CAS Number314045-39-1
SynonymsN,N'-[Sulfanediylbis(2,1-ethanediyl-1,3,4-thiadiazole-5,2-diyl)]bis(2-phenylacetamide); bis-2-(5-Phenylacetmido-1,2,4-Thiadiazol-2-yl)Ethyl Sulfide; BPTES; 3uo9; Bis-2-(5-phenylacetamido-1,3,4-thiadiazol-2-yl)ethyl sulfide
Molecular FormulaC24H24N6O2S3
Molecular Weight524.68
Density1.4±0.1 g/cm3
Appearancepowder
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 314045-39-1 |
| Catalog No. | 2A-1190700 |
| Chinese Name | BPTES |
| Synonyms | N,N'-[Sulfanediylbis(2,1-ethanediyl-1,3,4-thiadiazole-5,2-diyl)]bis(2-phenylacetamide); bis-2-(5-Phenylacetmido-1,2,4-Thiadiazol-2-yl)Ethyl Sulfide; BPTES; 3uo9; Bis-2-(5-phenylacetamido-1,3,4-thiadiazol-2-yl)ethyl sulfide |
| Molecular Formula | C24H24N6O2S3 |
| Molecular Weight | 524.68 |
| Density | 1.4±0.1 g/cm3 |
| Appearance | powder |
| Storage Condition | -20℃ |
| Application | BPTES is a selective allosteric inhibitor of glutaminase with an IC50 of 0.16 μM. |
| PubChem ID | 329825569 |
| MDL Number | MFCD01079848 |
| SMILES | O=C(Cc1ccccc1)Nc1nnc(CCSCCc2nnc(NC(=O)Cc3ccccc3)s2)s1 |
| InChI | 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 |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| Hazard Symbols | transportation |
| Bioactivity | BPTES is an allosteric and selective glutaminase inhibitor with an IC50 of 0.16 μM. Related Catalog Signaling Pathways >> Others >> Others Research Areas >> Cancer Target Glutaminase[1] In Vitro BPTES (10 µM) exhibits inhibition of PDAC cell proliferation[1]. BPTES preferentially slows growth of mutant IDH1 cells without inducing apoptosis. BPTES (10 µM) reduces glutaminase activity in both WT and mutant IDH1 expressing cells, diminishes glutamate and α-KG levels, and increases glycolytic intermediates while leaving total 2-HG levels unaffected[2]. BPTES (10 µM) shows a clear synergistic anti-cancer effect with 10 μM of 5-FU in A549 and EKVX cell lines, and results in a growth reduction response not only in EKVX and A549 but also in most of the NSCLC cell lines[3]. BPTES (10 µM) effectively reduces the levels of the metabolites of the TCA cycle, with no changes in the levels of metabolites in glycolysis and the pentose phosphate pathway. BPTES treatment reduces about 30% ATP production under normoxia, and an additional 10% reduction of ATP production is observed under hypoxia in EKVX[4]. In Vivo BPTES-NPs (BPTES nanoparticles, 1.2 mg BPTES in 100 µL nanoparticles, i.v.) significantly attenuates tumor growth in the patient-derived pancreatic orthotopic tumor model[1]. Kinase Assay D54 cells are seeded in a T75 flask at 5×105 cells, and IDH1 expression is induced with doxycycline 48 hrs before assaying. Cells are collected and resuspended in PBS, 0.1% Triton X-100, and Halt-Protease Inhibitor. Cells are lysed for 30 min on ice and centrifuged for 30 min at 12000 rpm at 4°C. Protein concentration is measured using the BCA Assay. Varying amounts of protein are added to IDH activity assay buffer (33 mM Tris, pH 7.6, 0.33 mM EDTA, 0.1 mM NADP+, 1.33 mM MnCl2, and 1.3 mM isocitrate), and changes in absorbance at 340 nm after 5 min is documented for each protein amount. Cell Assay Cells are plated at a density of 500 cells/well in a 96-well black clear bottom plate. At 24 hrs, media is changed to the appropriate media (DMEM with 4.5 g/L, 1.5 g/L or 0.1 g/L glucose, 10% FBS, pencillin/streptomycin, and 4 mM glutamine with or without doxycyline). 