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918091

Sigma-Aldrich

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:
2363144-29-8
Molecular Weight:
464.47 (free base basis)
UNSPSC Code:
12352101
NACRES:
NA.22

ligand

lenalidomide

Quality Level

100

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

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)

Other Notes

Technology Spotlight: Degrader Building Blocks for Targeted Protein Degradation

Portal: Building PROTAC® Degraders for Targeted Protein Degradation

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

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Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000104970

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Zhi-Wei Wang et al.
Trends in cell biology, 30(10), 749-751 (2020-08-29)
PROteolysis-TArgeting Chimeras (PROTACs) have been developed for targeting specific protein destruction. Two recent studies in Science Advances by Liu et al. and Reynders et al. reported a novel technology, PHOtochemically TArgeting Chimeras (PHOTACs) or opto-PROTAC, which is light-induced control of
Martin Reynders et al.
Science advances, 6(8), eaay5064-eaay5064 (2020-03-05)
PROTACs (PROteolysis TArgeting Chimeras) are bifunctional molecules that target proteins for ubiquitylation by an E3 ligase complex and subsequent degradation by the proteasome. They have emerged as powerful tools to control the levels of specific cellular proteins. We now introduce

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