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C1172

Sigma-Aldrich

ML-9

≥99% (TLC), powder

Synonym(s):

1-(5-Chloronaphthalene-1-sulfonyl)-1H-hexahydro-1,4-diazepine hydrochloride

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About This Item

Linear Formula:
C15H17N2O2SCl · HCl
CAS Number:
105637-50-1
Molecular Weight:
361.29
MDL number:
MFCD00065525
UNSPSC Code:
12352202
PubChem Substance ID:
24278297
NACRES:
NA.77

biological source

synthetic (organic)

assay

≥99% (TLC)

form

powder

color

white

solubility

ethanol: 10 mg/mL

storage temp.

2-8°C

SMILES string

Cl.Clc1cccc2c(cccc12)S(=O)(=O)N3CCCNCC3

InChI

1S/C15H17ClN2O2S.ClH/c16-14-6-1-5-13-12(14)4-2-7-15(13)21(19,20)18-10-3-8-17-9-11-18;/h1-2,4-7,17H,3,8-11H2;1H

InChI key

ZNRYCIVTNLZOGI-UHFFFAOYSA-N

Gene Information

human ... SLC2A1(6513) , SLC2A4(6517)

Application

ML-9 has been used in the inhibition of myosin light chain kinase (MLCK) and non-muscle myosin IIA (NMIIA) in human corneal epithelial cells and HeLa cells.

Biochem/physiol Actions

ML-9 is myosin light chain kinase inhibitor. It inhibits insulin-induced translocation of glucose transporters GLUT4 and GLUT1 in a dose-dependent manner. ML-9 also inhibits agonist-induced Ca2+ entry into endothelial cells and catecholamine secretion in intact and permeabilized chromaffin cells. ML-9 promotes cell death in cancer cells by triggering accumulation of autophagic vacuoles. ML-9 impacts phosphorylation of myosin light chain kinase and alters trabecular meshwork shape and decreases intraocular pressure in rabbit eyes.

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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M Saitoh et al.
The Journal of biological chemistry, 262(16), 7796-7801 (1987-06-05)
Systematically synthesized derivatives of ML-9, 1-(5-chloronaphthalenesulfonyl)-1H-hexahydro-1,4-diazepine, were found to inhibit both Ca2+-calmodulin-dependent and -independent smooth muscle myosin light chain kinases with a similar concentration dependence, and their inhibitions were of the competitive type with respect to ATP. Moreover, ML-9 as
Identification of ML-9 as a lysosomotropic agent targeting autophagy and cell death
Kondratskyi A, et al.
Cell Death & Disease, 5(4), e1193-e1193 (2014)
A myosin light chain kinase inhibitor, ML-9, lowers the intraocular pressure in rabbit eyes
Honjo M, et al.
Experimental Eye Research, 75(2), 135-142 (2002)
Inhibition of myosin light chain kinase can be targeted for the development of new therapies against herpes simplex virus type-1 infection
AntoineTE and Shukla D
Antiviral Therapy, 19(1), 15-29 (2014)
Effects of ML-9 on insulin stimulation of glucose transport in 3T3-L1 adipocytes.
Inoue G, et al.
The Journal of Biological Chemistry, 268(7), 5272-5278 (1993)
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