911771

Lenalidomide-Photoswitch1-NH₂ hydrochloride

≥95%

• Synonym(s): (E)-N-(4-Aminobutyl)-2-(4-((2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)diazenyl)-2,6-dimethoxyphenoxy)acetamide hydrochloride, PHOTAC template, Photoswitchable protein degrader building block for PROTAC^® research
• Empirical Formula (Hill Notation): C₂₇H₃₂N₆O₇ · xHCl
• CAS Number: 2363156-76-5
• Molecular Weight: 552.58 (free base basis)
• UNSPSC Code: 12352101

Properties

• ligand: lenalidomide
• Quality Level: 100
• assay: ≥95%
• form: powder or crystals
• reaction suitability: reactivity: carboxyl reactive; reagent type: ligand-linker conjugate
• availability: available only in USA
• functional group: amine
• storage temp.: 2-8°C
• SMILES string: NCCCCNC(COC1=C(OC)C=C(/N=N/C2=CC=CC3=C2CN(C4C(NC(CC4)=O)=O)C3=O)C=C1OC)=O.Cl

Description

Application

Learn more: Technology Spotlight: Degrader Building Blocks for Targeted Protein DegradationPortal: Building PROTAC^® Degraders for Targeted Protein DegradationProtein degrader building block Lenalidomide-Photoswitch1-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 >450 nm. As described in Reynders, et al, this conjugate was used to prepare PHOTAC-I-3 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.

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

Learn more:

• Technology Spotlight: Degrader Building Blocks for Targeted Protein Degradation
• Portal: Building PROTAC^® Degraders for Targeted Protein Degradation

Other Notes

1. PHOTACs enable optical control of protein degradation

2. 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: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable