Thalidomide 4'-oxyacetamide-alkylC4-azide

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Cat.No. 6300 - Thalidomide 4'-oxyacetamide-alkylC4-azide | C19H20N6O6 | CAS No. 2098488-36-7
Description: Cereblon ligand with alkyl linker and terminal azide for onward chemistry
Alternative Names: Azido-Thalidomide
Chemical Name: N-(4-Azidobutyl)-2-[[2-(2,6-dioxo-3-piperidinyl)-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]oxy]acetamide
Purity: ≥98% (HPLC)
Datasheet
Citations
Reviews
Literature (2)

Biological Activity

Click-activated Thalidomide (Cat.No. 0652); precursor to PROTAC® that hijacks cereblon as the E3 ubiquitin ligase component. Supplied with an azide functional handle at a position known not to significantly affect binding to cereblon, for ready click conjugation to a linker/target protein ligand.

This product has been recently renamed. The previous name for this product was Azido-Thalidomide

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

Technical Data

M. Wt 428.4
Formula C19H20N6O6
Storage Store at -20°C
Purity ≥98% (HPLC)
CAS Number 2098488-36-7
PubChem ID 131704500
InChI Key USWFAZSQVLTHHA-UHFFFAOYSA-N
Smiles [N-]=[N+]=NCCCCNC(COC1=C2C(N(C(C2=CC=C1)=O)C3CCC(NC3=O)=O)=O)=O

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 42.84 100

Preparing Stock Solutions

The following data is based on the product molecular weight 428.4. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.33 mL 11.67 mL 23.34 mL
5 mM 0.47 mL 2.33 mL 4.67 mL
10 mM 0.23 mL 1.17 mL 2.33 mL
50 mM 0.05 mL 0.23 mL 0.47 mL

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References

References are publications that support the biological activity of the product.

Schiedel et al (2018) Chemically induced degradation of sirtuin 2 (Sirt2) by a proteolysis targeting chimera (PROTAC) based on sirtuin rearranging ligands (SirReals). J.Med.Chem. 61 482 PMID: 28379698


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Keywords: Thalidomide 4'-oxyacetamide-alkylC4-azide, Thalidomide 4'-oxyacetamide-alkylC4-azide supplier, PROTACs, click-activated, thalidomide, E3, ligase, ligands, cereblon, Azido-Thalidomide, Cereblon, Ligands, Plus, Linkers, 6300, Tocris Bioscience

Citations for Thalidomide 4'-oxyacetamide-alkylC4-azide

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Literature in this Area

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Targeted Protein Degradation

Targeted Protein Degradation Research Product Guide

This brochure highlights the tools and services available from Bio-Techne to support Targeted Protein Degradation research, including:

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Targeted Protein Degradation

Targeted Protein Degradation Poster

Degraders (e.g. PROTACs) are bifunctional small molecules, that harness the Ubiquitin Proteasome System (UPS) to selectively degrade target proteins within cells. They consist of three covalently linked components: an E3 ubiquitin ligase ligand, a linker and a ligand for the target protein of interest. Authored in-house, this poster outlines the generation of a toolbox of building blocks for the development of Degraders. The characteristics and selection of each of these components are discussed. Presented at EFMC 2018, Ljubljana, Slovenia