919888

Thalidomide-Photoswitch3-NH₂ hydrochloride

≥95%

• Synonym(s): (E)-N-(4-((4-Aminophenyl)diazenyl)phenyl)-2-((2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)oxy)acetamide hydrochloride, Photoswitchable protein degrader building block for PROTAC^®
• Empirical Formula (Hill Notation): C₂₇H₂₂N₆O₆ · xHCl
• Molecular Weight: 526.50 (free base basis)
• UNSPSC Code: 12352101
• NACRES: NA.22

Properties

• ligand: thalidomide
• Quality Level: 100
• Assay: ≥95%
• form: solid
• reaction suitability: reactivity: carboxyl reactive; reagent type: ligand-linker conjugate
• functional group: amine
• storage temp.: 2-8°C
• SMILES string: O=C1N(C2C(NC(CC2)=O)=O)C(C3=C1C=CC=C3OCC(NC4=CC=C(/N=N/C5=CC=C(N)C=C5)C=C4)=O)=O.Cl

Description

Application

Protein degrader building block Thalidomide-Photoswitch3-NH₂ hydrochloride enables the synthesis of PHOtochemically TArgeting Chimeras (PHOTACs), or photoswitchable proteolysis-targeting chimeras (PROTACs) that can be reversibly activated with different wavelengths of light. Developed in the Trauner and Pagano labs, PHOTACs are inactive in the dark but are activated to the cis isomer via irradiation at 390 nm and reversibly deactivated at wavelengths above 450 nm. As described in Reynders et al, this conjugate was used to prepare PHOTAC-I-10 and PHOTAC-II-6 and contains a Cereblon (CRBN)-recruiting ligand, an azobenzene photoswitchable crosslinker, and pendant amine for reactivity with an acid on the target warhead. Light-mediated control of the resulting PHOTAC affords advanced temporal and spatial control of targeted protein degradation.

Suggested wavelengths for photoswitching:

• Switch to cis isomer: 390 nm (380-400 nm)
• Switch to trans isomer (thermally more stable isomer): >450 nm

Low-intensity light needed for photoactivation is not cytotoxic.

Browse our full offering of degrader building blocks that streamlines the synthesis of degrader libraries.

Learn more:
Technology Spotlight: Degrader Building Blocks for Targeted Protein Degradation

Portal: Building PROTAC Degraders for Targeted Protein Degradation

Product can be used with our line of photoreactors: Including Penn PhD (Z744035) & SynLED 2.0 (Z744080)

Other Notes

PHOTACs enable optical control of protein degradation

PhotoPROTACs: A Novel Biotechnology for Cancer Treatment

Legal Information

PROTAC is a registered trademark of Arvinas Operations, Inc., and is used under license

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable