Rational design of ratiometric near-infrared fluorescent pH probes with various pKa values, based on aminocyanine

Takuya Myochin; Kazuki Kiyose; Kenjiro Hanaoka; Hirotatsu Kojima; Takuya Terai; Tetsuo Nagano

doi:10.1021/ja1063058

Rational design of ratiometric near-infrared fluorescent pH probes with various pK_a values, based on aminocyanine

Takuya Myochin, Kazuki Kiyose, Kenjiro Hanaoka, Hirotatsu Kojima, Takuya Terai, Tetsuo Nagano

Research output: Contribution to journal › Article › peer-review

235 Citations (Scopus)

Abstract

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 pK_a values of these probes can be predicted from the calculated pK_a 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.

Original language	English
Pages (from-to)	3401-3409
Number of pages	9
Journal	Journal of the American Chemical Society
Volume	133
Issue number	10
DOIs	https://doi.org/10.1021/ja1063058
Publication status	Published - 2011 Mar 16
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja1063058

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abstract = "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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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

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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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Rational design of ratiometric near-infrared fluorescent pH probes with various pK_a values, based on aminocyanine

Abstract

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