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911771

Sigma-Aldrich

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

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About This Item

Empirical Formula (Hill Notation):
C27H32N6O7 · xHCl
CAS Number:
Molecular Weight:
552.58 (free base basis)
UNSPSC Code:
12352101

ligand

lenalidomide

Quality Level

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

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:

Legal Information

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

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