T4182

Sigma-Aldrich

Tyrphostin AG 1478

≥98%

Synonym(s):
N-(3-Chlorophenyl)-6,7-dimethoxy-4-quinazolinamine
Empirical Formula (Hill Notation):
C16H14ClN3O2
CAS Number:
Molecular Weight:
315.75
MDL number:
PubChem Substance ID:

Quality Level

assay

≥98%

form

solid

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

storage temp.

2-8°C

SMILES string

COc1cc2ncnc(Nc3cccc(Cl)c3)c2cc1OC

InChI

1S/C16H14ClN3O2/c1-21-14-7-12-13(8-15(14)22-2)18-9-19-16(12)20-11-5-3-4-10(17)6-11/h3-9H,1-2H3,(H,18,19,20)

InChI key

GFNNBHLJANVSQV-UHFFFAOYSA-N

Gene Information

human ... EGFR(1956)
mouse ... Egfr(13649)

Application

Tyrphostin AG 1478 has been used as epidermal growth factor receptor (EGFR) tyrosine kinase inhibitor to study its effect on desmoid cell mobility in boyden chamber motility assays. It has also been used to inhibit phosphorylation of c-Met by exogenous transforming growth factor α in epidermoid carcinoma cell line A431.

Packaging

1, 5 mg in ampule

Biochem/physiol Actions

Tyrphostin AG 1478 is an epidermal growth factor receptor (EGFR) tyrosine kinase inhibitor. It contributes to the development of hypomagnesemia and cardiac dysfunction in rats. Tyrphostin AG 1478 acts as a potential therapeutic agent for breast cancer.
Selective inhibitor of epidermal growth factor receptor protein

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Preparation Note

Tyrphostin AG 1478 dissolves in DMSO:MeOH (1:1) at 10 mg/ml to yield a clear, colorless solution. It is also soluble in methylene chloride (10 mg/ml), ethanol (10 mg/ml) and 0.1 N HCl (less than 0.4 mg/ml). However, it is insoluble in water, 2-hydroxypropyl-β-cyclodextrin, and 0.1 N NaOH.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Desmoid cell motility is induced in vitro by rhEGF
Joyner DE, et al.
Journal of Orthopaedic Research : Official Publication of the Orthopaedic Research Society, 27(9), 1258-1262 (2009)
Y Han et al.
Cancer research, 56(17), 3859-3861 (1996-09-01)
The effects of a new epidermal growth factor receptor (EGFR) tyrosine kinase inhibitor, tyrphostin AG 1478, were tested on three related human glioma cell lines: U87MG, which expressed endogenous wild-type (wt) EGFR, and two retrovirally infected U87MG cell populations which...
N Osherov et al.
European journal of biochemistry, 225(3), 1047-1053 (1994-11-01)
The precise role of src-type kinases as signal transducers has been under intensive investigation but only in a few instances has their role been revealed in any detail. Thus, src, fyn and yes are activated upon stimulation by platelet-derived growth...
Tyrphostin AG 1478 preferentially inhibits human glioma cells expressing truncated rather than wild-type epidermal growth factor receptors
Han Y, et al.
Cancer Research, 56, 3859-3861 (2019)
Sandra Rayego-Mateos et al.
The Journal of pathology, 244(2), 227-241 (2017-11-22)
Connective tissue growth factor (CCN2/CTGF) is a matricellular protein that is overexpressed in progressive human renal diseases, mainly in fibrotic areas. In vitro studies have demonstrated that CCN2 regulates the production of extracellular matrix (ECM) proteins and epithelial-mesenchymal transition (EMT)...
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