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安全信息

917729

Sigma-Aldrich

C5 Lenalidomide-piperazine-pyridine-alkyne-NH2 hydrochloride

≥95%

别名:

4-(4-(5-(3-Aminoprop-1-yn-1-yl)pyridin-2-yl)piperazin-1-yl)-N-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)butanamide, 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

经验公式（希尔记法）:
C29H33N7O4 · xHCl
分子量:
543.62 (free base basis)
MDL编号:
MFCD34166213
UNSPSC代码:
12352101
NACRES:
NA.22

ligand

C5 Lenalidomide

质量水平

100

方案

≥95%

表单

powder or crystals

反应适用性

reactivity: carboxyl reactive
reagent type: ligand-linker conjugate

官能团

amine

储存温度

2-8°C

SMILES字符串

O=C1N(C2CCC(NC2=O)=O)CC3=CC(NC(CCCN4CCN(C5=CC=C(C#CCN)C=N5)CC4)=O)=CC=C31.Cl

InChI

1S/C29H33N7O4.ClH/c30-11-1-3-20-5-9-25(31-18-20)35-15-13-34(14-16-35)12-2-4-26(37)32-22-6-7-23-21(17-22)19-36(29(23)40)24-8-10-27(38)33-28(24)39;/h5-7,9,17-18,24H,2,4,8,10-16,19,30H2,(H,32,37)(H,33,38,39);1H

InChI key

CLHMZJWSMMCSAI-UHFFFAOYSA-N

相关类别

应用

Protein degrader building block C5 Lenalidomide-piperazine-pyridine-alkyne-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 an acid on the target warhead. 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 terminal amine, parallel synthesis can be used to more quickly generate PROTAC libraries that feature variation in crosslinker length, composition, and E3 ligase ligand.

其他说明

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

法律信息

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

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储存分类代码

11 - Combustible Solids

WGK

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闪点(°F)

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闪点(°C)

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法规信息

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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
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.
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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

商品

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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