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S1318

Sigma-Aldrich

STO-609-acetic acid

≥95% (HPLC), solid

Synonym(s):

7-Oxo-7H-benzimidazo[2,1-a]benz[de]isoquinoline-3-carboxylic acid - acetic acid

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About This Item

Empirical Formula (Hill Notation):
C19H10N2O3 · C2H4O2
CAS Number:
1173022-21-3
Molecular Weight:
374.35
MDL number:
MFCD06411456
UNSPSC Code:
12352106
PubChem Substance ID:
329824472
NACRES:
NA.77

Quality Level

100

Assay

≥95% (HPLC)

form

solid

mp

>300 °C

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

CC(O)=O.OC(=O)c1ccc2-c3nc4ccccc4n3C(=O)c5cccc1c25

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 key

WNRSTFUVBWNELX-UHFFFAOYSA-N

General description

STO-609 reduces tumorigenicity of liver cancer cells in vivo. TO-609 reduces the activation of AMP (adenosine monophosphate)-activated protein kinase (AMPK) by ionomycin in a dose dependant manner.
1:1 adduct with acetic acid

Application

STO609 has been used as a calcium/calmodulin-dependent protein kinase kinase (CAMKK) inhibitor in mouse MLL-AF9 acute myeloid leukemia (AML) cells.

Biochem/physiol Actions

Selective Ca2+/Calmodulin-dependent protein kinase kinase (CaM-KK) antagonist. Inhibits CamKKa and CaMKKb with Ki = 80 and 15 ng/mL, respectively. Does not inhibit downstream CaM kinases (CaMKI and CaMKIV).

Features and Benefits

This compound is featured on the Ca/CaMKs page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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CAMKs support development of acute myeloid leukemia
Kang X, et al.
Journal of Hematology & Oncology, 11(1), 30-30 (2018)
Ca2+/calmodulin-dependent protein kinase kinase-beta acts upstream of AMP-activated protein kinase in mammalian cells
Woods A, et al.
Cell Metabolism, 2(1), 21-33 (2005)
The camKK2/camKIV relay is an essential regulator of hepatic cancer
Lin F, et al.
Hepatology, 62(2), 505-520 (2015)
Liping Shen et al.
Toxicology, 421, 22-29 (2019-04-04)
Voltage-gated sodium channels (VGSCs) represent molecular targets for a number of potent neurotoxins that affect the ion permeation or gating kinetics. BmK NT1, an α-scorpion toxin purified from Buthus martensii Karch (BMK), induces excitatory neurotoxicity by activation of VGSCs with
Nicholas D LeBlond et al.
International journal of molecular sciences, 21(23) (2020-12-03)
The dysregulation of macrophage lipid metabolism drives atherosclerosis. AMP-activated protein kinase (AMPK) is a master regulator of cellular energetics and plays essential roles regulating macrophage lipid dynamics. Here, we investigated the consequences of atherogenic lipoprotein-induced foam cell formation on downstream
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