Thalidomide-O-PEG4-Boc is a specialized E3 Ligase Ligand-Linker Conjugate designed for advanced PROTAC (Proteolysis Targeting Chimera) drug development and research. This compound features thalidomide, a well-established E3 ligase cereblon (CRBN) binder, connected via a four-unit polyethylene glycol (PEG4) linker and capped with a Boc-protected terminal group. The PEG4 spacer enhances solubility and flexibility, improving the efficacy and pharmacokinetics of resulting PROTAC molecules.
As an E3 ligase ligand-linker conjugate, Thalidomide-O-PEG4-Boc plays a pivotal role in targeted protein degradation strategies. It enables efficient recruitment of the CRBN E3 ubiquitin ligase, allowing for the development of innovative bifunctional molecules that induce selective ubiquitination and degradation of disease-related proteins. This versatile intermediate is ideal for researchers aiming to develop new therapeutics targeting cancer, neurodegenerative diseases, and other pathologies through the precise modulation of protein homeostasis. Thalidomide-O-PEG4-Boc is an essential building block in the construction of next-generation PROTACs, facilitating efficient and selective protein degradation for cutting-edge drug discovery and biomedical research.
Structure of 2411681-87-1
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Category
E3 Ligase Ligand-Linker Conjugate
Molecular Formula
C28H38N2O11
Molecular Weight
578.61
Appearance
Viscous Liquid
* For research and manufacturing use only. Not for human or clinical use.
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Thalidomide-O-PEG4-Boc is a versatile E3 ligase ligand-linker conjugate widely utilized in the development of targeted protein degradation tools known as PROTACs (Proteolysis Targeting Chimeras). This compound features thalidomide—a well-characterized ligand for the cereblon (CRBN) E3 ubiquitin ligase—chemically linked via a tetraethylene glycol (PEG4) spacer and capped with a Boc-protected amine. Its structure allows for enhanced solubility, flexible conjugation with various target binders, and increased stability, making it invaluable for medicinal chemistry and drug discovery projects.
Mechanism
Thalidomide-O-PEG4-Boc operates by harnessing thalidomide’s high affinity for cereblon, a component of the Cullin-4 E3 ubiquitin ligase complex. In PROTAC design, the molecule’s PEG4 linker provides optimal spatial arrangement and flexibility between two functional groups—facilitating the formation of a ternary complex between the E3 ligase and a target protein when coupled to a suitable ligand. This ternary complex triggers ubiquitination and subsequent proteasomal degradation of the target protein. The Boc group serves as a protective group for amine-functional group, allowing straightforward deprotection and further chemical modifications during PROTAC synthesis.
Applications
Thalidomide-O-PEG4-Boc is primarily used in the synthesis of cereblon-recruiting PROTACs for targeted protein degradation research. Researchers employ this conjugate to generate custom PROTAC molecules by attaching it to various ligands targeting disease-relevant proteins, facilitating the rapid prototyping of new therapeutics. In addition to therapeutic research, Thalidomide-O-PEG4-Boc can serve as a chemical biology tool for deciphering protein function, validating new drug targets, and studying the ubiquitin-proteasome system. Its PEG4 linker imparts improved aqueous solubility and cell permeability, making it especially suitable for applications in cellular systems and in vivo studies, enabling the next generation of targeted therapies.
• PEG4 linker provides increased water solubility and flexibility for improved cellular permeability in PROTAC applications.
• Boc-protected amine allows versatile conjugation, streamlining synthesis of CRBN-targeting PROTAC molecules.
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
CAS No.: 2411681-87-1
