TY - JOUR
T1 - Novel fluorescent probe for detecting hydroperoxides with strong emission in the visible range
AU - Soh, Nobuaki
AU - Ariyoshi, Tomoyuki
AU - Fukaminato, Tuyoshi
AU - Nakano, Koji
AU - Irie, Masahiro
AU - Imato, Toshihiko
N1 - Funding Information:
This work was supported by Industrial Technology Research Grant Program in 2005 (Grant No. 05A01507a to N.S.) from New Energy and Industrial Technology Development Organization (NEDO) of Japan, and by the Iketani Science and Technology Foundation (Grant No. 0171030A to N.S.).
PY - 2006/6/1
Y1 - 2006/6/1
N2 - A novel fluorescent probe, a swallow-tailed perylene derivative for detecting hydroperoxides (Spy-HP), containing perylene 3,4,9,10-tetracarboxyl bisimide as the main skeleton in the structure, was developed. Spy-HP reacted rapidly with hydroperoxides such as m-chloroperbenzoic acid (MCPBA) and cumene hydroperoxide to form its oxidized derivative, Spy-HPOx, and emitted an extremely strong fluorescence (Φ ∼ 1) in the visible range (λex = 524 nm and λem = 535 nm), as the result of canceling the photoinduced electron transfer (PET) effect. The reaction between Spy-HP and hydroperoxides proceeded quantitatively in strict stoichiometry, without being affected by autoxidation or photobleaching. Because of these prominent properties, Spy-HP is expected to be a novel and useful fluorescent probe to 'spy' on hydroperoxides in biosamples.
AB - A novel fluorescent probe, a swallow-tailed perylene derivative for detecting hydroperoxides (Spy-HP), containing perylene 3,4,9,10-tetracarboxyl bisimide as the main skeleton in the structure, was developed. Spy-HP reacted rapidly with hydroperoxides such as m-chloroperbenzoic acid (MCPBA) and cumene hydroperoxide to form its oxidized derivative, Spy-HPOx, and emitted an extremely strong fluorescence (Φ ∼ 1) in the visible range (λex = 524 nm and λem = 535 nm), as the result of canceling the photoinduced electron transfer (PET) effect. The reaction between Spy-HP and hydroperoxides proceeded quantitatively in strict stoichiometry, without being affected by autoxidation or photobleaching. Because of these prominent properties, Spy-HP is expected to be a novel and useful fluorescent probe to 'spy' on hydroperoxides in biosamples.
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U2 - 10.1016/j.bmcl.2006.02.078
DO - 10.1016/j.bmcl.2006.02.078
M3 - Article
C2 - 16554153
AN - SCOPUS:33646034579
SN - 0960-894X
VL - 16
SP - 2943
EP - 2946
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
IS - 11
ER -