Near-infrared fluorescent probes with higher quantum yields and neutral pKa values for the evaluation of intracellular pH

RSC Advances ◽  
2016 ◽  
Vol 6 (73) ◽  
pp. 69641-69646 ◽  
Author(s):  
Xinbo Song ◽  
Mingyu Hu ◽  
Chao Wang ◽  
Yi Xiao
Keyword(s):  
High Resolution ◽  
Intracellular Ph ◽  
Fluorescent Probes ◽  
Near Infrared ◽  
Quantum Yields ◽  
Pka Values

Near-infrared fluorescent probes for pH, named pH-A and pH-B, for labeling cells to produce high resolution fluorescent images reflect the changes of intracellular pH.

Novel near-infrared pH-sensitive cyanine-based fluorescent probes for intracellular pH monitoring

2019 ◽  
Vol 170 ◽  
pp. 107612 ◽  
Author(s):  
Di Jin ◽  
Bowei Wang ◽  
Yuqing Hou ◽  
Yuchao Du ◽  
Xue Li ◽  
...  
Keyword(s):  
Intracellular Ph ◽  
Fluorescent Probes ◽  
Near Infrared ◽  
Ph Monitoring ◽  
Ph Sensitive

scholarly journals Ratiometric Near-Infrared Fluorescent Probes Based on Hemicyanine Dyes Bearing Dithioacetal and Formal Residues for pH Detection in Mitochondria

Molecules ◽  
2021 ◽  
Vol 26 (7) ◽  
pp. 2088
Author(s):  
Yunnan Yan ◽  
Yibin Zhang ◽  
Shuai Xia ◽  
Shulin Wan ◽  
Tara Vohs ◽  
...  
Keyword(s):  
Fluorescent Probes ◽  
Near Infrared ◽  
Formyl Group ◽  
Pka Values ◽  
Theoretical Methods ◽  
Hemicyanine Dye ◽  
Hemicyanine Dyes ◽  
Experimental Values ◽  
Van Der Waals Radii ◽  
Ph Detection

Ratiometric near-infrared fluorescent probes (AH+ and BH+) have been prepared for pH determination in mitochondria by attaching dithioacetal and formal residues onto a hemicyanine dye. The reactive formyl group on probe BH+ allows for retention inside mitochondria as it can react with a protein primary amine residue to form an imine under slightly basic pH 8.0. Probes AH+ and BH+ display ratiometric fluorescent responses to pH changes through the protonation and deprotonaton of a hydroxy group in hemicyanine dyes with experimentally determined pKa values of 6.85 and 6.49, respectively. Calculated pKa values from a variety of theoretical methods indicated that the SMDBONDI method of accounting for solvent and van der Waals radii plus including a water molecule located near the site of protonation produced the closest overall agreement with the experimental values at 7.33 and 6.14 for AH+ and BH+ respectively.

scholarly journals Near-infrared fluorescent probes based on TBET and FRET rhodamine acceptors with different pKa values for sensitive ratiometric visualization of pH changes in live cells

2019 ◽  
Vol 7 (2) ◽  
pp. 198-209 ◽  
Author(s):  
Jianbo Wang ◽  
Shuai Xia ◽  
Jianheng Bi ◽  
Yibin Zhang ◽  
Mingxi Fang ◽  
...  
Keyword(s):  
Fluorescent Probes ◽  
Near Infrared ◽  
Live Cells ◽  
Pka Values ◽  
Ph Changes ◽  
Ph Variations

Three near-infrared ratiometric fluorescent probes with different pKa values were synthesized to achieve sensitive ratiometric visualization of pH variations in lysosomes.

scholarly journals Biocompatible Ir(III) Complexes as Oxygen Sensors for Phosphorescence Lifetime Imaging

Molecules ◽  
2021 ◽  
Vol 26 (10) ◽  
pp. 2898
Author(s):  
Ilya S. Kritchenkov ◽  
Anastasia I. Solomatina ◽  
Daria O. Kozina ◽  
Vitaly V. Porsev ◽  
Victor V. Sokolov ◽  
...  
Keyword(s):  
Near Infrared ◽  
Biological Systems ◽  
Aqueous Media ◽  
Oxygen Sensors ◽  
Quantum Yields ◽  
Complete Agreement ◽  
Phosphorescence Lifetime ◽  
Lifetime Imaging ◽  
Nir Emission ◽  
Phosphorescence Lifetime Imaging

Synthesis of biocompatible near infrared phosphorescent complexes and their application in bioimaging as triplet oxygen sensors in live systems are still challenging areas of organometallic chemistry. We have designed and synthetized four novel iridium [Ir(N^C)2(N^N)]+ complexes (N^C–benzothienyl-phenanthridine based cyclometalated ligand; N^N–pyridin-phenanthroimidazol diimine chelate), decorated with oligo(ethylene glycol) groups to impart these emitters’ solubility in aqueous media, biocompatibility, and to shield them from interaction with bio-environment. These substances were fully characterized using NMR spectroscopy and ESI mass-spectrometry. The complexes exhibited excitation close to the biological “window of transparency”, NIR emission at 730 nm, and quantum yields up to 12% in water. The compounds with higher degree of the chromophore shielding possess low toxicity, bleaching stability, absence of sensitivity to variations of pH, serum, and complex concentrations. The properties of these probes as oxygen sensors for biological systems have been studied by using phosphorescence lifetime imaging experiments in different cell cultures. The results showed essential lifetime response onto variations in oxygen concentration (2.0–2.3 μs under normoxia and 2.8–3.0 μs under hypoxia conditions) in complete agreement with the calibration curves obtained “in cuvette”. The data obtained indicate that these emitters can be used as semi-quantitative oxygen sensors in biological systems.

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