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Merck
CN

918091

Lenalidomide-Photoswitch2-NH2 hydrochloride

≥95%

Synonym(s):

(E)-N-(2-Aminoethyl)-2-(4-((2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)diazenyl)phenoxy)acetamide hydrochloride, PHOTAC template, Photoswitchable protein degrader building block for PROTAC® research

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About This Item

Empirical Formula (Hill Notation):
C23H24N6O5 · xHCl
CAS Number:
Molecular Weight:
464.47 (free base basis)
MDL number:
UNSPSC Code:
12352101
NACRES:
NA.22
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ligand

lenalidomide

Quality Level

assay

≥95%

form

powder or crystals

reaction suitability

reactivity: carboxyl reactive, reagent type: ligand-linker conjugate

functional group

amine

storage temp.

2-8°C

SMILES string

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

InChI key

SZBAHGLBGOFATH-RXQWRGDBSA-N

Application

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.

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)

Legal Information

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


Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Articles

Protein Degrader Building Blocks are a collection of crosslinker-E3 ligand conjugates with a pendant functional group for covalent linkage to a target ligand.





Global Trade Item Number

SKUGTIN
918091-50MG04065265086509