Disulfide/α-Amide-Bridged Doxorubicin Dimeric Prodrug : Effect of Aggregation Structures on pH/GSH Dual-Triggered Drug Release
Disulfide bonding has attracted intense interest in the tumor intracellular microenvironment-activated drug delivery systems (DDSs) in the last decades. Although various molecular structures of redox-responsive disulfide-containing DDSs have been developed, no investigation was reported on the effec...
| Veröffentlicht in: | Langmuir : the ACS journal of surfaces and colloids. - 1985. - 40(2024), 21 vom: 28. Mai, Seite 11098-11105 |
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| Format: | Online-Aufsatz |
| Sprache: | English |
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2024
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| Zugriff auf das übergeordnete Werk: | Langmuir : the ACS journal of surfaces and colloids |
| Schlagworte: | Journal Article Prodrugs Doxorubicin 80168379AG Disulfides Glutathione GAN16C9B8O Amides Drug Carriers |
| Zusammenfassung: | Disulfide bonding has attracted intense interest in the tumor intracellular microenvironment-activated drug delivery systems (DDSs) in the last decades. Although various molecular structures of redox-responsive disulfide-containing DDSs have been developed, no investigation was reported on the effect of aggregation structures. Here, the effect of aggregation structures on pH/GSH dual-triggered drug release was investigated with the simplest pH/GSH dual-triggered doxorubicin-based drug self-delivery system (DSDS), the disulfide/α-amide-bridged doxorubicin dimeric prodrug (DDOX), as a model. By fast precipitation or slow self-assembly, DDOX nanoparticles were obtained. With similar diameters, they exhibited different pH/GSH dual-triggered drug releases, demonstrating the effect of aggregation structures. The π-π stacking in different degrees was revealed by the UV-vis, fluorescence, and BET analysis of the DDOX nanoparticles. The effect of the π-π stacking between the dimeric prodrug and its activated products on drug release was also explored with the molecular simulation approach. The finding opens new ideas in the design of high-performance DDSs for future precise tumor treatment |
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| Beschreibung: | Date Completed 28.05.2024 Date Revised 28.05.2024 published: Print-Electronic Citation Status MEDLINE |
| ISSN: | 1520-5827 |
| DOI: | 10.1021/acs.langmuir.4c00663 |