Document Type
Article
Publication Date
4-6-2021
Department
Department of Chemistry
Abstract
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.
Publication Title
Molecules (Basel, Switzerland)
Recommended Citation
Yan, Y.,
Zhang, Y.,
Xia, S.,
Wan, S.,
Vohs, T.,
Tanasova, M.,
Luck, R.,
&
Lui, H.
(2021).
Ratiometric Near-Infrared Fluorescent Probes Based on Hemicyanine Dyes Bearing Dithioacetal and Formal Residues for pH Detection in Mitochondria.
Molecules (Basel, Switzerland),
26(7).
http://doi.org/10.3390/molecules26072088
Retrieved from: https://digitalcommons.mtu.edu/michigantech-p/14887
Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.
Version
Publisher's PDF