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927732

Sigma-Aldrich

C5 Lenalidomide-difluoroPEG1-C4-piperazine Hydrochloride

≥95%

Synonym(s):

2-(2,2-Difluoro-3-(4-(piperazin-1-yl)butoxy)propoxy)-N-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)acetamide Hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C26H35F2N5O6 · xHCl
Molecular Weight:
551.58 (free base basis)
NACRES:
NA.22

ligand

C5 Lenalidomide

Quality Level

100

Assay

≥95%

form

powder

storage temp.

2-8°C

SMILES string

O=C1N(C2CCC(NC2=O)=O)CC3=CC(NC(COCC(F)(F)COCCCCN4CCNCC4)=O)=CC=C31.Cl

Related Categories

Application

Protein degrader building block C5 Lenalidomide-difluoroPEG1-C4-piperazine Hydrochloride enables the synthesis of molecules for targeted protein degradation and PROTAC (proteolysis-targeting chimeras) technology. This conjugate contains a Cereblon (CRBN)-recruiting ligand, a fluorinated linker with both hydrophobic and hydrophilic moieties, and 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 PROTAC, many analogs are prepared to screen for optimal target degradation. When used with other protein degrader building blocks with a pendant amine, parallel synthesis can be used to more quickly generate PROTAC libraries that feature variation in crosslinker length, composition, and E3 ligase ligand.


Targeted Protein Degradation

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H361d,H373

Hazard Classifications

Repr. 2 - STOT RE 2

Target Organs

Blood

Storage Class Code

11 - Combustible Solids

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

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