Literature DB >> 21341656

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

Takuya Myochin1, Kazuki Kiyose, Kenjiro Hanaoka, Hirotatsu Kojima, Takuya Terai, Tetsuo Nagano.   

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.

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Year:  2011        PMID: 21341656     DOI: 10.1021/ja1063058

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  31 in total

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