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T7040

Sigma-Aldrich

Tyrphostin 1

≥98%

Synonym(s):

(4-Methoxybenzylidene)malononitrile

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About This Item

Linear Formula:
CH3OC6H4CH=C(CN)2
CAS Number:
2826-26-8
Molecular Weight:
184.19
MDL number:
MFCD00019787
UNSPSC Code:
12352200
PubChem Substance ID:
24278751
NACRES:
NA.77

Quality Level

200

assay

≥98%

form

solid

potency

>1250 μM IC50 (negative control)

mp

113-116 °C (lit.)

solubility

chloroform: soluble 50 mg/mL, clear, light yellow
DMSO: soluble

storage temp.

2-8°C

SMILES string

COc1ccc(cc1)\C=C(/C#N)C#N

InChI

1S/C11H8N2O/c1-14-11-4-2-9(3-5-11)6-10(7-12)8-13/h2-6H,1H3

InChI key

UOHFCPXBKJPCAD-UHFFFAOYSA-N

Gene Information

human ... EGFR(1956)

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Application

Tyrphostin 1 has been used to study its effect on the increase of transgene expression in HeLa and NIH3T3 cells.

Biochem/physiol Actions

Tyrphostin 1 is a small molecule inhibitor of epidermal growth factor (EGF) receptor kinase function. This molecule associates with the substrate subsite of the protein tyrosine kinase (PTK) domain. Tyrphostin 1 is also known to block EGF-dependent receptor autophosphorylation,. Furthermore, studies have reported that tyrphostin 1 can block Ca2+ channels and inhibit growth in vascular smooth muscle cells,.
EGFR tyrosine kinase inhibitor.

Features and Benefits

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Preparation Note

Tyrphostin 1 dissolves in chloroform at 50 mg/ml to yield a clear, light yellow solution. It is also soluble in DMSO.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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P R Standley et al.
The American journal of physiology, 276(4 Pt 1), E697-E705 (1999-04-13)
Vascular smooth muscle cells (VSMC) subjected to acute or chronic stretch display enhanced growth rates in vitro and in vivo. Clinical examples of vascular hyperplasia (e.g., systolic hypertension and postinjury restenosis) suggest that local insulin-like growth factor I (IGF-I) expression
K Qing et al.
Nature medicine, 5(1), 71-77 (1999-01-12)
Adeno-associated virus 2 (AAV)-based vectors have gained attention as a potentially useful alternative to the more commonly used retroviral and adenoviral vectors for human gene therapy. Although AAV uses the ubiquitously expressed cell surface heparan sulfate proteoglycan (HSPG) as a
Tamer Nasr et al.
European journal of medicinal chemistry, 84, 491-504 (2014-07-23)
Development of new antimicrobial agents is a good solution to overcome drug-resistance problems. In this context, new functionalized thiophene, acrylamide, arylhydrazone, pyrazole and pyridone derivatives bearing sulfisoxazole moiety were designed, synthesized and evaluated for their in vitro antibacterial and antifungal
S Wijetunge et al.
Biochemical and biophysical research communications, 189(3), 1620-1623 (1992-12-30)
Selective inhibitors of tyrosine kinases, tyrphostin 23 and genistein, produced concentration-dependent inhibition of voltage-operated calcium channel currents in vascular smooth muscle cells isolated from rabbit ear artery. The potency of these two structurally dissimilar inhibitors was similar to that reported
P Yaish et al.
Science (New York, N.Y.), 242(4880), 933-935 (1988-11-11)
A systematic series of low molecular weight protein tyrosine kinase inhibitors were synthesized; they had progressively increasing affinity over a 2500-fold range toward the substrate site of epidermal growth factor (EGF) receptor kinase domain. These compounds inhibited EGF receptor kinase
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