371963-M

H-89, Dihydrochloride

A cell-permeable, selective, reversible, ATP-competitive and potent inhibitor of protein kinase A (K_i = 48 nM).

• Synonym(s): H-89, Dihydrochloride, N-[2-(( p-Bromocinnamyl)amino)ethyl]-5-isoquinolinesulfonamide, 2HCl, PKA Inhibitor III, N-[2-((p-Bromocinnamyl)amino)ethyl]-5-isoquinolinesulfonamide, 2HCl, PKA Inhibitor III
• Empirical Formula (Hill Notation): C₂₀H₂₀BrN₃O₂S · 2HCl
• CAS Number: 127243-85-0
• Molecular Weight: 519.28
• MDL number: MFCD00214119
• UNSPSC Code: 12352200
• NACRES: NA.77
• Assay: ≥99% (HPLC)
• Form: film (crystalline)
• Storage condition: OK to freeze

Properties

• Quality Segment: 100
• assay: ≥99% (HPLC)
• form: film (crystalline)
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze
• color: clearoff-white
• solubility: DMSO: 200 mg/mL, water: 25 mg/mL
• storage temp.: 2-8°C
• SMILES string: [S](=O)(=O)(NCCNC\C=C\c3ccc(cc3)Br)c1c2c(cncc2)ccc1
• InChI: 1S/C20H20BrN3O2S/c21-18-8-6-16(7-9-18)3-2-11-22-13-14-24-27(25,26)20-5-1-4-17-15-23-12-10-19(17)20/h1-10,12,15,22,24H,11,13-14H2/b3-2+
• InChI key: ZKZXNDJNWUTGDK-NSCUHMNNSA-N

Description

General description

A cell-permeable, selective, reversible, ATP-competitive and potent inhibitor of protein kinase A (K_i = 48 nM). Inhibits other kinases only at much higher concentrations: CaM kinase II (K_i = 29.7 µM), casein kinase I (K_i = 38.3 µM), myosin light chain kinase (K_i = 28.3 µM), protein kinase C (K_i = 31.7 µM), and ROCK-II (IC₅₀ = 270 nM). May be used to discriminate between the effects of PKA and cAMP-regulated guanine-nucleotide-exchange factors (GEFs) such as GEFI, GEFII, or Epac (exchange protein directly activated by cAMP). Enhances radiation-induced apoptosis in the human cell line BM 13674. A 10 mM (1 mg/193 µl) solution of H-89, 2HCl (Cat. No. 371962) in DMSO is also available.

Biochem/physiol Actions

Primary Target
PKA

Target K_i: 48 nM for protein kinase A

Preparation Note

Following reconstitution, store in the refrigerator (4°C). Stock solutions are stable for at up to 4 months at 4°C.

Other Notes

Leemhuis, J., et al. 2002. J. Pharmacol. Exp. Ther.300, 1000.
Davies, S.P., et al. 2000. Biochem. J.351, 95.
Kawasaki, H., et al. 1998. Science 282, 2275.
de Rooij, J., et al. 1998. Nature 396, 474.
Findik, D., et al. 1995. J. Cell. Biochem.57, 12.
Geilen, C.C. 1992. FEBS Lett.309, 381.
Chijiwa, T., et al. 1990. J. Biol. Chem.265, 5267.
Combest, W.L., et al. 1988. J. Neurochem.51, 1581.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 1
• flash_point_f: Not applicable
• flash_point_c: Not applicable