4: Waghabi MC, Keramidas M, Calvet CM, Meuser M, de Nazaré C Soeiro M, Mendonça-Lima L, Araújo-Jorge TC, Feige JJ, Bailly S. SB-431542, a transforming growth factor beta inhibitor, impairs Trypanosoma cruzi infection in cardiomyocytes and parasite cycle completion. Antimicrob Agents Chemother. 2007 Aug;51(8):2905-10. Epub 2007 May 25. PubMed PMID: 17526757; PubMed Central PMCID: PMC1932517.

5: Hasegawa T, Nakao A, Sumiyoshi K, Tsuchihashi H, Ogawa H. SB-431542 inhibits TGF-beta-induced contraction of collagen gel by normal and keloid fibroblasts. J Dermatol Sci. 2005 Jul;39(1):33-8. PubMed PMID: 15978417.

6: Halder SK, Beauchamp RD, Datta PK. A specific inhibitor of TGF-beta receptor kinase, SB-431542, as a potent antitumor agent for human cancers. Neoplasia. 2005 May;7(5):509-21. PubMed PMID: 15967103; PubMed Central PMCID: PMC1501161.

7: Hjelmeland MD, Hjelmeland AB, Sathornsumetee S, Reese ED, Herbstreith MH, Laping NJ, Friedman HS, Bigner DD, Wang XF, Rich JN. SB-431542, a small molecule transforming growth factor-beta-receptor antagonist, inhibits human glioma cell line proliferation and motility. Mol Cancer Ther. 2004 Jun;3(6):737-45. PubMed PMID: 15210860.

8: Matsuyama S, Iwadate M, Kondo M, Saitoh M, Hanyu A, Shimizu K, Aburatani H, Mishima HK, Imamura T, Miyazono K, Miyazawa K. SB-431542 and Gleevec inhibit transforming growth factor-beta-induced proliferation of human osteosarcoma cells. Cancer Res. 2003 Nov 15;63(22):7791-8. PubMed PMID: 14633705.

9: Inman GJ, Nicolás FJ, Callahan JF, Harling JD, Gaster LM, Reith AD, Laping NJ, Hill CS. SB-431542 is a potent and specific inhibitor of transforming growth factor-beta superfamily type I activin receptor-like kinase (ALK) receptors ALK4, ALK5, and ALK7. Mol Pharmacol. 2002 Jul;62(1):65-74. PubMed PMID: 12065756.

10: Laping NJ, Grygielko E, Mathur A, Butter S, Bomberger J, Tweed C, Martin W, Fornwald J, Lehr R, Harling J, Gaster L, Callahan JF, Olson BA. Inhibition of transforming growth factor (TGF)-beta1-induced extracellular matrix with a novel inhibitor of the TGF-beta type I receptor kinase activity: SB-431542. Mol Pharmacol. 2002 Jul;62(1):58-64. PubMed PMID: 12065755.



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