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SML0601

Sigma-Aldrich

BPTES

≥95% (HPLC), powder, glutaminase GLS1 (KGA) inhibitor

Synonym(s):

Bis-2-(5-phenylacetamido-1,3,4-thiadiazol-2-yl)ethyl sulfide

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About This Item

Empirical Formula (Hill Notation):
C24H24N6O2S3
CAS Number:
314045-39-1
Molecular Weight:
524.68
MDL number:
MFCD01079848
UNSPSC Code:
12352200
PubChem Substance ID:
329825569
NACRES:
NA.77

product name

BPTES, ≥95% (HPLC)

Quality Level

100

Assay

≥95% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 10 mg/mL, clear

storage temp.

2-8°C

SMILES string

O=C(CC1=CC=CC=C1)NC2=NN=C(S2)CCSCCC3=NN=C(NC(CC4=CC=CC=C4)=O)S3

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

Application

Bis-2-(5-phenylacetamido-1,3,4-thiadiazol-2-yl)ethyl sulfide (BPTES) has been used as a glutaminase inhibitor.

Biochem/physiol Actions

BPTES is a selective inhibitor of Glutaminase GLS1 (KGA), which is found in the kidney and brain, and is positively regulated by myc and strongly expressed in many tumors and tumor cell lines. 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. BPTES was found to slow growth of glioma cells. BPTES is a noncompetitive inhibitor with a Ki of 3 μM.
Vaccinia virus (VACV) requires glutamine metabolism for its optimal replication. Inhibition of glutaminolysis by bis-2-(5-phenylacetamido-1,3,4-thiadiazol-2-yl)ethyl sulfide (BPTES) can be a potential method to treat poxvirus infections.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

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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Brian E Hsu et al.
Cell reports, 27(13), 3902-3915 (2019-06-27)
Neutrophils are phenotypically heterogeneous and exert either anti- or pro-metastatic functions. We show that cancer-cell-derived G-CSF is necessary, but not sufficient, to mobilize immature low-density neutrophils (iLDNs) that promote liver metastasis. In contrast, mature high-density neutrophils inhibit the formation of
Jitka Soukupova et al.
Scientific reports, 7(1), 12486-12486 (2017-10-04)
Transforming Growth Factor beta (TGF-β) induces tumor cell migration and invasion. However, its role in inducing metabolic reprogramming is poorly understood. Here we analyzed the metabolic profile of hepatocellular carcinoma (HCC) cells that show differences in TGF-β expression. Oxygen consumption
Roberta Palorini et al.
PLoS genetics, 12(3), e1005931-e1005931 (2016-03-16)
Cancer cells often rely on glycolysis to obtain energy and support anabolic growth. Several studies showed that glycolytic cells are susceptible to cell death when subjected to low glucose availability or to lack of glucose. However, some cancer cells, including
Lotte Kors et al.
Biochimica et biophysica acta. Molecular basis of disease, 1864(5 Pt A), 1883-1895 (2018-03-08)
NOD-like receptor (NLR)X1 (NLRX1) is an ubiquitously expressed inflammasome-independent NLR that is uniquely localized in mitochondria with as yet unknown effects on metabolic diseases. Here, we report that NLRX1 is essential in regulating cellular metabolism in non-immune parenchymal hepatocytes by
E Hendrick et al.
Oncogene, 36(34), 4859-4874 (2017-04-18)
The US FDA approval of broad-spectrum histone deacetylase (HDAC) inhibitors has firmly laid the cancer community to explore HDAC inhibition as a therapeutic approach for cancer treatment. Hitting one HDAC member could yield clinical benefit but this required a complete
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