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Ratiometric Near-Infrared Fluorescent Probes Based on Hemicyanine Dyes Bearing Dithioacetal and Formal Residues for pH Detection in Mitochondria
| Content Provider | MDPI |
|---|---|
| Author | Yan, Yunnan Zhang, Yibin Xia, Shuai Wan, Shulin Vohs, Tara Tanasova, Marina Luck, Rudy Liu, Haiying |
| Copyright Year | 2021 |
| Description | 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. |
| Starting Page | 2088 |
| e-ISSN | 14203049 |
| DOI | 10.3390/molecules26072088 |
| Journal | Molecules |
| Issue Number | 7 |
| Volume Number | 26 |
| Language | English |
| Publisher | MDPI |
| Publisher Date | 2021-04-06 |
| Access Restriction | Open |
| Subject Keyword | Molecules Organic Chemistry Near-infrared Fluorescence Ratiometric Imaging Mitochondria Fluorescent Probe |
| Content Type | Text |
| Resource Type | Article |
