Name: 2,5-dioxopyrrolidin-1-yl 17-oxo-4,7,10,13,19-pentaoxa-16-azadocos-21-yn-1-oate
Brand: BOC Sciences
Rating: 5 (1 reviews)

Synonyms

Propargyl-PEG6-NHS ester;

Appearance

Soild powder

Drug Delivery Systems: 2,5-dioxopyrrolidin-1-yl 17-oxo-4,7,10,13,19-pentaoxa-16-azadocos-21-yn-1-oate is utilized in the development of advanced drug delivery systems. Its unique structural properties allow it to enhance the solubility and bioavailability of poorly soluble compounds, making it an ideal candidate for formulating various therapeutic agents. By encapsulating drugs within this compound, researchers can achieve targeted delivery, reducing systemic side effects and increasing therapeutic efficacy. The compound's ability to form stable complexes with bioactive molecules facilitates controlled release profiles, which is crucial for maintaining effective drug concentrations over extended periods.

Bioconjugation Strategies: This compound plays a significant role in bioconjugation strategies, particularly in linking biomolecules such as peptides, proteins, and nucleic acids to drug carriers. Its reactive groups allow for specific conjugation to amino or carboxyl groups on biomolecules, creating stable linkages that enhance the therapeutic properties of the conjugated entity. By employing 2,5-dioxopyrrolidin-1-yl 17-oxo-4,7,10,13,19-pentaoxa-16-azadocos-21-yn-1-oate in bioconjugation, scientists can develop targeted therapies that minimize off-target effects and improve treatment outcomes for various diseases, including cancer and autoimmune disorders.

Nanomedicine Applications: In the field of nanomedicine, 2,5-dioxopyrrolidin-1-yl 17-oxo-4,7,10,13,19-pentaoxa-16-azadocos-21-yn-1-oate serves as a key component in the formulation of nanocarriers. These nanocarriers can encapsulate therapeutic agents, enabling precise delivery to diseased tissues while minimizing exposure to healthy cells. The compound's ability to form nanoparticles with favorable pharmacokinetics and biodistribution profiles is crucial in enhancing the therapeutic index of administered drugs. By leveraging its properties, researchers can develop innovative nanomedicine approaches that significantly improve patient outcomes through targeted and sustained drug delivery.

Sustainable Chemical Synthesis: Another critical application of 2,5-dioxopyrrolidin-1-yl 17-oxo-4,7,10,13,19-pentaoxa-16-azadocos-21-yn-1-oate is in sustainable chemical synthesis. Its multifunctional characteristics enable the development of greener synthesis methods that reduce waste and energy consumption in pharmaceutical production. By incorporating this compound into synthetic pathways, chemists can achieve higher yields and selectivity, minimizing the use of hazardous reagents and solvents. This aligns with the principles of green chemistry, promoting environmental sustainability in the production of pharmaceutical compounds and other valuable chemicals.

1. Absolute quantification of peptides by isotope dilution liquid chromatography-inductively coupled plasma mass spectrometry and gas chromatography/mass spectrometry

Lu Yang, Xiandeng Hou, Rui Liu, Yi Lv, Margaret McCooeye, Zoltán Mester Anal Chem . 2013 Apr 16;85(8):4087-93. doi: 10.1021/ac400158u.

Absolute quantitation of peptides/proteins in dilute calibration solutions used in various diagnostic settings is a major challenge. Here we report the absolute quantitation of peptides by non-species-specific isotope dilution liquid chromatography-inductively coupled plasma mass spectrometry (ID LC-ICPMS) based on stoichiometric Eu tagging. The method was validated by species-specific isotope dilution gas chromatography/mass spectrometry (GC/MS) analysis of constituent amino acids of the target peptide. Quantitative labeling of bradykinin peptide was accomplished with a commercially available 2',2″-(10-(2-((2,5-dioxopyrrolidin-1-yl)oxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl) triacetic acid (DOTA-NHS-ester) and subsequently tagged with Eu. A (151)Eu-enriched spike was used for the non-species-specific ID LC-ICPMS determination of bradykinin. The non-species-specific ID LC-ICPMS method was cross-validated by a species-specific ID GC/MS approach, which is based on the determination of phenylalanine in bradykinin to derive the concentration of the peptide in the sample. The hydrolysis of the peptide into amino acids was achieved by microwave digestion with 4 M methanesulfonic acid, and derivatization of phenylalanine with methyl chloroformate (MCF) was performed prior to its detection by GC/MS based on a (13)C-enriched phenylalanine spike. The accuracy of the method was confirmed at various concentration levels with a typical precision of better than 5% relative standard deviation (RSD) at 20 pmol for non-species-specific ID LC-ICPMS and 500 pmol for species-specific ID GC/MS. A detection limit (3 SD) of 7.2 fmol estimated for ID LC-ICPMS with a 10 μL injection volume from three procedure blanks was obtained for bradykinin, confirming the suitability of the method for the direct determination of peptides at trace levels. To the best of our knowledge, the proposed method is the first ICPMS peptide quantification strategy which employs an independent validation strategy using species-specific ID GC/MS for amino acid quantitation.

