TY - JOUR
T1 - Chemical reactions of 8-quinolinol derivatives and their applications to biochemical tools and enzyme inhibitors
AU - Aoki, Shin
AU - Ariyasu, Shinya
AU - Hanaya, Kengo
AU - Hisamatsu, Yosuke
AU - Sugai, Takeshi
PY - 2016
Y1 - 2016
N2 - 8-Quinolinol (8-hydroxyquioline, 8HQ) attracts much attention in material sciences and biorelated sciences, because of their simple structures, strong metal coordination properties, fluorescence properties, and extensive possibility of functionalization. In this review, five applications of 8HQ are described. The first application is 8HQ-linked macrocyclic tetraamines as fluorescent probes of zinc ions in living cell. The second and third sections provide the applications of 8HQ to inhibitors against dinuclear zinc hydrolase and to radioprotectors that can inhibit apoptosis of radiosensitive normal cells during radiotherapy. In the third section, finding of photochemical S-O bond cleavage reaction of 8HQ sulfonates (8HQS) under aqueous conditions, its mechanistic analysis and applications to photocleavable chemical linkers are described. Finally, the photophysical properties of iridium (III) complexes having 8HQ or its analogs will be presented. This knowledge will be useful in design and synthesis of useful molecules containing 8HQ units, in bioorganic chemistry, chemical biology, pharmaceutical science, material science, and other related scientific fields.
AB - 8-Quinolinol (8-hydroxyquioline, 8HQ) attracts much attention in material sciences and biorelated sciences, because of their simple structures, strong metal coordination properties, fluorescence properties, and extensive possibility of functionalization. In this review, five applications of 8HQ are described. The first application is 8HQ-linked macrocyclic tetraamines as fluorescent probes of zinc ions in living cell. The second and third sections provide the applications of 8HQ to inhibitors against dinuclear zinc hydrolase and to radioprotectors that can inhibit apoptosis of radiosensitive normal cells during radiotherapy. In the third section, finding of photochemical S-O bond cleavage reaction of 8HQ sulfonates (8HQS) under aqueous conditions, its mechanistic analysis and applications to photocleavable chemical linkers are described. Finally, the photophysical properties of iridium (III) complexes having 8HQ or its analogs will be presented. This knowledge will be useful in design and synthesis of useful molecules containing 8HQ units, in bioorganic chemistry, chemical biology, pharmaceutical science, material science, and other related scientific fields.
KW - 8-Quinolinol
KW - Biotin linker
KW - Luminescent metal complexes
KW - Metal enzyme inhibitors
KW - Metal ion probes
KW - Photolysis reactions
KW - Radioprotective agents
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M3 - Review article
AN - SCOPUS:84980417123
SN - 0037-9980
VL - 74
SP - 482
EP - 493
JO - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
JF - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
IS - 5
ER -