48 hours after plating, compounds or DMSO are added. Media and alamarBlue is added to a volume of 200 µL in each well. Fluorescence is measured at 48 hrs or 72 hrs (EGCG) using a Victor3 plate-reader. Animal Admin Four-week-old female Foxn1nuathymic nude mice are used for the assay. Freshly resected pancreatic tumor samples obtained from patients at the time of surgery are propagated from mouse to mouse as a live tumor bank. Once a tumor volume of 50 mm3 is reached (4 wk postimplantation), mice are treated with 12.5 mg/kg BPTES by intraperitoneal injection, 200 mg/kg CB-839 twice per d by oral gavage, 54 mg/kg BPTES-NPs (1.2 mg BPTES in 100 µL nanoparticles per mouse) by intravenous injection, blank-NPs (100 µL per mouse) by intravenous injection, 25 mg/kg gemcitabine intraperitoneally, 250 mg/kg metformin intraperitoneally daily, or a combination of BPTES-NPs with gemcitabine or metformin. BPTES-NPs are injected once every 3 d for a total of six injections over 16 d. References [1]. Elgogary A, et al. Combination therapy with BPTES nanoparticles and metformin targets the metabolic heterogeneity of pancreatic cancer. Proc Natl Acad Sci U S A. 2016 Sep 6;113(36):E5328-36. [2]. Meghan J. Seltzer, et al. Inhibition of glutaminase preferentially slows growth of glioma cells with mutant IDH1. Cancer Res. 2010 Nov 15; 70(22): 8981-8987. [3]. Lee JS, et al. Glutaminase 1 inhibition reduces thymidine synthesis in NSCLC. Biochem Biophys Res Commun. 2016 Aug 26;477(3):374-82 [4]. Lee JS, et al. Dual targeting of glutaminase 1 and thymidylate synthase elicits death synergistically in NSCLC. Cell Death Dis. 2016 Dec 8;7(12):e2511. Chemical & Physical Properties Density 1.4±0.1 g/cm3 Molecular Formula C24H24N6O2S3 Molecular Weight 524.681 Exact Mass 524.112305 PSA 198.52000 LogP 3.97 Index of Refraction 1.709 InChIKey MDJIPXYRSZHCFS-UHFFFAOYSA-N SMILES O=C(Cc1ccccc1)Nc1nnc(CCSCCc2nnc(NC(=O)Cc3ccccc3)s2)s1 Storage condition -20℃ |
| Use of | BPTES is an allosteric and selective glutaminase inhibitor with an IC50 of 0.16 μM. Properties Articles12 Name 2-phenyl-N-[5-[2-[2-[5-[(2-phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]ethylsulfanyl]ethyl]-1,3,4-thiadiazol-2-yl]acetamide Synonym More Synonyms BPTES Biological Activity Description BPTES is an allosteric and selective glutaminase inhibitor with an IC50 of 0.16 μM. Related Catalog Signaling Pathways >> Others >> Others Research Areas >> Cancer Glutaminase[1] References [1]. Elgogary A, et al. Combination therapy with BPTES nanoparticles and metformin targets the metabolic heterogeneity of pancreatic cancer. Proc Natl Acad Sci U S A. 2016 Sep 6;113(36):E5328-36. [3]. Lee JS, et al. Glutaminase 1 inhibition reduces thymidine synthesis in NSCLC. Biochem Biophys Res Commun. 2016 Aug 26;477(3):374-82 [4]. Lee JS, et al. Dual targeting of glutaminase 1 and thymidylate synthase elicits death synergistically in NSCLC. Cell Death Dis. 2016 Dec 8;7(12):e2511. Chemical & Physical Properties Molecular Formula C24H24N6O2S3 Exact Mass 524.112305 PSA 198.52000 Index of Refraction 1.709 InChIKey MDJIPXYRSZHCFS-UHFFFAOYSA-N Storage condition -20℃ |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available The above information is believed to be correct, but is not all-inclusive and should be used as a guide only. The information in this document is based on our current knowledge and is |
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