1-(4-((5-nitropyridin-2-yl)disulfanyl)butanoyloxy)-2,5-dioxopyrrolidine-3-sulfonic acid

  Cat No.: BADC-00479   Purity: ≥98% 4.5  

1-(4-((5-nitropyridin-2-yl)disulfanyl)butanoyloxy)-2,5-dioxopyrrolidine-3-sulfonic acid is a disulfide-containing crosslinker or linker building block for redox-responsive bioconjugation and ADC-related linker design. The disulfide bond provides a reduction-sensitive element, while the terminal reactive groups enable attachment to appropriately functionalized biomolecules or small-molecule partners. The molecule uses nhs/succinimidyl ester (amine-reactive) for antibody lysines/primary amines (common orientation) on one side and pyridyl-disulfide / activated disulfide handle for thiol-containing payloads or thiol exchange partners on the other, with disulfide trigger with c4/alkyl spacer segment providing the spacer/cleavable region. Conjugation orientation and reduction sensitivity should be evaluated in the context of the final construct because local substitution and neighboring groups can influence disulfide behavior.

1-(4-((5-nitropyridin-2-yl)disulfanyl)butanoyloxy)-2,5-dioxopyrrolidine-3-sulfonic acid

Structure of 663598-89-8

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Category
ADC Linker
Molecular Formula
C13H13N3O9S3
Molecular Weight
451.45
Shipping
Room temperature

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Synonyms
1-[4-[(5-nitropyridin-2-yl)disulfanyl]butanoyloxy]-2,5-dioxopyrrolidine-3-sulfonic acid;
IUPAC Name
SMILES
C1C(C(=O)N(C1=O)OC(=O)CCCSSC2=NC=C(C=C2)[N+](=O)[O-])S(=O)(=O)O
InChI
InChI=1S/C13H13N3O9S3/c17-11-6-9(28(22,23)24)13(19)15(11)25-12(18)2-1-5-26-27-10-4-3-8(7-14-10)16(20)21/h3-4,7,9H,1-2,5-6H2,(H,22,23,24)
InChIKey
AJTQYMNCOAZOGJ-UHFFFAOYSA-N
Appearance
Soild powder
Shipping
Room temperature

1-(4-((5-nitropyridin-2-yl)disulfanyl)butanoyloxy)-2,5-dioxopyrrolidine-3-sulfonic acid is a chemical compound with specialized applications in biochemical research and industrial processes. Here are some key applications of this compound:

Protein Labeling and Modification: This compound can be used to label and modify proteins through the disulfide bond. By attaching this molecule to specific cysteine residues on proteins, researchers can change the protein's functionality or track its location in cellular studies. This technique is vital for understanding protein dynamics and interactions.

Enzyme Inhibition Studies: This compound can act as an inhibitor for certain enzymes that interact with disulfide bonds or similar structures. By studying the inhibition effects of this molecule, scientists can gain insights into enzyme mechanisms and identify potential drug targets. This is crucial for the development of therapeutic agents against diseases involving these enzymes.

Redox Biology and Chemistry: The disulfide bond in this compound makes it useful for studies in redox biology, where the focus is on the oxidative and reductive processes in cells. Researchers can use it to probe redox-sensitive elements within biological systems. This enables the investigation of cellular stress responses and the development of antioxidant therapies.

Drug Delivery Systems: This compound can be incorporated into drug delivery systems that require precise release mechanisms. The disulfide bond can be selectively cleaved in reductive environments, allowing for targeted release of therapeutics within specific cellular compartments. This targeted approach enhances the efficacy and safety of drug delivery.

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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Historical Records: 3-(methylsulfonyl)-2,5-dioxopyrrolidin-1-yl 4-((5-nitropyridin-2-yl)disulfanyl)butanoate | Azonafide-PEABA | γ-Amanitin | MC-Val-Cit-PAB-Auristatin E | 1-{[4-({4-[(2,5-dioxo-3-sulfopyrrolidin-1-yl)oxy]-4-oxobutyl}disulfanyl)butanoyl]oxy}-2,5-dioxopyrrolidine-3-sulfonic acid | Hemiasterlin | MAC glucuronide α-hydroxy lactone-linked SN-38 | MC-Gly-Gly-{D-Phe}-Gly-NH-CH2-O-CH2COOH | Dideoxy-amanitin | 2,5-dioxo-1-(3-(pyridin-2-yldisulfanyl)propanoyloxy)pyrrolidine-3-sulfonic acid | 1-(4-((5-nitropyridin-2-yl)disulfanyl)butanoyloxy)-2,5-dioxopyrrolidine-3-sulfonic acid
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