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2,5-dioxopyrrolidin-1-yl 4-((5-nitropyridin-2-yl)disulfanyl)pentanoate

  CAS No.: 663598-61-6   Cat No.: BADC-00473   Purity: ≥98% 4.5  

2,5-dioxopyrrolidin-1-yl 4-((5-nitropyridin-2-yl)disulfanyl)pentanoate is a pyridyl disulfide-containing ADC linker with NHS ester function, designed for stable antibody attachment and selective intracellular release to improve antibody-drug conjugate therapeutic performance.

2,5-dioxopyrrolidin-1-yl 4-((5-nitropyridin-2-yl)disulfanyl)pentanoate

Structure of 663598-61-6

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Category
ADC Linker
Molecular Formula
C14H15N3O6S2
Molecular Weight
385.42
Shipping
Room temperature

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Synonyms
(2,5-dioxopyrrolidin-1-yl) 4-[(5-nitropyridin-2-yl)disulfanyl]pentanoate;
IUPAC Name
Canonical SMILES
CC(CCC(=O)ON1C(=O)CCC1=O)SSC2=NC=C(C=C2)[N+](=O)[O-]
InChI
InChI=1S/C14H15N3O6S2/c1-9(24-25-11-4-3-10(8-15-11)17(21)22)2-7-14(20)23-16-12(18)5-6-13(16)19/h3-4,8-9H,2,5-7H2,1H3
InChIKey
JFSJKWBYKAONEH-UHFFFAOYSA-N
Appearance
Soild powder
Shipping
Room temperature

2,5-Dioxopyrrolidin-1-yl 4-((5-nitropyridin-2-yl)disulfanyl)pentanoate, a unique chemical compound, finds significant applications in bioconjugation and molecular biology. Its ability to react with thiol groups enables it to form stable disulfide bonds, making it an essential tool in designing drug delivery systems. Conjugating drugs to specific molecules through disulfide bonds ensures that the drug is released in a controlled manner once it reaches the targeted site. This specificity enhances the efficacy and reduces the side effects of the drug, making it a valuable compound in pharmaceutical research and development.

In the field of proteomics, 2,5-dioxopyrrolidin-1-yl 4-((5-nitropyridin-2-yl)disulfanyl)pentanoate plays a crucial role in labeling and detecting protein interactions. By forming disulfide bridges with cysteine residues within proteins, it allows for the selective and stable attachment of probes used in mass spectrometry. This facilitates the identification and quantification of protein modifications and interactions, providing deeper insights into cellular functions and disease mechanisms. This application is critical for advancing our understanding of complex biological systems and for the development of new therapeutic strategies.

The compound is also extensively used in the development of biosensors. Its reactive disulfide group can be utilized to immobilize enzymes or other biomolecules onto sensor surfaces, creating highly sensitive and specific detection devices. These biosensors can detect a variety of analytes, from glucose in medical diagnostics to environmental pollutants. The robust and specific binding properties of 2,5-dioxopyrrolidin-1-yl 4-((5-nitropyridin-2-yl)disulfanyl)pentanoate ensure the longevity and reliability of these sensors, making them invaluable in both clinical and environmental monitoring applications.

Furthermore, 2,5-dioxopyrrolidin-1-yl 4-((5-nitropyridin-2-yl)disulfanyl)pentanoate is instrumental in synthesizing targeted therapies such as antibody-drug conjugates (ADCs). ADCs are a class of biopharmaceutical drugs designed as a targeted therapy for treating cancer. These conjugates work by linking a cytotoxic drug to an antibody via a disulfide bond, leveraging the antibody’s specificity to deliver the drug directly to cancer cells. This targeted approach minimizes damage to healthy cells and enhances the therapeutic index of the cytotoxic agents. As a result, this compound is critical in the ongoing efforts to develop more effective and less harmful cancer treatments.

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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