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Key Documents

Altri documenti

L4900

Sigma-Aldrich

Lonidamine

mitochondrial hexokinase inhibitor

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C15H10Cl2N2O2
Numero CAS:
50264-69-2
Peso molecolare:
321.16
Numero CE:
256-510-0
Numero MDL:
MFCD00866285
Codice UNSPSC:
12352202
ID PubChem:
24278515
NACRES:
NA.77

Livello qualitativo

200

Saggio

≥98% (TLC)

Forma fisica

powder

Solubilità

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

Stringa SMILE

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)
WDRYRZXSPDWGEB-UHFFFAOYSA-N

Applicazioni

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

Azioni biochim/fisiol

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.

Pittogrammi

Exclamation markHealth hazard
GHS07,GHS08

Avvertenze

Danger

Indicazioni di pericolo

H302 - H351 - H360

Classi di pericolo

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

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

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

Certificati d'analisi (COA)

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Sigma-Aldrich

T27006

2-Thenoyltrifluoroacetone

Sodium oxamate ≥98%

Sigma-Aldrich

O2751

Sodium oxamate

Oligomycin A ≥99% (HPLC)

Sigma-Aldrich

75351

Oligomycin A

Rotenone ≥95%

Sigma-Aldrich

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Sigma-Aldrich

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Supelco

PHR1084

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Curcumin ≥94% (curcuminoid content), ≥80% (Curcumin)

Sigma-Aldrich

C7727

Curcumin

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
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)
Morgane Le Bras et al.
Cancer research, 66(18), 9143-9152 (2006-09-20)
Mitochondrial membrane permeabilization (MMP) is a rate-limiting step of apoptosis, including in anticancer chemotherapy. Adenine nucleotide translocase (ANT) mediates the exchange of ADP and ATP on the inner mitochondrial membrane in healthy cells. In addition, ANT can cooperate with Bax
Eva Calviño et al.
Biochemical pharmacology, 82(11), 1619-1629 (2011-09-06)
Lonidamine is a safe, clinically useful anti-tumor drug, but its efficacy is generally low when used in monotherapy. We here demonstrate that lonidamine efficaciously cooperates with the anti-leukemic agent arsenic trioxide (ATO, Trisenox) to induce apoptosis in HL-60 and other
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Articoli

Aerobic Glycolysis and the Warburg Effect

We presents an article about the Warburg effect, and how it is the enhanced conversion of glucose to lactate observed in tumor cells, even in the presence of normal levels of oxygen. Otto Heinrich Warburg demonstrated in 1924 that cancer cells show an increased dependence on glycolysis to meet their energy needs, regardless of whether they were well-oxygenated or not.

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