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530030 Glutaminase Inhibitor II, BPTES - CAS 314045-39-1 - Calbiochem

A cell-permeable, potent, selective, reversible, and uncompetitive allosteric inhibitor of kidney-type glutaminase (GLS1). Does not affect the activity of liver glutaminase.

MSDS (material safety data sheet) or SDS, CoA and CoQ, dossiers, brochures and other available documents.

Synonyms: N,Nʹ-(5,5ʹ-(2,2ʹ-Thiobis(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

Primary Target: kidney-type glutaminase
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Overview

Replacement Information

Key Spec Table

CAS #Empirical Formula
314045-39-1C₂₄H₂₄N₆O₂S₃

Products

Catalogue NumberPackaging Qty/Pack
5300300001 Glass bottle 10 mg
Description
OverviewA cell-permeable bis-thiadiazole compound that selectively inhibits GLS1 (IC50 = 60 and 80 nM, respectively, against hKGA and hGAC), but not the liver-type GLS2/LGA (IC50 = 88 µM using hLGA) mitochondrial glutaminase (GA) activity by inducing an inactive GLS1 tetrameric conformation via a 2:1 inhibitor-to-tetramer stoichiometric binding. Shown to induce growth inhibition under aerobic/normoxic (up to 10 µM; 20% O2) and cell death under hypoxic (2 µM; 3% O2) in P493 B-cell lymphoma cultures in vitro and effectively suppress P493 tumor expansion in mice in vivo (12.5 mg/kg or 200 µg/animal via i.p.; q.o.d.).
Catalogue Number530030
Brand Family Calbiochem®
SynonymsN,Nʹ-(5,5ʹ-(2,2ʹ-Thiobis(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
References
ReferencesShukla, K., et al. 2012. J. Med. Chem. 55, 10551.
Thangavelu, K., et al. 2012. Proc. Natl. Acad. Sci. USA 109, 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.
Product Information
CAS number314045-39-1
FormYellow powder
Hill FormulaC₂₄H₂₄N₆O₂S₃
Chemical formulaC₂₄H₂₄N₆O₂S₃
ReversibleY
Structure formula ImageStructure formula Image
Quality LevelMQ100
Applications
Biological Information
Primary Targetkidney-type glutaminase
Primary Target IC<sub>50</sub>140 and 210 nM in HEK293 cells expressing wt-KGA and F318Y-cKGA, respectively
Purity≥94% by HPLC
Physicochemical Information
Cell permeableY
Dimensions
Materials Information
Toxicological Information
Safety Information according to GHS
Safety Information
Product Usage Statements
Storage and Shipping Information
Ship Code Ambient Temperature Only
Toxicity Standard Handling
Storage -20°C
Protect from Light Protect from light
Do not freeze Ok to freeze
Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.
Packaging Information
Packaged under inert gas Packaged under inert gas
Transport Information
Supplemental Information
Specifications
Global Trade Item Number
Catalogue Number GTIN
5300300001 04055977241198

Documentation

Glutaminase Inhibitor II, BPTES - CAS 314045-39-1 - Calbiochem SDS

Title

Safety Data Sheet (SDS) 

References

Reference overview
Shukla, K., et al. 2012. J. Med. Chem. 55, 10551.
Thangavelu, K., et al. 2012. Proc. Natl. Acad. Sci. USA 109, 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.
Data Sheet

Note that this data sheet is not lot-specific and is representative of the current specifications for this product. Please consult the vial label and the certificate of analysis for information on specific lots. Also note that shipping conditions may differ from storage conditions.

Revision29-April-2014 JSW
SynonymsN,Nʹ-(5,5ʹ-(2,2ʹ-Thiobis(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
DescriptionA cell-permeable bis-thiadiazole compound that selectively inhibits GLS1 (IC50 = 60 and 80 nM, respectively, against hKGA and hGAC), but not the liver-type GLS2/LGA (IC50 = 88 µM using hLGA), mitochondrial glutaminase (GA) activity by inducing an inactive GLS1 tetrameric conformation via a 2:1 inhibitor-to-tetramer stoichiometric binding, non-competitive against glutamine or phosphate binding. B-cell lymphoma line P493 is shown to depend primarily on glutamine metabolism for survival under hypoxic condition and cellular GLS1 inhibtion by BPTES treatment results in cell death (2 µM BPTES & 3% O2 for 4 d), while under aerobic/normoxic condition (20% O2 and up to 10 µM BPTES for 4 d) only growth inhibition is observed. Likewise, intraperitoneal administration (12.5 mg/kg or 200 µg/animal; q.o.d.) is demonstrated to be efficacious in suppressing P493 tumor expansion in mice in vivo.
FormYellow powder
Intert gas (Yes/No) Packaged under inert gas
CAS number314045-39-1
Chemical formulaC₂₄H₂₄N₆O₂S₃
Structure formulaStructure formula
Purity≥94% by HPLC
SolubilityDMSO (50 mg/ml)
Storage Protect from light
-20°C
Do Not Freeze Ok to freeze
Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.
Toxicity Standard Handling
ReferencesShukla, K., et al. 2012. J. Med. Chem. 55, 10551.
Thangavelu, K., et al. 2012. Proc. Natl. Acad. Sci. USA 109, 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.