Thalidomide-O-PEG2-Acid

 CAS No.: 2488752-64-1  Cat No.: BP-100190 4.5  

Thalidomide-O-PEG2-Acid is a high-purity E3 ligase ligand-linker conjugate designed for advanced PROTAC drug development. This compound features thalidomide, a well-established cereblon (CRBN) binding ligand, covalently attached via a two-unit polyethylene glycol (PEG2) spacer to a terminal carboxylic acid group. The PEG2 linker enhances water solubility and provides flexibility for conjugation, making it ideal for the synthesis of innovative PROTACs (Proteolysis Targeting Chimeras). As an essential building block, Thalidomide-O-PEG2-Acid enables researchers to create bifunctional molecules capable of recruiting the E3 ubiquitin ligase machinery to target specific proteins for degradation. Widely used in academic and pharmaceutical research, this reagent accelerates the development of next-generation therapeutics by facilitating the selective degradation of disease-associated proteins. Perfect for those working in targeted protein degradation and chemical biology, Thalidomide-O-PEG2-Acid is your reliable choice for creating customized PROTACs and exploring novel therapeutic targets.

Thalidomide-O-PEG2-Acid

Structure of 2488752-64-1

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Category
E3 Ligase Ligand-Linker Conjugate
Molecular Formula
C20H22N2O9
Molecular Weight
434.40

* For research and manufacturing use only. Not for human or clinical use.

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IUPACName
3-[2-[2-[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]oxyethoxy]ethoxy]propanoic acid
Synonyms
Thalidomide-O-PEG2-C2-acid
InChI Key
LDBBOUWQJLSTOP-UHFFFAOYSA-N
InChI
InChI=1S/C20H22N2O9/c23-15-5-4-13(18(26)21-15)22-19(27)12-2-1-3-14(17(12)20(22)28)31-11-10-30-9-8-29-7-6-16(24)25/h1-3,13H,4-11H2,(H,24,25)(H,21,23,26)
Canonical SMILES
C1CC(=O)NC(=O)C1N2C(=O)C3=C(C2=O)C(=CC=C3)OCCOCCOCCC(=O)O

Background Introduction

Thalidomide-O-PEG2-Acid is a specially designed E3 ligase ligand-linker conjugate widely used in targeted protein degradation research, particularly as a building block in PROTAC (Proteolysis Targeting Chimera) technology. Thalidomide serves as a high-affinity ligand for Cereblon (CRBN), a component of the CUL4-RBX1-DDB1-CRBN E3 ubiquitin ligase complex. The PEG2 linker provides enhanced solubility and optimal spacing for conjugating with various protein-targeting warheads, facilitating the formation of effective bifunctional degraders.

Mechanism

The mechanism of Thalidomide-O-PEG2-Acid centers on its role as the E3 ligase-binding moiety within PROTACs. The thalidomide portion specifically binds to CRBN, recruiting the E3 ubiquitin ligase complex. The attached PEG2 (polyethylene glycol) linker imparts flexibility and aqueous solubility, while the terminal carboxylic acid enables coupling to protein-targeting ligands (warheads) through amide or ester bond formation. When integrated into a PROTAC molecule, this conjugate mediates proximity-induced ubiquitination of the target protein, marking it for subsequent proteasomal degradation.

Applications

Thalidomide-O-PEG2-Acid is an essential intermediate for the synthesis of CRBN-recruiting PROTACs, molecular glues, and related protein degradation tools. It is valuable for drug discovery, chemical biology research, and mechanistic studies on targeted protein degradation. Researchers leverage Thalidomide-O-PEG2-Acid to develop customized PROTACs aimed at degrading disease-relevant proteins in oncology, immunology, and neurodegenerative research, thereby accelerating the advancement of next-generation therapeutics. Its structure, featuring a carboxylic acid functional group, allows for easy conjugation with various ligands and expands the toolbox for developing innovative bifunctional molecules.

• PEG2 linker increases aqueous solubility and flexibility for improved PROTAC design.
• Carboxylic acid functional group enables efficient coupling to a variety of E3 ligase ligands or target-binding ligands.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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* Total Molecular Weight:
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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Historical Records: DP-C-4

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