Competition between self-inclusion and drug binding explains the pH dependence of the cyclodextrin drug carrier - molecular modelling and electrochemistry studies.
| Title: | Competition between self-inclusion and drug binding explains the pH dependence of the cyclodextrin drug carrier - molecular modelling and electrochemistry studies. |
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| Authors: | Swiech O; University of Warsaw, Faculty of Chemistry, Pasteura 1 02-093 Warsaw, Poland. bilewicz@chem.uw.edu.pl.; Majdecki M; University of Warsaw, Faculty of Chemistry, Pasteura 1 02-093 Warsaw, Poland. bilewicz@chem.uw.edu.pl.; Debinski A; University of Warsaw, Faculty of Chemistry, Pasteura 1 02-093 Warsaw, Poland. bilewicz@chem.uw.edu.pl.; Krzak A; University of Warsaw, Faculty of Chemistry, Pasteura 1 02-093 Warsaw, Poland. bilewicz@chem.uw.edu.pl.; Stępkowski TM; Department of Radiobiology and Biological Dosimetry, Institute of Nuclear Chemistry and Technology, Dorodna 16, Warsaw, 03-195, Poland. m.kruszewski@ichtj.waw.pl.; Wójciuk G; Department of Radiobiology and Biological Dosimetry, Institute of Nuclear Chemistry and Technology, Dorodna 16, Warsaw, 03-195, Poland. m.kruszewski@ichtj.waw.pl.; Kruszewski M; Faculty of Medicine, University of Information Technology and Management in Rzeszów, ul. Sucharskiego 2, Rzeszów, 35-225, Poland. m.kruszewski@ichtj.waw.pl and Department of Molecular Biology and Translational Research, Institute of Rural Health, Jaczewskiego 2, Lublin, 20-090, Poland. m.kruszewski@ichtj.waw.pl.; Bilewicz R; University of Warsaw, Faculty of Chemistry, Pasteura 1 02-093 Warsaw, Poland. bilewicz@chem.uw.edu.pl. |
| Source: | Nanoscale [Nanoscale] 2016 Sep 22; Vol. 8 (37), pp. 16733-16742. |
| Publication Type: | Journal Article |
| Language: | English |
| Journal Info: | Publisher: RSC Pub Country of Publication: England NLM ID: 101525249 Publication Model: Print Cited Medium: Internet ISSN: 2040-3372 (Electronic) Linking ISSN: 20403364 NLM ISO Abbreviation: Nanoscale Subsets: MEDLINE |
| Imprint Name(s): | Original Publication: Cambridge, UK : RSC Pub. |
| MeSH Terms: | Models, Molecular*; Drug Carriers/*chemistry ; beta-Cyclodextrins/*chemistry; Doxorubicin/chemistry ; Thioctic Acid/chemistry ; Electrochemical Techniques ; HeLa Cells ; Humans ; Hydrogen-Ion Concentration |
| Abstract: | A non-toxic lipoic acid derivative of β cyclodextrin (βCDLip) with an electron-rich aromatic linker was studied as a carrier for the drug doxorubicin with the aim of decreasing the toxic side effects of this drug. The modified cyclodextrin strengthened the drug binding and differentiated the complex-forming ability with dependence on pH. The stability constants of the complexes were evaluated by voltammetry and spectrofluorometry. Molecular modelling provided deeper insight into the nature of the ligand structure itself and the drug-ligand interactions, showing the different contributions of the self-inclusion of the ligand substituent at different pH values. As a result, the modes of interaction of βCDLip with the drug and factors affecting the stabilities of the complex under the pH conditions of healthy and tumour cells could be discovered and explained. |
| Substance Nomenclature: | 0 (Drug Carriers); 0 (beta-Cyclodextrins); 73Y7P0K73Y (Thioctic Acid); 80168379AG (Doxorubicin) |
| Entry Date(s): | Date Created: 20161008 Date Completed: 20181001 Latest Revision: 20181001 |
| Update Code: | 20260130 |
| DOI: | 10.1039/c6nr05833g |
| PMID: | 27714103 |
| Database: | MEDLINE |
Journal Article