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IPA-3

CAS No.
42521-82-4
Chemical Name:
IPA-3
Synonyms
IPA 3;IPA 3;IPA3;1'-Dithiodi-2-naphthtol;1,1'-Dithiodi-2-naphthtol;2-Naphthalenol, 1,1'-dithiobis-;1,1′-Disulfanediyldinaphthalen-2-ol;Bis(2-hydroxy-1-naphthyl) disulfide;1,1'-Dithiodi-2-naphthtol USP/EP/BP;1,1'-Disulfanediylbis(naphthalen-2-ol);p21-Activated Kinase Inhibitor III, IPA-3
CBNumber:
CB02518903
Molecular Formula:
C20H14O2S2
Molecular Weight:
350.45
MDL Number:
MFCD00388917
MOL File:
42521-82-4.mol
MSDS File:
SDS
Last updated:2023-06-30 15:45:59

IPA-3 Properties

Melting point 172℃
Boiling point 543.7±35.0 °C(Predicted)
Density 1.46±0.1 g/cm3(Predicted)
storage temp. 2-8°C
solubility DMSO: >20mg/mL
pka 7.52±0.50(Predicted)
form Yellow solid
color off-white to yellow
Water Solubility Soluble in DMSO or ethanol. Insoluble in water.
Sensitive Light Sensitive
Stability Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
CAS DataBase Reference 42521-82-4
FDA UNII 3XFG6MQ9G2

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS05,GHS09
Signal word  Danger
Hazard statements  H318-H410
Precautionary statements  P273-P280-P305+P351+P338-P501
Hazard Codes  Xi,N
Risk Statements  41-50/53
Safety Statements  26-39-60-61
RIDADR  UN 3077 9 / PGIII
WGK Germany  3
HazardClass  9
NFPA 704
0
3 0

IPA-3 price More Price(31)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 506106 p21-Activated Kinase Inhibitor III, IPA-3 42521-82-4 5mg $144 2024-03-01 Buy
Sigma-Aldrich 506106 p21-Activated Kinase Inhibitor III, IPA-3 42521-82-4 25mg $490 2024-03-01 Buy
Alfa Aesar J65848 p21-Activated Kinase Inhibitor III, IPA-3 42521-82-4 5mg $122 2023-06-20 Buy
Alfa Aesar J65848 p21-Activated Kinase Inhibitor III, IPA-3 42521-82-4 10mg $205 2023-06-20 Buy
Cayman Chemical 14759 IPA-3 ≥95% 42521-82-4 5mg $57 2024-03-01 Buy
Product number Packaging Price Buy
506106 5mg $144 Buy
506106 25mg $490 Buy
J65848 5mg $122 Buy
J65848 10mg $205 Buy
14759 5mg $57 Buy

IPA-3 Chemical Properties,Uses,Production

Description

IPA-3 (42521-82-4) is a selective allosteric inhibitor of Group 1 p21-activated kinase (PAK1 IC50?= 2.5 μM)1?via covalent binding to the PAK1 regulatory domain preventing binding to the upstream activator Cdc422. IPA-3 has been shown to induce cell death in human leukemic cell lines3, significantly inhibit TGFβ1-induced prostate cell epithelial to mesenchymal transition4?and inhibit the growth of liver cancer cells5.

Uses

p21-activated kinase 1 (PAK1) is a member of a family non-receptor serine/threonine kinases that are vital to normal cell function. Binding of various upstream partners to PAK1 results in release of an autoinhibitory domain that blocks activity of the kinase domain. PAK1 expression and activity is upregulated in several human cancers and is a potential therapeutic target for cancer intervention. IPA-3 is a cell-permeable allosteric inhibitor of PAK1 that is non-competitive with respect to ATP binding (IC50 = 2.5 μM). It does not, however, inhibit the activity of PAK1 that has been pre-activated with Cdc42. IPA-3 binds covalently to the PAK1 regulatory domain (apparent Kd = 1.9 uM) and prevents binding to the upstream activator Cdc42.[Cayman Chemical]

Uses

Acts as an allosteric inhibitor of Pak1

Definition

ChEBI: An organic disulfide obtained by oxidative dimerisation of 1-sulfanylnaphthalen-2-ol.

Biological Activity

IPA-3 is a selective non-ATP competitive Pak1 inhibitor with IC50 of 2.5 μM in a cell-free assay, no inhibition to group II PAKs (PAKs 4-6).

