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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%

Synonym(s):

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

Empirical Formula (Hill Notation):
C17H16N2O4
CAS Number:
2207541-23-7
Molecular Weight:
312.32
MDL number:
MFCD32903468
UNSPSC Code:
12352101
NACRES:
NA.21

Quality Level

100

Assay

≥95.0%

form

powder

functional group

hydroxyl

storage temp.

2-8°C

SMILES string

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

Related Categories

Application

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

Other Notes

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

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H360D

Hazard Classifications

Repr. 1B

Storage Class Code

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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