Saltar al contenido
Merck
Todas las fotos(2)

Documentos clave

Ver Toda la documentación

L4900

Sigma-Aldrich

Lonidamine

mitochondrial hexokinase inhibitor

Sinónimos:

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

Iniciar sesiónpara Ver la Fijación de precios por contrato y de la organización
Todas las fotos(2)

About This Item

Fórmula empírica (notación de Hill):
C15H10Cl2N2O2
Número de CAS:
50264-69-2
Peso molecular:
321.16
EC Number:
256-510-0
MDL number:
MFCD00866285
UNSPSC Code:
12352202
PubChem Substance ID:
24278515
NACRES:
NA.77
En este momento no podemos mostrarle ni los precios ni la disponibilidad

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

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.
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.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Repr. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Elija entre una de las versiones más recientes:

Certificados de análisis (COA)

Lot/Batch Number
0000375988
0000332130
0000239443
0000239443
0000332130

¿No ve la versión correcta?

Si necesita una versión concreta, puede buscar un certificado específico por el número de lote.

Busque por un COA

¿Ya tiene este producto?

Encuentre la documentación para los productos que ha comprado recientemente en la Biblioteca de documentos.

Visite la Librería de documentos

Lara Milane et al.
Nanomedicine : nanotechnology, biology, and medicine, 7(4), 435-444 (2011-01-12)
The aim of this study was to assess the biodistribution and pharmacokinetics of epidermal growth factor receptor (EGFR)-targeted polymer-blend nanoparticles loaded with the anticancer drugs lonidamine and paclitaxel. Plasma, tumor, and tissue distribution profiles were quantified in an orthotopic animal
H Ben-Horin et al.
Cancer research, 55(13), 2814-2821 (1995-07-01)
The mechanism of action of the antineoplastic drug lonidamine (LND) on MCF-7 human breast cancer cells was studied with the use of 31P and 13C nuclear magnetic resonance (NMR) spectroscopy. The cells were embedded in alginate microcapsules, perfused with growth
Lara Milane et al.
Molecular pharmaceutics, 8(1), 185-203 (2010-10-15)
Multi-drug resistant (MDR) cancer is a significant clinical obstacle and is often implicated in cases of recurrent, nonresponsive disease. Targeted nanoparticles were made by synthesizing a poly(D,L-lactide-co-glycolide)/poly(ethylene glycol)/epidermal growth factor receptor targeting peptide (PLGA/PEG/EGFR-peptide) construct for incorporation in poly(epsilon-caprolactone) (PCL)
Marilisa P Dimmito et al.
Biomolecules, 9(9) (2019-09-19)
The endocannabinoid system represents an integrated neuronal network involved in the control of several organisms' functions, such as feeding behavior. A series of hybrids of 5-(4-chlorophenyl)-1-(2,4-dichloro-phenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide (mimonabant), a well-known inverse agonist of the type-1 cannabinoid receptor (CB1), once used as
Yolanda Sánchez et al.
The Journal of pharmacology and experimental therapeutics, 335(1), 114-123 (2010-07-08)
Arsenic trioxide (ATO, Trisenox) is an important antileukemic drug, but its efficacy is frequently low when used as a single agent. Here, we demonstrate that the apoptotic action of ATO is greatly increased when combined with subcytotoxic curcumin concentrations in
Ver todos los artículos relacionados

Artículos

Aerobic Glycolysis and the Warburg Effect

Warburg effect enhances glucose to lactate conversion in tumor cells, regardless of oxygen levels; impacting cancer metabolism since 1924.

Aerobic Glycolysis and the Warburg Effect

Warburg effect enhances glucose to lactate conversion in tumor cells, regardless of oxygen levels; impacting cancer metabolism since 1924.

Aerobic Glycolysis and the Warburg Effect

Warburg effect enhances glucose to lactate conversion in tumor cells, regardless of oxygen levels; impacting cancer metabolism since 1924.

Aerobic Glycolysis and the Warburg Effect

Warburg effect enhances glucose to lactate conversion in tumor cells, regardless of oxygen levels; impacting cancer metabolism since 1924.

Questions

Reviews

No rating value

Active Filters

Nuestro equipo de científicos tiene experiencia en todas las áreas de investigación: Ciencias de la vida, Ciencia de los materiales, Síntesis química, Cromatografía, Analítica y muchas otras.

Póngase en contacto con el Servicio técnico