SML1743
ETaKG
≥95% (HPLC), α-ketoglutarate prodrug, oil
Synonym(s):
2-Oxo-pentanedioic acid 5-ethyl ester 1-(3-trifluoromethyl-benzyl) ester, 5-Ethyl 1-(3-(trifluoromethyl)benzyl) 2-oxopentanedioate
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About This Item
Empirical Formula (Hill Notation):
C15H15F3O5
CAS Number:
Molecular Weight:
332.27
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Assay:
≥95% (HPLC)
Form:
oil
Product Name
ETaKG, ≥95% (HPLC)
Quality Segment
assay
≥95% (HPLC)
form
oil
color
colorless to light yellow
storage temp.
2-8°C
SMILES string
O=C(C(CCC(OCC)=O)=O)OCC1=CC=CC(C(F)(F)F)=C1
InChI
1S/C15H15F3O5/c1-2-22-13(20)7-6-12(19)14(21)23-9-10-4-3-5-11(8-10)15(16,17)18/h3-5,8H,2,6-7,9H2,1H3
InChI key
OKDCLZOKKGLMIX-UHFFFAOYSA-N
Biochem/physiol Actions
A cell-permeable, bioavailable & aqueous stable α-ketoglutarate prodrug that selectively induces PHD-dependent cell death in hypoxic cells
ETaKG is a cell-permeable, aqueous stable, bioavailable, non-toxic α-ketoglutarate/2-oxoglutarate (α-KG/2-OG) diester derivative that readily undergoes hydrolysis by cytosolic esterases to α-KG. The monoester analog, TaKG is also membrane permeant. ETaKG elevates intracellular [α-KG] by ~15-fold in a prologned fashion, destabilizes HIF-1α/2α and reactivates prolyl hydroxylases (PHDs) in hypoxic HCT116, A431 and RPE cells at 2 mM. Further, shown to selectively trigger PHD-dependent cell death in hypoxic cells and decreases cellular [ATP] and glucose uptake. ETaKG has shown to reduce glucose metabolism, elevate [α-KG] levels and suppress A375 xenograft tumor growth (750 mg/kg of mice, p.o., q.d., 14 days). Also, induces mTORC1 lysosomal translocation and stimulates mTORC1 activity in the absence of glutaminolysis in U2OS cells.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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