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SML0601

Sigma-Aldrich

BPTES

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

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C24H24N6O2S3
Numéro CAS:
314045-39-1
Poids moléculaire :
524.68
Numéro MDL:
MFCD01079848
Code UNSPSC :
12352200
ID de substance PubChem :
329825569
Nomenclature NACRES :
NA.77

Nom du produit

BPTES, ≥95% (HPLC)

Niveau de qualité

100

Essai

≥95% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 10 mg/mL, clear

Température de stockage

2-8°C

Chaîne SMILES 

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)

Clé InChI

MDJIPXYRSZHCFS-UHFFFAOYSA-N

Application

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

Actions biochimiques/physiologiques

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

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

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Certificats d'analyse (COA)

Lot/Batch Number
105M4614V
084M4619V
013M4610V
083M4616V

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

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
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
Jorge Domínguez-Andrés et al.
PLoS pathogens, 13(9), e1006632-e1006632 (2017-09-19)
Monocytes are innate immune cells that play a pivotal role in antifungal immunity, but little is known regarding the cellular metabolic events that regulate their function during infection. Using complementary transcriptomic and immunological studies in human primary monocytes, we show
T Q Tran et al.
Oncogene, 36(14), 1991-2001 (2016-10-11)
Cancer cells depend on glutamine to sustain their increased proliferation and manage oxidative stress, yet glutamine is often depleted at tumor sites owing to excessive cellular consumption and poor vascularization. We have previously reported that p53 protein, although a well-known
Hayden Weng Siong Tan et al.
Nature communications, 8(1), 338-338 (2017-08-25)
Activation of autophagy and elevation of glutamine synthesis represent key adaptations to maintain amino acid balance during starvation. In this study, we investigate the role of autophagy and glutamine on the regulation of mTORC1, a critical kinase that regulates cell
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Articles

Glutamate/GABA Synthesis and Metabolism

Glutamine is a common precursor for the biosynthesis of both glutamate and GABA. Glutamine can be transported in and out of neurons and astrocytes utilizing different glutamine carriers. The neurotransmitter glutamate can be synthesized from glutamine by the action of phosphate-activated glutaminase.

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