Lenalidomide-Photoswitch2-NH₂ hydrochloride

C₂₃H₂₄N₆O₅ · xHCl

464.47 (free base basis)

Protein degrader building block Lenalidomide-Photoswitch2-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-II-5 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.

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100

≥95%

powder or crystals

2-8℃

NCCNC(COC1=CC=C(/N=N/C2=CC=CC3=C2CN(C4C(NC(CC4)=O)=O)C3=O)C=C1)=O.Cl

11 - Combustible Solids

WGK 3