![N-(2-[P-BROMOCINNAMYLAMINO]ETHYL)-5-ISOQUINOLINESULFONAMIDE HYDROCHLORIDE structure, CAS 127243-85-0](/structures/210000/187523_1_127243_85_0.png)
CAS Number127243-85-0
SynonymsN-(2-{[(2E)-3-(4-Bromophenyl)-2-propen-1-yl]amino}ethyl)-5-isoquinolinesulfonamide; MFCD00214119; N-(2-((3-(4-Bromophenyl)allyl)amino)ethyl)isoquinoline-5-sulfonamide dihydrochloride; N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide; H-89; N-(2-{[(2E)-3-(4-bromophenyl)prop-2-en-1-yl]amino}ethyl)isoquinoline-5-sulfonamide; H-89 dihydrochloride; H 89
Molecular FormulaC20H20BrN3O2S
Molecular Weight519.28
Density1.4±0.1 g/cm3
Boiling Point639.7±65.0 °C at 760 mmHg
Melting Point195-200°C
Appearanceoff-white powder
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 127243-85-0 |
| Catalog No. | 2A-3186215 |
| Chinese Name | H-89二盐酸盐 |
| Synonyms | N-(2-{[(2E)-3-(4-Bromophenyl)-2-propen-1-yl]amino}ethyl)-5-isoquinolinesulfonamide; MFCD00214119; N-(2-((3-(4-Bromophenyl)allyl)amino)ethyl)isoquinoline-5-sulfonamide dihydrochloride; N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide; H-89; N-(2-{[(2E)-3-(4-bromophenyl)prop-2-en-1-yl]amino}ethyl)isoquinoline-5-sulfonamide; H-89 dihydrochloride; H 89 |
| Molecular Formula | C20H20BrN3O2S |
| Molecular Weight | 519.28 |
| Density | 1.4±0.1 g/cm3 |
| Boiling Point | 639.7±65.0 °C at 760 mmHg |
| Melting Point | 195-200°C |
| Appearance | off-white powder |
| Water Solubility | H2O: ≥10 mg/mL |
| Storage Condition | Sealed in a cool, dry environment at 2-8 ºC |
| Application | H-89 is a potent protein kinase A inhibitor with an IC50 value of 48 nM. It has a weak inhibitory effect on PKG, PKC, Casein Kinase and other kinases. |
| PubChem ID | 645252 |
| MDL Number | MFCD00214119 |
| SMILES | O=S(=O)(NCCNCC=Cc1ccc(Br)cc1)c1cccc2cnccc12 |
| InChI | 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 |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| Bioactivity | H-89 is a potent inhibitor of cyclic AMP-dependent protein kinase (protein kinase A) with IC50 of 48 nM and has weak inhibition on PKG, PKC, Casein Kinase, and others kinases. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Protein Tyrosine Kinase/RTK >> PKA Signaling Pathways >> Stem Cell/Wnt >> PKA Research Areas >> Others Target IC50: 48 nM (protein kinase A) In Vitro H-89 inhibits protein kinase A, in competitive fashion against ATP. H-89 causes a dose-dependent inhibition of the forskolin-induced protein phosphorylation, with no decrease in intracellular cyclic AMP levels in PC12D cells. H-89 significantly inhibits the forskolin-induced neurite outgrowth from PC12D cells. H-89 (30 μM) inhibits significantly cAMP-dependent histone IIb phosphorylation activity in PC12D cell lysates[1]. H-89 (1-2 μM) significantly slows the repriming rate in rat skinned fibres, most likely due to it deleteriously affecting the T-system potential. H-89 (10-100 μM) inhibits net Ca2+ uptake by the SR and affectes the Ca32-sensitivity of the contractile apparatus in rat skinned fibres[2]. In Vivo H-89 (0.2 mg/100g, i.p.) significantly increases seizure latency and threshold in PTZ-treated animals. H-89 (0.05, 0.2 mg/100 g, i.p.) prevents the epileptogenic activity of bucladesine (300 nM) with significant increase of seizure latency and seizure threshold[3]. Kinase Assay Kinase activities are assayed at 30°C for 2-5 min by measuring the transfer of 32P from [γ-32P]ATP to substrates. The reaction is terminated by adding 1 mL of 20% trichloroacetic acid, following the addition of 100 μg of bovine serum albumin as a carrier protein. The sample is centrifuged at 3000 rpm for 10 min, the pellet is resuspended in 5% trichloroacetic acid solution, the final pellet is dissolved in 1 mL of 1 N NaOH and the radioactivity is measured in a liquid scintillation counter. Cell Assay After 48 h in culture, PCl2D cells are cultured