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NHS-SS-Ph

  CAS No.: 2750799-12-1   Cat No.: BADC-01630 4.5  

NHS-SS-Ph is a cleavable ADC linker featuring a disulfide bond and NHS ester for stable antibody conjugation and controlled intracellular drug release in targeted cancer therapies.

NHS-SS-Ph

Structure of 2750799-12-1

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Category
ADC Linker
Molecular Formula
C16H17NO7S2
Molecular Weight
399.44

* 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-[2-(2,5-dioxopyrrolidin-1-yl)oxycarbonyloxyethyldisulfanyl]ethyl benzoate
Canonical SMILES
C1CC(=O)N(C1=O)OC(=O)OCCSSCCOC(=O)C2=CC=CC=C2
InChI
InChI=1S/C16H17NO7S2/c18-13-6-7-14(19)17(13)24-16(21)23-9-11-26-25-10-8-22-15(20)12-4-2-1-3-5-12/h1-5H,6-11H2
InChIKey
VCMZIGLIZQEWHS-UHFFFAOYSA-N
Appearance
Colorless to light yellow Oil

NHS-SS-Ph is a specialized ADC linker reagent widely used in the development of antibody-drug conjugates (ADCs) and targeted bioconjugation applications. Featuring a disulfide (SS) bond and an N-hydroxysuccinimide (NHS) ester, this linker enables site-specific conjugation to primary amines on monoclonal antibodies or ADC cytotoxins. The phenyl (Ph) group provides structural stability and hydrophobicity, while the disulfide bond allows controlled intracellular cleavage for payload release in tumor cells. In ADC linker design, NHS-SS-Ph facilitates predictable, efficient, and modular conjugation strategies while preserving antibody functionality.

In payload conjugation applications, NHS-SS-Ph is compatible with a wide variety of ADC cytotoxins, including microtubule inhibitors, DNA-targeting agents, and other potent therapeutic payloads. The NHS ester ensures rapid, reproducible, and mild conjugation to antibodies, while the disulfide bond allows selective cleavage under intracellular reducing conditions, enabling controlled release of the cytotoxic payload. The phenyl spacer supports linker stability and reduces steric hindrance, facilitating homogeneous ADC construction. Researchers can use NHS-SS-Ph to optimize linker length, improve payload delivery, and construct high-performance ADCs suitable for preclinical and industrial applications.

From an application perspective, NHS-SS-Ph is extensively utilized in oncology-focused ADC research, targeted drug delivery systems, and protein bioconjugation studies. Its combination of NHS ester, disulfide bond, and phenyl spacer allows efficient, site-specific, and flexible conjugation strategies while maintaining antibody structure and activity. By incorporating NHS-SS-Ph into ADC linker design, developers can construct stable, cleavable, and effective linker-payload conjugates, supporting tumor-specific delivery, enhanced pharmacokinetics, and improved therapeutic performance in modern ADC development.

What is NHS-SS-Ph used for in ADC development?

NHS-SS-Ph is a disulfide-containing bifunctional linker with an NHS ester for amine conjugation. It allows the attachment of cytotoxic payloads to antibodies and facilitates intracellular release via disulfide cleavage in reducing environments.

3/9/2018

We are interested in how stable NHS-SS-Ph is during storage.

NHS-SS-Ph should be stored at -20°C under inert conditions and protected from moisture. The disulfide and NHS ester groups remain stable under proper storage, ensuring reproducible conjugation efficiency in ADC synthesis.

10/8/2018

We are interested in which conjugation reactions are compatible with NHS-SS-Ph.

NHS-SS-Ph reacts with primary amines on antibodies through its NHS ester. The disulfide bond allows controlled intracellular cleavage, making it suitable for constructing reducible ADC linkers with precise drug release properties.

1/12/2019

Good afternoon! Can NHS-SS-Ph be used in preclinical ADC studies?

Yes, NHS-SS-Ph has been successfully applied in preclinical ADC development. The disulfide linker ensures stability in circulation and efficient release of the payload in the reducing intracellular environment of target cells.

1/11/2022

Good afternoon! What detection and analytical methods are recommended for NHS-SS-Ph?

NHS-SS-Ph identity and reactivity can be confirmed using NMR spectroscopy, mass spectrometry, and HPLC. These techniques allow verification of the disulfide-containing structure and NHS ester functionality, ensuring reliable performance in conjugation reactions and maintaining stability under controlled reaction conditions.

14/12/2018

— Dr. Michael Brown, Protein Chemist (USA)

NHS-SS-Ph linker from BOC Sciences was supplied with high purity, enabling clean ADC conjugations. Very satisfied with the results.

1/12/2019

— Prof. Isabelle Dupont, Biochemist (France)

The disulfide-containing NHS-SS-Ph allowed precise payload release under intracellular conditions. Quality and delivery were reliable.

14/12/2018

— Dr. Thomas Keller, ADC Developer (Germany)

Batch reproducibility of NHS-SS-Ph was remarkable, ensuring consistent conjugation efficiency across multiple projects.

1/11/2022

— Ms. Rachel Evans, Research Scientist (UK)

The linker’s solubility profile was ideal for our aqueous conjugation protocols. NHS-SS-Ph performed as advertised.

3/9/2018

— Dr. Sofia Lindberg, Medicinal Chemist (Sweden)

BOC Sciences provided excellent technical support along with NHS-SS-Ph. Delivery timing was perfect for our critical experiments.

— Mr. Alex Johnson, Bioconjugation Analyst (Canada)

Using NHS-SS-Ph linker improved payload stability and conjugation reproducibility. Excellent overall service.

10/8/2018

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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