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Tetrazine-Ph-SS-amine

  CAS No.:   Cat No.: BADC-01335   Purity: > 99% 4.5  

Tetrazine-Ph-SS-amine combines tetrazine for click chemistry, aromatic disulfide for cleavage, and amine functionality. Ideal for precise ADC conjugation and controlled drug release in antibody-drug conjugates.

Tetrazine-Ph-SS-amine

Structure of

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Category
ADC Linker
Molecular Formula
C14H18N6OS2
Molecular Weight
350.46
Shipping
Room temperature
Storage
-20°C

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

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Capabilities & Facilities

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IUPAC Name
Solubility
10 mm in DMSO
Shelf Life
-20°C 3 years powder; -80°C 2 years in solvent
Shipping
Room temperature
Storage
-20°C

Tetrazine-Ph-SS-amine is a highly functional ADC linker designed for advanced antibody-drug conjugate (ADC) construction and targeted bioconjugation. Featuring a tetrazine reactive group, a phenyl-disulfide (Ph-SS) cleavable unit, and a terminal amine, this linker enables rapid and selective bioorthogonal conjugation while incorporating a reduction-sensitive cleavage site. The Ph-SS disulfide bond allows controlled intracellular release of ADC cytotoxins within reducing environments, while the tetrazine group facilitates inverse-electron-demand Diels–Alder (IEDDA) reactions with trans-cyclooctene (TCO)-functionalized payloads. In ADC linker design, Tetrazine-Ph-SS-amine supports modular payload attachment and maintains antibody stability during conjugation.

In payload conjugation applications, Tetrazine-Ph-SS-amine is compatible with a wide range of ADC cytotoxins, including microtubule inhibitors, DNA-interacting agents, and other potent therapeutic molecules. The disulfide bond ensures selective intracellular cleavage, releasing the payload specifically in tumor cells. The tetrazine group allows rapid bioorthogonal attachment of azide or TCO-functionalized drugs, while the terminal amine provides additional reactive functionality for secondary modifications. The combination of cleavable disulfide and tetrazine chemistry facilitates the construction of homogeneous ADCs with optimized pharmacokinetics and controlled intracellular release profiles.

From an application perspective, Tetrazine-Ph-SS-amine is widely utilized in oncology-focused ADC research, protein bioconjugation studies, and reduction-sensitive drug delivery systems. Its combination of tetrazine reactivity, cleavable Ph-SS bond, and amine functionality ensures efficient, site-specific conjugation while preserving antibody integrity. Leveraging this linker in ADC designs allows the creation of stable, customizable linker-payload conjugates that deliver cytotoxic agents precisely within tumor cells, enhancing therapeutic precision and efficacy.

What is Tetrazine-Ph-SS-amine and its role in ADCs?

Tetrazine-Ph-SS-amine is a redox-sensitive linker containing a disulfide bond and a tetrazine moiety. It allows site-specific ADC conjugation and intracellular payload release in reducing environments such as the cytosol, exploiting disulfide cleavage for controlled drug delivery.

11/12/2019

We would like to know how Tetrazine-Ph-SS-amine enables controlled payload release.

The disulfide bond in Tetrazine-Ph-SS-amine is stable extracellularly but cleaved in the reducing intracellular environment. This cleavage releases the attached payload selectively within target cells, minimizing off-target toxicity while maintaining ADC stability in plasma.

12/2/2018

We would like to know which conjugation chemistry is used with Tetrazine-Ph-SS-amine.

Conjugation occurs via inverse electron-demand Diels-Alder reaction between the tetrazine and strained alkenes on the antibody or payload. The disulfide segment provides redox-sensitive release, allowing combination of site-specific conjugation and stimuli-responsive delivery.

3/9/2020

Good morning! What considerations are critical when using Tetrazine-Ph-SS-amine in ADCs?

Key considerations include controlling the reduction potential during formulation, verifying conjugation efficiency, and ensuring the disulfide bond remains intact until internalization. Proper handling preserves linker stability and predictable payload release.

7/7/2021

Good morning! What quality control tests are recommended for Tetrazine-Ph-SS-amine?

Quality control for Tetrazine-Ph-SS-amine typically involves HPLC for purity assessment, NMR for structural verification, and mass spectrometry to confirm molecular weight. These tests ensure the disulfide-containing linker meets structural and functional expectations for ADC synthesis without specifying exact purity values.

12/9/2018

— Dr. Sarah Collins, Protein Chemist (USA)

Tetrazine-Ph-SS-amine linker provided efficient bioorthogonal conjugation with controlled disulfide cleavage.

3/9/2020

— Prof. Markus Fischer, Medicinal Chemist (Germany)

High-purity Tetrazine-Ph-SS-amine enabled reproducible ADC synthesis and payload release.

12/9/2018

— Dr. Claudia Rossi, ADC Scientist (Italy)

BOC Sciences delivered the linker with excellent documentation and batch consistency.

7/7/2021

— Ms. Emily Parker, R&D Manager (UK)

Using this linker, we achieved reproducible conjugation and controlled intracellular payload release.

11/12/2019

— Dr. Henrik Larsen, Bioconjugation Specialist (Denmark)

The Ph-SS moiety provided controlled cleavage, improving ADC design flexibility.

— Mr. Felix Johnson, Senior Scientist (France)

Tetrazine-Ph-SS-amine linker consistently performed well in bioorthogonal and disulfide-sensitive applications.

12/2/2018

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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