Ro-31-7549 Monohydrate | CAS# 125313-65-7 | PKC Inhibitor

MedKoo Cat#: 564514 | Name: Ro-31-7549 monohydrate

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ro-31-7549 Monohydrate is a cell permeable, reversible, selective protein kinase C (PKC) inhibitor.

Chemical Structure

Ro-31-7549 monohydrate

CAS#125313-65-7

Theoretical Analysis

MedKoo Cat#: 564514

Name: Ro-31-7549 monohydrate

CAS#: 125313-65-7

Chemical Formula: C26H28N4O5

Exact Mass: 0.0000

Molecular Weight: 476.53

Elemental Analysis: C, 65.53; H, 5.92; N, 11.76; O, 16.79

Price and Availability

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1mg	USD 345.00

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Synonym

Ro317549 Monohydrate; Ro-317549 Monohydrate; Ro 31-7549 Monohydrate; Ro-31-7549 Monohydrate

IUPAC/Chemical Name

3-(1-(3-Aminopropyl)-1H-indol-3-yl)-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione acetate monohydrate

InChi Key

LBUSOQPTLSCLFN-UHFFFAOYSA-N

InChi Code

InChI=1S/C24H22N4O2.C2H4O2.H2O/c1-27-13-17(15-7-2-4-9-19(15)27)21-22(24(30)26-23(21)29)18-14-28(12-6-11-25)20-10-5-3-8-16(18)20;1-2(3)4;/h2-5,7-10,13-14H,6,11-12,25H2,1H3,(H,26,29,30);1H3,(H,3,4);1H2

SMILES Code

O=C(C(C1=CN(CCCN)C2=C1C=CC=C2)=C3C4=CN(C)C5=C4C=CC=C5)NC3=O.CC(O)=O.O

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

To be determined

Shelf Life

>3 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).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Ro-31-7549 has an IC50 value of 158 nM for rat brain PKC. Ro-31-7549 acts at the ATP binding site of PKC. Ro-31-7549 exhibits some degree of PKC isozyme specificity (IC50 = 53 nM for PKCα, 195 nM for PKCβI, 163 nM for PKCβII, 213 nM for PKCγ, and 175 nM for PKCε). Ro-31-7549 inhibits carbachol-evoked noradrenaline release (IC50 = 600 nM).

In vitro activity:

PKCα activity was effectively suppressed by Ro-31-7549 and reversal of intracellular accumulation of doxorubicin was observed by inhibition of PKCα activity in MCF-7/ADR cells compared with their intrinsic drug resistance. These findings suggest a potential treatment of multidrug resistance of cancer drug by inhibiting PKCα activity with conventional anticancer drugs. Reference: Tumour Biol. 2016 Feb;37(2):1901-8. https://pubmed.ncbi.nlm.nih.gov/26323260/

In vivo activity:

In a rat subarachnoid hemorrhage model of delayed cerebral vasospasm, it was found that the application of RO-31-7549 reduced the expression of endothelin receptors and reduced cerebral vasospasm. These findings suggest that the inhibition of PKC signaling pathway could effectively reduce delayed cerebral vasospasm after a subarachnoid hemorrhage. Reference: J Integr Neurosci. 2012 Dec;11(4):439-51. https://pubmed.ncbi.nlm.nih.gov/23351051/

Preparing Stock Solutions

The following data is based on the product molecular weight 476.53 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Kim CW, Asai D, Kang JH, Kishimura A, Mori T, Katayama Y. Reversal of efflux of an anticancer drug in human drug-resistant breast cancer cells by inhibition of protein kinase Cα (PKCα) activity. Tumour Biol. 2016 Feb;37(2):1901-8. doi: 10.1007/s13277-015-3963-4. Epub 2015 Sep 2. PMID: 26323260. 2. Harmon CS, Nevins TD, Ducote J, Lutz D. Bisindolylmaleimide protein-kinase-C inhibitors delay the decline in DNA synthesis in mouse hair follicle organ cultures. Skin Pharmacol. 1997;10(2):71-8. doi: 10.1159/000211471. PMID: 9257375. 3. Sun L, Zhang W, Wang X, Song J, Li M. Inhibition of protein kinase C signal reduces ET receptor expression and basilar vasospasm after subarachnoid hemorrhage in rats. J Integr Neurosci. 2012 Dec;11(4):439-51. doi: 10.1142/S0219635212500288. Epub 2012 Dec 28. PMID: 23351051. 4. Kang JH, Asai D, Toita R, Kitazaki H, Katayama Y. Plasma protein kinase C (PKC)alpha as a biomarker for the diagnosis of cancers. Carcinogenesis. 2009 Nov;30(11):1927-31. doi: 10.1093/carcin/bgp210. Epub 2009 Aug 26. PMID: 19710177.

