Name: Thalidomide-O-COOH
Brand: BOC Sciences
Rating: 5 (1 reviews)

Size

Price

Stock

Quantity

$--

In stock

Purity

≥ 98%

Appearance

Beige Powder

ShelfLife

2 years

Storage

-20 °C

IUPACName

2-[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]oxyacetic acid

Synonyms

E3 ligase Ligand 3; Thalidomide-Acid; Thalidomide-carboxylic acid; 2-((2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)oxy)acetic acid; 2-[[2-(2,6-Dioxo-3-piperidinyl)-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]oxy]acetic acid

Boiling Point

660.5±55.0 °C (Predicted)

Density

1.606±0.06 g/cm3 (Predicted)

InChI Key

ZVWIXIGBWIEDFO-UHFFFAOYSA-N

InChI

InChI=1S/C15H12N2O7/c18-10-5-4-8(13(21)16-10)17-14(22)7-2-1-3-9(12(7)15(17)23)24-6-11(19)20/h1-3,8H,4-6H2,(H,19,20)(H,16,18,21)

Canonical SMILES

C1CC(=O)NC(=O)C1N2C(=O)C3=C(C2=O)C(=CC=C3)OCC(=O)O

Background Introduction

Thalidomide-O-COOH is a functionalized derivative of thalidomide, featuring a carboxylic acid group for straightforward conjugation. As a cereblon (CRBN) E3 ligase ligand, this molecule is widely used in the design and synthesis of PROTACs (Proteolysis Targeting Chimeras), enabling targeted protein degradation applications in biomedical research and drug discovery.

Mechanism

Thalidomide-O-COOH binds selectively to the CRBN protein, a substrate receptor component of the CRL4 E3 ubiquitin ligase complex. When used as part of a PROTAC molecule, it acts as an E3 ligase recruiter. The carboxylic acid moiety allows for easy linker attachment, facilitating the covalent connection to a target protein ligand. Upon successful linking, the resulting bifunctional PROTAC molecule brings the E3 ligase and the target protein into close proximity, enabling ubiquitination and subsequent proteasomal degradation of the target protein.

Applications

Thalidomide-O-COOH is a key building block in the synthesis of CRBN-based PROTACs, allowing researchers to design molecules for selective protein degradation of disease-relevant targets. It is ideal for chemical biology studies, mechanism-of-action investigations, and early-stage drug development in oncology, neurodegenerative diseases, and immune disorders. Additionally, it is utilized in developing next-generation targeted therapies with improved selectivity and reduced off-target effects.

• Carboxylic acid functionality enables versatile coupling with amine-containing partners for PROTAC assembly.
• Specifically designed for efficient and reliable CRBN E3 ligase recruitment in targeted protein degradation applications.

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* 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