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N3-Cystamine-Suc-OSu

  CAS No.: 1987341-40-1   Cat No.: BADC-01807 4.5  

N3-Cystamine-Suc-OSu is an azide-functionalized cleavable disulfide ADC linker intermediate with NHS ester reactivity, facilitating site-specific antibody conjugation and controlled intracellular payload release in ADCs.

N3-Cystamine-Suc-OSu

Structure of 1987341-40-1

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ADC Linker
Molecular Formula
C12H17N5O5S2
Molecular Weight
375.42

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

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Popular Publications Citing BOC Sciences Products
IUPAC Name
(2,5-dioxopyrrolidin-1-yl) 4-[2-(2-azidoethyldisulfanyl)ethylamino]-4-oxobutanoate
Canonical SMILES
C1CC(=O)N(C1=O)OC(=O)CCC(=O)NCCSSCCN=[N+]=[N-]
InChI
InChI=1S/C12H17N5O5S2/c13-16-15-6-8-24-23-7-5-14-9(18)1-4-12(21)22-17-10(19)2-3-11(17)20/h1-8H2,(H,14,18)
InChIKey
IUENXPTVPBUBED-UHFFFAOYSA-N

N3-Cystamine-Suc-OSu is a compound that combines cystamine, a disulfide-containing compound, with a succinyl group (Suc) and an N-hydroxysuccinimide ester (OSu) functionality. This structure imparts a range of useful properties, including the ability to form covalent bonds with nucleophilic groups, such as thiols in proteins or peptides. N3-Cystamine-Suc-OSu is widely utilized in bioconjugation and drug delivery applications due to its high reactivity, versatility, and ability to target specific biomolecules. Its design allows for selective attachment to biomolecules, making it valuable for a variety of therapeutic and research purposes.

One of the primary applications of N3-Cystamine-Suc-OSu is in the development of targeted drug delivery systems. The cystamine unit, with its disulfide bond, can be selectively cleaved in the reducing environment of cancer cells or certain disease tissues, leading to the release of the conjugated drug. The succinyl and OSu groups enable efficient conjugation to a wide variety of therapeutic agents, including peptides, antibodies, and small molecules. By linking these agents to N3-Cystamine-Suc-OSu, researchers can develop drugs that are activated in specific cellular environments, enhancing drug efficacy and minimizing systemic toxicity.

Another important application of N3-Cystamine-Suc-OSu is in protein labeling and modification. The compound’s high reactivity towards thiol groups makes it an ideal reagent for covalently attaching labels or functional groups to proteins, antibodies, or peptides. This feature is especially useful in the creation of protein-based diagnostic tools, where the addition of fluorescent or enzymatic tags allows for the detection and quantification of target proteins. The succinyl group further enhances the solubility of the compound, making it suitable for use in a wide range of bioconjugation reactions.

N3-Cystamine-Suc-OSu also plays a crucial role in the synthesis of disulfide-linked bioconjugates. The cystamine component, with its two thiol-reactive arms, allows for the formation of stable disulfide bonds, which can be used to link biomolecules together. This property is particularly useful in the design of antibody-drug conjugates (ADCs) and other biotherapeutic agents, where the disulfide bond provides a reversible link that is cleaved under specific conditions, such as within the tumor microenvironment. By using N3-Cystamine-Suc-OSu, researchers can create ADCs that selectively release their cytotoxic payloads in response to environmental cues, improving therapeutic outcomes.

Additionally, N3-Cystamine-Suc-OSu is valuable in the development of crosslinked polymers and hydrogels for drug delivery. The compound can be incorporated into polymeric networks to create materials that respond to changes in the cellular or extracellular environment. For example, the disulfide linkage can be cleaved in the presence of reducing agents, allowing the controlled release of drugs or biologically active molecules from the polymer matrix. This makes N3-Cystamine-Suc-OSu an important component in the design of responsive drug delivery systems and bioactive materials.

What is N3-Cystamine-Suc-OSu and its role in ADC construction?

N3-Cystamine-Suc-OSu is a bifunctional linker featuring an azide group and a disulfide bond for reducible conjugation in ADCs. It allows attachment of payloads to antibodies with controlled intracellular release triggered by the reductive environment of target cells.

6/8/2021

We would like to know how N3-Cystamine-Suc-OSu facilitates payload release.

The disulfide bond in N3-Cystamine-Suc-OSu is cleavable in intracellular reducing environments, such as high glutathione concentrations in tumor cells, enabling site-specific release of the cytotoxic drug while remaining stable in circulation.

29/8/2017

We would like to know what conjugation chemistries are compatible with N3-Cystamine-Suc-OSu.

This linker is reactive toward primary amines via the N-hydroxysuccinimide (OSu) ester and can participate in azide-alkyne click chemistry, allowing versatile attachment to antibodies and payloads with controlled orientation.

7/8/2021

Good afternoon! What precautions are required for handling N3-Cystamine-Suc-OSu?

Due to the reactivity of the OSu ester and disulfide bond, N3-Cystamine-Suc-OSu should be handled under inert, anhydrous conditions. Light and moisture exposure should be minimized to prevent degradation before conjugation.

9/9/2021

Good afternoon! What storage conditions are recommended for N3-Cystamine-Suc-OSu to maintain stability?

N3-Cystamine-Suc-OSu should be stored at low temperature, typically -20°C, in a dry and inert atmosphere to prevent hydrolysis and degradation. Avoid repeated freeze-thaw cycles and prolonged exposure to moisture or light to preserve its chemical integrity and reactivity.

24/12/2017

— Dr. Emily Carter, Senior Scientist (USA)

N3-Cystamine-Suc-OSu linker provided excellent azide functionality for click chemistry conjugations.

7/8/2021

— Prof. David Müller, Medicinal Chemist (Germany)

BOC Sciences’ N3-Cystamine-Suc-OSu showed high purity and batch consistency, enabling reproducible results.

24/12/2017

— Dr. Anna Rossi, Bioconjugation Specialist (Italy)

The disulfide and azide functionalities facilitated controlled payload release and conjugation.

9/9/2021

— Mr. James Thompson, R&D Manager (UK)

Using N3-Cystamine-Suc-OSu, we achieved efficient and reproducible ADC yields.

6/8/2021

— Dr. Laura Jensen, ADC Project Lead (Denmark)

Excellent solubility and reactivity improved our high-throughput conjugation workflow.

— Ms. Sophie Martin, Senior Researcher (France)

High-quality linker and timely delivery allowed us to meet project deadlines.

29/8/2017

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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