3-(2,4-Dichloro-5-methoxyphenyl)-2,3-dihydro-2-thioxo-4(1H)-quinazolinone

3-(2,4-Dichloro-5-methoxyphenyl)-2,3-dihydro-2-thioxo-4(1H)-quinazolinone Basic information
Product Name:3-(2,4-Dichloro-5-methoxyphenyl)-2,3-dihydro-2-thioxo-4(1H)-quinazolinone
Synonyms:3-(2,4-Dichloro-5-methoxyphenyl)-2,3-dihydro-2-thioxo-4(1H)-quinazolinone;Mdivi 1;Mdivi1/Mdivi-1;Mitochondrial division inhibitor 1;3-(2,4-DICHLORO-5-METHOXYPHENYL)-2-THIOXO-2,3-DIHYDROQUINAZOLIN-4(1H)-ONE EXACT;Mitochondrial Division Inhibitor, mdivi-1;4(1H)-Quinazolinone, 3-(2,4-dichloro-5-methoxyphenyl)-2,3-dihydro-2-thioxo-;3-(2,4-Dichloro-5-methoxyphenyl)-2,3-dihydro-2-thioxo-4(1H)-quinazolinone Mdivi-1
CAS:338967-87-6
MF:C15H10Cl2N2O2S
MW:353.22
EINECS:
Product Categories:Inhibitors
Mol File:338967-87-6.mol
3-(2,4-Dichloro-5-methoxyphenyl)-2,3-dihydro-2-thioxo-4(1H)-quinazolinone Structure
3-(2,4-Dichloro-5-methoxyphenyl)-2,3-dihydro-2-thioxo-4(1H)-quinazolinone Chemical Properties
Melting point 289 °C
Boiling point 522.5±60.0 °C(Predicted)
density 1.57±0.1 g/cm3(Predicted)
storage temp. -20°C
solubility DMSO: >20mg/mL
pka9.91±0.20(Predicted)
form White solid
color White
Stability:Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
Safety Information
WGK Germany 3
HS Code 2933.59.8000
MSDS Information
3-(2,4-Dichloro-5-methoxyphenyl)-2,3-dihydro-2-thioxo-4(1H)-quinazolinone Usage And Synthesis
DescriptionMdivi 1 is a mitochondrial division inhibitor. It inhibits the GTPase activity of yeast, but not human, dynamin-1 (Dnm1; IC50 = ~1-10 μM for the recombinant yeast enzyme) and human dynamin-related protein 1 (DRP1) in A549 lung cancer cells when used at a concentration of 50 μM. Mdivi 1 (50 μM) inhibits mitochondrial fragmentation and DRP1 self-assembly induced by staurosporine in COS cells overexpressing DRP1. It induces apoptosis in, and inhibits colony formation of, A549 cells when used at concentrations of 25 and 50 μM, respectively. Mdivi 1 (1 μM) decreases doxorubicin-induced increases in infarct-to-risk ratios in a Langendorff isolated perfused rat heart model of ischemia-reperfusion injury. It reduces the severity of lung injury in a mouse model of LPS-induced acute lung injury when administered at a dose of 20 mg/kg.
UsesMdivi-1 is an inhibitor of mitochondrial division DRP1 and Dynamin I.
UsesMdivi-1 has been used:
  • in embryonic thoracic aorta A7r5 cells to inhibit cell migration and proliferation
  • in mitochondrial network reshaping and reactive oxygen species (ROS) production studies in oligodendrocyte precursor cells (OPCs)
  • to induce mitochondrial damage in lung fibroblasts

General DescriptionMitochondrial Division Inhibitor 1 (Mdivi-1) is a quinazolinone derivative and is cell permeable. It traverses blood-brain barrier and elicits protective functionality in heart and brain ischemia-reperfusion injury.
Biological ActivityMdivi-1 (Mitochondrial division inhibitor 1) is a selective and cell-penetrating inhibitor of mitochondrial division, inhibits DRP1 (dynamin-related GTPase) and Dynamin I (Dnm1) with IC50 of 1-10 μM. Mdivi-1 reduces mitophagy and increases apoptosis.
Biochem/physiol ActionsMdivi-1 is a cell-permeable selective inhibitor of mitochondrial division DRP (dynamin-related GTPase) and inhibitor of the mitochondrial division dynamin (Dnm1). Mitochondrial fusion and division play important roles in the regulation of apoptosis. Mdivi-1 is the first selective inhibitor of mitochondrial division dynamins. In principle, Mdivi-1 represents a class of therapeutics for stroke, myocardial infarction, and neurodegenerative diseases.
in vivoThe protein expression of Drp1 and GFAP is significantly increased during early neural development in the retina of ischemic mice. The use of Mdivi-1 blocked apoptosis in the ischemic retina and significantly increased RGC survival after two weeks of ischemia. In normal mouse retina, the expression of Drp1 is mainly distributed in the ganglion cell layer (GCL), the inner plexiform layer, the inner nuclear layer (INL) and the outer plexiform layer. In the ganglion cell layer, Drp1 is strongly immunoreactive. Drp1 protein expression was increased in GCLs 12 h after ischemia induction. Mdivi-1 did not alter the increase in Drp1 protein expression but significantly decreased GFAP protein expression.
in vitroMdivi-1 is a membrane-crossing quinazolone that inhibits the cleavage of DRPs (dynamin-associated GTPases) by yeast Dnm1 and human Drp1, and induces mitochondrial fusion into a nest-like structure efficiently and reversibly. Extracellular studies suggest that mdivi-1 blocks the ATPase activity (IC50<10 μM) and self-assembly of Dnm1 through allosteric regulation. Mdivi-1 potently inhibited STS and C8-Bid-induced MOMP (increased mitochondrial outer membrane permeability) in HeLa cells and extracellular murine hepatocyte mitochondrial preparations, respectively. In cells, mdivi-1 further inhibited apoptosis by inhibiting mitochondrial outer membrane permeability. In general, mivi-1 represents a class of therapies for the treatment of stroke, myocardial infarction and neurodegenerative diseases.
storageStore at -20°C
References1) Cassidy-Stone et al. (2008), Chemical inhibition of the mitochondrial division dynamin reveals its role in Bax/Bak-dependent mitochondrial outer membrane permeabilization; Dev. Cell, 14 193 2) Lackner et al. (2010), Small molecule inhibitors of mitochondrial division: tools that translate basic biological research into medicine; Chem. Biol., 17 578
3-(2,4-Dichloro-5-methoxyphenyl)-2,3-dihydro-2-thioxo-4(1H)-quinazolinone Preparation Products And Raw materials
FCCP DECYLUBIQUINONE CARBONYL CYANIDE 3-CHLOROPHENYLHYDRAZONE Afatinib Phenylsilane SB 203580 BA, 3NH4 Lopinavir BONGKREKIC ACID SB 431542 Melatonine p-Anisidine 7-CHLORO-5-(2-CHLOROPHENYL)-1,5-DIHYDRO-4,1-BENZOTHIAZEPIN-2(3H)-ONE Phenyltrichlorosilane Y27632 (hydrochloride) N4-(9-Ethyl-9H-carbazol-3-yl)-N2-(3-Morpholin-4-yl-propyl)-pyriMidine-2,4-diaMine CHLOROPHENYLSILANE 97 COENZYME Q2

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