C20-GLU-AEEA-AEEA-OSU
[CAS# 1188328-38-2]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: C20-GLU-AEEA-AEEA-OSU
• Synonyms: 19-((S)-1-Carboxy-3-{2-[2-({2-[2-(2,5-dioxo-pyrrolidin-1-yloxycarbonylmethoxy)ethoxy]ethyl-carbamoyl}methoxy)ethoxy]ethylcarbamoyl}propylcarbamoyl)nonadecanoic acid; 20-[[(1S)-1-carboxy-4-[2-[2-[2-[2-[2-[2-(2,5-dioxopyrrolidin-1-yl)oxy-2-oxoethoxy]ethoxy]ethylamino]-2-oxoethoxy]ethoxy]ethylamino]-4-oxobutyl]amino]-20-oxoicosanoic acid
• Molecular Formula: C₄₁H₇₀N₄O₁₅
• Molecular Weight: 859.01
• CAS Registry Number: 1188328-38-2
• SMILES: C1CC(=O)N(C1=O)OC(=O)COCCOCCNC(=O)COCCOCCNC(=O)CC[C@@H](C(=O)O)NC(=O)CCCCCCCCCCCCCCCCCCC(=O)O

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovery and Applications

C20-GLU-AEEA-AEEA-OSU is a synthetic molecule specifically designed for bioconjugation applications and the development of advanced drug delivery systems. This compound combines a hydrophobic C20 lipid chain, a glutamic acid (GLU) core, and multiple AEEA (aminoethoxyethanol) spacers, capped with an N-hydroxysuccinimide (OSU) ester. The structure ensures versatility, solubility, and reactivity, making it ideal for modifying biomolecules or creating functionalized materials.

The discovery of C20-GLU-AEEA-AEEA-OSU is rooted in the need for multifunctional reagents capable of forming stable conjugates with peptides, proteins, or other bioactive molecules. The inclusion of the C20 chain introduces lipophilic characteristics, enhancing its compatibility with lipid-based delivery systems. The glutamic acid moiety offers multiple attachment sites, while the OSU group ensures efficient coupling with primary amines under mild conditions.

Synthesis of C20-GLU-AEEA-AEEA-OSU involves several steps, starting with the preparation of the lipid tail and glutamic acid core. The AEEA spacers are then added sequentially using amide bond formation. Finally, the OSU ester is introduced through a reaction with N-hydroxysuccinimide and a coupling agent, such as dicyclohexylcarbodiimide (DCC). This step ensures high reactivity while maintaining the molecule’s structural integrity.

The applications of this compound are diverse. It is extensively used in the preparation of liposomes and micelles for drug delivery, where its amphiphilic nature facilitates the encapsulation of hydrophobic drugs. The reactive OSU ester allows conjugation with targeting ligands or therapeutic agents, enabling precision delivery to specific cellular or tissue targets. Additionally, C20-GLU-AEEA-AEEA-OSU finds use in biomaterial development, such as fabricating functionalized surfaces for biosensors or creating hydrogels for controlled drug release.

This molecule represents a significant advancement in chemical biology and materials science, offering a flexible platform for the development of novel therapeutic and diagnostic tools.

References

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