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920797

Sigma-Aldrich

C5 Lenalidomide-pyridine-PEG1-piperazine hydrochloride

≥95%

Synonym(s):

N-(2-(2,6-Dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)-2-(6-(3-(piperazin-1-yl)propoxy)pyridin-3-yl)acetamide hydrochloride, Crosslinker−E3 Ligase ligand conjugate, Protein degrader building block for PROTAC® research, Template for synthesis of targeted protein degrader

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About This Item

Empirical Formula (Hill Notation):
C27H32N6O5 · xHCl
Molecular Weight:
520.58 (free base basis)
UNSPSC Code:
12352101
NACRES:
NA.22

ligand

C5 Lenalidomide

Quality Level

100

assay

≥95%

form

powder or crystals

reaction suitability

reactivity: carboxyl reactive
reagent type: ligand-linker conjugate

functional group

amine

storage temp.

2-8°C

SMILES string

O=C1N(C2CCC(NC2=O)=O)CC3=CC(NC(CC4=CC=C(OCCCN5CCNCC5)N=C4)=O)=CC=C31.Cl

Related Categories

Application

Protein degrader building block C5 Lenalidomide-pyridine-PEG1-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 with alternative exit vector, a linker with added rigidity, 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.

Other Notes

Technology Spotlight: Degrader Building Blocks for Targeted Protein Degradation

Portal: Building PROTAC® Degraders for Targeted Protein Degradation

Targeted Protein Degradation by Small Molecules

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

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wgk_germany

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

Articles

Degrader Building Blocks for Targeted Protein Degradation

Protein Degrader Building Blocks are a collection of crosslinker-E3 ligand conjugates with a pendant functional group for covalent linkage to a target ligand.

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