Highly Selective Fluorescent Probe for Hypochlorite Anion based on β-position C=N functionalized BODIPY Derivative and Their Applications in Bioimaging
碩士 === 國立交通大學 === 應用化學系碩博士班 === 102 === In this thesis, we used the BODIPY derivatives HBP and BODH as the fluorescent probes for HOCl. Both of them exhibited high selectivity and high sensitivity for hypochlorite ions over others ROS (reactive oxygen species) and RNS (reactive nitrogen species). Th...
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ndltd-TW-102NCTU55000762019-05-15T21:50:57Z http://ndltd.ncl.edu.tw/handle/ugfh95 Highly Selective Fluorescent Probe for Hypochlorite Anion based on β-position C=N functionalized BODIPY Derivative and Their Applications in Bioimaging 以修飾碳氮雙鍵在 β位-BODIPY 之衍生物作為高選擇性次氯酸根離子螢光感測分子之合成與應用 Chen, Wei-Chieh 陳瑋杰 碩士 國立交通大學 應用化學系碩博士班 102 In this thesis, we used the BODIPY derivatives HBP and BODH as the fluorescent probes for HOCl. Both of them exhibited high selectivity and high sensitivity for hypochlorite ions over others ROS (reactive oxygen species) and RNS (reactive nitrogen species). The strong green fluorescence of BODIPY is restored after reaction with hypochlorite ions. The design of two fluorescent probe is based on the functionalization with unbridged C=N in β-position of BODIPY. It was found that unbridged C=N structure will quench the fluorescent due to the C=N isomerization, which is the predominant decay process of excited states. However, when the reaction of the probe HBP with hypochlorite ions, a oxidative intramolecular cyclization will convert the unbridged C=N to a bridged C=N which suppressed the C=N isomerization and then restore the fluorescence. For BODH, the unbridged C=N contained functional group will be converted to aldehyde by the oxidation of hypochlorite ions. Because the fluorescent quenching mechanism was terminated, the fluorescence of BODIPY was restored. Finally, confocal microscopy imaging using RAW264.7 cells showed that the two probes could be used as effective fluorescent probes for detecting HOCl in living cells. Wu, Shu-Pao 吳淑褓 2014 學位論文 ; thesis 89 zh-TW |
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碩士 === 國立交通大學 === 應用化學系碩博士班 === 102 === In this thesis, we used the BODIPY derivatives HBP and BODH as the fluorescent probes for HOCl. Both of them exhibited high selectivity and high sensitivity for hypochlorite ions over others ROS (reactive oxygen species) and RNS (reactive nitrogen species). The strong green fluorescence of BODIPY is restored after reaction with hypochlorite ions.
The design of two fluorescent probe is based on the functionalization with unbridged C=N in β-position of BODIPY. It was found that unbridged C=N structure will quench the fluorescent due to the C=N isomerization, which is the predominant decay process of excited states. However, when the reaction of the probe HBP with hypochlorite ions, a oxidative intramolecular cyclization will convert the unbridged C=N to a bridged C=N which suppressed the C=N isomerization and then restore the fluorescence. For BODH, the unbridged C=N contained functional group will be converted to aldehyde by the oxidation of hypochlorite ions. Because the fluorescent quenching mechanism was terminated, the fluorescence of BODIPY was restored.
Finally, confocal microscopy imaging using RAW264.7 cells showed that the two probes could be used as effective fluorescent probes for detecting HOCl in living cells.
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author2 |
Wu, Shu-Pao |
author_facet |
Wu, Shu-Pao Chen, Wei-Chieh 陳瑋杰 |
author |
Chen, Wei-Chieh 陳瑋杰 |
spellingShingle |
Chen, Wei-Chieh 陳瑋杰 Highly Selective Fluorescent Probe for Hypochlorite Anion based on β-position C=N functionalized BODIPY Derivative and Their Applications in Bioimaging |
author_sort |
Chen, Wei-Chieh |
title |
Highly Selective Fluorescent Probe for Hypochlorite Anion based on β-position C=N functionalized BODIPY Derivative and Their Applications in Bioimaging |
title_short |
Highly Selective Fluorescent Probe for Hypochlorite Anion based on β-position C=N functionalized BODIPY Derivative and Their Applications in Bioimaging |
title_full |
Highly Selective Fluorescent Probe for Hypochlorite Anion based on β-position C=N functionalized BODIPY Derivative and Their Applications in Bioimaging |
title_fullStr |
Highly Selective Fluorescent Probe for Hypochlorite Anion based on β-position C=N functionalized BODIPY Derivative and Their Applications in Bioimaging |
title_full_unstemmed |
Highly Selective Fluorescent Probe for Hypochlorite Anion based on β-position C=N functionalized BODIPY Derivative and Their Applications in Bioimaging |
title_sort |
highly selective fluorescent probe for hypochlorite anion based on β-position c=n functionalized bodipy derivative and their applications in bioimaging |
publishDate |
2014 |
url |
http://ndltd.ncl.edu.tw/handle/ugfh95 |
work_keys_str_mv |
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