Rational Design of Ratiometric Near-Infrared Fluorescent pH Probes with Various pKa Values, Based on Aminocyanine
- 22 February 2011
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 133 (10), 3401-3409
- https://doi.org/10.1021/ja1063058
Abstract
Novel ratiometric, near-infrared fluorescent pH probes with various pKa 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.Keywords
This publication has 21 references indexed in Scilit:
- Fluorescent Indicators for Intracellular pHChemical Reviews, 2009
- Solid‐State Gas Sensors Developed from Functional Difluoroboradiazaindacene DyesChemistry – A European Journal, 2009
- Selective molecular imaging of viable cancer cells with pH-activatable fluorescence probesNature Medicine, 2008
- Imaging in the era of molecular oncologyNature, 2008
- Optimized pH-responsive cyanine fluorochromes for detection of acidic environmentsChemical Communications, 2007
- Synthesis and spectroscopic characterisation of heptamethincyanine NIR dyes for their use in optochemical sensorsDyes and Pigments, 2006
- Mono‐ and Di(dimethylamino)styryl‐Substituted Borondipyrromethene and Borondiindomethene Dyes with Intense Near‐Infrared FluorescenceChemistry – An Asian Journal, 2006
- Development of a Ratiometric Fluorescent Zinc Ion Probe in Near-Infrared Region, Based on Tricarbocyanine ChromophoreJournal of the American Chemical Society, 2006
- Design, synthesis and evaluation of near-infrared fluorescent pH indicators in a physiologically relevant rangeChemical Communications, 2005
- Bioinorganic Photochemistry: Frontiers and MechanismsChemical Reviews, 2005