2. Design, synthesis and biological evaluation of new hybrid anticonvulsants derived from N-benzyl-2-(2,5-dioxopyrrolidin-1-yl)propanamide and 2-(2,5-dioxopyrrolidin-1-yl)butanamide derivatives

Anna Rapacz, Barbara Filipek, Katarzyna Kieć-Kononowicz, Krzysztof Kamiński, Gniewomir Latacz, Jarogniew J Łuszczki, Jolanta Obniska Bioorg Med Chem . 2015 May 15;23(10):2548-61. doi: 10.1016/j.bmc.2015.03.038.

The purpose of this study was to synthesize the library of 33 new N-benzyl-2-(2,5-dioxopyrrolidin-1-yl)propanamides, 2-(3-methyl-2,5-dioxopyrrolidin-1-yl)propanamides, and 2-(2,5-dioxopyrrolidin-1-yl)butanamides as potential new hybrid anticonvulsant agents. These hybrid molecules join the chemical fragments of well-known antiepileptic drugs (AEDs) such as ethosuximide, levetiracetam, and lacosamide. The coupling reaction of the 2-(2,5-dioxopyrrolidin-1-yl)propanoic acid, 2-(3-methyl-2,5-dioxopyrrolidin-1-yl)propanoic acid, or 2-(2,5-dioxopyrrolidin-1-yl)butanoic acid with the appropriately substituted benzylamines in the presence of the coupling reagent, N,N-carbonyldiimidazole (CDI) generated the final compounds 4-36. Spectral data acquired via (1)H NMR, (13)C NMR, and LC-MS confirmed the chemical structures of the newly prepared compounds. The initial anticonvulsant screening was performed in mice intraperitoneally (ip), using the maximal electroshock seizure (MES) and subcutaneous pentylenetetrazole (scPTZ) seizure tests. The rotarod test determined the acute neurological toxicity (NT). The results of preliminary pharmacological screening revealed that 25 compounds showed protection in half or more of the animals tested in the MES and/or scPTZ seizure models at the fixed dose of 100mg/kg. The broad spectra of activity across the preclinical seizure models displayed compounds 4, 7, 8, 13, 15-18, 24, and 26. The quantitative pharmacological studies in mice demonstrated the highest protection for compounds 4 (ED50 MES=67.65 mg/kg, ED50scPTZ=42.83 mg/kg); 8 (ED50 MES=54.90 mg/kg, ED50scPTZ=50.29 mg/kg); and 20 (ED50scPTZ=47.39 mg/kg). These compounds were distinctly more potent and provided better safety profiles in the rotarod test compared to valproic acid or ethosuximide, which were used as model AEDs. Compound 8 underwent only a slight metabolic change by the human liver microsomes (HLMs), and also did not affect the activity of human cytochrome P450 isoform, CYP3A4, in the in vitro assays.

Catalog	Product Name	CAS
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BADC-00520	2,5-Dioxopyrrolidin-1-yl 3-(benzyloxy)propanoate	1134280-63-9
BADC-00521	2,5-Dioxopyrrolidin-1-yl 3-((2-Fluorobenzyl)oxy)propanoate	1134280-64-0
BADC-00522	2,5-Dioxopyrrolidin-1-yl 3-((2,4-Difluorobenzyl)oxy)propanoate	1134280-65-1
BADC-00526	2,5-Dioxopyrrolidin-1-yl 4-((2-(1,3-Dioxoisoindolin-2-Yl)ethyl)disulfanyl)butanoate	1190203-91-8
BADC-00476	2,5-dioxopyrrolidin-1-yl 2-(dimethylamino)-4-(pyridin-2-yldisulfanyl)butanoate	1193111-73-7
BADC-00527	2,5-Dioxopyrrolidin-1-yl 3-(4-Methoxyphenoxy)propanoate	1199815-10-5
BADC-00429	2,5-dioxopyrrolidin-1-yl 7,10,13-trioxa-4-azahexadec-1-yn-16-oate	1214319-94-4