Selective Sugar Recognition by Anthracene-Type Boronic Acid Fluorophore/Cyclodextrin Supramolecular Complex Under Physiological pH Condition
We synthesized novel PET (photoinduced electron transfer)-type fluorescence glucose probe 1 [(4-(anthracen-2-yl-carbamoyl)-3-fluorophenyl)boronic acid], which has a phenylboronic acid (PBA) moiety as the recognition site and anthracene as the fluorescent part. Although the PBA derivatives dissociate...
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Frontiers Media S.A.
2019-11-01
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| Series: | Frontiers in Chemistry |
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| Online Access: | https://www.frontiersin.org/article/10.3389/fchem.2019.00806/full |
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| author | Ko Sugita Yuji Tsuchido Yuji Tsuchido Chisato Kasahara Maria Antonietta Casulli Shoji Fujiwara Shoji Fujiwara Takeshi Hashimoto Takashi Hayashita |
| author_facet | Ko Sugita Yuji Tsuchido Yuji Tsuchido Chisato Kasahara Maria Antonietta Casulli Shoji Fujiwara Shoji Fujiwara Takeshi Hashimoto Takashi Hayashita |
| author_sort | Ko Sugita |
| collection | DOAJ |
| description | We synthesized novel PET (photoinduced electron transfer)-type fluorescence glucose probe 1 [(4-(anthracen-2-yl-carbamoyl)-3-fluorophenyl)boronic acid], which has a phenylboronic acid (PBA) moiety as the recognition site and anthracene as the fluorescent part. Although the PBA derivatives dissociate and bind with sugar in the basic condition, our new fluorescent probe can recognize sugars in the physiological pH by introducing an electron-withdrawing fluorine group into the PBA moiety. As a result, the pKa value of this fluorescent probe was lowered and the probe was able to recognize sugars at the physiological pH of 7.4. The sensor was found to produce two types of fluorescent signals, monomer fluorescence and dimer fluorescence, by forming a supramolecular 2:1 complex of 1 with glucose inside a γ-cyclodextrin (γ-CyD) cavity. Selective ratiometric sensing of glucose by the 1/γ-CyD complex was achieved in water at physiological pH. |
| first_indexed | 2024-12-11T05:22:15Z |
| format | Article |
| id | doaj.art-53f9b7877198447594f56aa27fdb66b7 |
| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-12-11T05:22:15Z |
| publishDate | 2019-11-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Chemistry |
| spelling | doaj.art-53f9b7877198447594f56aa27fdb66b72022-12-22T01:19:40ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462019-11-01710.3389/fchem.2019.00806501469Selective Sugar Recognition by Anthracene-Type Boronic Acid Fluorophore/Cyclodextrin Supramolecular Complex Under Physiological pH ConditionKo Sugita0Yuji Tsuchido1Yuji Tsuchido2Chisato Kasahara3Maria Antonietta Casulli4Shoji Fujiwara5Shoji Fujiwara6Takeshi Hashimoto7Takashi Hayashita8Department of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, Tokyo, JapanDepartment of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, Tokyo, JapanDepartment of Life Science and Medical Bioscience, Graduate School of Advanced Science and Engineering, Waseda University (TWIns), Tokyo, JapanDepartment of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, Tokyo, JapanDepartment of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, Tokyo, JapanDepartment of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, Tokyo, JapanDepartment of Current Legal Studies, Faculty of Law, Meiji Gakuin University, Yokohama, JapanDepartment of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, Tokyo, JapanDepartment of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, Tokyo, JapanWe synthesized novel PET (photoinduced electron transfer)-type fluorescence glucose probe 1 [(4-(anthracen-2-yl-carbamoyl)-3-fluorophenyl)boronic acid], which has a phenylboronic acid (PBA) moiety as the recognition site and anthracene as the fluorescent part. Although the PBA derivatives dissociate and bind with sugar in the basic condition, our new fluorescent probe can recognize sugars in the physiological pH by introducing an electron-withdrawing fluorine group into the PBA moiety. As a result, the pKa value of this fluorescent probe was lowered and the probe was able to recognize sugars at the physiological pH of 7.4. The sensor was found to produce two types of fluorescent signals, monomer fluorescence and dimer fluorescence, by forming a supramolecular 2:1 complex of 1 with glucose inside a γ-cyclodextrin (γ-CyD) cavity. Selective ratiometric sensing of glucose by the 1/γ-CyD complex was achieved in water at physiological pH.https://www.frontiersin.org/article/10.3389/fchem.2019.00806/fullcyclodextrinboronic acidsupramolecular chemistryfluorescencesugar recognition |
| spellingShingle | Ko Sugita Yuji Tsuchido Yuji Tsuchido Chisato Kasahara Maria Antonietta Casulli Shoji Fujiwara Shoji Fujiwara Takeshi Hashimoto Takashi Hayashita Selective Sugar Recognition by Anthracene-Type Boronic Acid Fluorophore/Cyclodextrin Supramolecular Complex Under Physiological pH Condition Frontiers in Chemistry cyclodextrin boronic acid supramolecular chemistry fluorescence sugar recognition |
| title | Selective Sugar Recognition by Anthracene-Type Boronic Acid Fluorophore/Cyclodextrin Supramolecular Complex Under Physiological pH Condition |
| title_full | Selective Sugar Recognition by Anthracene-Type Boronic Acid Fluorophore/Cyclodextrin Supramolecular Complex Under Physiological pH Condition |
| title_fullStr | Selective Sugar Recognition by Anthracene-Type Boronic Acid Fluorophore/Cyclodextrin Supramolecular Complex Under Physiological pH Condition |
| title_full_unstemmed | Selective Sugar Recognition by Anthracene-Type Boronic Acid Fluorophore/Cyclodextrin Supramolecular Complex Under Physiological pH Condition |
| title_short | Selective Sugar Recognition by Anthracene-Type Boronic Acid Fluorophore/Cyclodextrin Supramolecular Complex Under Physiological pH Condition |
| title_sort | selective sugar recognition by anthracene type boronic acid fluorophore cyclodextrin supramolecular complex under physiological ph condition |
| topic | cyclodextrin boronic acid supramolecular chemistry fluorescence sugar recognition |
| url | https://www.frontiersin.org/article/10.3389/fchem.2019.00806/full |
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