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5.30030

Glutaminase Inhibitor II, BPTES

Synonym(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

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About This Item

Empirical Formula (Hill Notation):
C24H24N6O2S3
CAS Number:
314045-39-1
Molecular Weight:
524.68
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD01079848
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assay

≥94% (HPLC)

Quality Level

100

form

powder

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze, protect from light

color

yellow

solubility

DMSO: 50 mg/mL

storage temp.

−20°C

SMILES string

[s]1c(nnc1CCSCCc3[s]c(nn3)NC(=O)Cc4ccccc4)NC(=O)Cc2ccccc2

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)

InChI key

MDJIPXYRSZHCFS-UHFFFAOYSA-N

General description

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.

Biochem/physiol Actions

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

Packaging

Packaged under inert gas

Preparation Note

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

Other Notes

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.

Legal Information

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

Disclaimer

Toxicity: Standard Handling (A)

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Glutaminase 1 regulates the release of extracellular vesicles during neuroinflammation through key metabolic intermediate alpha-ketoglutarate
Beiqing W, et al.
Journal of Neuroinflammation (2018)
Charles J McDonald et al.
Neurochemistry international, 88, 10-14 (2014-12-17)
The GLS1 gene encodes a mitochondrial glutaminase that is highly expressed in brain, kidney, small intestine and many transformed cells. Recent studies have identified multiple lysine residues in glutaminase that are sites of N-acetylation. Interestingly, these sites are located within

Global Trade Item Number

SKUGTIN
530030000104055977241198