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Chemical name: 2-(2-Pyridithio)ethyl-p-nitrophenylcarbonate // Synonyms: oPy-SS-OPNP, 4-nitrophenyl 2-(2-pyridithio)ethyl carbonate, 4-nitrophenyl (2-(pyridin-2-yldisulfaneyl)ethyl) carbonate
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.
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
Stabilizing p-Dithiobenzyl Urethane Linkers without Rate-Limiting Self-Immolation for Traceless Drug Release; Y. Zheng, Y. Shen, X. Meng, Y. Wu, Y. Zhao and C. Wu; ChemMedChem 2019; 14: 1196-1203. https://doi.org/10.1002/cmdc.201900248
Discovery of an SSTR2-Targeting Maytansinoid Conjugate (PEN-221) with Potent Activity in Vitro and in Vivo; B. H. White, K. Whalen, K. Kriksciukaite, R. Alargova, T. Au Yeung, P. Bazinet, A. Brockman, M. DuPont, H. Oller, C. A. Lemelin, P. Lim Soo, B. Moreau, S. Perino, J. M. Quinn, G. Sharma, R. Shinde, B. Sweryda-Krawiec, R. Wooster and M. T. Bilodeau; Journal of medicinal chemistry 2019; 62: 2708-2719. https://doi.org/10.1021/acs.jmedchem.8b02036
Reduction-Triggered Transformation of Disulfide-Containing Micelles at Chemically Tunable Rates; Z. Deng, S. Yuan, R. X. Xu, H. Liang and S. Liu; Angew Chem Int Ed Engl 2018; 57: 8896-8900. https://doi.org/10.1002/anie.201802909
Biomarker-Based Metabolic Labeling for Redirected and Enhanced Immune Response; S. Li, B. Yu, J. Wang, Y. Zheng, H. Zhang, M. J. Walker, Z. Yuan, H. Zhu, J. Zhang, P. G. Wang and B. Wang; ACS Chem Biol 2018; 13: 1686-1694. https://doi.org/10.1021/acschembio.8b00350
Conjugation Chemistry-Dependent T-Cell Activation with Spherical Nucleic Acids; K. Skakuj, S. Wang, L. Qin, A. Lee, B. Zhang and C. A. Mirkin; J Am Chem Soc 2018; 140: 1227-1230. https://doi.org/10.1021/jacs.7b12579
Development of Efficient Chemistry to Generate Site-Specific Disulfide-Linked Protein- and Peptide-Payload Conjugates: Application to THIOMAB Antibody-Drug Conjugates; J. D. Sadowsky, T. H. Pillow, J. Chen, F. Fan, C. He, Y. Wang, G. Yan, H. Yao, Z. Xu, S. Martin, D. Zhang, P. Chu, J. Dela Cruz-Chuh, A. O'Donohue, G. Li, G. Del Rosario, J. He, L. Liu, C. Ng, D. Su, G. D. Lewis Phillips, K. R. Kozak, S. F. Yu, K. Xu, D. Leipold and J. Wai; Bioconjug Chem 2017; 28: 2086-2098. https://doi.org/10.1021/acs.bioconjchem.7b00258
Modulated Fragmentation of Proapoptotic Peptide Nanoparticles Regulates Cytotoxicity; T. Suma, J. Cui, M. Mullner, S. Fu, J. Tran, K. F. Noi, Y. Ju and F. Caruso; J Am Chem Soc 2017; 139: 4009-4018. https://doi.org/10.1021/jacs.6b11302
Design, synthesis, and evaluation of water-soluble morpholino-decorated paclitaxel prodrugs with remarkably decreased toxicity; S. Feng, K. Chen, C. Wang, X. Jiang, H. Dong, Z. Gong and K. Liu; Bioorg Med Chem Lett 2016; 26: 3598-602. https://doi.org/10.1016/j.bmcl.2016.06.012
An immunosuppressive antibody-drug conjugate; R. E. Wang, T. Liu, Y. Wang, Y. Cao, J. Du, X. Luo, V. Deshmukh, C. H. Kim, B. R. Lawson, M. S. Tremblay, T. S. Young, S. A. Kazane, F. Wang and P. G. Schultz; J Am Chem Soc 2015; 137: 3229-32. https://doi.org/10.1021/jacs.5b00620
A small-molecule drug conjugate for the treatment of carbonic anhydrase IX expressing tumors; N. Krall, F. Pretto, W. Decurtins, G. J. Bernardes, C. T. Supuran and D. Neri; Angew Chem Int Ed Engl 2014; 53: 4231-5. https://doi.org/10.1002/anie.201310709
Multifunctionalization of magnetic nanoparticles for controlled drug release: a general approach; A. Latorre, P. Couleaud, A. Aires, A. L. Cortajarena and A. Somoza; Eur J Med Chem 2014; 82: 355-62. https://doi.org/10.1016/j.ejmech.2014.05.078
Overcoming multidrug resistance of small-molecule therapeutics through conjugation with releasable octaarginine transporters; E. A. Dubikovskaya, S. H. Thorne, T. H. Pillow, C. H. Contag and P. A. Wender; Proc Natl Acad Sci U S A 2008; 105: 12128-33. https://doi.org/10.1073/pnas.0805374105
Conjugating Aptamber and Mitomycin C with Reductant-Responsive Linker Leading to Synergistically Enhanced Anticancer Effect; Q. Yang, Z. Deng, D. Wang, J. He, D. Zhang, Y. Tan, T. Peng, X.-Q. Wang, W. Tan; J. Am. Chem. Soc. 2020; 142(5): 2532-2540. https://doi.org/10.1021/jacs.9b12409.
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