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930792

Sigma-Aldrich

3-[1,3-Dihydro-4-(4-hydroxy-1-butyn-1-yl)-1-oxo-2H-isoindol-2-yl]-2,6-piperidinedione

≥95.0%

Sinonimo/i:

2,6-Piperidinedione, 3-[1,3-dihydro-4-(4-hydroxy-1-butyn-1-yl)-1-oxo-2H-isoindol-2-yl]

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About This Item

Formula empirica (notazione di Hill):
C17H16N2O4
Numero CAS:
2207541-23-7
Peso molecolare:
312.32
Numero MDL:
MFCD32903468
Codice UNSPSC:
12352101
NACRES:
NA.21

Livello qualitativo

100

Saggio

≥95.0%

Stato

powder

Gruppo funzionale

hydroxyl

Temperatura di conservazione

2-8°C

Stringa SMILE

O=C1NC(=O)C(N2C(=O)C=3C=CC=C(C#CCCO)C3C2)CC1

InChI

1S/C17H16N2O4/c20-9-2-1-4-11-5-3-6-12-13(11)10-19(17(12)23)14-7-8-15(21)18-16(14)22/h3,5-6,14,20H,2,7-10H2,(H,18,21,22)
CXYDJLZSIZXGEC-UHFFFAOYSA-N

Categorie correlate

Applicazioni

3-[1,3-Dihydro-4-(4-hydroxy-1-butyn-1-yl)-1-oxo-2H-isoindol-2-yl]-2,6-piperidinedione is a functionalized cereblon (CRBN) ligand used in the development of lenalidomide-based protein degrader building blocks. Can be activated by many nucleophiles or form ether linkages through its terminal hydroxyl group. A basic building block for development of a protein degrader library.

Technology Spotlight: Degrader Building Blocks for Targeted Protein Degradation

Protein Degrader Building Blocks

Altre note

Targeted Protein Degradation by Small Molecules

Destruction of DNA-Binding Proteins by Programmable Oligonucleotide PROTAC (O′PROTAC): Effective Targeting of LEF1 and ERG

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

Pittogrammi

Health hazard
GHS08

Avvertenze

Danger

Indicazioni di pericolo

H360D

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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Certificati d'analisi (COA)

Lot/Batch Number
0000204095
0000191390
0000191390
0000204095

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Jingwei Shao et al.
Advanced science (Weinheim, Baden-Wurttemberg, Germany), 8(20), e2102555-e2102555 (2021-08-17)
DNA-binding proteins, including transcription factors (TFs), play essential roles in various cellular processes and pathogenesis of diseases, deeming to be potential therapeutic targets. However, these proteins are generally considered undruggable as they lack an enzymatic catalytic site or a ligand-binding
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
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
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

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