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929360

Sigma-Aldrich

Opto-pomalidomide

≥95%

Sinonimo/i:

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

Formula empirica (notazione di Hill):
C23H20N4O10
Peso molecolare:
512.43
Codice UNSPSC:
12352101
NACRES:
NA.21

ligand

pomalidomide

Livello qualitativo

Saggio

≥95%

Forma fisica

powder

Temperatura di conservazione

2-8°C

Stringa SMILE

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

Applicazioni

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

Note legali

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

Pittogrammi

Health hazard

Avvertenze

Danger

Indicazioni di pericolo

Classi di pericolo

Repr. 1B

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable


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Jing Liu et al.
Science advances, 6(8), eaay5154-eaay5154 (2020-03-05)
By hijacking endogenous E3 ligase to degrade protein targets via the ubiquitin-proteasome system, PROTACs (PRoteolysis TArgeting Chimeras) provide a new strategy to inhibit protein targets that were regarded as undruggable before. However, the catalytic nature of PROTAC potentially leads to
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
Kedra Cyrus et al.
Molecular bioSystems, 7(2), 359-364 (2010-10-06)
Conventional genetic approaches have provided a powerful tool in the study of proteins. However, these techniques often preclude selective manipulation of temporal and spatial protein functions, which is crucial for the investigation of dynamic cellular processes. To overcome these limitations
Philipp M Cromm et al.
Cell chemical biology, 24(9), 1181-1190 (2017-06-27)
Traditional pharmaceutical drug discovery is almost exclusively focused on directly controlling protein activity to cure diseases. Modulators of protein activity, especially inhibitors, are developed and applied at high concentration to achieve maximal effects. Thereby, reduced bioavailability and off-target effects can
Momar Toure et al.
Angewandte Chemie (International ed. in English), 55(6), 1966-1973 (2016-01-13)
The current inhibitor-based approach to therapeutics has inherent limitations owing to its occupancy-based model: 1) there is a need to maintain high systemic exposure to ensure sufficient in vivo inhibition, 2) high in vivo concentrations bring potential for off-target side effects, and 3) there is

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