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SML2226

Sigma-Aldrich

BC-LI-0186

≥98% (HPLC)

Synonym(s):

4-(4-Isopropyl-2,3-dimethyl-5-oxo-2,5-dihydro-1H-pyrazol-1-yl)-N-(2-phenoxyethyl)benzenesulfonamide, 4-[2,5-Dihydro-2,3-dimethyl-4-(1-methylethyl)-5-oxo-1H-pyrazol-1-yl]-N-(2-phenoxyethyl)benzenesulfonamide

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About This Item

Empirical Formula (Hill Notation):
C22H27N3O4S
CAS Number:
695207-56-8
Molecular Weight:
429.53
UNSPSC Code:
12352200
NACRES:
NA.77
Pricing and availability is not currently available.

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

O=C(C(C(C)C)=C(C)N1C)N1C2=CC=C(S(NCCOC3=CC=CC=C3)(=O)=O)C=C2

InChI

1S/C22H27N3O4S/c1-16(2)21-17(3)24(4)25(22(21)26)18-10-12-20(13-11-18)30(27,28)23-14-15-29-19-8-6-5-7-9-19/h5-13,16,23H,14-15H2,1-4H3

InChI key

SQYWMHPZMHDCHP-UHFFFAOYSA-N

Biochem/physiol Actions

BC-LI-0186 is a selective blocker of Leucyl-tRNA synthetase (LRS; LeuRS) and Ras-related GTP-binding protein D (RagD) interaction (IC50 = 46.11 nM) by competing against RagD for LRS VC domain binding (KD = 42.1 nM) without affecting LRS-Vps34, LRS-EPRS, RagB-RagD association, mTORC1 complex formation or the activities of 12 kinases. BC-LI-0186 inhibits Leu-dependent LRS lysosomal membrane localization (10 μM), RagD GTPase and mTORC1 activation (IC50 = 81.4 nM against Leu-induced S6K phosphorylation), but not ARF1 activation, AKT S473 phosphorylation, Glu- or Arg-dependent S6K phosphorylation, nor the cytosolic and mitochondrial LRS catalytic activities. BC-LI-0186 effectively suppresses the growth of rapamycin-resistant MCT116 MM cancer cells with mTOR-S2035I mutation both in cultures (GI50 = 42.03) and in mice in vivo (by 40% in 2 wks; 20 mg/kg/day i.p.).
Leucyl-tRNA synthetase (LRS) and RagD interaction blocker that inhibits Leu-dependent LRS lysosomal localization, RagD and mTOR activation.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Hyosun Choi et al.
Biochemical and biophysical research communications, 493(2), 1129-1135 (2017-09-09)
Leucyl-tRNA synthetase (LRS) plays major roles in providing leucine-tRNA and activating mechanistic target of rapamycin complex 1 (mTORC1) through intracellular leucine sensing. mTORC1 activated by amino acids affects the influence on physiology functions including cell proliferation, protein synthesis and autophagy
Jong Hyun Kim et al.
Nature communications, 8(1), 732-732 (2017-10-01)
Leucyl-tRNA synthetase (LRS) is known to function as leucine sensor in the mammalian target of rapamycin complex 1 (mTORC1) pathway. However, the pathophysiological significance of its activity is not well understood. Here, we demonstrate that the leucine sensor function for mTORC1

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