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919888

Sigma-Aldrich

Thalidomide-Photoswitch3-NH2 hydrochloride

≥95%

Synonyme(s) :

(E)-N-(4-((4-Aminophenyl)diazenyl)phenyl)-2-((2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)oxy)acetamide hydrochloride, Photoswitchable protein degrader building block for PROTAC®

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About This Item

Formule empirique (notation de Hill):
C27H22N6O6 · xHCl
Poids moléculaire :
526.50 (free base basis)
Code UNSPSC :
12352101
Nomenclature NACRES :
NA.22

ligand

thalidomide

Niveau de qualité

100

Pureté

≥95%

Forme

solid

Pertinence de la réaction

reactivity: carboxyl reactive
reagent type: ligand-linker conjugate

Groupe fonctionnel

amine

Température de stockage

2-8°C

Chaîne SMILES 

O=C1N(C2C(NC(CC2)=O)=O)C(C3=C1C=CC=C3OCC(NC4=CC=C(/N=N/C5=CC=C(N)C=C5)C=C4)=O)=O.Cl

Catégories apparentées

Application

Protein degrader building block Thalidomide-Photoswitch3-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-I-10 and PHOTAC-II-6 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.

Learn more:
Technology Spotlight: Degrader Building Blocks for Targeted Protein Degradation

Portal: Building PROTAC Degraders for Targeted Protein Degradation

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

Autres remarques

PHOTACs enable optical control of protein degradation

PhotoPROTACs: A Novel Biotechnology for Cancer Treatment

Informations légales

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

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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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