Development of a fluorescent indicator for the bioimaging of nitric oxide.
Nitric oxide (NO) has been reported to play various roles as a signal transmitter. However, detailed functions of NO have yet to be clarified. We have developed a fluorescent indicator for NO imaging in living cells. The N-nitrosation of newly designed and synthesized 4-((3-amino-2-naphthyl)aminomethyl)benzoic acid (DAN-1) by NO yielded the highly fluorescent triazole-form. The membrane permeable ester derivative of DAN-1 (DAN-1 EE) was applied to the imaging of NO produced in activated rat aortic smooth muscle cells. After DAN-1 EE has been loaded into cells, the ester bond is hydrolyzed by intracellular esterase, yielding original DAN-1 with less permeability. The fluorescence intensity of the cells loaded with DAN-1 EE increased according to NO production. The imaging method with fluorescent indicators will be significant for the functional clarification of NO in vivo.
Kojima
H
H
Graduate School of Pharmaceutical Sciences, the University of Tokyo, Japan.
Sakurai
K
K
Kikuchi
K
K
Kawahara
S
S
Kirino
Y
Y
Nagoshi
H
H
Hirata
Y
Y
Akaike
T
T
Maeda
H
H
Nagano
T
T
D015081:2-Naphthylamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000818:Animals; D001013:Aorta, Thoracic / Q000737:chemistry / Q000166:cytology / Q000378:metabolism; D001565:Benzoates / Q000138:chemical synthesis* / Q000737:chemistry; D003952:Diagnostic Imaging; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D009131:Muscle, Smooth, Vascular / Q000737:chemistry / Q000166:cytology / Q000378:metabolism; D009569:Nitric Oxide / Q000032:analysis / Q000378:metabolism*; D051381:Rats; D017208:Rats, Wistar; D013056:Spectrophotometry, Ultraviolet
C110816:4-((3-amino-2-naphthyl)aminomethyl)benzoic acid; D001565:Benzoates; D005456:Fluorescent Dyes; C110817:ethyl 4-((3-amino-2-naphthyl)aminomethyl)benzoate; D009569:Nitric Oxide; D015081:2-Naphthylamine