bis-2-(5-PhenylacetMido-1,2,4-Thiadiazol-2-yl)Ethyl Sulfide Chemical Properties

Density 

1.420±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO: soluble10mg/mL, clear

form 

powder

pka

9.13±0.50(Predicted)

color 

white to beige

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 months.

InChIKey

HBFNKZVNDOYJDJ-UHFFFAOYSA-N

SMILES

S(CCN1CN=C(NC(=O)CC2=CC=CC=C2)S1)CCN1CN=C(NC(=O)CC2=CC=CC=C2)S1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

HS Code 

2934999090

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

bis-2-(5-PhenylacetMido-1,2,4-Thiadiazol-2-yl)Ethyl Sulfide Usage And Synthesis

Description

BPTES (314045-39-1) is a potent and selective allosteric1 inhibitor of kidney-type glutaminase (GLS1), IC50 = 3.3 μM2.? Selective for GLS1 over GLS2, g-glutamyl transpeptidase and glutamate dehydrogenase. Shuts down an alternative energy-generating glutaminolysis pathway in P493 cells under both glucose deprivation or hypoxia.3 Reduces the growth of P493 cell xenografts by 50% over a 10 day treatment.4 BPTES inhibition of glutamine utilization in cancer cells increases PD-L1 expression.5 Clears senescent cells and improves various age-related disorders in a geriatric mouse model.6

Uses

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

Biochem/physiol Actions

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.

in vivo

storage

Store at -20°C

References

[1] BYRON DELABARRE*. Full-Length Human Glutaminase in Complex with an Allosteric Inhibitor[J]. Biochemistry Biochemistry, 2011, 50 50: 10764-10770. DOI:10.1021/bi201613d
[2] KRUPA SHUKLA. Design, Synthesis, and Pharmacological Evaluation of Bis-2-(5-phenylacetamido-1,2,4-thiadiazol-2-yl)ethyl Sulfide 3 (BPTES) Analogs as Glutaminase Inhibitors[J]. Journal of Medicinal Chemistry, 2012, 55 23: 10551-10563. DOI:10.1021/jm301191p
[3] ANNE LE. Glucose-independent glutamine metabolism via TCA cycling for proliferation and survival in B cells.[J]. Cell metabolism, 2012, 15 1: 110-121. DOI:10.1016/j.cmet.2011.12.009
[4] YAN XIANG. Targeted inhibition of tumor-specific glutaminase diminishes cell-autonomous tumorigenesis.[J]. The Journal of clinical investigation, 2015: 2293-2306. DOI:10.1172/jci75836
[5] JUN-KYU BYUN. Inhibition of Glutamine Utilization Synergizes with Immune Checkpoint Inhibitor to Promote Antitumor Immunity.[J]. Molecular Cell, 2020: 592-606.e8. DOI:10.1016/j.molcel.2020.10.015
[6] CHRISTOPHER PAN  Jason W L. Targeting metabolism to influence aging[J]. Science, 2021, 371 6526. DOI:10.1126/science.abf6368

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