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929360

Opto-pomalidomide

≥95%

Synonym(s):

4,5-Dimethoxy-2-nitrobenzyl 3-(4-amino-1,3-dioxoisoindolin-2-yl)-2,6-dioxopiperidine-1-carboxylate

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About This Item

Empirical Formula (Hill Notation):
C23H20N4O10
Molecular Weight:
512.43
MDL number:
MFCD34704573
UNSPSC Code:
12352101
NACRES:
NA.21
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ligand

pomalidomide

Quality Level

100

assay

≥95%

form

powder

storage temp.

2-8°C

SMILES string

NC1=C2C(C(N(C2=O)C3C(N(C(CC3)=O)C(OCC4=C(C=C(C(OC)=C4)OC)[N+]([O-])=O)=O)=O)=O)=CC=C1

InChI

1S/C23H20N4O10/c1-35-16-8-11(15(27(33)34)9-17(16)36-2)10-37-23(32)26-18(28)7-6-14(21(26)30)25-20(29)12-4-3-5-13(24)19(12)22(25)31/h3-5,8-9,14H,6-7,10,24H2,1-2H3

InChI key

VIMWIXPVAGZBOD-UHFFFAOYSA-N

Application

Protein degrader building block Opto-pomalidomide enables the synthesis of molecules for light-induced targeted protein degradation and PROTAC® (proteolysis-targeting chimeras) research. This conjugate contains a Cereblon (CRBN) recruiting ligand, a rigid linker, and a nitroveratryloxycarbonyl group that can undergo photolysis to form a pendant amine for reactivity with a carboxylic acid on the target ligand. Because even slight alterations in ligands and crosslinkers can affect ternary complex formation between the target, E3 ligase, and degrader, many analogs are prepared to screen for optimal target degradation. When used with other protein degrader building blocks with a terminal amine, parallel synthesis can be used to more quickly generate degrader libraries that feature variation in crosslinker length, composition, and E3 ligase ligand.


Technology Spotlight: Degrader Building Blocks for Targeted Protein Degradation


Protein Degrader Building Blocks

Other Notes

Targeted Protein Degradation by Small Molecules

Light-induced control of protein destruction by opto-PROTAC

Small-Molecule PROTACS: New Approaches to Protein Degradation

Targeted Protein Degradation: from Chemical Biology to Drug Discovery

Impact of linker length on the activity of PROTACs

Legal Information

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

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H360D

Hazard Classifications

Repr. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Daniel P Bondeson et al.
Annual review of pharmacology and toxicology, 57, 107-123 (2016-10-13)
Protein homeostasis networks are highly regulated systems responsible for maintaining the health and productivity of cells. Whereas therapeutics have been developed to disrupt protein homeostasis, more recently identified techniques have been used to repurpose homeostatic networks to effect degradation of