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2,5-dioxopyrrolidin-1-yl 4-((3-(dimethylcarbamoyl)pyridin-4-yl)disulfanyl)pentanoate

  CAS No.: 663599-10-8   Cat No.: BADC-00470   Purity: ≥98% 4.5  

2,5-dioxopyrrolidin-1-yl 4-((3-(dimethylcarbamoyl)pyridin-4-yl)disulfanyl)pentanoate features cleavable disulfide and NHS ester groups, allowing precise antibody-payload conjugation and controlled intracellular release to enhance ADC targeting and cytotoxicity in cancer treatment.

2,5-dioxopyrrolidin-1-yl 4-((3-(dimethylcarbamoyl)pyridin-4-yl)disulfanyl)pentanoate

Structure of 663599-10-8

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Category
ADC Linker
Molecular Formula
C17H21N3O5S2
Molecular Weight
411.50
Shipping
-20°C (International: -20°C)

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Synonyms
(2,5-dioxopyrrolidin-1-yl) 4-[[3-(dimethylcarbamoyl)pyridin-4-yl]disulfanyl]pentanoate;
IUPAC Name
Canonical SMILES
CC(CCC(=O)ON1C(=O)CCC1=O)SSC2=C(C=NC=C2)C(=O)N(C)C
InChI
InChI=1S/C17H21N3O5S2/c1-11(4-7-16(23)25-20-14(21)5-6-15(20)22)26-27-13-8-9-18-10-12(13)17(24)19(2)3/h8-11H,4-7H2,1-3H3
InChIKey
AFGUQHOCEUTKEQ-UHFFFAOYSA-N
Appearance
Soild powder
Shipping
-20°C (International: -20°C)

One key application of 2,5-dioxopyrrolidin-1-yl 4-((3-(dimethylcarbamoyl)pyridin-4-yl)disulfanyl)pentanoate is in biochemical research as a cross-linking reagent. Cross-linking reagents are pivotal in studying protein-protein interactions, providing insights into the spatial arrangement and functional connectivity within protein complexes. This compound can be particularly useful in stabilizing transient protein interactions, which are often difficult to study using conventional techniques. By creating stable covalent bonds between interacting proteins, researchers can more easily isolate and identify the components of complex biochemical pathways. This application is especially valuable in understanding diseases at the molecular level, enabling the development of targeted therapeutic strategies.

Another significant application of 2,5-dioxopyrrolidin-1-yl 4-((3-(dimethylcarbamoyl)pyridin-4-yl)disulfanyl)pentanoate is in the synthesis of antibody-drug conjugates (ADCs). ADCs are an innovative class of biopharmaceutical drugs designed to selectively target and kill cancer cells while minimizing damage to normal tissues. The compound serves as a linker that connects cytotoxic drugs to monoclonal antibodies, which specifically bind to cancer cell antigens. The disulfide bond within the structure is particularly advantageous as it offers a controlled release mechanism—once inside the target cell, the bond can be cleaved, releasing the cytotoxic agent to exert its therapeutic effect. This precise targeting capability enhances the efficacy and safety profile of cancer treatments.

The compound also finds application in the field of targeted protein degradation, specifically in the development of proteolysis-targeting chimeras (PROTACs). PROTACs are molecules designed to selectively degrade specific proteins by harnessing the cell’s ubiquitin-proteasome system. In this context, 2,5-dioxopyrrolidin-1-yl 4-((3-(dimethylcarbamoyl)pyridin-4-yl)disulfanyl)pentanoate can be used as a linker that joins a ligand capable of binding the target protein with another ligand that recruits an E3 ubiquitin ligase. This bifunctional molecule brings the target protein into proximity with the ubiquitin-proteasome machinery, resulting in its degradation. This approach offers a novel therapeutic strategy, especially for treating diseases caused by aberrant protein function, such as cancer and neurodegenerative disorders.

Additionally, this compound can be employed in the realm of redox biology as a disulfide exchange reagents. Disulfide exchange reactions are crucial in the formation and isomerization of disulfide bonds, which play a vital role in protein folding and stability. The presence of a disulfide bond in 2,5-dioxopyrrolidin-1-yl 4-((3-(dimethylcarbamoyl)pyridin-4-yl)disulfanyl)pentanoate allows it to act as a modulator of thiol-disulfide balance within cells. This capability can be exploited to probe cellular redox states and to study the mechanisms of diseases related to oxidative stress. Furthermore, manipulating disulfide bonds in peptides and proteins using this reagent can lead to the development of novel biopharmaceuticals with improved stability and activity profiles.

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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