In vitro protocol:

In vivo protocol:

1. Sun L, Zhang W, Wang X, Song J, Li M. Inhibition of protein kinase C signal reduces ET receptor expression and basilar vasospasm after subarachnoid hemorrhage in rats. J Integr Neurosci. 2012 Dec;11(4):439-51. doi: 10.1142/S0219635212500288. Epub 2012 Dec 28. PMID: 23351051. 2. Kang JH, Asai D, Toita R, Kitazaki H, Katayama Y. Plasma protein kinase C (PKC)alpha as a biomarker for the diagnosis of cancers. Carcinogenesis. 2009 Nov;30(11):1927-31. doi: 10.1093/carcin/bgp210. Epub 2009 Aug 26. PMID: 19710177.

1: Bömers JP, Holm A, Kazantzi S, Edvinsson L, Mathiesen TI, Haanes KA. Protein kinase C-inhibition reduces critical weight loss and improves functional outcome after experimental subarachnoid haemorrhage. J Stroke Cerebrovasc Dis. 2024 Jul;33(7):107728. doi: 10.1016/j.jstrokecerebrovasdis.2024.107728. Epub 2024 Apr 19. PMID: 38643942. 2: Magee CP, Le BD, Siripathane YH, Wilkins DG, Hanson GR, Fleckenstein AE. Methcathinone decreases dopamine transporter function: Role of protein kinase C. J Neurochem. 2021 Oct;159(1):116-127. doi: 10.1111/jnc.15483. Epub 2021 Aug 13. PMID: 34320222. 3: Kim CW, Asai D, Kang JH, Kishimura A, Mori T, Katayama Y. Reversal of efflux of an anticancer drug in human drug-resistant breast cancer cells by inhibition of protein kinase Cα (PKCα) activity. Tumour Biol. 2016 Feb;37(2):1901-8. doi: 10.1007/s13277-015-3963-4. Epub 2015 Sep 2. PMID: 26323260. 4: Filla MS, Clark R, Peters DM. A syndecan-4 binding peptide derived from laminin 5 uses a novel PKCε pathway to induce cross-linked actin network (CLAN) formation in human trabecular meshwork (HTM) cells. Exp Cell Res. 2014 Oct 1;327(2):171-82. doi: 10.1016/j.yexcr.2014.07.035. Epub 2014 Aug 13. PMID: 25128150; PMCID: PMC4164596. 5: Sun L, Zhang W, Wang X, Song J, Li M. Inhibition of protein kinase C signal reduces ET receptor expression and basilar vasospasm after subarachnoid hemorrhage in rats. J Integr Neurosci. 2012 Dec;11(4):439-51. doi: 10.1142/S0219635212500288. Epub 2012 Dec 28. PMID: 23351051. 6: Cataldi A, Zara S, Rapino M, Patruno A, di Giacomo V. Human gingival fibroblasts stress response to HEMA: A role for protein kinase C α. J Biomed Mater Res A. 2013 Feb;101(2):378-84. doi: 10.1002/jbm.a.34337. Epub 2012 Jul 30. PMID: 22847994. 7: Wiejak J, Dunlop J, Stoyle C, Lappin G, McIlroy A, Pediani JD, Gao S, Yarwood SJ. The protein kinase C inhibitor, Ro-31-7459, is a potent activator of ERK and JNK MAP kinases in HUVECs and yet inhibits cyclic AMP-stimulated SOCS-3 gene induction through inactivation of the transcription factor c-Jun. Cell Signal. 2012 Aug;24(8):1690-9. doi: 10.1016/j.cellsig.2012.04.016. Epub 2012 Apr 25. PMID: 22561846; PMCID: PMC3383993. 8: Lawal AO, Ellis EM. Nrf2-mediated adaptive response to cadmium-induced toxicity involves protein kinase C delta in human 1321N1 astrocytoma cells. Environ Toxicol Pharmacol. 2011 Jul;32(1):54-62. doi: 10.1016/j.etap.2011.03.010. Epub 2011 Mar 15. PMID: 21787730. 9: Bogatcheva NV, Zemskova MA, Gorshkov BA, Kim KM, Daglis GA, Poirier C, Verin AD. Ezrin, radixin, and moesin are phosphorylated in response to 2-methoxyestradiol and modulate endothelial hyperpermeability. Am J Respir Cell Mol Biol. 2011 Dec;45(6):1185-94. doi: 10.1165/rcmb.2011-0092OC. Epub 2011 Jun 9. PMID: 21659656; PMCID: PMC3262663. 