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919896

Sigma-Aldrich

C5 Lenalidomide-dipiperazine-NH2 hydrochloride

Synonym(s):

4-(4-(2-Aminoethyl)piperazine-1-carbonyl)-N-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)piperazine-1-carboxamide, 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):
C25H34N8O5 · xHCl
Molecular Weight:
526.59 (free base basis)
UNSPSC Code:
12352101
NACRES:
NA.22

ligand

C5 Lenalidomide

Quality Level

100

form

solid

reaction suitability

reactivity: carboxyl reactive
reagent type: ligand-linker conjugate

storage temp.

2-8°C

SMILES string

O=C(N(CC1)CCN1C(NC2=CC(C3)=C(C=C2)C(N3C(C4=O)CCC(N4)=O)=O)=O)N5CCN(CC5)CCN.Cl

Related Categories

Application

Protein degrader building block C5 Lenalidomine-dipiperazine-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, a rigid linker, 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

Legal Information

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

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901511

(S,R,S)-AHPC-PEG3-NH2 hydrochloride, ≥95%

901517

(S,R,S)-AHPC-PEG2-Alkyne, ≥95%

901516

Pomalidomide-PEG1-NH2 hydrochloride, ≥95%

901513

Pomalidomide-PEG2-NH2 hydrochloride, ≥95%

901523

Pomalidomide-PEG1-Alkyne, ≥98%

901533

(S,R,S)-AHPC-PEG3-Alkyne, ≥95%

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(S,R,S)-AHPC-C6-CO2H hydrochloride

901531

Pomalidomide-PEG3-Alkyne, ≥95%

901529

Pomalidomide-PEG2-Alkyne, ≥95%

901527

Pomalidomide-PEG1-CO2H, ≥95%

901526

Pomalidomide-PEG2-CO2H, 95%

901525

Pomalidomide-C9-CO2H, ≥95%

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Lenalidomide, ≥95%

901860

(S,R,S)-AHPC-PEG6-NH2 hydrochloride, ≥95%

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(S,R,S)-AHPC-PEG5-Alkyne

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(S,R,S)-AHPC-PEG4-Alkyne

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

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(S,R,S)-AHPC-PEG4-NH2 hydrochloride, ≥95%

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903833

Pomalidomide-PEG2-azide

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Pomalidomide-PEG1-azide

903957

(S,R,S)-AHPC-PEG1-azide

904651

(S,R,S)-AHPC-PEG3-azide, ≥95%

904724

Pomalidomide-PEG2-butyl iodide, ≥95%

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Pomalidomide-C6-PEG3-butyl iodide, ≥95%

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Pomalidomide-PEG3-azide

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Pomalidomide-C6-PEG3-butyl azide, ≥95%

904813

(S,R,S)-AHPC-PEG2-azide

904821

(S,R,S)-AHPC-C6-PEG3-butyl azide, ≥95%

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904872

Pomalidomide-PEG2-butyl azide, ≥95%

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(S,R,S)-AHPC-PEG6-butyl azide, ≥95%

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(S,R,S)-AHPC-C6-PEG1-C3-PEG1-butyl azide, ≥95%

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(S,R,S)-AHPC-PEG6-butyl amine hydrochloride, ≥95%

905216

(S,R,S)-AHPC-PEG2-butyl azide, ≥95%

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(S,R,S)-AHPC-C6-PEG3-butyl amine hydrochloride, ≥95%

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(S,R,S)-AHPC-C6-PEG3-butyl chloride, ≥95%

905402

(S,R,S)-AHPC-C6-PEG1-C3-PEG1-butyl chloride, 95%

906050

Pomalidomide-C6-PEG1-C3-PEG1-butyl iodide, ≥95%

906123

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

907677

(S,R,S)-AHPC-PEG6-butyl chloride

909351

(S,R,S)-AHPC-PEG5-azide, ≥98%

909378

(S,R,S)-AHPC-PEG6-Azide, ≥95%

909416

Fluorinated VHL spy molecule 1

909432

Fluorinated VHL Spy Molecule 2, ≥98%

909440

Fluorinated VHL spy molecule 3, ≥95%

909459

Fluorinated VHL Spy Molecule 4, ≥98%

909262

(S,R,S)-AHPC-PEG4-Azide, ≥95%

910600

(S,R,S)-AHPC-PEG2-butyl CO2H, ≥95%

910597

(S,R,S)-AHPC-PEG6-butyl alkyne, ≥95%

910554

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910546

(S,R,S)-AHPC-C6-PEG3-butyl alkyne, ≥95%

910538

(S,R,S)-AHPC-PEG2-butyl alkyne, ≥95%

910511

Pomalidomide-C6-PEG3-butyl alkyne, ≥95.0%

910503

Pomalidomide-PEG2-butyl alkyne, ≥95%

911801

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911720

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911712

C5 Lenalidomine-C6-NH2 hydrochloride, ≥95%

911755

C5 Lenalidomide-PEG5-NH2 hydrochloride

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C5 Lenalidomine-C3-NH2 hydrochloride, ≥95%

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911747

C5 Lenalidomide-PEG3-NH2 hydrochloride, ≥95%

915572

Pomalidomide-dipiperazine-NH2 hydrochloride, ≥95%

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920789

Pomalidomide-pyridine-PEG1-piperazine hydrochloride

920797

C5 Lenalidomide-pyridine-PEG1-piperazine hydrochloride, ≥95%

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923931

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923877

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924202

5-Amino-Thalidomide, ≥95%

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
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
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

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