5.30030

Glutaminase Inhibitor II, BPTES

• Synonyme(s) : Glutaminase Inhibitor II, BPTES, N,Nʹ-(5,5ʹ-(2,2ʹ-Thio bis(ethane-2,1-diyl)) bis(1,3,4-thiadiazole-5,2-diyl)) bis(2-phenylacetamide), Kidney-Type Glutaminase Inhibitor II, GAC Inhibitor II, GLS1 Inhibitor II, KGA Inhibitor II
• Formule empirique (notation de Hill): C₂₄H₂₄N₆O₂S₃
• Numéro CAS: 314045-39-1
• Poids moléculaire : 524.68
• Numéro MDL: MFCD01079848
• Code UNSPSC : 12352200
• Nomenclature NACRES : NA.77

Propriétés

• Pureté: ≥94% (HPLC)
• Niveau de qualité: 100
• Forme: powder
• Fabricant/nom de marque: Calbiochem^®
• Conditions de stockage: OK to freeze; protect from light
• Couleur: yellow
• Solubilité: DMSO: 50 mg/mL
• Température de stockage: −20°C
• InChI: 1S/C24H24N6O2S3/c31-19(15-17-7-3-1-4-8-17)25-23-29-27-21(34-23)11-13-33-14-12-22-28-30-24(35-22)26-20(32)16-18-9-5-2-6-10-18/h1-10H,11-16H2,(H,25,29,31)(H,26,30,32)
• Clé InChI: MDJIPXYRSZHCFS-UHFFFAOYSA-N

Description

Description générale

Glutaminase Inhibitor II,Bis-2-(5-phenylacetamido-1,2,4-thiadiazol-2-yl)ethyl sulfide (BPTES)is a cell-permeable bis-thiadiazole compound that selectivelyinhibits glutaminase-1(GLS1). It does not inhibit the liver-type GLS-2 mitochondrialglutaminase activity. It exerts its effect by inducing an inactive GLS1tetrameric conformation via a 2:1 inhibitor-to-tetramer stoichiometric binding.BPTES blocks the growth under aerobic/ normoxic conditions, and promotes celldeath under hypoxic conditions in P493 B-cell lymphoma cultures invitro, and effectively suppresses P493 tumor expansion in mice invivo.BPTES has been observedto be active in several cancer cells as it prevents cancer cellproliferation.

Application

Glutaminase Inhibitor II, BPTES has been used asa glutaminase inhibitor to study its effects on the release of extracellularvesicles (EVs) in human immunodeficiency virus (HIV-1) infected macrophages.

Actions biochimiques/physiologiques

Cell permeable: yes

Primary Target
kidney-type glutaminase

Reversible: yes

Target IC₅₀: 140 and 210 nM in HEK293 cells expressing wt-KGA and F318Y-cKGA, respectively

Conditionnement

Packaged under inert gas

Avertissement

Toxicity: Standard Handling (A)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Autres remarques

Shukla, K., et al. 2012. J. Med. Chem.55, 10551.

Thangavelu, K., et al. 2012. Proc. Natl. Acad. Sci. USA109, 7705.
Le, A., et al. 2012. Cell Metab.15, 110.
DeLaBarre, B., et al. 2011. Biochemistry 50, 10764.
Seltzer, M.J., et al. 2010. Cancer Res.70, 8981.
Robinson, M.M., et al. 2007. Biochem. J.406, 407.

Informations légales

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Informations sur la sécurité

• Pictogrammes: GHS07
• Mention d'avertissement: Warning
• Mentions de danger: H315 - H319 - H335
• Conseils de prudence: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Classification des risques: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Organes cibles: Respiratory system
• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable