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919896

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)
MDL number:
MFCD34166228
UNSPSC Code:
12352101
NACRES:
NA.22
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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

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

InChI key

YIVQCHPIDFGEDN-UHFFFAOYSA-N

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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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.

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

Global Trade Item Number

SKUGTIN
919896-50MG04065265680455