Biochem/physiol Actions

IPA-3 is an allosteric inhibitor of Pak1. It binds to autoinhibitory domain of Pak1 (p21 activated kinase), highly selective amongst kinases. Pak1 is implicated in tumorigenesis and metastasis.

in vitro

IPA-3 is a non ATP-competitive, allosteric inhibitor of p21-activated kinase 1 (Pak1). PIR3.5 is the control compound of IPA-3. IPA-3 prevents Cdc42-stimulated Pak1 autophosphorylation on Thr423. IPA-3 also prevents sphingosine-dependent Pak1 autophosphorylation. IPA-3 does not target exposed cysteine residues on Pak1. The disulfide bond of IPA-3 is critical for inhibition of Pak1 and in vitro reduction by the reducing agent dithiothreitol (DTT) abolishes Pak1 inhibition by IPA-3. IPA-3 inhibits activation of Pak1 by diverse activators, but does not inhibit preactivated Pak1. IPA-3 inhibits PDGF-stimulated Pak activation in mouse embryonic fibroblasts. IPA-3 inhibits Pak1 activation in part by binding covalently to the regulatory domain of Pak1. IPA-3 binds Pak1 covalently in a time- and temperature-dependent manner. IPA-3 prevents binding of the Pak1 activator Cdc42. IPA-3 binds directly to the Pak1 autoregulatory domain. IPA-3 reversibly inhibits PMA-induced membrane ruffling in cells.

storage

Store at -20°C

References

1) Deacon?et al.?(2008)?An isoform-selective, small-molecule inhibitor targets the autoregulatory mechanism of p21-activated kinase; Chem.Biol.,?14?322 2) Viaud and Peterson (2009)?An allosteric kinase inhibitor binds the p21-activated kinase (PAK) autoregulatory domain covalently; Mol. Cancer Ther.,?8?2559 3) Kuzelova?et al. (2014)?Group 1 PAK Inhibitor IPA-3 Induces Cell Death and Affects Cell Adhesivity to Fibronectin in Human Hematopoietic Cells; PLoS One,?9?e92560 4) Al-Azayzih?et al.?(2015)?P21 Activated Kinase-1 Mediates Transforming Growth factor b1-Induced Prostate Cancer Cell Epithelial to Mesenchymal transition; Biochim. Biophys. Acta,?1853?1229 5) Wong?et al.?(2013)?IPA-3 Inhibits the Growth of Liver Cancer Cells By Suppressing PAK1 and NF-kB Activation; PLoS One,?8?e68843

IPA-3 Preparation Products And Raw materials

Raw materials

Preparation Products

IPA-3 Suppliers

Global( 106)Suppliers
Supplier Tel Email Country ProdList Advantage
Hubei xin bonus chemical co. LTD
86-13657291602 linda@hubeijusheng.com CHINA 22968 58
Career Henan Chemica Co
+86-0371-86658258 15093356674; laboratory@coreychem.com China 30256 58
Dideu Industries Group Limited
+86-29-89586680 +86-15129568250 1026@dideu.com China 29831 58
InvivoChem
+1-708-310-1919 +1-13798911105 sales@invivochem.cn United States 6393 58
TargetMol Chemicals Inc.
+1-781-999-5354 support@targetmol.com United States 19973 58
Wuhan Topule Biopharmaceutical Co., Ltd
+8618327326525 masar@topule.com China 8475 58
Amadis Chemical Company Limited
571-89925085 sales@amadischem.com China 132020 58
3B Pharmachem (Wuhan) International Co.,Ltd. 821-50328103-801 18930552037 3bsc@sina.com China 15848 69
VDM Biochemicals 0330-2528181 sales@vdmbio.com United States 510 64
Jinan Trio PharmaTech Co., Ltd. +86 (531) 88811783 sales@trio-pharmatech.com (International market) China 1856 62
1,1'-Dithiodi-2-naphthtol IPA 3 p21-Activated Kinase Inhibitor III, IPA-3 Bis(2-hydroxy-1-naphthyl) disulfide 2-Naphthalenol, 1,1'-dithiobis- 1,1′-Disulfanediyldinaphthalen-2-ol 1,1'-Disulfanediylbis(naphthalen-2-ol) IPA 3;IPA3 p21-Activated Kinase Inhibitor III, IPA-3 - CAS 42521-82-4 - Calbiochem 1-[(2-hydroxy-1-naphthyl)disulfanyl]naphthalen-2-ol 1'-Dithiodi-2-naphthtol 1,1'-Dithiodi-2-naphthtol USP/EP/BP inhibit,Inhibitor,IPA-3,p21 activated kinases,PAK 42521-82-4 Inhibitors PAK Inhibitor III, IPA-3 PAK Inhibitor III 1,1'-disulfanediylbis(naphthalen-2-ol)