Bioimaging of thiazolidine-4-one-based new probes, fluorimetric detection of Cu2+ “on-off” sensor property, DFT calculation, molecular docking studies, and multiple real samples application
Thiazolidinones have been the subject of various research areas for their biological activities, thus they were promising scaffolds to develop new drug agents. A novel thiazolidine 4-one-based fluorescent chemosensor probes PS (thiazolidine) and BO (oxazolidine) were designed and synthesized. Both p...
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| Published in | Food chemistry Vol. 463; no. Pt 2; p. 141269 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Elsevier Ltd
15.01.2025
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| Subjects | |
| Online Access | Get full text |
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| Abstract | Thiazolidinones have been the subject of various research areas for their biological activities, thus they were promising scaffolds to develop new drug agents. A novel thiazolidine 4-one-based fluorescent chemosensor probes PS (thiazolidine) and BO (oxazolidine) were designed and synthesized. Both probes showed specific recognition against Cu2+ via a “turn-off” fluorescence response in ACN/H2O (v/v: 50/50) stock solution (10 mM, pH = 7.0) with a detection limit of (for BO: 1.9 nM and PS: 1.03 nM). Finally, the detection of chemosensory PS and BO showed positive potential for the determination of Cu2+ in real food samples, drinking water, and mung beans. The compounds were characterized by diferent chemical and spectroscopic methods. The proposed binding mode for PS and BO with Cu2+ was confirmed by DFT calculation, and also they elucidated by bioimaging studies against MCF-7 live cell lines. Additionally, the docking experiment was performed on XylE and hAChE targets.
•Novel sensors with high fluorescence emission based on thiazolidin-4-one have been developed.•BO and PS sensors showed high selectivity and “turn-off” detection for Cu2+.•Both BO (1.9 nM) and PS (1.03 nM) have low detection limits.•Both BO and PS exerted excellent cell-permeability and potentially responded to changes of Cu+2 in MCF-7 cells.•The applicability of both sensors to multiple real samples was determined. |
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| AbstractList | Thiazolidinones have been the subject of various research areas for their biological activities, thus they were promising scaffolds to develop new drug agents. A novel thiazolidine 4-one-based fluorescent chemosensor probes PS (thiazolidine) and BO (oxazolidine) were designed and synthesized. Both probes showed specific recognition against Cu²⁺ via a "turn-off" fluorescence response in ACN/H₂O (v/v: 50/50) stock solution (10 mM, pH = 7.0) with a detection limit of (for BO: 1.9 nM and PS: 1.03 nM). Finally, the detection of chemosensory PS and BO showed positive potential for the determination of Cu²⁺ in real food samples, drinking water, and mung beans. The compounds were characterized by diferent chemical and spectroscopic methods. The proposed binding mode for PS and BO with Cu²⁺ was confirmed by DFT calculation, and also they elucidated by bioimaging studies against MCF-7 live cell lines. Additionally, the docking experiment was performed on XylE and hAChE targets. Thiazolidinones have been the subject of various research areas for their biological activities, thus they were promising scaffolds to develop new drug agents. A novel thiazolidine 4-one-based fluorescent chemosensor probes PS (thiazolidine) and BO (oxazolidine) were designed and synthesized. Both probes showed specific recognition against Cu2+ via a "turn-off" fluorescence response in ACN/H2O (v/v: 50/50) stock solution (10 mM, pH = 7.0) with a detection limit of (for BO: 1.9 nM and PS: 1.03 nM). Finally, the detection of chemosensory PS and BO showed positive potential for the determination of Cu2+ in real food samples, drinking water, and mung beans. The compounds were characterized by diferent chemical and spectroscopic methods. The proposed binding mode for PS and BO with Cu2+ was confirmed by DFT