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Lonidamine

SIGMA/L4900 - mitochondrial hexokinase inhibitor

Synonym: 1-(2,4-Dichlorobenzyl)-1H-indazole-3-carboxylic acid; Diclondazolic acid

CAS Number: 50264-69-2
Empirical Formula (Hill Notation): C15H10Cl2N2O2
Molecular Weight: 321.16
EC Number: 256-510-0
MDL Number: MFCD00866285
Linear Formula: C15H10Cl2N2O2
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-L4900-5MG 5 mg
 $182.00
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45-L4900-25MG 25 mg
 $623.00
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This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: L4900-25MG

 

assay ≥98% (TLC)
form powder
InChI 1S/C15H10Cl2N2O2/c16-10-6-5-9(12(17)7-10)8-19-13-4-2-1-3-11(13)14(18-19)15(20)21/h1-7H,8H2,(H,20,21)
InChI key WDRYRZXSPDWGEB-UHFFFAOYSA-N
Quality Level 200 
SMILES string OC(=O)c1nn(Cc2ccc(Cl)cc2Cl)c3ccccc13
solubility chloroform: methanol (1:1): 9.80-10.20 mg/mL, clear, colorless to light yellow
Application: Lonidamine has been used:
• as an inhibitor of glycolysis to study its effects on the epithelial-mesenchymal transition (EMT) mechanism in cancer stem cells (CSC)
• as mitochondrial permeability transition (MPT)- inducing drug to study its effects on temozolomide-resistant glioblastoma cell line
• as mitochondrial hexokinase inhibitor to measure reactive oxygen species (ROS) in human acute myeloid leukemia cells
Biochem/physiol Actions: Inhibits the energy metabolism of neoplastic cells by interfering with hexokinase and disrupting uncoupler-stimulated mitochondrial electron transport; damages cell and mitochondrial membranes.
Biochem/physiol Actions: Lonidamine (LND) is an indazole derivative and is an anti-spermatogenic agent. It exhibits anti-tumor activity by sensitizing tumors to photodynamic, chemo-, radiotherapy, and hyperthermia. LND also interferes with energy metabolism by blocking glycolysis, adenosine diphosphate (ADP-), and uncoupler-stimulated respiration on various nicotinamide adenine dinucleotide (NAD-) and flavin adenine dinucleotide (FAD)-linked substrates, hexokinase activity, and oxygen uptake in Ehrlich ascites tumor cells. It blocks lactate export and pyruvate uptake into the mitochondria by inhibiting proton-linked monocarboxylate transporter (MCT) and mitochondrial pyruvate carrier (MPC), respectively.
Packaging: 5, 25 mg in glass bottle
Purity ≥98% (TLC)
UNSPSC 12352202

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