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Magnesium tetrapyrazinoporphyrazines: tuning of the pKa of red-fluorescent pH indicators
摘要： Magnesium (II) tetrapyrazinoporphyrazines (TPyzPzs) are excellent red fluorophores (λF ~ 663 nm, ΦF ~ 0.53 in THF). In this work, a series of magnesium (II) complexes of unsymmetrical TPyzPzs bearing one or two phenol substituents was prepared. Suitable substitutions on the phenolic moiety tuned its pKa in the range of 5.5 to 13. Deprotonation of the phenolic group at higher pH induced a strong donor (phenolate) in the macrocycle that led to pH-dependent quenching of the red fluorescence of these indicators. pH sensing was proven in water solutions after incorporation of TPyzPs into two delivery systems – microemulsions and liposomes. The latter also serves as a simple model of biomembranes. Finally, a wavelength-ratiometric probe was constructed by incorporation of a TPyzPz indicator and lipophilic pH-nonsensitive BODIPY dye into liposomes. Synthetic precursors for TPyzPzs, substituted pyrazine-2,3-dicarbonitriles, also represent donor-acceptor system and the pH-dependent changes in absorption spectra may be easily visible to the naked eye.
关键词： pH indicators,microemulsions,fluorescence,BODIPY,wavelength-ratiometric probe,liposomes,tetrapyrazinoporphyrazines,magnesium complexes
更新于2025-11-20 15:33:11
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Ratiometric Fluorescent Detection of Intracellular Singlet Oxygen by Semiconducting Polymer Dots
摘要： Singlet oxygen (1O2) plays important roles in many biological processes. However, it is very difficult to detect 1O2 in the intracellular environment owing to its relatively low concentration and short lifetime. Here, we developed a ratiometric probe based on semiconducting polymer dots (Pdots) that can sensitively detect 1O2 in live cells. An organic dye, singlet oxygen sensor green (SOSG), was doped in polyfluorene Pdots, and excitation energy was efficiently transferred from the polymer to the SOSG dye. Accordingly, the Pdots showed constant blue fluorescence as a reference, and increased green fluorescence upon singlet oxygen generation. The ratiometric response of Pdots was examined in the intracellular environment by in-situ 1O2 generation with a photosensitizer and light irradiation. Both spectroscopic measurements and confocal imaging were performed to monitor intracellular 1O2 generation during photodynamic therapy using the Pdot probe. Our results indicate that the SOSG-doped Pdots are promising for intracellular 1O2 detection.
关键词： Semiconducting polymer dots,Intracellular detection,Singlet oxygen,Photodynamic therapy,Ratiometric probe
更新于2025-09-11 14:15:04
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A 1,8 Naphthalimide anchor Rhodamine B Based FRET Probe for Ratiometric Detection of Cr3+ion in Living Cells
摘要： A 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetaldehydeanchored rhodamine B based probe, RDNAP detects Cr3+ ion by fluorescence resonance energy transfer (FRET) process in aqueous buffered acetonitrile media (7:3, v/v). Conversely, conjugation of 2-(1,3-dioxo-6-(piperidin-1-yl)-1H-benzo[de]isoquinolin-2(3H)-yl)acetaldehyde with rhodamine B provides another probe, RDNAP-PY that undergoes Cr3+assisted ratiometric fluorescence and colorimetric change in the same media. RDNAP-PY provides higher FRET efficiency and detects as low as 1.81×10?6 M Cr3+with an association constant, 15.9 × 104 M-1. Other common ions do not interfere. RDNAP-PY efficiently images intracellular Cr3+ in live Hep3B, MCF-7, HeLa, SiHa and HEK 293T cells under fluorescence microscope in a ratiometric and time dependent manner. 1H NMR titration and DFT studies strongly support experimental findings.
关键词： 1,8 Naphthalimide,Live cell imaging,Ratiometric probe,fluorescence resonance energy transfer,DFT calculation
更新于2025-09-09 09:28:46