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T7040

Sigma-Aldrich

Tyrphostin 1

≥98%

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Synonym(s):
(4-Methoxybenzylidene)malononitrile
Linear Formula:
CH3OC6H4CH=C(CN)2
CAS Number:
Molecular Weight:
184.19
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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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1 of 4

This Item
T4182T7165B9934
Tyrphostin 1 ≥98%

Sigma-Aldrich

T7040

Tyrphostin 1

Tyrphostin AG 1478 ≥98%

Sigma-Aldrich

T4182

Tyrphostin AG 1478

Tyrphostin 23 ≥98%

Sigma-Aldrich

T7165

Tyrphostin 23

BTA-1 ≥98% (HPLC), solid

Sigma-Aldrich

B9934

BTA-1

form

solid

form

solid

form

powder

form

solid

solubility

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

solubility

0.1 M HCl: soluble <0.4 mg/mL, DMSO:methanol (1:1): soluble 10 mg/mL, clear, colorless, ethanol: soluble 10 mg/mL, methylene chloride: soluble 10 mg/mL, 0.1 M NaOH: insoluble, 2-hydroxypropyl-β-cyclodextrin: insoluble, H2O: insoluble

solubility

DMSO: soluble 50 mg/mL, clear, yellow to brownish-yellow

solubility

DMSO: soluble ~10 mg/mL

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

potency

>1250 μM IC50 (negative control)

potency

-

potency

35 μM IC50

potency

-

mp

113-116 °C (lit.)

mp

-

mp

-

mp

-

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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
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
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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