Amine-containing drugs often show poor pharmacological properties, but these disadvantages can be overcome by using a prodrug approach involving self-immolative linkers. Accordingly, we designed l-lactate linkers as ideal candidates for amine delivery. Furthermore, we designed linkers bearing two different cargos (aniline and phenol) for preferential amine cargo release within 15 min. Since the linkers carrying secondary amine cargo showed high stability at physiological pH, we used our strategy to prepare phosphate-based prodrugs of the antibiotic Ciprofloxacin. Therefore, our study will facilitate the rational design of new and more effective drug delivery systems for amine-containing drugs.

• Keywords
• 31P-NMR spectroscopy, amine-containing drugs, phosphate-based linkers, prodrugs, self-immolative linkers,
• MeSH
• Amines chemistry   MeSH
• Anti-Bacterial Agents chemistry   MeSH
• Ciprofloxacin chemistry   MeSH
• Phosphates chemistry   MeSH
• Hydrogen-Ion Concentration MeSH
• Lactic Acid chemistry   MeSH
• Pharmaceutical Preparations chemistry   MeSH
• Drug Delivery Systems methods   MeSH
• Prodrugs chemistry   MeSH
• Publication type
• Journal Article MeSH
• Names of Substances
• Amines MeSH
• Anti-Bacterial Agents MeSH
• Ciprofloxacin MeSH
• Phosphates MeSH
• Lactic Acid MeSH
• Pharmaceutical Preparations MeSH
• Prodrugs MeSH