Thalidomide-NH-C8-NH2 hydrochloride is a specialized E3 ligase ligand-linker conjugate widely used in the development and synthesis of PROTACs (Proteolysis Targeting Chimeras). This compound features a thalidomide-based ligand—a well-established cereblon (CRBN) E3 ligase recruiter—chemically linked via an optimized eight-carbon (C8) flexible spacer to a terminal amine group (NH2), presented as the hydrochloride salt to ensure stability and ease of handling.
Structure of 2446474-06-0
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Category
E3 Ligase Ligand-Linker Conjugate
Molecular Formula
C₂₁H₂₉ClN₄O₄
Molecular Weight
436.93
* For research and manufacturing use only. Not for human or clinical use.
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Thalidomide-NH-C8-NH2 hydrochloride is a specialized E3 ligase ligand-linker conjugate designed for advanced PROTAC (Proteolysis Targeting Chimera) research. It comprises a thalidomide-based moiety known to recruit the cereblon (CRBN) E3 ubiquitin ligase, linked via an eight-carbon alkyl chain terminated with an amine group (NH2) for ready conjugation. The hydrochloride form enhances its solubility and stability, making it exceptionally useful for the construction of bespoke PROTAC molecules.
Mechanism
This molecule functions as a bifunctional PROTAC linker component. The thalidomide motif binds to the CRBN E3 ligase, facilitating the recruitment of ubiquitin-proteasome machinery. The C8 alkyl chain serves as an optimal linker, providing spatial flexibility and chemical reactivity through its terminal amine group. Researchers can utilize this amine handle to attach a variety of target protein-binding ligands via amide coupling or other chemoselective conjugation strategies. When incorporated into a complete PROTAC, Thalidomide-NH-C8-NH2 hydrochloride effectively enables the targeted ubiquitination and subsequent degradation of disease-relevant proteins.
Applications
Thalidomide-NH-C8-NH2 hydrochloride is widely applied in medicinal chemistry, drug discovery, and targeted protein degradation research. Its primary application is as a building block for the synthesis of custom PROTAC molecules targeting proteins implicated in cancer, neurodegenerative diseases, and immune disorders. The compound's chemical structure allows for rapid and efficient assembly of CRBN-based PROTACs, facilitating structure-activity relationship (SAR) studies, high-throughput screening, and the development of next-generation therapeutic agents. It is a valuable tool for both academic and industrial researchers aiming to harness the full potential of targeted protein degradation technologies.
• Long-chain amine linker (C8) improves solubility and flexibility in PROTAC design, enabling efficient target engagement.
• Ideal for CRBN-based PROTAC synthesis, ensuring high stability and robust E3 ligase recruitment.
* 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.: 2446474-06-0
