Synonym
SB-202190 hydrochloride; SB-202190 HCl
IUPAC/Chemical Name
4-[4-(4-fluorophenyl)-5-(4-pyridinyl)-1H-imidazol-2-yl]-phenol, monohydrochloride
InChi Key
XOQSUTIMRLPFPB-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H14FN3O.ClH/c21-16-5-1-13(2-6-16)18-19(14-9-11-22-12-10-14)24-20(23-18)15-3-7-17(25)8-4-15;/h1-12,25H,(H,23,24);1H
SMILES Code
FC(C=C1)=CC=C1C2=C(C3=CC=NC=C3)NC(C4=CC=C(O)C=C4)=N2.Cl
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
>3 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-202190 has IC50s of 50 nM and 100 nM for p38α and p38β2, respectively. SB-202190 binds to the ATP pocket of the active recombinant human p38 kinase with a Kd of 38 nM. SB-202190 has anti-cancer activity and rescued memory deficits. SB-202190 also induces autophagy.
In vitro activity:
SB-202190 can be used to predict BRAF-activating mutations in patient-derived organoids and discover new BRAF variants. It affects Erk1-2 phosphorylation differently in colorectal cancer organoids. In 20 organoid cultures, SB-202190 induced phosphorylation, while it inhibited this process in 5 organoid cultures. SB-202190 mimicked the biochemical activity of Dabrafenib, particularly in BRAF-mutated organoid growth.
Reference: Cells. 2023 Feb 20;12(4):664. https://pubmed.ncbi.nlm.nih.gov/36831331/
In vivo activity:
In a rat model of vascular dementia, using SB-202190 to block the p38 MAPK pathway after permanent bilateral carotid occlusion led to reduced apoptosis of hippocampal neurons and an improvement in spatial learning and memory. The rats treated with SB-202190 showed faster escape times in the Morris water maze, spent more time in the platform quadrant during probe trials, had lower levels of neuronal apoptosis, higher Bcl-2 expression, and lower caspase-3 expression compared to the vascular dementia model group.
Reference: Biomed Res Int. 2013;2013:215798. https://pubmed.ncbi.nlm.nih.gov/24455679/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
83.3 |
226.56 |
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
367.81
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. Costa D, Venè R, Coco S, Longo L, Tosetti F, Scabini S, Mastracci L, Grillo F, Poggi A, Benelli R. SB202190 Predicts BRAF-Activating Mutations in Primary Colorectal Cancer Organoids via Erk1-2 Modulation. Cells. 2023 Feb 20;12(4):664. doi: 10.3390/cells12040664. PMID: 36831331; PMCID: PMC9954675.
2. Yang C, Zhu Z, Tong BC, Iyaswamy A, Xie WJ, Zhu Y, Sreenivasmurthy SG, Senthilkumar K, Cheung KH, Song JX, Zhang HJ, Li M. A stress response p38 MAP kinase inhibitor SB202190 promoted TFEB/TFE3-dependent autophagy and lysosomal biogenesis independent of p38. Redox Biol. 2020 May;32:101445. doi: 10.1016/j.redox.2020.101445. Epub 2020 Jan 28. PMID: 32037305; PMCID: PMC7264467.
3. Guo K, Ma J, Liang W. Effects of SB202190 on expression levels of IL-6 and NF-κB in flap ischemia-reperfusion injury. Exp Ther Med. 2018 Sep;16(3):2522-2526. doi: 10.3892/etm.2018.6442. Epub 2018 Jul 13. PMID: 30210603; PMCID: PMC6122530.
4. Yang S, Zhou G, Liu H, Zhang B, Li J, Cui R, Du Y. Protective effects of p38 MAPK inhibitor SB202190 against hippocampal apoptosis and spatial learning and memory deficits in a rat model of vascular dementia. Biomed Res Int. 2013;2013:215798. doi: 10.1155/2013/215798. Epub 2013 Dec 25. PMID: 24455679; PMCID: PMC3886604.
In vitro protocol:
1. Costa D, Venè R, Coco S, Longo L, Tosetti F, Scabini S, Mastracci L, Grillo F, Poggi A, Benelli R. SB202190 Predicts BRAF-Activating Mutations in Primary Colorectal Cancer Organoids via Erk1-2 Modulation. Cells. 2023 Feb 20;12(4):664. doi: 10.3390/cells12040664. PMID: 36831331; PMCID: PMC9954675.
2. Yang C, Zhu Z, Tong BC, Iyaswamy A, Xie WJ, Zhu Y, Sreenivasmurthy SG, Senthilkumar K, Cheung KH, Song JX, Zhang HJ, Li M. A stress response p38 MAP kinase inhibitor SB202190 promoted TFEB/TFE3-dependent autophagy and lysosomal biogenesis independent of p38. Redox Biol. 2020 May;32:101445. doi: 10.1016/j.redox.2020.101445. Epub 2020 Jan 28. PMID: 32037305; PMCID: PMC7264467.
In vivo protocol:
1. Guo K, Ma J, Liang W. Effects of SB202190 on expression levels of IL-6 and NF-κB in flap ischemia-reperfusion injury. Exp Ther Med. 2018 Sep;16(3):2522-2526. doi: 10.3892/etm.2018.6442. Epub 2018 Jul 13. PMID: 30210603; PMCID: PMC6122530.
2. Yang S, Zhou G, Liu H, Zhang B, Li J, Cui R, Du Y. Protective effects of p38 MAPK inhibitor SB202190 against hippocampal apoptosis and spatial learning and memory deficits in a rat model of vascular dementia. Biomed Res Int. 2013;2013:215798. doi: 10.1155/2013/215798. Epub 2013 Dec 25. PMID: 24455679; PMCID: PMC3886604.
1. Jiang, Y., Chen, C., Li, Z., et al. Characterization of the structure and function of a new mitogen-activated protein kinase (p38β). J. Biol. Chem. 271(30), 17920-17926 (1996).
2. Davies, S.P., Reddy, H., Caivano, M., et al. Specificity and mechanism of action of some commonly used protein kinase inhibitors. Biochem. J. 351(1), 95-105 (2000).
3. Fox, T., Coll, J.T., Xie, X., et al. A single amino acid substitution makes ERK2 susceptible to pyridinyl imidazole inhibitors of p38 MAP kinase. Protein Sci. 7(11), 2249-2255 (1998).
4. Fu, X., Lawson, M.A., Kelley, K.W., et al. HIV-1 Tat activates indoleamine 2,3 dioxygenase in murine organotypic hippocampal slice cultures in a p38 mitogen-activated protein kinase-dependent manner. J. Neuroinflammation 8(88), 1-12 (2011).
5. Riis, J.L., Johansen, C., Vestergaard, C., et al. CCL27 expression is regulated by both p38 MAPK and IKKβ signalling pathways. Cytokine 56(3), 699-707 (2011).
6. Röthig, A., Schreckenberg, R., Weber, K., et al. Effects of nicotine on PTHrP and PTHrP receptor expression in rat coronary endothelial cells. Cell Physiol. Biochem. 29, 485-492 (2012).
