Ratiometric Near-Infrared Fluorescent Probes Based on Hemicyanine Dyes Bearing Dithioacetal and Formal Residues for pH Detection in Mitochondria
Ratiometric near-infrared fluorescent probes (<b>AH<sup>+</sup></b> and <b>BH<sup>+</sup></b>) have been prepared for pH determination in mitochondria by attaching dithioacetal and formal residues onto a hemicyanine dye. The reactive formyl group on pr...
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| Format: | Article |
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MDPI AG
2021-04-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/7/2088 |
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| author | Yunnan Yan Yibin Zhang Shuai Xia Shulin Wan Tara Vohs Marina Tanasova Rudy L. Luck Haiying Liu |
| author_facet | Yunnan Yan Yibin Zhang Shuai Xia Shulin Wan Tara Vohs Marina Tanasova Rudy L. Luck Haiying Liu |
| author_sort | Yunnan Yan |
| collection | DOAJ |
| description | Ratiometric near-infrared fluorescent probes (<b>AH<sup>+</sup></b> and <b>BH<sup>+</sup></b>) have been prepared for pH determination in mitochondria by attaching dithioacetal and formal residues onto a hemicyanine dye. The reactive formyl group on probe <b>BH<sup>+</sup></b> 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 <b>AH<sup>+</sup></b> and <b>BH<sup>+</sup></b> display ratiometric fluorescent responses to pH changes through the protonation and deprotonaton of a hydroxy group in hemicyanine dyes with experimentally determined p<i>K</i>a values of 6.85 and 6.49, respectively. Calculated p<i>K</i><sub>a</sub> values from a variety of theoretical methods indicated that the SMD<sub>BONDI</sub> 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 <b>AH<sup>+</sup></b> and <b>BH<sup>+</sup></b> respectively. |
| first_indexed | 2024-03-10T12:35:20Z |
| format | Article |
| id | doaj.art-f6526b7d98434b0dbd16ecf4d979d2f7 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T12:35:20Z |
| publishDate | 2021-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-f6526b7d98434b0dbd16ecf4d979d2f72023-11-21T14:20:16ZengMDPI AGMolecules1420-30492021-04-01267208810.3390/molecules26072088Ratiometric Near-Infrared Fluorescent Probes Based on Hemicyanine Dyes Bearing Dithioacetal and Formal Residues for pH Detection in MitochondriaYunnan Yan0Yibin Zhang1Shuai Xia2Shulin Wan3Tara Vohs4Marina Tanasova5Rudy L. Luck6Haiying Liu7Department of Chemistry, Michigan Technological University, Houghton, MI 49931, USADepartment of Chemistry, Michigan Technological University, Houghton, MI 49931, USADepartment of Chemistry, Michigan Technological University, Houghton, MI 49931, USADepartment of Chemistry, Michigan Technological University, Houghton, MI 49931, USADepartment of Chemistry, Michigan Technological University, Houghton, MI 49931, USADepartment of Chemistry, Michigan Technological University, Houghton, MI 49931, USADepartment of Chemistry, Michigan Technological University, Houghton, MI 49931, USADepartment of Chemistry, Michigan Technological University, Houghton, MI 49931, USARatiometric near-infrared fluorescent probes (<b>AH<sup>+</sup></b> and <b>BH<sup>+</sup></b>) have been prepared for pH determination in mitochondria by attaching dithioacetal and formal residues onto a hemicyanine dye. The reactive formyl group on probe <b>BH<sup>+</sup></b> 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 <b>AH<sup>+</sup></b> and <b>BH<sup>+</sup></b> display ratiometric fluorescent responses to pH changes through the protonation and deprotonaton of a hydroxy group in hemicyanine dyes with experimentally determined p<i>K</i>a values of 6.85 and 6.49, respectively. Calculated p<i>K</i><sub>a</sub> values from a variety of theoretical methods indicated that the SMD<sub>BONDI</sub> 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 <b>AH<sup>+</sup></b> and <b>BH<sup>+</sup></b> respectively.https://www.mdpi.com/1420-3049/26/7/2088near-infrared fluorescenceratiometric imagingpHmitochondriafluorescent probe |
| spellingShingle | Yunnan Yan Yibin Zhang Shuai Xia Shulin Wan Tara Vohs Marina Tanasova Rudy L. Luck Haiying Liu Ratiometric Near-Infrared Fluorescent Probes Based on Hemicyanine Dyes Bearing Dithioacetal and Formal Residues for pH Detection in Mitochondria Molecules near-infrared fluorescence ratiometric imaging pH mitochondria fluorescent probe |
| title | Ratiometric Near-Infrared Fluorescent Probes Based on Hemicyanine Dyes Bearing Dithioacetal and Formal Residues for pH Detection in Mitochondria |
| title_full | Ratiometric Near-Infrared Fluorescent Probes Based on Hemicyanine Dyes Bearing Dithioacetal and Formal Residues for pH Detection in Mitochondria |
| title_fullStr | Ratiometric Near-Infrared Fluorescent Probes Based on Hemicyanine Dyes Bearing Dithioacetal and Formal Residues for pH Detection in Mitochondria |
| title_full_unstemmed | Ratiometric Near-Infrared Fluorescent Probes Based on Hemicyanine Dyes Bearing Dithioacetal and Formal Residues for pH Detection in Mitochondria |
| title_short | Ratiometric Near-Infrared Fluorescent Probes Based on Hemicyanine Dyes Bearing Dithioacetal and Formal Residues for pH Detection in Mitochondria |
| title_sort | ratiometric near infrared fluorescent probes based on hemicyanine dyes bearing dithioacetal and formal residues for ph detection in mitochondria |
| topic | near-infrared fluorescence ratiometric imaging pH mitochondria fluorescent probe |
| url | https://www.mdpi.com/1420-3049/26/7/2088 |
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