in test medium containing 30 μM H-89 for 1 h and then exposed to fresh medium that contained both 10 μM forskolin and 30 μM H-89. Cells are scraped off with a rubber policeman and sonicated in the presence of 0.5 mL of 6% trichloroacetic acid. To extract trichloroacetic acid, 2 mL of petroleum ether is added, the preparation mixed and centrifuged at 3000 rpm for 10 min. After aspiration of the upper layer, the residue sample solution is used for determination. Animal Admin Male albino mice weighing 20-25 g are obtained. Pentoxifylline (25, 50, 100 mg/kg), bucladesine (50, 100, 300 nM/mouse) and H-89 (0.05, 0.1, 0.2 mg/100 g) are administered intraperitoneally (i.p.) 30 min before intravenous (i.v.) infusion of PTZ. In combination groups, the first and second components are injected 45 and 30 min before PTZ infusion. In all groups, the respective control animalsreceive an appropriate volume of vehicle. For the i.v. infusion, the needle is inserted into the lateral tail vein, fixed to the tail vein by a narrow piece of adhesive tape, and the animal is allowed to move freely. PTZ solution is infused at a concentration rate of 1 mL/min. References [1]. Chijiwa T, et al. Inhibition of forskolin-induced neurite outgrowth and protein phosphorylation by a newly synthesized selective inhibitor of cyclic AMP-dependent protein kinase, N-[2-(p-bromocinnamylamino)ethyl]-5-isoquinolinesulfonamide (H-89), of PC12D [2]. Blazev R, et al. Effects of the PKA inhibitor H-89 on excitation-contraction coupling in skinned and intact skeletal muscle fibres. J Muscle Res Cell Motil. 2001;22(3):277-86. [3]. Hosseini-Zare MS, et al. Effects of pentoxifylline and H-89 on epileptogenic activity of bucladesine in pentylenetetrazol-treated mice. Eur J Pharmacol. 2011 Nov 30;670(2-3):464-70. Chemical & Physical Properties Density 1.4±0.1 g/cm3 Boiling Point 639.7±65.0 °C at 760 mmHg Melting Point 195-200°C Molecular Formula C20H20BrN3O2S Molecular Weight 446.361 Flash Point 340.7±34.3 °C Exact Mass 445.045959 PSA 79.47000 LogP 3.03 Vapour Pressure 0.0±1.9 mmHg at 25°C Index of Refraction 1.653 InChIKey ZKZXNDJNWUTGDK-NSCUHMNNSA-N SMILES O=S(=O)(NCCNCC=Cc1ccc(Br)cc1)c1cccc2cnccc12 Storage condition 2-8°C Water Solubility H2O: ≥10 mg/mL |
| Use of | H-89 is a potent inhibitor of cyclic AMP-dependent protein kinase (protein kinase A) with IC50 of 48 nM and has weak inhibition on PKG, PKC, Casein Kinase, and others kinases. Properties Name N-[2-(p-Bromocinnamylamino)ethyl]-5-Isoquinoline Sulfonamide Synonym More Synonyms H-89 dihydrochloride Biological Activity Description H-89 is a potent inhibitor of cyclic AMP-dependent protein kinase (protein kinase A) with IC50 of 48 nM and has weak inhibition on PKG, PKC, Casein Kinase, and others kinases. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Protein Tyrosine Kinase/RTK >> PKA Signaling Pathways >> Stem Cell/Wnt >> PKA Research Areas >> Others IC50: 48 nM (protein kinase A) References [1]. Chijiwa T, et al. Inhibition of forskolin-induced neurite outgrowth and protein phosphorylation by a newly synthesized selective inhibitor of cyclic AMP-dependent protein kinase, N-[2-(p-bromocinnamylamino)ethyl]-5-isoquinolinesulfonamide (H-89), of PC12D [2]. Blazev R, et al. Effects of the PKA inhibitor H-89 on excitation-contraction coupling in skinned and intact skeletal muscle fibres. J Muscle Res Cell Motil. 2001;22(3):277-86. [3]. Hosseini-Zare MS, et al. Effects of pentoxifylline and H-89 on epileptogenic activity of bucladesine in pentylenetetrazol-treated mice. Eur J Pharmacol. 2011 Nov 30;670(2-3):464-70. Chemical & Physical Properties Molecular Formula C20H20BrN3O2S Exact Mass 445.045959 PSA 79.47000 Index of Refraction 1.653 InChIKey ZKZXNDJNWUTGDK-NSCUHMNNSA-N |
| Transport Info | Product name: H-89 dihydrochloride |
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