PD 98059 Chemical Properties

Melting point:

164～165℃

Boiling point:

453.1±45.0 °C(Predicted)

Density 

1.300±0.06 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

ethanol: 0.6 mg/mL

pka

1.21±0.10(Predicted)

form 

solid

color 

yellow

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.

InChI

InChI=1S/C16H13NO3/c1-19-14-8-4-6-11(16(14)17)15-9-12(18)10-5-2-3-7-13(10)20-15/h2-9H,17H2,1H3

InChIKey

QFWCYNPOPKQOKV-UHFFFAOYSA-N

SMILES

C1(C2=CC=CC(OC)=C2N)OC2=CC=CC=C2C(=O)C=1

CAS DataBase Reference

167869-21-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

22-60-36

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

HS Code 

29322090

MSDS

• Language:English Provider:SigmaAldrich

PD 98059 Usage And Synthesis

Description

PD 98059 is a noncompetitive inhibitor of the MAPK pathway. It prevents the activation of MEK by Raf or MEK kinase (a MAP3K) with an IC₅₀ value of 2-7 μM but does not inhibit Raf-activated MAP2K1. It inhibits Raf activation of MAP2K2 with an IC₅₀ value of 50 μM. PD 98059 also phosphorylates and activates AMP-activated protein kinase (AMPK) in a dose-dependent manner (EC₅₀ = 35 μM in HEK293 cells). It increases the ratios of ADP to ATP and AMP to ATP and increases phosphorylation of the AMPK target acetyl-CoA carboxylase (ACC).

Uses

PD 98059 is a selective inhibitor of MEK and blocker of MAPK.

Definition

ChEBI: A member of the class of monomethoxyflavones that is 3'-methoxyflavone bearing an additional amino substituent at position 2'

General Description

Selective, reversible, and cell-permeable inhibitor of MAP kinase kinase (MEK) that acts by inhibiting the activation of MAP kinase and subsequent phosphorylation of MAP kinase substrates. Pretreatment of PC-12 cells with PD 98059 completely blocks the 4-fold increase in MAP kinase activity produced by nerve growth factor (NGF; IC₅₀ = 2 μM); however, it has no effect on NGF-dependent tyrosine phosphorylation of the p140^trk receptor or its substrate Shc and does not block NGF-dependent activation of PI 3-kinase. Blocks LPS-induced activation of TNF-α gene expression. Inhibits cell growth and reverses the phenotype of ras-transformed BALB3T3 mouse fibroblasts and rat kidney cells. A 5 mg/ml solution of PD 98059 (Cat. No. 513001) in anhydrous DMSO is also available.

Biological Activity

Specific inhibitor of mitogen-activated protein kinase kinase (MAPKK / MEK). Acts by binding to the inactivated form of MEK, thereby preventing its phosphorylation by cRAF or MEK kinase (IC 50 = 2-7 μ M). Inhibits cell growth and proliferation in acute myelogenous leukemia (AML) cell lines; causes G 1 arrest by blocking p53-dependent p21 induction. Also available as part of the MAPK Cascade Inhibitor Tocriset™ and MAPK Inhibitor Tocriset™ .

Biochem/physiol Actions

PD 98,059 is a flavonoid and specific inhibitor of mitogen-activated protein kinase kinase (MAPKK). In mice, PD 98,059 helps to block zymosan stimulated organ dysfunction syndrome and non-septic shock. It is known to inhibit in vitro hypertrophy. PD 98,059 also induces cartilage formation in mesenchymal stromal cells.

storage

Room temperature

References

[1] D R ALESSI. PD 098059 is a specific inhibitor of the activation of mitogen-activated protein kinase kinase in vitro and in vivo.[J]. The Journal of Biological Chemistry, 1995, 270 46: 27489-27494. DOI:10.1074/jbc.270.46.27489
[2] D T DUDLEY. A synthetic inhibitor of the mitogen-activated protein kinase cascade.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1995, 92 17: 7686-7689. DOI:10.1073/pnas.92.17.7686
[3] HITOSHI HOTOKEZAKA. U0126 and PD98059, specific inhibitors of MEK, accelerate differentiation of RAW264.7 cells into osteoclast-like cells.[J]. The Journal of Biological Chemistry, 2002, 277 49: 47366-47372. DOI:10.1074/jbc.m208284200
[4] XIAOXIA QI. BMP4 supports self-renewal of embryonic stem cells by inhibiting mitogen-activated protein kinase pathways.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2004, 101 16: 6027-6032. DOI:10.1073/pnas.0401367101

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