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

  CAS No.: 890409-87-7   Cat No.: BADC-00471   Purity: ≥98% 4.5  

3-(methylsulfonyl)-2,5-dioxopyrrolidin-1-yl 4-((5-nitropyridin-2-yl)disulfanyl)pentanoate enables stable antibody conjugation through NHS ester and disulfide chemistry, allowing tumor-triggered payload release and improved therapeutic efficacy in ADC cancer therapy.

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

Structure of 890409-87-7

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Category
ADC Linker
Molecular Formula
C15H17N3O8S3
Molecular Weight
463.51
Shipping
-20°C (International: -20°C)

* For research and manufacturing use only. We do not sell to patients.

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Popular Publications Citing BOC Sciences Products
Synonyms
(3-methylsulfonyl-2,5-dioxopyrrolidin-1-yl) 4-[(5-nitropyridin-2-yl)disulfanyl]pentanoate;
IUPAC Name
Canonical SMILES
CC(CCC(=O)ON1C(=O)CC(C1=O)S(=O)(=O)C)SSC2=NC=C(C=C2)[N+](=O)[O-]
InChI
InChI=1S/C15H17N3O8S3/c1-9(27-28-12-5-4-10(8-16-12)18(22)23)3-6-14(20)26-17-13(19)7-11(15(17)21)29(2,24)25/h4-5,8-9,11H,3,6-7H2,1-2H3
InChIKey
QGJALSNSJKAIFI-UHFFFAOYSA-N
Appearance
Soild powder
Shipping
-20°C (International: -20°C)

3-(methylsulfonyl)-2,5-dioxopyrrolidin-1-yl 4-((5-nitropyridin-2-yl)disulfanyl)pentanoate is a heterobifunctional ADC linker designed for thiol-reactive conjugation. The 5-nitropyridin-2-yl disulfide moiety enables selective payload release under reductive tumor conditions, while the methylsulfonyl-activated NHS ester facilitates efficient coupling to antibody amines. The pentanoate spacer provides flexibility and reduces steric interference in ADC linker design.

In ADC payload applications, the disulfide group allows controlled cytotoxin release inside target cells. The linker maintains solubility, preserves antibody-antigen interaction, and supports consistent drug-to-antibody ratios (DAR) and reproducible pharmacokinetics.

3-(methylsulfonyl)-2,5-dioxopyrrolidin-1-yl 4-((5-nitropyridin-2-yl)disulfanyl)pentanoate is compatible with a variety of cytotoxic payloads, including auristatins and DNA-damaging agents. Its stability in plasma and reductive cleavage in the tumor microenvironment ensure targeted payload delivery.

This linker is applied in ADC research requiring reliable thiol-specific conjugation, controlled payload release, and reproducible synthesis of antibody-drug conjugates for oncology therapeutics.

What is 3-(methylsulfonyl)-2,5-dioxopyrrolidin-1-yl 4-((5-nitropyridin-2-yl)disulfanyl)pentanoate and its role in ADCs?

This compound is a bifunctional disulfide linker with a reactive NHS ester, designed for conjugation of amine-containing antibodies and thiol-containing payloads. The disulfide moiety enables controlled intracellular release of cytotoxins in ADCs.

12/2/2018

Dear team, how does this linker facilitate intracellular payload release?

The disulfide bond is cleavable under intracellular reducing conditions, allowing selective release of the payload within target cells, enhancing ADC specificity while remaining stable in systemic circulation.

22/12/2021

Dear team, what payloads are suitable for this disulfide linker?

It can conjugate cytotoxins, peptides, and small molecules with thiol or amine groups. The linker maintains ADC solubility and reduces steric hindrance due to its pentanoate and PEG-like structure.

29/9/2016

Good morning! What are the optimal conditions for conjugation?

Perform conjugation in polar aprotic solvents or buffered aqueous solutions (pH 7–8) at controlled temperatures to maximize NHS ester reactivity while preventing premature disulfide reduction.

12/6/2021

Good morning! How should 3-(methylsulfonyl)-2,5-dioxopyrrolidin-1-yl 4-((5-nitropyridin-2-yl)disulfanyl)pentanoate be stored and handled for optimal stability?

This compound should be stored at low temperatures in airtight containers under inert atmosphere. Avoid exposure to light and moisture. Proper handling includes using gloves and avoiding prolonged exposure to air to prevent premature hydrolysis or loss of functional groups essential for ADC conjugation.

29/8/2020

— Dr. Olivia Brown, Senior Researcher (UK)

This linker offered excellent reactivity and stability in ADC development, making 3-(methylsulfonyl)-2,5-dioxopyrrolidin-1-yl 4-((5-nitropyridin-2-yl)disulfanyl)pentanoate an ideal choice.

29/9/2016

— Mr. David Wilson, Chemistry Scientist (USA)

Batch-to-batch consistency of this product allowed seamless integration into our workflow.

29/8/2020

— Dr. Sofia Rossi, Biochemist (Italy)

3-(methylsulfonyl)-2,5-dioxopyrrolidin-1-yl 4-((5-nitropyridin-2-yl)disulfanyl)pentanoate performed reliably in multi-step conjugations.

12/6/2021

— Ms. Hannah Schmidt, ADC Scientist (Germany)

We achieved high conjugation efficiency with minimal optimization using this linker.

12/2/2018

— Dr. Mark Taylor, Bioconjugation Specialist (Canada)

Documentation and QC reports were comprehensive, supporting regulatory submissions.

— Prof. Claire Dubois, Chemical Biologist (France)

This reagent performed exceptionally in our cross-linking experiments. BOC Sciences’ 3-(methylsulfonyl)-2,5-dioxopyrrolidin-1-yl 4-((5-nitropyridin-2-yl)disulfanyl)pentanoate met all our specifications and delivery was prompt.

22/12/2021

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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