Tyrphostin 9

Selective EGFR/PDGFR inhibitor CAS# 10537-47-0

Tyrphostin 9

2D Structure

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3D structure

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Tyrphostin 9

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Chemical Properties of Tyrphostin 9

Cas No. 10537-47-0 SDF Download SDF
PubChem ID 5614 Appearance Powder
Formula C18H22N2O M.Wt 282.38
Type of Compound N/A Storage Desiccate at -20°C
Synonyms AG 17; Tyrphostin 9; Malonoben
Solubility DMSO : ≥ 100 mg/mL (354.13 mM)
H2O : < 0.1 mg/mL (insoluble)
*"≥" means soluble, but saturation unknown.
Chemical Name 2-[(3,5-ditert-butyl-4-hydroxyphenyl)methylidene]propanedinitrile
SMILES CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)C=C(C#N)C#N
Standard InChIKey MZOPWQKISXCCTP-UHFFFAOYSA-N
Standard InChI InChI=1S/C18H22N2O/c1-17(2,3)14-8-12(7-13(10-19)11-20)9-15(16(14)21)18(4,5)6/h7-9,21H,1-6H3
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Tyrphostin 9

DescriptionPotent uncoupler of oxidative phosphorylation.

Tyrphostin 9 Dilution Calculator

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Tyrphostin 9 Molarity Calculator

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Preparing Stock Solutions of Tyrphostin 9

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.5413 mL 17.7066 mL 35.4133 mL 70.8265 mL 88.5332 mL
5 mM 0.7083 mL 3.5413 mL 7.0827 mL 14.1653 mL 17.7066 mL
10 mM 0.3541 mL 1.7707 mL 3.5413 mL 7.0827 mL 8.8533 mL
50 mM 0.0708 mL 0.3541 mL 0.7083 mL 1.4165 mL 1.7707 mL
100 mM 0.0354 mL 0.1771 mL 0.3541 mL 0.7083 mL 0.8853 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Tyrphostin 9

Tyrphostin 9 is an inhibitor of PDGFR with IC50 value of ~2.5μM [1].

Tyrphostin 9 is generated as specific inhibitor of PDGFR in 1991. It also has inhibitory effect on the proliferation of SMC. Tyrphostin 9 potently inhibits the PDGF-dependent SMC proliferation with IC50 value of 40nM and inhibits the PDGF-dependent autophosphorylation of PDGFR with IC50 value of ~2.5μM. Besides that, Tyrphostin 9 also affects the phosphorylation of PLCγ (IC50 value of about 2.5μM) and the PDGF-dependent c-fos expression. Moreover, Tyrphostin 9 is found to be an inhibitor of EGFR with IC50 value of 460μM [1, 2].

In the rat carotid artery injury model, treatment of Tyrphostin 9 significantly reduces neointimal hyperplasia through inhibiting the tyrosine phosphorylation in injured arteries [1].

References:
[1] Levitzki A. PDGF receptor kinase inhibitors for the treatment of restenosis. Cardiovascular research, 2005, 65(3): 581-586.
[2] Levitzki A. Tyrphostins—potential antiproliferative agents and novel molecular tools. Biochemical pharmacology, 1990, 40(5): 913-918.

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References on Tyrphostin 9

Some biochemical and physiochemical properties of the potent uncoupler SF 6847 (3,5-di-tert-butyl-4-hydroxybenzylidenemalononitrile).[Pubmed:237542]

Biochim Biophys Acta. 1975 Jun 17;387(3):519-32.

Various physicochemical and biochemical properties of the most potent uncoupler of oxidative phosphorylation known to date 3,5-di-tert-butyl-4-hydroxybenzylidenemalononitrile (SF 6847), such as pH dependence of the uncoupling activity and binding to mitochondria, spectral properties in the presence of different types of liposomes, biopolymers and mitochondria, and effects on model membrane systems have been investigated. From the results, it is concluded that the uncoupler most likely is localized in the phospholipid part of the membrane.

Description

Tyrphostin A9, a PDGFR inhibitor, is a potent inducer of mitochondrial fission. Tyrphostin A9 emerged as the most potent and selective of 51 tyrosine kinase inhibitors tested against the TNF-induced respiratory burst. Tyrphostin A9 has anti-influenza virus activities.

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