N-[18-(1,1-Dimethylethoxy)-1,18-dioxooctadecyl]-L-glutamic acid 1-(1,1-dimethylethyl) 5-(2,5-dioxo-1-pyrrolidinyl) ester
[CAS# 1188328-22-4]

Identification

• Classification: Biochemical >> Amino acids and their derivatives
• Name: N-[18-(1,1-Dimethylethoxy)-1,18-dioxooctadecyl]-L-glutamic acid 1-(1,1-dimethylethyl) 5-(2,5-dioxo-1-pyrrolidinyl) ester
• Synonyms: 1-O-tert-butyl 5-O-(2,5-dioxopyrrolidin-1-yl) (2S)-2-[[18-[(2-methylpropan-2-yl)oxy]-18-oxooctadecanoyl]amino]pentanedioate
• Molecular Formula: C₃₅H₆₀N₂O₉
• Molecular Weight: 652.86
• CAS Registry Number: 1188328-22-4
• SMILES: CC(C)(C)OC(=O)CCCCCCCCCCCCCCCCC(=O)N[C@@H](CCC(=O)ON1C(=O)CCC1=O)C(=O)OC(C)(C)C

Properties

• Solubility: Insoluble (2.5E^-4 g/L) (25 ºC), Calc.^*
• Density: 1.09±0.1 g/cm³ (20 ºC 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2018 ACD/Labs)

Discovory and Applicatios

N-[18-(1,1-Dimethylethoxy)-1,18-dioxooctadecyl]-L-glutamic acid 1-(1,1-dimethylethyl) 5-(2,5-dioxo-1-pyrrolidinyl) ester, often referred to by its abbreviated chemical name, is a synthetic molecule with potential applications in pharmaceutical and biomedical fields. This compound belongs to a class of molecules designed for drug delivery systems, specifically as prodrugs or carriers for therapeutic agents. It has been investigated for its ability to enhance the solubility, stability, and bioavailability of drugs, particularly hydrophobic compounds.

The discovery of this compound was part of ongoing research aimed at improving drug delivery methods. Traditional pharmaceutical formulations often face challenges in effectively delivering poorly soluble drugs to their target sites. Researchers developed N-[18-(1,1-Dimethylethoxy)-1,18-dioxooctadecyl]-L-glutamic acid derivatives to address these issues by modifying the physicochemical properties of the parent compounds, enhancing their compatibility with biological systems.

One of the most notable applications of this molecule lies in its role as a component of lipid-based drug delivery systems. Its long-chain hydrophobic structure, combined with hydrophilic functional groups, allows it to form stable micelles or nanoparticles in aqueous environments. This amphiphilic nature facilitates the encapsulation of hydrophobic drugs, protecting them from degradation and enabling controlled release at the target site. Additionally, the ester and amide linkages in its structure are designed to be cleaved under physiological conditions, ensuring the release of the active drug in its intended form.

Another important application of this compound is in targeted drug delivery. The L-glutamic acid moiety can be modified with targeting ligands, such as antibodies or peptides, to direct the drug-loaded nanoparticles to specific cells or tissues. This approach has shown promise in cancer therapy, where selective delivery to tumor cells can reduce off-target effects and improve therapeutic efficacy.

The synthesis of N-[18-(1,1-Dimethylethoxy)-1,18-dioxooctadecyl]-L-glutamic acid 1-(1,1-dimethylethyl) 5-(2,5-dioxo-1-pyrrolidinyl) ester involves multiple steps, typically starting with the preparation of a protected L-glutamic acid derivative. The introduction of the long alkyl chain and the functional ester groups is achieved through reactions such as esterification, amidation, and selective deprotection. Careful control of reaction conditions is necessary to ensure high yield and purity of the final product.

In recent years, researchers have explored the potential of this compound in combination therapies, where it serves as a carrier for multiple drugs simultaneously. By co-encapsulating chemotherapeutic agents and imaging molecules, it enables both treatment and diagnostic imaging in a single platform, a concept known as theranostics.

The environmental and biocompatibility aspects of this compound are also under investigation. Studies suggest that its components can be metabolized into non-toxic byproducts, making it a suitable candidate for clinical applications. However, further research is needed to fully understand its pharmacokinetics and long-term safety profile.

Overall, N-[18-(1,1-Dimethylethoxy)-1,18-dioxooctadecyl]-L-glutamic acid 1-(1,1-dimethylethyl) 5-(2,5-dioxo-1-pyrrolidinyl) ester represents a significant advancement in the field of drug delivery. Its ability to improve the solubility, stability, and targeting of therapeutic agents highlights its potential to enhance treatment outcomes across various medical conditions.