920754

C5 Lenalidomide-benzyl-piperazine hydrochloride

Name: C5 Lenalidomide-benzyl-piperazine hydrochloride
Brand: ALDRICH
Price: 434 USD
Availability: InStock

Synonym(s):

N-(2-(2,6-Dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)-4-(piperazin-1-ylmethyl)benzamide hydrochloride, Crosslinker−E3 Ligase ligand conjugate, Protein degrader building block for PROTAC^® research, Template for synthesis of targeted protein degrader

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50 MG

$434.00

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About This Item

Empirical Formula (Hill Notation):

C₂₅H₂₇N₅O₄ · xHCl

Molecular Weight:

461.51 (free base basis)

UNSPSC Code:

12352200

NACRES:

NA.22

Key Documents

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ligand

C5 Lenalidomide

Quality Level

100

form

solid

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(C4=CC=C(CN5CCNCC5)C=C4)=O)=CC=C31.Cl

InChI key

FYDHHUZWYCJEBY-UHFFFAOYSA-N

Related Categories

Chemical Biology

Protein Degrader Building Blocks

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1 of 4

This Item	921327	920746	920762
Sigma-Aldrich 920754 C5 Lenalidomide-benzyl-piperazine hydrochloride	Sigma-Aldrich 921327 C5 Lenalidomide-PEG₆-Butyl NH₂ hydrochloride	Sigma-Aldrich 920746 Pomalidomide-benzyl-piperazine hydrochloride	Sigma-Aldrich 920762 (S,R,S)-AHPC-benzyl-piperazine hydrochloride
reaction suitability reactivity: carboxyl reactive, reagent type: ligand-linker conjugate	reaction suitability reactivity: carboxyl reactive, reagent type: ligand-linker conjugate	reaction suitability reactivity: carboxyl reactive, reagent type: ligand-linker conjugate	reaction suitability reactivity: carboxyl reactive, reagent type: ligand-linker conjugate
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
form solid	form powder or crystals	form solid	form solid
storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C
ligand C5 Lenalidomide	ligand C5 Lenalidomide	ligand pomalidomide	ligand VH032
functional group amine	functional group amine	functional group amine	functional group amine

Application

Protein degrader building block C5 Lenalidomide-benzyl-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, 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

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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Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number

0000503077

0000344408

0000353954

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Targeted Protein Degradation by Small Molecules.

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

Impact of linker length on the activity of PROTACs.

Kedra Cyrus et al.

Molecular bioSystems, 7(2), 359-364 (2010-10-06)

Conventional genetic approaches have provided a powerful tool in the study of proteins. However, these techniques often preclude selective manipulation of temporal and spatial protein functions, which is crucial for the investigation of dynamic cellular processes. To overcome these limitations

Small-Molecule PROTACS: New Approaches to Protein Degradation.

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

Targeted Protein Degradation: from Chemical Biology to Drug Discovery.

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

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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