Lonidamine mitochondrial hexokinase inhibitor ยี่ห้อ Sigma

PROPERTIES

Quality Level

200

Assay

≥98% (TLC)

form

powder

solubility

chloroform: methanol (1:1): 9.80-10.20 mg/mL, clear, colorless to light yellow

SMILES string

OC(=O)c1nn(Cc2ccc(Cl)cc2Cl)c3ccccc13

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

DESCRIPTION

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

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.

Inhibits the energy metabolism of neoplastic cells by interfering with hexokinase and disrupting uncoupler-stimulated mitochondrial electron transport; damages cell and mitochondrial membranes.