TY - JOUR
T1 - Rational design of ratiometric near-infrared fluorescent pH probes with various pKa values, based on aminocyanine
AU - Myochin, Takuya
AU - Kiyose, Kazuki
AU - Hanaoka, Kenjiro
AU - Kojima, Hirotatsu
AU - Terai, Takuya
AU - Nagano, Tetsuo
PY - 2011/3/16
Y1 - 2011/3/16
N2 - Novel ratiometric, near-infrared fluorescent pH probes with various pK a values have been designed and synthesized on the basis of aminocyanine bearing a diamine moiety, and their photochemical properties were evaluated. Under acidic conditions, these pH probes showed a 46- to 83-nm red shift of the absorption maximum. This change is sufficiently large to permit their use as ratiometric pH probes, and is reversible, whereas monoamine-substituted aminocyanines showed irreversible changes because of their instability under acidic conditions. Furthermore, the pKa values of these probes can be predicted from the calculated pKa values of the diamine moieties, obtained from the SciFinder database. This design strategy is very simple and flexible, and should be applicable to develop NIR pH probes for various applications.
AB - Novel ratiometric, near-infrared fluorescent pH probes with various pK a values have been designed and synthesized on the basis of aminocyanine bearing a diamine moiety, and their photochemical properties were evaluated. Under acidic conditions, these pH probes showed a 46- to 83-nm red shift of the absorption maximum. This change is sufficiently large to permit their use as ratiometric pH probes, and is reversible, whereas monoamine-substituted aminocyanines showed irreversible changes because of their instability under acidic conditions. Furthermore, the pKa values of these probes can be predicted from the calculated pKa values of the diamine moieties, obtained from the SciFinder database. This design strategy is very simple and flexible, and should be applicable to develop NIR pH probes for various applications.
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U2 - 10.1021/ja1063058
DO - 10.1021/ja1063058
M3 - Article
C2 - 21341656
AN - SCOPUS:79952605400
VL - 133
SP - 3401
EP - 3409
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 10
ER -