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911747

Sigma-Aldrich

C5 Lenalidomide-PEG3-NH2 hydrochloride

≥95%

Synonym(s):

2-(2-(2-(2-Aminoethoxy)ethoxy)ethoxy)-N-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)acetamide hydrochloride, C5 Lenalidomide conjugate, 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):
C21H28N4O7 · xHCl
Molecular Weight:
448.47 (free base basis)
UNSPSC Code:
12352101

ligand

C5 Lenalidomide

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(COCCOCCOCCN)=O)=CC=C31.Cl

Application

Protein degrader builiding block C5 Lenalidomide-PEG3-NH2 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 and a PEGylated crosslinker with pendant amine for reactivity with an acid on the target warhead. Because even slight alterations in ligands, warheads, 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 terminal amine, parallel synthesis can be used to more quickly generate PROTAC libraries that feature variation in crosslinker length, composition, and E3 ligase ligand.

Automate your CRBN-PEG based PROTACs with Synple Automated Synthesis Platform (SYNPLE-SC002)

Other Notes

Degrader Building Blocks for Targeted Protein Degradation.

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

Legal Information

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

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(S,R,S)-AHPC-PEG5-NH2 hydrochloride

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Pomalidomide-PEG6-butyl amine hydrochloride, ≥95%

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Pomalidomide-C6-PEG3-butyl amine hydrochloride, ≥98%

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(S,R,S)-AHPC-PEG2-butyl amine hydrochloride

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Pomalidomide-PEG2-butyl amine hydrochloride, ≥95%

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911690

C5 Lenalidomide, ≥95%

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911739

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911747

C5 Lenalidomide-PEG3-NH2 hydrochloride, ≥95%

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911763

C5 Lenalidomide-PEG1-piperazine hydrochloride, ≥95%

913987

Pomalidomide-C6-PEG1-C3-PEG1-butyl amine hydrochloride, ≥95%

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C5 Lenalidomide-piperazine-pyridine-alkyne-NH2 hydrochloride, ≥95%

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917559

(S,R,S)-AHPC-C6-NH2 hydrochloride, ≥95%

919357

(S,R,S)-AHPC-PEG1-piperazine hydrochloride, ≥95%

918350

C5 Lenalidomide-alkyne-piperidine hydrochloride, ≥95%

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919969

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Pomalidomide-benzyl-piperazine hydrochloride

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C5 Lenalidomide-benzyl-piperazine hydrochloride

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Pomalidomide-pyridine-PEG1-piperazine hydrochloride

920797

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C5 Lenalidomide-methylamino-PEG1-NH2 hydrochloride, ≥95%

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pictograms

Health hazard
GHS08

signalword

Warning

Hazard Classifications

Repr. 2 - STOT RE 2

target_organs

Blood

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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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
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

Partial PROTACs are a collection of crosslinker-E3 ligand conjugates with a pendant functional group for covalent linkage to a target ligand.

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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