Highly Selective Fluorescent Probe for Hypochlorite Anion based on β-position C=N functionalized BODIPY Derivative and Their Applications in Bioimaging

• Main Authors: Chen, Wei-Chieh, 陳瑋杰
• Other Authors: Wu, Shu-Pao
• Format: Others
• Language: zh-TW
• Published: 2014
• Online Access: http://ndltd.ncl.edu.tw/handle/ugfh95

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.