Chemical name: 2-(pyridin-2-yldisulfaneyl)ethyl (4-(hydroxymethyl)phenyl)carbamate // Synonyms: oPy-SS-PAB

  • Product code:RL-3890
  • CAS No.:2362536-42-1
  • Formula:C15H16N2O3S2
  • Molecular weight:336,42 g/mol

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This compound can be easily converted in situ into the corresponding chloro derivative and then coupled to a molecule containing a tertiary amine.

The linkage of a drug to its carrier via a disulfide-based self-immolative linker allows for the specific intracellular release of the active molecule upon glutathione reduction and linker cleavage. The overall red/ox potential in the human blood is oxidative, making disulfide linkages stable during circulation. In contrast, the intracellular milieu of mammalian cells is characterized by an overall reductive potential, thus allowing to revert the disulfide bond formation. Pyridyl disulfides undergo a disulfide exchange reaction with sulfhydryl groups to form disulfide bonds over a broad pH range also suitable for physiological pH. During the reaction, a disulfide exchange occurs between the biomolecule’s thiol group and the reagent’s 2-pyridyldithiol group. As a result, pyridine-2-thione is released, which can be followed spectrophotometrically (λmax = 343 nm) to monitor the progress of the reaction. The p-nitrophenylcarbonate activating group reacts preferably with amines or other nucleophiles and allows further derivatization, e.g. with the desired drug molecule.

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Disulfide-Based Self-Immolative Linkers and Functional Bioconjugates for Biological Applications; Z. Deng, J. Hu and S. Liu; Macromol Rapid Commun 2020; 41: e1900531. https://doi.org/10.1002/marc.201900531

Targeted drug delivery through the traceless release of tertiary and heteroaryl amines from antibody-drug conjugates; L. R. Staben, S. G. Koenig, S. M. Lehar, R. Vandlen, D. Zhang, J. Chuh, S.-F. Yu, C. Ng, J. Guo, Y. Liu, A. Fourie-O’Donohue, M. Go, X. Linghu, N. L. Segraves, T. Wang, J. Chen, B. Wei, G. D. Lewis Phillips, K. Xu, K. R. Kozak, S. Mariathasan, J. A. Flygare, T. H. Pillow; Nat. Chem. 2016; 8: 1112-1119. https://doi.org/10.1038/nchem.2635

Novel N-Methylated Cyclodepsipeptide Prodrugs for Targeted Cancer Therapy; C. Wu, Z. Cheng, D. Lu, K. Liu, Y. Cheng, P. Wang, Y. Zhou, M. Li, X. Shao, H. Li, W. Su, L. Fang; J. Med. Chem. 2021; 64(2): 991-1000. https://doi.org/10.1021/acs.jmedchem.0c01387

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