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Peer-reviewedCC BY 3.0Chemical Science

Electric field-dependent excited-state twisting in donor–acceptor thiazolothiazole dyes establishes a new class of cell membrane voltage sensors

  • Pranamita Chakraborti1
  • Rui Fu2,3,4,5
  • Lucia M. Wert1
  • Charlie A. L. Darby1
  • Joy D. Amuzu1
  • Daphne Oettinger2,3,4
  • Aditya Nandy6
  • Yamuna Krishnan2,3,4,5
  • Michael G. Walter1
6 affiliations
  1. 1Department of Chemistry, University of North Carolina at Charlotte Charlotte NC 28223 USA
  2. 2Department of Chemistry, The University of Chicago Chicago IL 60637 USA
  3. 3Neuroscience Institute, The University of Chicago Chicago IL 60637 USA
  4. 4Institute of Biophysical Dynamics, The University of Chicago Chicago IL 60637 USA
  5. 5Immunoengineering and Bioengineering Institute, The University of Chicago USA
  6. 6Department of Chemical and Biomolecular Engineering, University of California, Los Angeles Los Angeles CA 90095 USA
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Abstract

Voltage sensitive dyes (VSDs) are versatile and powerful reporters of the membrane potential across cell membranes. Thiazolothiazole (TTz) dyes are a promising new class of VSDs with high photostability and low cytotoxicity. However, the mechanistic basis of their voltage sensitivity is unknown. To address this, we developed a new generation of asymmetrically substituted TTz dyes (asym-TTz). They exhibit strong solvatofluorochromism with large Stokes shifts and exceptionally large changes in dipole moments (23–29 D), representing an 80% increase over those of previously reported TTz VSDs. An asym-TTz derivative, TwistTz-P, bearing a carboxyphenyl acceptor group, shows sustained cellular membrane localization and a voltage sensitivity of ∼10% ΔF/F per 100 mV. Computational analysis of TwistTz-P under varying electric fields revealed a pronounced twist on both sides of the TTz bridging unit in the excited state. The degree of twisting was voltage-dependent, exhibiting an increase upon depolarization, consistent with the experimentally observed fluorescence decrease at an identical voltage. In another asym-TTz dye (FlatTz-P), where a carboxypyrazinyl acceptor group was incorporated, excited-state twisting under varying electric fields was negligible and demonstrated no voltage sensitivity. These observations establish electric field-dependent excited-state twisting as a new voltage sensing mechanism, and, additionally, provide a new strategy for creating highly sensitive VSDs.

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Cite

BibTeXRIS
BibTeX
@article{chakraborti2026electric,
  title = {{Electric field-dependent excited-state twisting in donor–acceptor thiazolothiazole dyes establishes a new class of cell membrane voltage sensors}},
  author = {Pranamita Chakraborti and Rui Fu and Lucia M. Wert and Charlie A. L. Darby and Joy D. Amuzu and Daphne Oettinger and Aditya Nandy and Yamuna Krishnan and Michael G. Walter},
  journal = {Chemical Science},
  year = {2026},
  month = aug,
  doi = {10.1039/d6sc04210d},
  url = {https://doi.org/10.1039/d6sc04210d},
  note = {CC BY 3.0},
}
RIS
TY  - JOUR
TI  - Electric field-dependent excited-state twisting in donor–acceptor thiazolothiazole dyes establishes a new class of cell membrane voltage sensors
AU  - Pranamita Chakraborti
AU  - Rui Fu
AU  - Lucia M. Wert
AU  - Charlie A. L. Darby
AU  - Joy D. Amuzu
AU  - Daphne Oettinger
AU  - Aditya Nandy
AU  - Yamuna Krishnan
AU  - Michael G. Walter
PY  - 2026
DA  - 2026/08/25
JO  - Chemical Science
DO  - 10.1039/d6sc04210d
UR  - https://doi.org/10.1039/d6sc04210d
AB  - Voltage sensitive dyes (VSDs) are versatile and powerful reporters of the membrane potential across cell membranes. Thiazolothiazole (TTz) dyes are a promising new class of VSDs with high photostability and low cytotoxicity. However, the mechanistic basis of their voltage sensitivity is unknown. To address this, we developed a new generation of asymmetrically substituted TTz dyes (asym-TTz). They exhibit strong solvatofluorochromism with large Stokes shifts and exceptionally large changes in dipole moments (23–29 D), representing an 80% increase over those of previously reported TTz VSDs. An asym-TTz derivative, TwistTz-P, bearing a carboxyphenyl acceptor group, shows sustained cellular membrane localization and a voltage sensitivity of ∼10% ΔF/F per 100 mV. Computational analysis of TwistTz-P under varying electric fields revealed a pronounced twist on both sides of the TTz bridging unit in the excited state. The degree of twisting was voltage-dependent, exhibiting an increase upon depolarization, consistent with the experimentally observed fluorescence decrease at an identical voltage. In another asym-TTz dye (FlatTz-P), where a carboxypyrazinyl acceptor group was incorporated, excited-state twisting under varying electric fields was negligible and demonstrated no voltage sensitivity. These observations establish electric field-dependent excited-state twisting as a new voltage sensing mechanism, and, additionally, provide a new strategy for creating highly sensitive VSDs.
SN  - 2041-6520
SN  - 2041-6539
ER  -