Design strategy for germanium-rhodamine based pH-activatable near-infrared fluorescence probes suitable for biological applications

Koide, Yuichiro; Kojima, Ryosuke; Hanaoka, Kenjiro; Numasawa, Koji; Komatsu, Toshimitsu; Nagano, Tetsuo; Kobayashi, Hisataka; Urano, Yasuteru

doi:10.1038/s42004-019-0194-4

Cited by 34 publications

(26 citation statements)

References 35 publications

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“…A pH‐activable germanium‐rhodamine based near IR fluorescence probe 35 [66] is a fluorescence ‘turn on’ probe in an acidic pH, with a high signal‐to‐noise ratio near IR region. It was found to be suitable for pH monitoring in the range of 5.0–6.4, with a p K a value of 5.46.…”

Section: Rhodamine‐based Ph Probesmentioning

confidence: 99%

Recent Advances in Small Molecule‐Based Intracellular pH Probes

et al. 2021

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Intracellular pH plays an important role in many biological and pathological processes. Small‐molecule based pH probes are found to be the most effective for pH sensing because of ease of preparation, high sensitivity, and quick response. They have many advantages such as small perturbation to the functions of the target, functional adaptability, cellular component‐specific localization, etc. The present review highlights the flurry of recent activity in the development of such probes. The probes are categorized based on the type of fluorophore used like quinoline, coumarin, BODIPY, rhodamine, indolium, naphthalimide, etc., and their analytical performance is discussed.

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Section: Rhodamine‐based Ph Probesmentioning

confidence: 99%

Recent Advances in Small Molecule‐Based Intracellular pH Probes

et al. 2021

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“…The ability to locally, and with high precision, determine pH and/or the presence of specific metal ions using fluorescent molecules is important for several disciplines, including biology − and environmental monitoring. − Detection of transition metal ions is crucial to the diagnosis and/or prevention of diseases caused by dysregulation of metal-ion homeostasis, such as anemia and Alzheimer’s disease . In biology, protons play a critical role in living cells to support various biological activities .…”

Section: Introductionmentioning

confidence: 99%

A Highly Luminescent Nitrogen-Doped Nanographene as an Acid- and Metal-Sensitive Fluorophore for Optical Imaging

Jin

Yang

et al. 2021

J. Am. Chem. Soc.

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Dibenzo[hi,st]ovalene (DBOV) has excellent photophysical properties, including strong fluorescence and high ambient stability. Moreover, the optical blinking properties of DBOV have enabled optical super-resolution single-molecule localization microscopy with an imaging resolution beyond the diffraction limit. Various organic and inorganic fluorescent probes have been developed for super-resolution imaging, but those sensitive to pH and/or metal ions have remained elusive. Here, we report a diaza-derivative of DBOV (N-DBOV), synthesized in eight steps with a total yield of 15%. Nitrogen (N)-bearing zigzag edges were formed through oxidative cyclization of amino groups in the last step. UV–vis and fluorescence spectroscopy of N-DBOV revealed its promising optical properties comparable to those of the parent DBOV, while cyclic voltammetry and density functional theory calculations highlighted its lower orbital energy levels and potential n-type semiconductor character. Notably, in contrast to that of the parent DBOV, the strong luminescence of N-DBOV is dependent on pH and the presence of heavy metal ions, indicating the potential of N-DBOV in sensing applications. N-DBOV also exhibited pH-responsive blinking, which enables pH-sensitive super-resolution imaging. Therefore, N-DBOV appears to be a highly promising candidate for fluorescence sensing in biology and environmental analytics.

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“…Over the years, a wide range of activity-based probes have been designed and developed to detect a number of metal ions, 2,3 pH fluctuations 4 and biologically relevant enzymes [5][6][7] in real-time. In particular, enzymes represent important biomarkers for diagnosis and monitoring the progression of a number of chronic diseases such as Parkinson's disease, 8 arthritis 9 and many types of cancer.…”

Section: Introductionmentioning

confidence: 99%