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MedKoo Cat#: 555213 | Name: STO-609 acetate
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Description:

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

STO-609 is a cell-permeable inhibitor of calcium/calmodulin-dependent kinase kinases (CaMKK) isoforms CaMKKα and CaMKKβ (Ki = 80 and 15 ng/ml, respectively). STO-609 is a selective and cell-permeable inhibitor of CaM-KK and that it may be a useful tool for evaluating the physiological significance of the CaM-KK-mediated pathway in vivo as well as in vitro.

Chemical Structure

STO-609 acetate
STO-609 acetate
CAS#1173022-21-3 (acetate)

Theoretical Analysis

MedKoo Cat#: 555213

Name: STO-609 acetate

CAS#: 1173022-21-3 (acetate)

Chemical Formula: C21H14N2O5

Exact Mass: 0.0000

Molecular Weight: 374.35

Elemental Analysis: C, 67.38; H, 3.77; N, 7.48; O, 21.37

Price and Availability

Size Price Availability Quantity
5mg USD 300.00 2 Weeks
10mg USD 550.00 2 Weeks
25mg USD 950.00 2 Weeks
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Related CAS #
52029-86-4 (free base) 1173022-21-3 (acetate)
Synonym
STO-609 acetate; STO 609; STO609;
IUPAC/Chemical Name
7-oxo-7H-benzimidazo[2,1-a]benz[de]isoquinoline-3-carboxylic acid, monoacetate
InChi Key
WNRSTFUVBWNELX-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H10N2O3.C2H4O2/c22-18-13-5-3-4-10-11(19(23)24)8-9-12(16(10)13)17-20-14-6-1-2-7-15(14)21(17)18;1-2(3)4/h1-9H,(H,23,24);1H3,(H,3,4)
SMILES Code
O=C(C1=C2C3=C(C4=NC5=CC=CC=C5N4C(C3=CC=C2)=O)C=C1)O.CC(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
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).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
STO-609 is a CaMKK inhibitor (IC50s = 120 and 40 ng/ml for CaMKKα and CaMKKβ, respectively). It is selective for CaMKKs over CaMKI, CaMKII, CaMKIV, MLCK, PKC, PKA, and p42 MAPK (IC50s = ≥10,000 ng/ml for all).
In vitro activity:
STO-609, a CaMKK inhibitor, blocked MRS2957-induced AMPK activation in MIN6 cells. Silencing the CaMKKβ gene in MIN6 cells also reduced AMPK phosphorylation when treated with MRS2957, confirming that P2Y6R activates AMPK via the CaMKKβ pathway. Reference: Biochem Pharmacol. 2013 Apr 1; 85(7): 991–998. https://pubmed.ncbi.nlm.nih.gov/23333427/
In vivo activity:
STO-609 treatment to inhibit CaMKK2 function confers protection against non-alcoholic fatty liver disease. In a murine model, STO-609S treatment significantly improved hepatic steatosis. Prolonged STO-609S treatment had no effect on body weight but slightly improved glycemia, which is consistent with its acute effects. Reference: Sci Rep. 2017; 7: 11793. https://pubmed.ncbi.nlm.nih.gov/28924233/
Solvent mg/mL mM
Solubility
DMSO 1.0 2.67
100 mM NaOH 10.0 26.71
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 374.35 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.

