Soh Nobuaki, Ariyoshi Tomoyuki, Fukaminato Tuyoshi, Nakano Koji, Irie Masahiro, Imato Toshihiko
Department of Applied Chemistry, Graduate School of Engineering, Kyushu University, 744, Moto-oka, Nishi-ku, Fukuoka 819-0395, Japan.
Bioorg Med Chem Lett. 2006 Jun 1;16(11):2943-6. doi: 10.1016/j.bmcl.2006.02.078. Epub 2006 Mar 22.
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 (phi approximately 1) in the visible range (lambda(ex) = 524 nm and lambda(em) = 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.
开发了一种新型荧光探针——用于检测氢过氧化物的燕尾状苝衍生物（Spy-HP），其结构中以苝3,4,9,10-四羧基双酰亚胺为主要骨架。Spy-HP与间氯过氧苯甲酸（MCPBA）和氢过氧化异丙苯等氢过氧化物迅速反应，形成其氧化衍生物Spy-HPOx，并在可见光范围内（λ(ex)=524 nm，λ(em)=535 nm）发出极强的荧光（φ约为1），这是由于光致电子转移（PET）效应被消除的结果。Spy-HP与氢过氧化物之间的反应以严格的化学计量比定量进行，不受自氧化或光漂白的影响。由于这些突出的性质，Spy-HP有望成为一种新型且有用的荧光探针，用于“窥探”生物样品中的氢过氧化物。
