OPSS-PAB-OpNC

Nombre químico: 2-(pyridin-2-yldisulfaneyl)ethyl (4-((((4-nitrophenoxy)carbonyl)oxy)methyl)phenyl)carbamate // Sinónimos: oPy-SS-PAB-OPNP

Nº Artículo:RL-3820
Nº CAS:2362536-70-5
Fórmula:C₂₂H₁₉N₃O₇S₂
Storage temperature:-20°C
Masa molecular:501,53 g/mol

from 200,00 €

Grouped product items
Unidad de venta	Precio	Unidad de almacenamiento de stock (SKU)	Disponibilidad
50 mg	200,00 €	RL-3820.0050	peticón
100 mg	350,00 €	RL-3820.0100	peticón
250 mg	700,00 €	RL-3820.0250	peticón

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description

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 (ëmax = 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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references

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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

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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

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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

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