T7040
Tyrphostin 1
≥98%
Synonym(s):
(4-Methoxybenzylidene)malononitrile
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About This Item
Linear Formula:
CH3OC6H4CH=C(CN)2
CAS Number:
Molecular Weight:
184.19
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
Product Name
Tyrphostin 1, ≥98%
InChI
1S/C11H8N2O/c1-14-11-4-2-9(3-5-11)6-10(7-12)8-13/h2-6H,1H3
SMILES string
COc1ccc(cc1)\C=C(/C#N)C#N
InChI key
UOHFCPXBKJPCAD-UHFFFAOYSA-N
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
Quality Level
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
EGFR tyrosine kinase inhibitor.
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,.
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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
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
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
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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