Steric and stereoscopic disulfide construction for cross-linkage via N-dithiophthalimides
Disulfide bonds are a significant motif in life and drug-delivery systems. In particular, steric hindrance and stereoscopic disulfide linkers are closely associated with the stability of antibody-drug conjugates, which affects the potency, selectivity, and pharmacokinetics of drugs. However, limited...
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| Veröffentlicht in: | Chemical science (Cambridge) 2020-04, Vol.11 (15), p.3903-3908 |
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| creator | Gao, Wen-Chao Tian, Jun Shang, Yu-Zhu Jiang, Xuefeng |
| description | Disulfide bonds are a significant motif in life and drug-delivery systems. In particular, steric hindrance and stereoscopic disulfide linkers are closely associated with the stability of antibody-drug conjugates, which affects the potency, selectivity, and pharmacokinetics of drugs. However, limited availability and diversity of tertiary thiols impede the construction of steric and stereoscopic disulfides for cross-linkage in biochemistry and pharmaceuticals. Through modulating the mask effect of disulfurating reagents, we develop a facile and robust strategy for construction of diverse steric and stereoscopic disulfides via N-dithiophthalimides. The practical cross-linkage of biomolecules including amino acids, saccharides, and nucleosides with different drugs and fluorescent molecules is successfully established through hindered disulfide linkers. |
| doi_str_mv | 10.1039/d0sc01060j |
| format | Article |
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| subjects | Amino acids Antibodies Biomolecules Carbohydrates Chemistry Chemistry, Multidisciplinary Crosslinking Crystallography Disulfides Drug delivery systems Drugs Fluorescence NMR Nuclear magnetic resonance Physical Sciences Reagents Science & Technology Selectivity Stereoscopy Steric hindrance Thiols |
| title | Steric and stereoscopic disulfide construction for cross-linkage via N-dithiophthalimides |
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