Cyanine Conformational Restraint in the Far-Red Range

Megan S. Michie, Ralph Götz, Christian Franke, Matthew Bowler, Nikita Kumari, Valentin Magidson, Marcia Levitus, Jadranka Loncarek, Markus Sauer, Martin J. Schnermann

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Far-red cyanine fluorophores find extensive use in modern microscopy despite modest quantum yields. To improve the photon output of these molecules, we report a synthetic strategy that blocks the major deactivation pathway: excited-state trans-to-cis polyene rotation. In the key transformation, a protected dialdehyde precursor undergoes a cascade reaction to install the requisite tetracyclic ring system. The resulting molecules exhibit the characteristic features of conformational restraint, including improved fluorescence quantum yield and extended lifetime. Moreover, these compounds recover from hydride reduction with dramatically improved efficiency. These observations enable efficient single-molecule localization microscopy in oxygenated buffer without addition of thiols. Enabled by modern organic synthesis, these studies provide a new class of far-red dyes with promising spectroscopic and chemical properties.

Original languageEnglish (US)
Pages (from-to)12406-12409
Number of pages4
JournalJournal of the American Chemical Society
Volume139
Issue number36
DOIs
StatePublished - Sep 13 2017

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Polyenes
Synthetic Chemistry Techniques
Photons
Sulfhydryl Compounds
Microscopy
Buffers
Coloring Agents
Fluorescence
Quantum yield
Molecules
Microscopic examination
Fluorophores
Excited states
Hydrides
Chemical properties
Dyes
Single Molecule Imaging

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Michie, M. S., Götz, R., Franke, C., Bowler, M., Kumari, N., Magidson, V., ... Schnermann, M. J. (2017). Cyanine Conformational Restraint in the Far-Red Range. Journal of the American Chemical Society, 139(36), 12406-12409. https://doi.org/10.1021/jacs.7b07272

Cyanine Conformational Restraint in the Far-Red Range. / Michie, Megan S.; Götz, Ralph; Franke, Christian; Bowler, Matthew; Kumari, Nikita; Magidson, Valentin; Levitus, Marcia; Loncarek, Jadranka; Sauer, Markus; Schnermann, Martin J.

In: Journal of the American Chemical Society, Vol. 139, No. 36, 13.09.2017, p. 12406-12409.

Research output: Contribution to journalArticle

Michie, MS, Götz, R, Franke, C, Bowler, M, Kumari, N, Magidson, V, Levitus, M, Loncarek, J, Sauer, M & Schnermann, MJ 2017, 'Cyanine Conformational Restraint in the Far-Red Range', Journal of the American Chemical Society, vol. 139, no. 36, pp. 12406-12409. https://doi.org/10.1021/jacs.7b07272
Michie MS, Götz R, Franke C, Bowler M, Kumari N, Magidson V et al. Cyanine Conformational Restraint in the Far-Red Range. Journal of the American Chemical Society. 2017 Sep 13;139(36):12406-12409. https://doi.org/10.1021/jacs.7b07272
Michie, Megan S. ; Götz, Ralph ; Franke, Christian ; Bowler, Matthew ; Kumari, Nikita ; Magidson, