期刊
MOLECULES
卷 26, 期 7, 页码 -出版社
MDPI
DOI: 10.3390/molecules26072088
关键词
near-infrared fluorescence; ratiometric imaging; pH; mitochondria; fluorescent probe
资金
- National Institute of General Medical Sciences of the National Institutes of Health [R15GM114751, 2R15GM114751-02]
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 probes display ratiometric fluorescent responses to pH changes through the protonation and deprotonation of a hydroxy group in hemicyanine dyes, with experimentally determined pKa values.
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 pK(a) 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.
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