A proteasome assembly modulator
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TCH-165

Item No. 40454

Technical Information
Formal Name
rel-(4R,5R)-4,5-dihydro-2-(4-methoxyphenyl)-4-phenyl-1-(phenylmethyl)-5-[4-[(phenylmethyl)amino]phenyl]-1H-imidazole-4-carboxylic acid, ethyl ester
CAS Number
1446350-60-2
Molecular Formula
C39H37N3O3
Formula Weight
Purity
≥98%
Formulation
A solid
DMSO: SolubleMethanol: Soluble
SMILES
CCOC([C@@]1(C2=CC=CC=C2)[C@@H](C3=CC=C(NCC4=CC=CC=C4)C=C3)N(C(C5=CC=C(C=C5)OC)=N1)CC6=CC=CC=C6)=O
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    TCH-165 is a modulator of proteasome assembly.1 It selectively activates the chymotrypsin-like, trypsin-like, and caspase-like activities of the 20S proteasome (EC50s = 4.2, 3.2, and 4.7 µM, respectively) over the same activities of the 26S proteasome (EC50s = >70 µM for all) but also inhibits the chymotrypsin-like activity of the 20S proteasome (IC50 = 1.44 µM) in cell-free assays.1,2 TCH-165 (10 µM) increases the 20S proteasome-dependent degradation of the intrinsically disordered proteins α-synuclein and tau.1 It enhances disassembly of the 26S proteasome with a concomitant increase in 20S proteasome levels in HEK293T cells in a time-and concentration-dependent manner. TCH-165 (100 mg/kg, p.o.) decreases tumor volume in an RPMI-8226 multiple myeloma mouse xenograft model.3 It decreases infarct volume as a percentage of the area at risk in a mouse model of cardiac ischemia-reperfusion injury induced by left anterior descending coronary artery occlusion when administered at a dose of 50 mg/kg.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Njomen, E., Osmulski, P.A., Jones, C.L., et alSmall molecule modulation of proteasome assembly. Biochemistry 57(28), 4214-4224 (2018).

    2. Azevedo, L.M., Lansdell, T.A., Ludwig, J.R., et alInhibition of the human proteasome by imidazoline scaffolds. J. Med. Chem. 56(14), 5974-5978 (2013).

    3. Njomen, E., Vanecek, A., Lansdell, T.A., et alSmall molecule 20S proteasome enhancer regulates MYC protein stability and exhibits antitumor activity in multiple myeloma. Biomedicines 10(5), 938 (2022).

    4. Gao, J., Su, H.-X., Li, P.-B., et alTCH-165 attenuates cardiac ischaemia/reperfusion injury by balancing mitochondrial dynamics via increasing proteasome activity. Eur. J. Pharmacol. 957, 176011 (2023).