calculation, and also they elucidated by bioimaging studies against MCF-7 live cell lines. Additionally, the docking experiment was performed on XylE and hAChE targets.Thiazolidinones have been the subject of various research areas for their biological activities, thus they were promising scaffolds to develop new drug agents. A novel thiazolidine 4-one-based fluorescent chemosensor probes PS (thiazolidine) and BO (oxazolidine) were designed and synthesized. Both probes showed specific recognition against Cu2+ via a "turn-off" fluorescence response in ACN/H2O (v/v: 50/50) stock solution (10 mM, pH = 7.0) with a detection limit of (for BO: 1.9 nM and PS: 1.03 nM). Finally, the detection of chemosensory PS and BO showed positive potential for the determination of Cu2+ in real food samples, drinking water, and mung beans. The compounds were characterized by diferent chemical and spectroscopic methods. The proposed binding mode for PS and BO with Cu2+ was confirmed by DFT calculation, and also they elucidated by bioimaging studies against MCF-7 live cell lines. Additionally, the docking experiment was performed on XylE and hAChE targets. Thiazolidinones have been the subject of various research areas for their biological activities, thus they were promising scaffolds to develop new drug agents. A novel thiazolidine 4-one-based fluorescent chemosensor probes PS (thiazolidine) and BO (oxazolidine) were designed and synthesized. Both probes showed specific recognition against Cu2+ via a “turn-off” fluorescence response in ACN/H2O (v/v: 50/50) stock solution (10 mM, pH = 7.0) with a detection limit of (for BO: 1.9 nM and PS: 1.03 nM). Finally, the detection of chemosensory PS and BO showed positive potential for the determination of Cu2+ in real food samples, drinking water, and mung beans. The compounds were characterized by diferent chemical and spectroscopic methods. The proposed binding mode for PS and BO with Cu2+ was confirmed by DFT calculation, and also they elucidated by bioimaging studies against MCF-7 live cell lines. Additionally, the docking experiment was performed on XylE and hAChE targets. •Novel sensors with high fluorescence emission based on thiazolidin-4-one have been developed.•BO and PS sensors showed high selectivity and “turn-off” detection for Cu2+.•Both BO (1.9 nM) and PS (1.03 nM) have low detection limits.•Both BO and PS exerted excellent cell-permeability and potentially responded to changes of Cu+2 in MCF-7 cells.•The applicability of both sensors to multiple real samples was determined. |
| ArticleNumber | 141269 |
| Author | Başçeken, Sinan Baran, Arif Karakiliç, Emel Eskiler, Gamze Güney Uzuner, Uğur |
| Author_xml | – sequence: 1 givenname: Emel surname: Karakiliç fullname: Karakiliç, Emel organization: Department of Chemistry, Science Faculty, Sakarya University, 54187, Sakarya, Turkey – sequence: 2 givenname: Sinan surname: Başçeken fullname: Başçeken, Sinan organization: Department of Chemistry, Faculty of Arts and Sciences, Hitit University, 19030 Çorum, Turkey – sequence: 3 givenname: Gamze Güney surname: Eskiler fullname: Eskiler, Gamze Güney organization: Department of Medical Biolog, Faculty of Medicine, Sakarya University, 54187, Sakarya, Turkey – sequence: 4 givenname: Uğur surname: Uzuner fullname: Uzuner, Uğur organization: Department of Molecular Biology and Genetics Department, Science Faculty, Karadeniz Technical University, 61080 Trabzon, Turkey – sequence: 5 givenname: Arif surname: Baran fullname: Baran, Arif email: abaran@sakarya.edu.tr organization: Department of Chemistry, Science Faculty, Sakarya University, 54187, Sakarya, Turkey |
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| SubjectTerms | bioimaging detection limit DFT Docking drugs fluorescence Fluorescent fluorometry food chemistry MCF-7 cells Multiple real samples spectroscopy Thiazolidine-4-one |
| Title | Bioimaging of thiazolidine-4-one-based new probes, fluorimetric detection of Cu2+ “on-off” sensor property, DFT calculation, molecular docking studies, and multiple real samples application |
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