SML3911
TCH-165
≥98% (HPLC)
Synonym(s):
Ethyl (4R,5R)-rel-1-benzyl-5-(4-(benzylamino)phenyl)-2-(4-methoxyphenyl)-4-phenyl-4,5-dihydro-1H-imidazole-4-carboxylate, rel-Ethyl (4R,5R)-4,5-dihydro-2-(4-methoxyphenyl)-4-phenyl-1-(phenylmethyl)-5-[4-[(phenylmethyl)amino]phenyl]-1H-imidazole-4-carboxylate
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About This Item
Quality Segment
assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 2 mg/mL, clear
storage temp.
-10 to -25°C
SMILES string
N2([C@@H]([C@](N=C2c6ccc(cc6)OC)(c5ccccc5)C(=O)OCC)c3ccc(cc3)NCc4ccccc4)Cc1ccccc1
InChI
1S/C39H37N3O3/c1-3-45-38(43)39(33-17-11-6-12-18-33)36(31-19-23-34(24-20-31)40-27-29-13-7-4-8-14-29)42(28-30-15-9-5-10-16-30)37(41-39)32-21-25-35(44-2)26-22-32/h4-26,36,40H,3,27-28H2,1-2H3/t36-,39-/m1/s1
InChI key
XXDLWRCUPASJGY-AEGYFVCZSA-N
Biochem/physiol Actions
TCH-165 is a cell-permeable and potent activator of 20S proteasome assembly that favors a proteolytically active, open-gate 20S proteasome subcomplex and enhances 20S-mediated proteolysis (nearly 10-fold ≤1.5 µM) to the detriment of the 26S proteasome, in a time- and dose-dependent manner. TCH-165 restores proteostasis and enhances degradation of intrinsically disordered proteins (IDPs) both in purified protein assays and in cell culture (α-synuclein, tau441, c-MYC, cFos, ornithine decarboxylase). TCH 165 degrades SNAP29 and syntaxin 17 and reduces autophagosome-lysosome fusion. TCH165 inhibits cancer cell proliferation, impedes in vivo tumor growth, and offers neuroprotection from distinct dipeptide repeat (DPR) protein toxicity and is well tolerated in vivo (in mice and in dogs) at therapeutic concentrations.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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