10: Eddaoudi A, Townsend-Nicholson A, Timms JF, Schorge S, Jayasinghe SN. Molecular characterisation of post-bio-electrosprayed human brain astrocytoma cells. Analyst. 2010 Oct;135(10):2600-12. doi: 10.1039/c0an00213e. Epub 2010 Aug 6. PMID: 20694206. 11: Lagranha CJ, Deschamps A, Aponte A, Steenbergen C, Murphy E. Sex differences in the phosphorylation of mitochondrial proteins result in reduced production of reactive oxygen species and cardioprotection in females. Circ Res. 2010 Jun 11;106(11):1681-91. doi: 10.1161/CIRCRESAHA.109.213645. Epub 2010 Apr 22. PMID: 20413785; PMCID: PMC3127199. 12: Kang JH, Asai D, Toita R, Kitazaki H, Katayama Y. Plasma protein kinase C (PKC)alpha as a biomarker for the diagnosis of cancers. Carcinogenesis. 2009 Nov;30(11):1927-31. doi: 10.1093/carcin/bgp210. Epub 2009 Aug 26. PMID: 19710177. 13: Oh YJ, Youn JH, Ji Y, Lee SE, Lim KJ, Choi JE, Shin JS. HMGB1 is phosphorylated by classical protein kinase C and is secreted by a calcium- dependent mechanism. J Immunol. 2009 May 1;182(9):5800-9. doi: 10.4049/jimmunol.0801873. PMID: 19380828. 14: Elkins JM, Amos A, Niesen FH, Pike AC, Fedorov O, Knapp S. Structure of dystrophia myotonica protein kinase. Protein Sci. 2009 Apr;18(4):782-91. doi: 10.1002/pro.82. PMID: 19309729; PMCID: PMC2762590. 15: Kang JH, Asai D, Yamada S, Toita R, Oishi J, Mori T, Niidome T, Katayama Y. A short peptide is a protein kinase C (PKC) alpha-specific substrate. Proteomics. 2008 May;8(10):2006-11. doi: 10.1002/pmic.200701045. PMID: 18425734. 16: Ansar S, Edvinsson L. Subtype activation and interaction of protein kinase C and mitogen-activated protein kinase controlling receptor expression in cerebral arteries and microvessels after subarachnoid hemorrhage. Stroke. 2008 Jan;39(1):185-90. doi: 10.1161/STROKEAHA.107.487827. Epub 2007 Nov 21. PMID: 18032736. 17: Klinger JR, Murray JD, Casserly B, Alvarez DF, King JA, An SS, Choudhary G, Owusu-Sarfo AN, Warburton R, Harrington EO. Rottlerin causes pulmonary edema in vivo: a possible role for PKCdelta. J Appl Physiol (1985). 2007 Dec;103(6):2084-94. doi: 10.1152/japplphysiol.00695.2007. Epub 2007 Sep 27. PMID: 17901241. 18: Santiskulvong C, Rozengurt E. Protein kinase Calpha mediates feedback inhibition of EGF receptor transactivation induced by Gq-coupled receptor agonists. Cell Signal. 2007 Jun;19(6):1348-57. doi: 10.1016/j.cellsig.2007.01.006. Epub 2007 Jan 19. PMID: 17307332. 19: Kang JH, Katayama Y, Han A, Shigaki S, Oishi J, Kawamura K, Toita R, Han XM, Mori T, Niidome T. Mass-tag technology responding to intracellular signals as a novel assay system for the diagnosis of tumor. J Am Soc Mass Spectrom. 2007 Jan;18(1):106-12. doi: 10.1016/j.jasms.2006.09.004. Epub 2006 Oct 13. PMID: 17046276. 20: Beg SS, Hansen-Schwartz JA, Vikman PJ, Xu CB, Edvinsson LI. Protein kinase C inhibition prevents upregulation of vascular ET(B) and 5-HT(1B) receptors and reverses cerebral blood flow reduction after subarachnoid haemorrhage in rats. J Cereb Blood Flow Metab. 2007 Jan;27(1):21-32. doi: 10.1038/sj.jcbfm.9600313. Epub 2006 May 17. PMID: 16736053.