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SML0524

Sigma-Aldrich

ML277

≥98% (HPLC)

Synonym(s):

(2R)-N-[4-(4-Methoxyphenyl)-1,3-thiazol-2-yl]-1-(4-methylphenyl)sulfonylpiperidine-2-carboxamide, (R)-N-(4-(4-Methoxyphenyl)thiazol-2-yl)-1-tosylpiperidine-2-carboxamide, CID-53347902, VU0458298-2, VU0458298-3

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About This Item

Empirical Formula (Hill Notation):
C23H25N3O4S2
CAS Number:
1401242-74-7
Molecular Weight:
471.59
MDL number:
MFCD23704792
UNSPSC Code:
12352200
PubChem Substance ID:
329825530
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear

storage temp.

2-8°C

SMILES string

COc1ccc(cc1)-c2cnc(NC(=O)[C@H]3CCCCN3S(=O)(=O)c4ccc(C)cc4)s2

InChI

1S/C23H25N3O4S2/c1-16-6-12-19(13-7-16)32(28,29)26-14-4-3-5-20(26)22(27)25-23-24-15-21(31-23)17-8-10-18(30-2)11-9-17/h6-13,15,20H,3-5,14H2,1-2H3,(H,24,25,27)/t20-/m1/s1

InChI key

UKSXJENCMIVQMU-HXUWFJFHSA-N

Application

ML277 has been used as the KCNQ1 activator to treat cells in lung metastasis assay.

Biochem/physiol Actions

ML277 is a potent activator of KCNQ1 (Kv7.1) channels with >100-fold selectivity versus KCNQ2 and KCNQ4 and no activity against the hERG potassium channel up to 30 μM. KCNQ1 is a voltage-gated potassium channel required for repolarization phase of the cardiac action potential. Mutations in the KCNQ1 gene are associated with long QT syndrome (LQTS), a disorder in which the heart muscles take longer than normal to recover after each heart beat and can lead to dangerous arrhythmias such as atrial fibrillation. Activators of KCNQ1 channels could have potential use in treatments of LQTS. ML277 is the first selective and potent activator found, with an EC50 of 260 nM.

Features and Benefits

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Xiaohong Wei et al.
PloS one, 13(3), e0192122-e0192122 (2018-03-27)
Pre-eclampsia is associated with altered maternal and placental vascular reactivity. Kv7 channels (encoded by KCNQ 1-5 genes) are a potential contributor to the regulation of vascular tone in CPAs (chorionic plate arteries) during normal pregnancy. The aim of this study
Gaelle Lentini et al.
PloS one, 12(12), e0189556-e0189556 (2017-12-16)
During the infection process, Apicomplexa discharge their secretory organelles called micronemes, rhoptries and dense granules to sustain host cell invasion, intracellular replication and to modulate host cell pathways and immune responses. Herein, we describe the Toxoplasma gondii Deg-like serine protein
Hypermethylated KCNQ1 acts as a tumor suppressor in hepatocellular carcinoma
Fan H, et al.
Biochemical and Biophysical Research Communications, 503(4), 3100-3107 (2018)
Dmitry Tsvetkov et al.
British journal of pharmacology, 174(2), 150-162 (2016-12-22)
K We used Kcnq1 R-L3 produced similar concentration-dependent relaxations (EC We conclude that K
Haiyan Fan et al.
Biochemical and biophysical research communications, 503(4), 3100-3107 (2018-08-27)
Potassium (K+) channels are dysregulated in tumor tissues and functionally these channels contribute significantly to the malignant phenotypes of the cancer cells, including cell apoptosis, chemo- and radio-resistance, proliferation, and migration. However, little is known about the potential implications of

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