H-89 Dihydrochloride
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 530379

CAS#: 130964-39-5 (2HCl)

Description: H-89 is a specific adenylyl cyclase inhibitor (DDA) and a cyclic AMP-dependent protein kinase inhibitor. H-89 blocks the action of equine growth hormone on in vitro maturation of equine oocytes. H-89 decreases the gain of excitation-contraction coupling and attenuates calcium sparks in the absence of beta-adrenergic stimulation. H-89 potentiates adipogenesis in 3T3-L1 cells by activating insulin signaling independently of protein kinase A.


Price and Availability

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Price

100mg
USD 750
1g
USD 2950
Size
Price

200mg
USD 1250
2g
USD 4150
Size
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500mg
USD 1950
5g
Ask price

H-89 Dihydrochloride, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 530379
Name: H-89 Dihydrochloride
CAS#: 130964-39-5 (2HCl)
Chemical Formula: C20H22BrCl2N3O2S
Exact Mass:
Molecular Weight: 519.279
Elemental Analysis: C, 46.26; H, 4.27; Br, 15.39; Cl, 13.65; N, 8.09; O, 6.16; S, 6.17


Related CAS #: 127243-85-0 (free base)   130964-39-5 (2HCl)   1000995-75-4 (free base)   1049740-55-7 (2HCl   hydrate)    

Synonym: H-89 Dihydrochloride; H-89; H89; H 89 HCl.

IUPAC/Chemical Name: N-[2-[[3-(4-Bromophenyl)-2-propen-1-yl]amino]ethyl]-5-Isoquinolinesulfonamide dihydrochloride

InChi Key: GELOGQJVGPIKAM-WTVBWJGASA-N

InChi Code: InChI=1S/C20H20BrN3O2S.2ClH/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;2*1H/b3-2+;;

SMILES Code: O=S(C1=CC=CC2=C1C=CN=C2)(NCCNC/C=C/C3=CC=C(Br)C=C3)=O.[H]Cl.[H]Cl


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Pereira GR, Lorenzo PL, Carneiro GF, Bilodeau-Goeseels S, Kastelic J, Liu IK. A specific adenylyl cyclase inhibitor (DDA) and a cyclic AMP-dependent protein kinase inhibitor (H-89) block the action of equine growth hormone on in vitro maturation of equine oocytes. Zygote. 2015 Dec;23(6):795-801. doi: 10.1017/S0967199414000434. PubMed PMID: 25257826.

2: He H, Genovese KJ, Swaggerty CL, Nisbet DJ, Kogut MH. Nitric oxide as a biomarker of intracellular Salmonella viability and identification of the bacteriostatic activity of protein kinase A inhibitor H-89. PLoS One. 2013;8(3):e58873. doi: 10.1371/journal.pone.0058873. PubMed PMID: 23554945; PubMed Central PMCID: PMC3598854.

3: Parks RJ, Howlett SE. H-89 decreases the gain of excitation-contraction coupling and attenuates calcium sparks in the absence of beta-adrenergic stimulation. Eur J Pharmacol. 2012 Sep 15;691(1-3):163-72. doi: 10.1016/j.ejphar.2012.07.012. PubMed PMID: 22796673.

4: Pflug A, Johnson KA, Engh RA. Anomalous dispersion analysis of inhibitor flexibility: a case study of the kinase inhibitor H-89. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2012 Aug 1;68(Pt 8):873-7. doi: 10.1107/S1744309112028655. PubMed PMID: 22869112; PubMed Central PMCID: PMC3412763.

5: Hosseini-Zare MS, Salehi F, Seyedi SY, Azami K, Ghadiri T, Mobasseri M, Gholizadeh S, Beyer C, Sharifzadeh M. 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. doi: 10.1016/j.ejphar.2011.09.026. PubMed PMID: 21946102.

6: Suzuki R, Niimura S. Hatching and distribution of actin filaments in mouse blastocysts whose activities of protein kinase A were suppressed by H-89. J Reprod Dev. 2010 Feb;56(1):103-9. PubMed PMID: 19881218.

7: Herbst KJ, Allen MD, Zhang J. The cAMP-dependent protein kinase inhibitor H-89 attenuates the bioluminescence signal produced by Renilla Luciferase. PLoS One. 2009 May 21;4(5):e5642. doi: 10.1371/journal.pone.0005642. PubMed PMID: 19461967; PubMed Central PMCID: PMC2680982.

8: Sharif R, Aghsami M, Gharghabi M, Sanati M, Khorshidahmad T, Vakilzadeh G, Mehdizadeh H, Gholizadeh S, Taghizadeh G, Sharifzadeh M. Melatonin reverses H-89 induced spatial memory deficit: Involvement of oxidative stress and mitochondrial function. Behav Brain Res. 2017 Jan 1;316:115-124. doi: 10.1016/j.bbr.2016.08.040. PubMed PMID: 27555536.

