Acetylated Trifluoromethyl Diboronic Acid Anthracene with a Large Stokes Shift and Long Excitation Wavelength as a Glucose-Selective Probe
Continuous control of blood glucose levels is important for the effective treatment of diabetes. The short-term use of enzymatic continuous monitoring systems involves expensive maintenance and is inconvenient, which limits their widespread use by diabetes patients. The fluorescent diboronic anthrac...
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MDPI AG
2022-03-01
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| Series: | Applied Sciences |
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| Online Access: | https://www.mdpi.com/2076-3417/12/6/2782 |
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| author | Hongsik Choi Inhyeok Song Chul Soon Park Heung-seop Yim Joong Hyun Kim |
| author_facet | Hongsik Choi Inhyeok Song Chul Soon Park Heung-seop Yim Joong Hyun Kim |
| author_sort | Hongsik Choi |
| collection | DOAJ |
| description | Continuous control of blood glucose levels is important for the effective treatment of diabetes. The short-term use of enzymatic continuous monitoring systems involves expensive maintenance and is inconvenient, which limits their widespread use by diabetes patients. The fluorescent diboronic anthracene-embedded system has demonstrated in vivo continuous glucose monitoring for 12 times longer than enzymatic systems by protecting the dye from reactive oxygen species. However, its small Stokes shift and low excitation and emission wavelength should be heavily considered for easy fabrication. We successfully synthesized a derivative of bis-phenyl boronate with a large Stokes shift and long excitation wavelength by adding an acetyl moiety to the anthracene ring. This resulted in a ~90-nm Stokes shift and 15-nm and 80-nm redshifts of the excitation and emission wavelengths, respectively. The fluorescence of the synthesized probe increased proportionally with the glucose concentration because the formation of the boronic acid-glucose complex prevented photoinduced electron transfer. The association constant and quantum yield for acetyl-substituted diboronic anthracene with glucose was 20% and 13% higher than that of the analog, respectively. While keeping resistance to the oxidation by reactive oxygen species, the improved optical properties and glucose-detecting performances of the newly synthesized dye will allow better pairing of the source and detecting unit for in vivo continuous glucose monitoring, leading to easy fabrication and then contributing more to utilization by diabetes patients. |
| first_indexed | 2024-03-09T13:52:24Z |
| format | Article |
| id | doaj.art-c60187af3aee44658b708d1375572b16 |
| institution | Directory Open Access Journal |
| issn | 2076-3417 |
| language | English |
| last_indexed | 2024-03-09T13:52:24Z |
| publishDate | 2022-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Applied Sciences |
| spelling | doaj.art-c60187af3aee44658b708d1375572b162023-11-30T20:48:35ZengMDPI AGApplied Sciences2076-34172022-03-01126278210.3390/app12062782Acetylated Trifluoromethyl Diboronic Acid Anthracene with a Large Stokes Shift and Long Excitation Wavelength as a Glucose-Selective ProbeHongsik Choi0Inhyeok Song1Chul Soon Park2Heung-seop Yim3Joong Hyun Kim4Drug Manufacturing Center, Daegu-Gyeongbuk Medical Innovation Foundation, 80 Chumbok-ro, Dong-gu, Daegu City 41061, KoreaDrug Manufacturing Center, Daegu-Gyeongbuk Medical Innovation Foundation, 80 Chumbok-ro, Dong-gu, Daegu City 41061, KoreaDrug Manufacturing Center, Daegu-Gyeongbuk Medical Innovation Foundation, 80 Chumbok-ro, Dong-gu, Daegu City 41061, KoreaDrug Manufacturing Center, Daegu-Gyeongbuk Medical Innovation Foundation, 80 Chumbok-ro, Dong-gu, Daegu City 41061, KoreaDrug Manufacturing Center, Daegu-Gyeongbuk Medical Innovation Foundation, 80 Chumbok-ro, Dong-gu, Daegu City 41061, KoreaContinuous control of blood glucose levels is important for the effective treatment of diabetes. The short-term use of enzymatic continuous monitoring systems involves expensive maintenance and is inconvenient, which limits their widespread use by diabetes patients. The fluorescent diboronic anthracene-embedded system has demonstrated in vivo continuous glucose monitoring for 12 times longer than enzymatic systems by protecting the dye from reactive oxygen species. However, its small Stokes shift and low excitation and emission wavelength should be heavily considered for easy fabrication. We successfully synthesized a derivative of bis-phenyl boronate with a large Stokes shift and long excitation wavelength by adding an acetyl moiety to the anthracene ring. This resulted in a ~90-nm Stokes shift and 15-nm and 80-nm redshifts of the excitation and emission wavelengths, respectively. The fluorescence of the synthesized probe increased proportionally with the glucose concentration because the formation of the boronic acid-glucose complex prevented photoinduced electron transfer. The association constant and quantum yield for acetyl-substituted diboronic anthracene with glucose was 20% and 13% higher than that of the analog, respectively. While keeping resistance to the oxidation by reactive oxygen species, the improved optical properties and glucose-detecting performances of the newly synthesized dye will allow better pairing of the source and detecting unit for in vivo continuous glucose monitoring, leading to easy fabrication and then contributing more to utilization by diabetes patients.https://www.mdpi.com/2076-3417/12/6/2782diboronic acidsstokes shiftphotoinduced energy transferdiabetesglucose sensor |
| spellingShingle | Hongsik Choi Inhyeok Song Chul Soon Park Heung-seop Yim Joong Hyun Kim Acetylated Trifluoromethyl Diboronic Acid Anthracene with a Large Stokes Shift and Long Excitation Wavelength as a Glucose-Selective Probe Applied Sciences diboronic acids stokes shift photoinduced energy transfer diabetes glucose sensor |
| title | Acetylated Trifluoromethyl Diboronic Acid Anthracene with a Large Stokes Shift and Long Excitation Wavelength as a Glucose-Selective Probe |
| title_full | Acetylated Trifluoromethyl Diboronic Acid Anthracene with a Large Stokes Shift and Long Excitation Wavelength as a Glucose-Selective Probe |
| title_fullStr | Acetylated Trifluoromethyl Diboronic Acid Anthracene with a Large Stokes Shift and Long Excitation Wavelength as a Glucose-Selective Probe |
| title_full_unstemmed | Acetylated Trifluoromethyl Diboronic Acid Anthracene with a Large Stokes Shift and Long Excitation Wavelength as a Glucose-Selective Probe |
| title_short | Acetylated Trifluoromethyl Diboronic Acid Anthracene with a Large Stokes Shift and Long Excitation Wavelength as a Glucose-Selective Probe |
| title_sort | acetylated trifluoromethyl diboronic acid anthracene with a large stokes shift and long excitation wavelength as a glucose selective probe |
| topic | diboronic acids stokes shift photoinduced energy transfer diabetes glucose sensor |
| url | https://www.mdpi.com/2076-3417/12/6/2782 |
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