ML-7 HYDROCHLORIDE Chemical Properties

Melting point:

246-249°C dec.

storage temp. 

-20°C

solubility 

insoluble in EtOH; ≥15.95 mg/mL in DMSO; ≥8.82 mg/mL in H2O with gentle warming and ultrasonic

form 

powder

color 

white

InChI

1S/C15H17IN2O2S.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

InChIKey

KDDALCDYHZIZMH-UHFFFAOYSA-N

SMILES

Cl.Ic1cccc2c(cccc12)S(=O)(=O)N3CCCNCC3

Safety Information

WGK Germany 

3

Storage Class

11 - Combustible Solids

MSDS

• Language:English Provider:SigmaAldrich

ML-7 HYDROCHLORIDE Usage And Synthesis

Description

ML-7 inhibits smooth muscle myosin light chain kinase (MLCK) with a K_i value of 0.3 μM and displays reversible, ATP-competitive inhibition of Ca²⁺-calmodulin-dependent and -independent smooth muscle MLCKs. It exhibits a 10-fold more potent inhibition of MLCK than its parent compound ML-9 .

Chemical Properties

Off-White to Yellow Fine Crystalline Solid

Uses

A potent and selective inhibitor of myosin light chain kinase.

Uses

ML-7 has been used as a myosin light chain kinase (MLCK) inhibitor in various experiments.

Biochem/physiol Actions

Selective myosin light chain kinase inhibitor.

Synthesis

It is synthesized in two steps. 1) Synthesis of 1-(5-iodonaphthalene-1-sulfonyl)-1H-hexahydro-1,4-diazepine: A toluene solution of homopiperazine reacts with a solution of 5-iodo-1-naphthalenesulfonyl chloride. After filtration, the filtrate is washed with water. The organic phase is purified over a silica gel pad. The resulting solid is crystallized from isopropanol and dried to give the product. 2) Preparation of the hydrochloride (ML-7 HYDROCHLORIDE): The product from step 1 is dissolved in isopropanol by heating. After cooling, 6N HCl is added. The mixture is cooled and filtered. The solid is crystallized from water, filtered, washed, and vacuum-dried to yield the title hydrochloride.

in vitro

rats with myocardial infarction were intravenously infused with rhnrg-1. the cmlck expression and phosphorylated mlc-2v were up-regulated in rat treated with rhnrg-1 significantly. moreover, the restoration of rhnrg-1-induced sarcomeric organization in serum-free cultured neonatal rat cardiomyocytes with rhnrg-1 was inhibited by ml-7 [1].

in vivo

administration of ml-7 from 10 min before ischemia to the first 10 min of reperfusion led to a significant recovery of heart contractility. gel analyses of two-dimensional electrophoresis revealed eight proteins with decreased levels in i/r hearts. six proteins involved in energy metabolism, which were cytochrome b-c1 complex subunit 1, atp synthase beta subunit, cytochrome c oxidase subunit, mitochondrial nadhdehydrogenase, nadhdehydrogenase iron-sulfur protein 8, and succinyl-coa ligase subunit. the other two protein levels decreased in i/r hearts, which were peroxiredoxin-2 and tubulin. in addition, ml-7 treatment increased the level of succinyl-coa ligase, which was a key enzyme involved in the citric acid cycle [2].

storage

room temperature (desiccate)

References

[1] gu x,liu x,xu d,li x,yan m,qi y,yan w,wang w,pan j,xu y,xi b,cheng l,jia j,wang k,ge j,zhou m. cardiac functional improvement in rats with myocardial infarction by up-regulating cardiac myosin light chain kinase with neuregulin. cardiovasc res.2010 nov 1;88(2):334-43.
[2] lin hb,cadete vj,sawicka j,wozniak m,sawicki g. effect of the myosin light chain kinase inhibitor ml-7 on the proteome of hearts subjected to ischemia-reperfusion injury. j proteomics.2012 sep 18;75(17):5386-95.

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