AminoBODIPY Conjugates for Targeted Drug Delivery Systems and Real-Time Monitoring of Drug ReleaseClick to copy article linkArticle link copied!
- Martin PorubskýMartin PorubskýDepartment of Organic Chemistry, Faculty of Science, Palacký University, Tr. 17. Listopadu 12, 771 46 Olomouc, Czech RepublicMore by Martin Porubský
- Soňa GurskáSoňa GurskáInstitute of Molecular and Translational Medicine, Faculty of Medicine and Dentistry, Palacký University, Hněvotínská 5, 779 00 Olomouc, Czech RepublicMore by Soňa Gurská
- Jarmila StankováJarmila StankováInstitute of Molecular and Translational Medicine, Faculty of Medicine and Dentistry, Palacký University, Hněvotínská 5, 779 00 Olomouc, Czech RepublicMore by Jarmila Stanková
- Marián HajdúchMarián HajdúchInstitute of Molecular and Translational Medicine, Faculty of Medicine and Dentistry, Palacký University, Hněvotínská 5, 779 00 Olomouc, Czech RepublicMore by Marián Hajdúch
- Petr DžubákPetr DžubákInstitute of Molecular and Translational Medicine, Faculty of Medicine and Dentistry, Palacký University, Hněvotínská 5, 779 00 Olomouc, Czech RepublicMore by Petr Džubák
- Jan Hlaváč*Jan Hlaváč*Email: [email protected]Department of Organic Chemistry, Faculty of Science, Palacký University, Tr. 17. Listopadu 12, 771 46 Olomouc, Czech RepublicMore by Jan Hlaváč
Abstract
In this work, we report two concepts of drug delivery based on small-molecule drug conjugates with the ability of specific targeting and drug release monitoring via ratiometric fluorescence. The functionality of these concepts has been verified by two model systems consisting of three parts: (i) fluorescent aminoBODIPY for real-time detection of conjugate cleavage, (ii) a c(RGDfK) peptide specific for αvβ3 integrin receptors targeting angiogenesis in most solid tumors or redBODIPY for conjugate cleavage monitoring via FRET, and (iii) pegylated-2-phenyl-3-hydroxy-4(1H)-quinolinone (3HQ) as a model drug. The model drug release is based on a self-immolative disulfide linker sensitive to environments containing thiols, especially glutathione, which is overexpressed in cancer cells. The results show effective thiol-mediated cleavage of the fluorescent reporter and the subsequent liberation of the drug in a tube. The conjugate with c(RGDfK) was confirmed to penetrate the cells via interaction with integrin receptors. Drug release from this conjugate is possible to monitor inside the cells. Further, the synthetic approach to the conjugates and the method of fluorescence monitoring of the drug release have also been described.
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This article is cited by 4 publications.
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- Martin Porubsky, Jiří Hodoň, Jarmila Stanková, Petr Dzubak, Marian Hajduch, Milan Urban, Jan Hlaváč. Near-Infrared Ph-Switchable Bodipy Photosensitizers for Dual Biotin/Crgd Targeted Photodynamic Therapy. 2024https://doi.org/10.2139/ssrn.4854259
- Bhaskar C. Das, Parthiban Chokkalingam, Pavithra Masilamani, Srushti Shukla, Sasmita Das. Stimuli-Responsive Boron-Based Materials in Drug Delivery. International Journal of Molecular Sciences 2023, 24
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