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921327

Sigma-Aldrich

C5 Lenalidomide-PEG6-Butyl NH2 hydrochloride

≥95%

Synonym(s):

24-Amino-N-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)-3,6,9,12,15,18-hexaoxatetracosanamide hydrochloride, 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):
C31H48N4O10 · xHCl
Molecular Weight:
636.73 (free base basis)
NACRES:
NA.22

ligand

C5 Lenalidomide

Quality Level

100

Assay

≥95%

form

powder or crystals

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(COCCOCCOCCOCCOCCOCCCCCCN)=O)=CC=C31.Cl

Application

Protein degrader builiding block C5 Lenalidomide-PEG6-Butyl 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 PEGylated 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 terminal amine, parallel synthesis can be used to more quickly generate PROTAC libraries that feature variation in crosslinker length, composition, and E3 ligase ligand.

Technology Spotlight:Degrader Building Blocks for Targeted Protein Degradation

Portal:Building PROTAC® Degraders for Targeted Protein Degradation

Other Notes

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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901513

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901832

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905224

Pomalidomide-PEG6-butyl amine hydrochloride, ≥95%

905208

Pomalidomide-C6-PEG3-butyl amine hydrochloride, ≥98%

911003

Pomalidomide-PEG2-butyl amine hydrochloride, ≥95%

911666

Pomalidomide-C6-NH2 hydrochloride, ≥95%

911658

Pomalidomide-C3-NH2 hydrochloride, ≥95%

911720

C5 Lenalidomide-C9-NH2 hydrochloride, ≥95%

911712

C5 Lenalidomine-C6-NH2 hydrochloride, ≥95%

911755

C5 Lenalidomide-PEG5-NH2 hydrochloride

911704

C5 Lenalidomine-C3-NH2 hydrochloride, ≥95%

911739

C5 Lenalidomide-PEG1-NH2 hydrochloride, ≥95%

911747

C5 Lenalidomide-PEG3-NH2 hydrochloride, ≥95%

911763

C5 Lenalidomide-PEG1-piperazine hydrochloride, ≥95%

913987

Pomalidomide-C6-PEG1-C3-PEG1-butyl amine hydrochloride, ≥95%

915572

Pomalidomide-dipiperazine-NH2 hydrochloride, ≥95%

916536

Pomalidomide-piperazine-pyridine-alkyne-NH2 hydrochloride

917729

C5 Lenalidomide-piperazine-pyridine-alkyne-NH2 hydrochloride, ≥95%

917303

C5 Lenalidomide-C6-PEG1-C3-PEG1-Butyl NH2 hydrochloride, ≥95%

918350

C5 Lenalidomide-alkyne-piperidine hydrochloride, ≥95%

918091

Lenalidomide-Photoswitch2-NH2 hydrochloride, ≥95%

919969

C5 Lenalidomide-PEG2-Butyl NH2 hydrochloride, ≥95%

919896

C5 Lenalidomide-dipiperazine-NH2 hydrochloride

920738

Pomalidomide-C9-NH2 hydrochloride

920754

C5 Lenalidomide-benzyl-piperazine hydrochloride

920789

Pomalidomide-pyridine-PEG1-piperazine hydrochloride

920797

C5 Lenalidomide-pyridine-PEG1-piperazine hydrochloride, ≥95%

920800

C5 Lenalidomide-methylamino-PEG1-NH2 hydrochloride, ≥95%

921300

C5 Lenalidomide-pyrimidine-piperazine-PEG1-NH2 hydrochloride, ≥95%

921319

Pomalidomide-methylamino-PEG1-NH2 hydrochloride

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

921327-BULK:
921327-VAR:
921327-50MG:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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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