TY - JOUR
T1 - Swallow-tailed perylene derivative
T2 - A new tool for fluorescent imaging of lipid hydroperoxides
AU - Soh, Nobuaki
AU - Ariyoshi, Tomoyuki
AU - Fukaminato, Tuyoshi
AU - Nakajima, Hizuru
AU - Nakano, Koji
AU - Imato, Toshihiko
PY - 2007
Y1 - 2007
N2 - A swallow-tailed perylene derivative including a triphenylphosphine moiety was synthesized and applied to the detection and the live-cell imaging of lipid hydroperoxides. The novel probe, named Spy-LHP, reacted rapidly and quantitatively with lipid hydroperoxides to form the corresponding oxide, Spy-LHPOx, which emits extremely strong fluorescence (Φ ∼ 1) in the visible range (λem = 535 nm, 574 nm). Spy-LHP was highly selective for lipid hydroperoxides, and the addition of other reactive oxygen species (ROS) including hydrogen peroxides, hydroxyl radical, superoxide anion, nitric oxide, peroxynitrite, and alkylperoxyl radical, caused no significant increase in the fluorescence intensity. The probe exhibited good localization to cellular membranes and was successfully applied to the confocal laser scanning microscopy (CLSM) imaging of lipid hydroperoxides in live J774A.1 cells, in which lipid peroxidation was proceeded by the stimulation of 2,2-azobis(2-amidinopropane)dihydrochloride (AAPH). These findings establish Spy-LHP as a promising new tool for investigating the physiology of lipid hydroperoxides.
AB - A swallow-tailed perylene derivative including a triphenylphosphine moiety was synthesized and applied to the detection and the live-cell imaging of lipid hydroperoxides. The novel probe, named Spy-LHP, reacted rapidly and quantitatively with lipid hydroperoxides to form the corresponding oxide, Spy-LHPOx, which emits extremely strong fluorescence (Φ ∼ 1) in the visible range (λem = 535 nm, 574 nm). Spy-LHP was highly selective for lipid hydroperoxides, and the addition of other reactive oxygen species (ROS) including hydrogen peroxides, hydroxyl radical, superoxide anion, nitric oxide, peroxynitrite, and alkylperoxyl radical, caused no significant increase in the fluorescence intensity. The probe exhibited good localization to cellular membranes and was successfully applied to the confocal laser scanning microscopy (CLSM) imaging of lipid hydroperoxides in live J774A.1 cells, in which lipid peroxidation was proceeded by the stimulation of 2,2-azobis(2-amidinopropane)dihydrochloride (AAPH). These findings establish Spy-LHP as a promising new tool for investigating the physiology of lipid hydroperoxides.
UR - http://www.scopus.com/inward/record.url?scp=36148957430&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=36148957430&partnerID=8YFLogxK
U2 - 10.1039/b713223a
DO - 10.1039/b713223a
M3 - Article
C2 - 18004455
AN - SCOPUS:36148957430
SN - 1477-0520
VL - 5
SP - 3762
EP - 3768
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 23
ER -