BPTES

Specifications / Handling

More Information
Product Details
Synonyms	Bis-2-(5-phenylacetamido-1,3,4-thiadiazol-2-yl)ethyl sulfide
Product Type	Chemical
Properties
Formula	C₂₄H₂₄N₆O₂S₃
MW	524.7
CAS	314045-39-1
Purity Chemicals	≥95% (HPLC)
Appearance	White to off-white solid.
Solubility	Soluble in DMSO (10mg/ml) or DMF (10mg/ml). Sparingly soluble in aqueous buffers.
Identity	Determined by ¹H-NMR.
InChi Key	MDJIPXYRSZHCFS-UHFFFAOYSA-N
Smiles	O=C(CC1=CC=CC=C1)NC2=NN=C(CCSCCC3=NN=C(NC(CC4=CC=CC=C4)=O)S3)S2
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Keep cool and dry. Protect from moisture and oxygen.
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

Description

Selective, allosteric non-competitive inhibitor of glutaminase 1 (GLS1), selective for GLS1 over GLS2, glutamate dehydrogenase, and γ-glutamyl transpeptidase, consequently inhibiting glutaminolysis.
Useful agent for immunometabolism research. Glutaminase converts glutamine to glutamate, which is an important excitatory neurotransmitter in brain and can be further oxidized to α-ketoglutarate to feed the tricarboxylic acid (TCA) cycle and to glutathione, which is important for controlling the level of reactive oxygen species (ROS), particularly important for cancer cell growth.
Anticancer agent. Increases the production of reactive oxygen species and reduces ATP levels in hypoxic cells, induces cell death of P493 human lymphoma B cells in vitro and delays tumor xenograft growth in vivo.

Product References

Novel mechanism of inhibition of rat kidney-type glutaminase by bis-2-(5-phenylacetamido-1,2,4-thiadiazol-2-yl)ethyl sulfide (BPTES): M.M. Robinson, et al.; Biochem. J. 406, 407 (2007)
Inhibition of glutaminase preferentially slows growth of glioma cells with mutant IDH1: M.J. Seltzer, et al.; Cancer Res. 70, 8981 (2010)
Full-length human glutaminase in complex with an allosteric inhibitor: B. DeLaBarre, et al.; Biochemistry 50, 10764 (2011)
BPTES inhibition of hGA(124-551), a truncated form of human kidney-type glutaminase: E.W. Hartwick & N.P. Curthoys; J. Enzyme Inhib. Med. Chem. 27, 861 (2012)
Glucose-independent glutamine metabolism via TCA cycling for proliferation and survival in B cells: A. Le, et al.; Cell Metab. 15, 110 (2012)
Design, synthesis, and pharmacological evaluation of bis-2-(5-phenylacetamido-1,2,4-thiadiazol-2-yl)ethyl sulfide 3 (BPTES) analogs as glutaminase inhibitors: K. Shukla, et al.; J. Med. Chem. 55, 10551 (2012)
Availability of the key metabolic substrates dictates the respiratory response of cancer cells to the mitochondrial uncoupling: A.V. Zhdanov, et al.; Biochim. Biophys. Acta 1837, 51 (2014)
Small molecule glutaminase inhibitors block glutamate release from stimulated microglia: A.G. Thomas, et al.; BBRC 443, 32 (2014)
Targeted inhibition of tumor-specific glutaminase diminishes cell-autonomous tumorigenesis: Y. Xiang, et al.; J. Clin. Invest. 125, 2293 (2015)
Design and evaluation of novel glutaminase inhibitors: L.A. McDermott, et al.; Bioorg. Med. Chem. 24, 1819 (2016)
Glutaminase 1 inhibition reduces thymidine synthesis in NSCLC: J.S. Lee, et al.; BBRC 477, 374 (2016)
Inhibition of Glutaminolysis Inhibits Cell Growth via Down-regulating Mtorc1 Signaling in Lung Squamous Cell Carcinoma: X. Ye, et al.; Anticancer Res. 36, 6021 (2016)
A guide to immunometabolism for immunologists: L.A. O'Neill, et al.; Nat. Rev. Immunol. 16, 553 (2016) (Review)
Characterization of the interactions of potent allosteric inhibitors with glutaminase C, a key enzyme in cancer cell glutamine metabolism: Q. Huang, et al.; J. Biol. Chem. 293, 3535 (2018)

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