STO-609 acetate | CAS#1173022-21-3

STO-609 acetate
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 555213

CAS#: 1173022-21-3 (acetate)

Description: 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

CAS# 1173022-21-3 (acetate)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 555213
Name: STO-609 acetate
CAS#: 1173022-21-3 (acetate)
Chemical Formula: C21H14N2O5
Exact Mass: 0.00
Molecular Weight: 374.350
Elemental Analysis: C, 67.38; H, 3.77; N, 7.48; O, 21.37

Price and Availability

Size	Price	Availability
5mg	USD 300	2 Weeks
10mg	USD 550	2 Weeks
25mg	USD 950	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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: 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)

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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	1.0	2.67
	100 mM NaOH	10.0	26.71

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.

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.

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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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STO-609 acetate featured