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919896

Sigma-Aldrich

C5 Lenalidomide-dipiperazine-NH2 hydrochloride

Sinônimo(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

Fórmula empírica (Notação de Hill):
C25H34N8O5 · xHCl
Peso molecular:
526.59 (free base basis)
Número MDL:
MFCD34166228
Código UNSPSC:
12352101
NACRES:
NA.22
Preço e disponibilidade não estão disponíveis no momento.

ligand

C5 Lenalidomide

Nível de qualidade

100

Formulário

solid

adequação da reação

reactivity: carboxyl reactive
reagent type: ligand-linker conjugate

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

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

InChI

1S/C25H34N8O5.ClH/c26-5-6-29-7-9-31(10-8-29)25(38)32-13-11-30(12-14-32)24(37)27-18-1-2-19-17(15-18)16-33(23(19)36)20-3-4-21(34)28-22(20)35;/h1-2,15,20H,3-14,16,26H2,(H,27,37)(H,28,34,35);1H

chave InChI

YIVQCHPIDFGEDN-UHFFFAOYSA-N

Categorias relacionadas

Aplicação

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.

Outras notas

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

Informações legais

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

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Daniel P Bondeson et al.
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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

Artigos

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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