Recalculate based on batch purity %
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. Ma Z, Wen D, Wang X, Yang L, Liu T, Liu J, Zhu J, Fang X. Growth inhibition of human gastric adenocarcinoma cells in vitro by STO-609 is independent of calcium/calmodulin-dependent protein kinase kinase-beta and adenosine monophosphate-activated protein kinase. Am J Transl Res. 2016 Feb 15;8(2):1164-71. PMID: 27158402; PMCID: PMC4846959. 2. Balasubramanian R, Maruoka H, Jayasekara PS, Gao ZG, Jacobson KA. AMP-activated protein kinase as regulator of P2Y(6) receptor-induced insulin secretion in mouse pancreatic β-cells. Biochem Pharmacol. 2013 Apr 1;85(7):991-8. doi: 10.1016/j.bcp.2012.11.029. Epub 2013 Jan 17. PMID: 23333427; PMCID: PMC3594329. 3. York B, Li F, Lin F, Marcelo KL, Mao J, Dean A, Gonzales N, Gooden D, Maity S, Coarfa C, Putluri N, Means AR. Pharmacological inhibition of CaMKK2 with the selective antagonist STO-609 regresses NAFLD. Sci Rep. 2017 Sep 18;7(1):11793. doi: 10.1038/s41598-017-12139-3. PMID: 28924233; PMCID: PMC5603587.
In vitro protocol:
1. Ma Z, Wen D, Wang X, Yang L, Liu T, Liu J, Zhu J, Fang X. Growth inhibition of human gastric adenocarcinoma cells in vitro by STO-609 is independent of calcium/calmodulin-dependent protein kinase kinase-beta and adenosine monophosphate-activated protein kinase. Am J Transl Res. 2016 Feb 15;8(2):1164-71. PMID: 27158402; PMCID: PMC4846959. 2. Balasubramanian R, Maruoka H, Jayasekara PS, Gao ZG, Jacobson KA. AMP-activated protein kinase as regulator of P2Y(6) receptor-induced insulin secretion in mouse pancreatic β-cells. Biochem Pharmacol. 2013 Apr 1;85(7):991-8. doi: 10.1016/j.bcp.2012.11.029. Epub 2013 Jan 17. PMID: 23333427; PMCID: PMC3594329.
In vivo protocol:
1. York B, Li F, Lin F, Marcelo KL, Mao J, Dean A, Gonzales N, Gooden D, Maity S, Coarfa C, Putluri N, Means AR. Pharmacological inhibition of CaMKK2 with the selective antagonist STO-609 regresses NAFLD. Sci Rep. 2017 Sep 18;7(1):11793. doi: 10.1038/s41598-017-12139-3. PMID: 28924233; PMCID: PMC5603587.
1: York B, Li F, Lin F, Marcelo KL, Mao J, Dean A, Gonzales N, Gooden D, Maity S, Coarfa C, Putluri N, Means AR. Pharmacological inhibition of CaMKK2 with the selective antagonist STO-609 regresses NAFLD. Sci Rep. 2017 Sep 18;7(1):11793. doi: 10.1038/s41598-017-12139-3. PubMed PMID: 28924233; PubMed Central PMCID: PMC5603587. 2: Gerner L, Munack S, Temmerman K, Lawrence-Dörner AM, Besir H, Wilmanns M, Jensen JK, Thiede B, Mills IG, Morth JP. Using the fluorescent properties of STO-609 as a tool to assist structure-function analyses of recombinant CaMKK2. Biochem Biophys Res Commun. 2016 Jul 22;476(2):102-7. doi: 10.1016/j.bbrc.2016.05.045. Epub 2016 May 11. PubMed PMID: 27178209. 3: Ma Z, Wen D, Wang X, Yang L, Liu T, Liu J, Zhu J, Fang X. Growth inhibition of human gastric adenocarcinoma cells in vitro by STO-609 is independent of calcium/calmodulin-dependent protein kinase kinase-beta and adenosine monophosphate-activated protein kinase. Am J Transl Res. 2016 Feb 15;8(2):1164-71. eCollection 2016. PubMed PMID: 27158402; PubMed Central PMCID: PMC4846959. 4: Fujiwara Y, Hiraoka Y, Fujimoto T, Kanayama N, Magari M, Tokumitsu H. Analysis of Distinct Roles of CaMKK Isoforms Using STO-609-Resistant Mutants in Living Cells. Biochemistry. 2015 Jun 30;54(25):3969-77. doi: 10.1021/acs.biochem.5b00149. Epub 2015 Jun 18. PubMed PMID: 26050738. 5: Kukimoto-Niino M, Yoshikawa S, Takagi T, Ohsawa N, Tomabechi Y, Terada T, Shirouzu M, Suzuki A, Lee S, Yamauchi T, Okada-Iwabu M, Iwabu M, Kadowaki T, Minokoshi Y, Yokoyama S. Crystal structure of the Ca²⁺/calmodulin-dependent protein kinase kinase in complex with the inhibitor STO-609. J Biol Chem. 2011 Jun 24;286(25):22570-9. doi: 10.1074/jbc.M111.251710. Epub 2011 Apr 19. PubMed PMID: 21504895; PubMed Central PMCID: PMC3121401. 6: Monteiro P, Gilot D, Langouet S, Fardel O. Activation of the aryl hydrocarbon receptor by the calcium/calmodulin-dependent protein kinase kinase inhibitor 7-oxo-7H-benzimidazo[2,1-a]benz[de]isoquinoline-3-carboxylic acid (STO-609). Drug Metab Dispos. 2008 Dec;36(12):2556-63. doi: 10.1124/dmd.108.023333. Epub 2008 Aug 28. PubMed PMID: 18755850. 7: Tokumitsu H, Inuzuka H, Ishikawa Y, Kobayashi R. A single amino acid difference between alpha and beta Ca2+/calmodulin-dependent protein kinase kinase dictates sensitivity to the specific inhibitor, STO-609. J Biol Chem. 2003 Mar 28;278(13):10908-13. Epub 2003 Jan 22. PubMed PMID: 12540834. 8: Tokumitsu H, Inuzuka H, Ishikawa Y, Ikeda M, Saji I, Kobayashi R. STO-609, a specific inhibitor of the Ca(2+)/calmodulin-dependent protein kinase kinase. J Biol Chem. 2002 May 3;277(18):15813-8. Epub 2002 Feb 26. Erratum in: J Biol Chem. 2003 Feb 7;278(6):4368. PubMed PMID: 11867640.

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