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Merck
CN

911712

C5 Lenalidomine-C6-NH2 hydrochloride

≥95%

Synonym(s):

7-Amino-N-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)heptanamide 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):
C20H26N4O4 · xHCl
Molecular Weight:
386.44 (free base basis)
MDL number:
MFCD32857272
UNSPSC Code:
12352101
NACRES:
NA.22

Key Documents

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Product Name

C5 Lenalidomine-C6-NH2 hydrochloride, ≥95%

InChI key

BQPYHWPMMOFXIA-UHFFFAOYSA-N

SMILES string

O=C1N(C2CCC(NC2=O)=O)CC3=CC(NC(CCCCCCN)=O)=CC=C31.Cl

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

Quality Level

100

Related Categories

Application

Protein degrader builiding block C5 Lenalidomide-C6-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 an alkyl-chain 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.

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

pictograms

Health hazard
GHS08

signalword

Warning

Hazard Classifications

Repr. 2 - STOT RE 2

target_organs

Blood

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000490919
0000490919
0000211780
0000211780
0000367030

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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
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

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.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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