17-((S)-1-Carboxy-3-{2-[2-({2-[2-(2,5-dioxo-pyrrolidin-1-yloxycarbonylmethoxy)ethoxy]ethylcarbamoyl}methoxy)ethoxy]ethylcarbamoyl}propylcarbamoyl)-heptadecanoic acid
[CAS# 1169630-40-3]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: 17-((S)-1-Carboxy-3-{2-[2-({2-[2-(2,5-dioxo-pyrrolidin-1-yloxycarbonylmethoxy)ethoxy]ethylcarbamoyl}methoxy)ethoxy]ethylcarbamoyl}propylcarbamoyl)-heptadecanoic acid
• Synonyms: HO-Ste-Glu(AEEA-AEEA-Osu)-OH;18-[[(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]-18-oxooctadecanoic acid
• Molecular Formula: C₃₉H₆₆N₄O₁₅
• Molecular Weight: 830.96
• CAS Registry Number: 1169630-40-3
• EC Number: 815-717-1
• SMILES: C1CC(=O)N(C1=O)OC(=O)COCCOCCNC(=O)COCCOCCNC(=O)CC[C@@H](C(=O)O)NC(=O)CCCCCCCCCCCCCCCCC(=O)O

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.532, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302
• Precautionary Statements: P264-P270-P301+P312-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319

Discovory and Applicatios

17-((S)-1-Carboxy-3-{2-[2-({2-[2-(2,5-dioxo-pyrrolidin-1-yloxycarbonylmethoxy)ethoxy]ethylcarbamoyl}methoxy)ethoxy]ethylcarbamoyl}propylcarbamoyl)-heptadecanoic acid is a complex synthetic compound with applications in drug delivery and bioconjugation technologies. Its discovery is rooted in efforts to design multifunctional molecules capable of linking therapeutic agents to carrier systems, such as polymers or nanoparticles, for targeted delivery. The molecular structure of this compound is highly specialized, with multiple functional groups that make it ideal for controlled release systems in pharmaceutical research and biotechnological applications.

The structural complexity of this compound arises from its long fatty acid chain (heptadecanoic acid) and multiple carbamoyl and ester linkages. The presence of 2,5-dioxo-pyrrolidin-1-yloxycarbonyl (often referred to as N-hydroxysuccinimide ester, or NHS ester) makes the compound highly reactive toward primary amines. This reactivity is pivotal in bioconjugation, where NHS esters are commonly used to attach bioactive molecules, such as peptides, proteins, or drugs, to carriers like polymers or nanoparticles. The NHS ester group, in particular, facilitates the formation of stable amide bonds between the compound and biological molecules, allowing for precise and efficient conjugation in various biotechnological processes.

One of the primary applications of 17-((S)-1-Carboxy-3-{2-[2-({2-[2-(2,5-dioxo-pyrrolidin-1-yloxycarbonylmethoxy)ethoxy]ethylcarbamoyl}methoxy)ethoxy]ethylcarbamoyl}propylcarbamoyl)-heptadecanoic acid is in the field of targeted drug delivery. Its ability to conjugate therapeutic agents to long-chain fatty acids or polymers enables the controlled release of drugs within the body. The compound’s multiple reactive sites allow for the attachment of drugs or bioactive molecules, which can then be delivered to specific tissues or cells, enhancing the efficacy of treatments while minimizing side effects. In particular, this compound has been explored in the development of liposomal drug delivery systems, where it serves as a linker between the drug and the liposome, enabling the encapsulation of therapeutic agents for controlled release.

In addition to its use in drug delivery, this compound is also employed in the development of diagnostic tools and biosensors. The NHS ester groups provide sites for conjugating biomolecules, such as antibodies or enzymes, to surfaces or nanoparticles. This capability allows for the creation of highly specific and sensitive diagnostic assays, where the biomolecule attached to the compound can interact with a target analyte. As a result, this compound has potential applications in medical diagnostics, including the detection of disease markers and pathogens.

The discovery of 17-((S)-1-Carboxy-3-{2-[2-({2-[2-(2,5-dioxo-pyrrolidin-1-yloxycarbonylmethoxy)ethoxy]ethylcarbamoyl}methoxy)ethoxy]ethylcarbamoyl}propylcarbamoyl)-heptadecanoic acid stemmed from research aimed at developing versatile linker molecules for bioconjugation and drug delivery. The goal was to create a compound with multiple functional groups capable of attaching a wide range of molecules, including hydrophobic and hydrophilic drugs, peptides, and proteins. Its long fatty acid chain enhances its lipophilicity, making it suitable for incorporation into lipid-based drug delivery systems, while its water-soluble NHS ester groups provide the reactivity needed for bioconjugation.

In pharmaceutical applications, the compound’s role as a linker molecule has proven valuable in the design of prodrugs, where the active drug is chemically modified to improve its pharmacokinetics or targeting ability. Upon administration, the drug is gradually released from the compound, allowing for controlled and sustained drug delivery. This has potential benefits in treatments requiring long-term drug administration, such as chronic diseases or cancer therapies.

The versatility of 17-((S)-1-Carboxy-3-{2-[2-({2-[2-(2,5-dioxo-pyrrolidin-1-yloxycarbonylmethoxy)ethoxy]ethylcarbamoyl}methoxy)ethoxy]ethylcarbamoyl}propylcarbamoyl)-heptadecanoic acid in bioconjugation and drug delivery continues to be explored in various research and industrial settings. Its ability to link biomolecules to carriers and its potential for controlled release make it a valuable tool in the development of new therapeutic and diagnostic technologies.