9: Azimi L, Kachooeian M, Khodagholi F, Yans A, Heysieattalab S, Vakilzadeh G, Vosoughi N, Sanati M, Taghizadeh G, Sharifzadeh M. Protective effects of salicylate on PKA inhibitor (H-89)-induced spatial memory deficit via lessening autophagy and apoptosis in rats. Pharmacol Biochem Behav. 2016 Oct 27. pii: S0091-3057(16)30185-X. doi: 10.1016/j.pbb.2016.10.008. [Epub ahead of print] PubMed PMID: 27984096.

10: Zhao S, Yang J, Li C, Xing S, Yu Y, Liu S, Pu F, Ma D. [Protein kinase A inhibitor H-89 blocks polyploidization of SP600125-induced CMK cells by regulating phosphorylation of ribosomal protein S6 kinase 1]. Xi Bao Yu Fen Zi Mian Yi Xue Za Zhi. 2016 Oct;32(10):1321-1326. Chinese. PubMed PMID: 27667455.

11: Park WS, Son YK, Kim N, Youm JB, Warda M, Ko JH, Ko EA, Kang SH, Kim E, Earm YE, Han J. Direct modulation of Ca(2+)-activated K(+) current by H-89 in rabbit coronary arterial smooth muscle cells. Vascul Pharmacol. 2007 Feb;46(2):105-13. PubMed PMID: 17052962.

12: Sharifzadeh M, Aghsami M, Gholizadeh S, Tabrizian K, Soodi M, Khalaj S, Ranjbar A, Hosseini-Sharifabad A, Roghani A, Karimfar MH. Protective effects of chronic lithium treatment against spatial memory retention deficits induced by the protein kinase AII inhibitor H-89 in rats. Pharmacology. 2007;80(2-3):158-65. PubMed PMID: 17534126.

13: Kato Y, Ozaki N, Yamada T, Miura Y, Oiso Y. H-89 potentiates adipogenesis in 3T3-L1 cells by activating insulin signaling independently of protein kinase A. Life Sci. 2007 Jan 9;80(5):476-83. PubMed PMID: 17056071.

14: Pearman C, Kent W, Bracken N, Hussain M. H-89 inhibits transient outward and inward rectifier potassium currents in isolated rat ventricular myocytes. Br J Pharmacol. 2006 Aug;148(8):1091-8. PubMed PMID: 16799649; PubMed Central PMCID: PMC1752020.

15: Alamdary SZ, Digaleh H, Khodagholi F. Dual contradictory effect of H-89 on neuronal retraction, death and inflammation in differentiated PC12 cells subjected to oxidative stress. J Mol Neurosci. 2013 Nov;51(3):1030-7. doi: 10.1007/s12031-013-0092-7. PubMed PMID: 23949609.

16: Sun Park W, Kyoung Son Y, Kim N, Boum Youm J, Joo H, Warda M, Ko JH, Earm YE, Han J. The protein kinase A inhibitor, H-89, directly inhibits KATP and Kir channels in rabbit coronary arterial smooth muscle cells. Biochem Biophys Res Commun. 2006 Feb 24;340(4):1104-10. PubMed PMID: 16403438.

17: Son YK, Park WS, Kim SJ, Earm YE, Kim N, Youm JB, Warda M, Kim E, Han J. Direct inhibition of a PKA inhibitor, H-89 on KV channels in rabbit coronary arterial smooth muscle cells. Biochem Biophys Res Commun. 2006 Mar 24;341(4):931-7. PubMed PMID: 16455049.

18: Makaula S, Lochner A, Genade S, Sack MN, Awan MM, Opie LH. H-89, a non-specific inhibitor of protein kinase A, promotes post-ischemic cardiac contractile recovery and reduces infarct size. J Cardiovasc Pharmacol. 2005 Apr;45(4):341-7. PubMed PMID: 15772523.

19: Meja KK, Catley MC, Cambridge LM, Barnes PJ, Lum H, Newton R, Giembycz MA. Adenovirus-mediated delivery and expression of a cAMP-dependent protein kinase inhibitor gene to BEAS-2B epithelial cells abolishes the anti-inflammatory effects of rolipram, salbutamol, and prostaglandin E2: a comparison with H-89. J Pharmacol Exp Ther. 2004 May;309(2):833-44. PubMed PMID: 14747610.

20: Chang CZ, Wu SC, Kwan AL, Lin CL. Magnesium Lithospermate B Implicates 3'-5'-Cyclic Adenosine Monophosphate/Protein Kinase A Pathway and N-Methyl-d-Aspartate Receptors in an Experimental Traumatic Brain Injury. World Neurosurg. 2015 Oct;84(4):954-63. doi: 10.1016/j.wneu.2015.05.075. PubMed PMID: 26093361.