167869-21-8

Basic information

• Product Name: PD 98059
• Synonyms: 2-(2-AMINO-3-METHOXYPHENYL)-4H-1-BENZOPYRAN-4-ONE;2-(2-AMINO-3-METHOXY-PHENYL)CHROMEN-4-ONE;2'-AMINO-3'-METHOXYFLAVONE;PD 98059;PD 098,059;PD 98059 in Solution;PD 098,059 (2-(2-AMINO-3-METHOXYPHENYL)- 4H-1-BENZOPYRAN-4-ONE;PD 98059, 99+%
• CAS NO: 167869-21-8
• Molecular Formula: C16H13NO3
• Molecular Weight: 267.28
• Product Categories: FLAVONE;pharmacetical;Protein Kinase;Signalling;inhibitor;MAPK;Inhibitors
• Mol File: 167869-21-8.mol
• Article Data: 1

Chemical Properties

• Melting Point: 164～165℃
• Boiling Point: 453.142 °C at 760 mmHg
• Flash Point: 221.938 °C
• Appearance: yellow/solid
• Density: 1.3 g/cm³
• Vapor Pressure: 2.12E-08mmHg at 25°C
• Refractive Index: 1.651
• Storage Temp.: −20°C
• Solubility: ethanol: 0.6 mg/mL
• PKA: 1.21±0.10(Predicted)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
• CAS DataBase Reference: PD 98059(CAS DataBase Reference)
• NIST Chemistry Reference: PD 98059(167869-21-8)
• EPA Substance Registry System: PD 98059(167869-21-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-60-36
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 167869-21-8(Hazardous Substances Data)

Usage

Description

PD 98059, a monomethoxyflavone derivative, is a selective, reversible, and cell-permeable inhibitor of MAP kinase kinase (MEK). It functions by inhibiting the activation of MAP kinase and the subsequent phosphorylation of MAP kinase substrates. PD 98059 is also a noncompetitive inhibitor of the MAPK pathway, preventing the activation of MEK by Raf or MEK kinase (a MAP3K) with an IC50 value of 2-7 μM. Additionally, it phosphorylates and activates AMP-activated protein kinase (AMPK) in a dose-dependent manner.
Used in Pharmaceutical Industry:
PD 98059 is used as a research tool for studying the role of MEK and MAPK in cellular processes. Its ability to inhibit MEK activation makes it valuable in understanding the MAPK signaling pathway and its implications in various diseases.
Used in Cancer Research:
PD 98059 is used as a selective inhibitor of MEK and a blocker of MAPK for investigating the effects of MEK inhibition on cancer cell growth and proliferation. It helps researchers explore the potential of MEK inhibitors as therapeutic agents in cancer treatment.
Used in Cellular Signaling Studies:
PD 98059 is used as a pharmacological agent to modulate the MAPK pathway, allowing researchers to study the effects of MAPK signaling on various cellular processes, such as cell growth, differentiation, and apoptosis.
Used in Drug Discovery:
PD 98059 serves as a lead compound in the development of new drugs targeting the MEK-MAPK pathway. Its properties and mechanism of action provide insights for designing more potent and selective MEK inhibitors for therapeutic applications.
Used in Toxicology and Safety Assessment:
PD 98059 is used in toxicological studies to evaluate the safety and potential side effects of MEK inhibition. Understanding its effects on cellular processes and signaling pathways can help in assessing the risks associated with MEK inhibitor-based therapies.

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.

References

1) Alessi et al. (1995), PD 098059 is a specific inhibitor of the activation of mitogen-activated protein kinase kinase in vitro and in vivo; J. Biol. Chem., 270 27489 2) Dudley et al. (1995), A synthetic inhibitor of the mitogen-activated protein kinase cascade; Proc. Natl. Acad. Sci., 92 7686 3) Hotokezaka et al. (2002) U0126 and PD98059, specific inhibitors of MEK, accelerate differentiation of RAW264.7 cells into osteoclast-like cells; J. Biol. Chem., 277 47366 4) Xiaoxia et al. (2004) BMP4 supports self-renewal of embryonic stem cells by inhibiting mitogen-activated protein kinase pathways; Proc. Natl. Acad. Sci. USA 101 6027

InChI:InChI=1/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

Upstream product

• 4920-80-3 3-methoxy-2-nitrobenzoic acid 
• 118-93-4 o-hydroxyacetophenone 

Relevant articles and documents

Synthesis process for 2-(2-amino-3-methoxyphenyl)chromone

The invention belongs to the technical field of polymer synthesis, and relates to a synthesis process for 2-(2-amino-3-methoxyphenyl)chromone. The synthesis process comprises the following steps: 1) synthesizing a first intermediate, namely 2-nitro-3-meth