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910511

Sigma-Aldrich

Pomalidomide-C6-PEG3-butyl alkyne

≥95.0%

Synonym(e):

N-(2-(2,6-Dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)-6-(2-(2-(oct-7-yn-1-yloxy)ethoxy)ethoxy)hexanamide, Crosslinker–E3 Ligase ligand conjugate, Pomalidomide conjugate, Pomalidomide-6-2-2-6-alkyne, Protein degrader building block for PROTAC® research, Template for synthesis of targeted protein degrader

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About This Item

Empirische Formel (Hill-System):
C31H41N3O8
Molekulargewicht:
583.67
UNSPSC-Code:
51171641

Assay

≥95.0%

Form

(Liquid or Semi-solid or Paste or Solid)

Eignung der Reaktion

reaction type: click chemistry
reagent type: ligand-linker conjugate

Funktionelle Gruppe

alkyne

Lagertemp.

2-8°C

SMILES String

O=C(C(CC1)N(C2=O)C(C3=C2C=CC=C3NC(CCCCCOCCOCCOCCCCCCC#C)=O)=O)NC1=O

Anwendung

Protein degrader builiding block Pomalidomide-C6-PEG3-butyl alkyne enables the synthesis of molecules for targeted protein degradation and PROTAC (proteolysis-targeting chimeras) technology. This conjugate contains a Cereblon (CRBN)-recruiting ligand, a linker with both hydrophobic and hydrophilic moieties, and a pendant alkyne for click chemistry with an azide 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 alkyne, parallel synthesis can be used to more quickly generate PROTAC libraries that feature variation in crosslinker length, composition, and E3 ligase ligand.

Sonstige Hinweise

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

Rechtliche Hinweise

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

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Lagerklassenschlüssel

13 - Non Combustible Solids

WGK

WGK 3

Flammpunkt (°C)

Not applicable

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Die Dokumentenbibliothek aufrufen

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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)
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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
Daniel P Bondeson et al.
Annual review of pharmacology and toxicology, 57, 107-123 (2016-10-13)
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Artikel

Partial PROTACs for Targeted Protein Degradation

Partial PROTACs are a collection of crosslinker-E3 ligand conjugates with a pendant functional group for covalent linkage to a target ligand.

Degrader Building Blocks for Targeted Protein Degradation

Partial PROTACs are a collection of crosslinker-E3 ligand conjugates with a pendant functional group for covalent linkage to a target ligand.

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