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919888

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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A propos de cet article

Formule empirique (notation de Hill) :
C27H22N6O6 · xHCl
Poids moléculaire :
526.50 (free base basis)
MDL number:
MFCD34166227
UNSPSC Code:
12352101
NACRES:
NA.22
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ligand

thalidomide

Quality Level

100

assay

≥95%

form

solid

reaction suitability

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

functional group

amine

storage temp.

2-8°C

SMILES string

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

InChI

1S/C27H22N6O6.ClH/c28-15-4-6-17(7-5-15)31-32-18-10-8-16(9-11-18)29-23(35)14-39-21-3-1-2-19-24(21)27(38)33(26(19)37)20-12-13-22(34)30-25(20)36;/h1-11,20H,12-14,28H2,(H,29,35)(H,30,34,36);1H/b32-31+;

InChI key

LEIFAZYMMHNBAT-MRRLHAJBSA-N

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)

Other Notes

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

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Articles

Degrader Building Blocks for Targeted Protein Degradation

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

Numéro d'article de commerce international

RéférenceGTIN
919888-50MG04065265630702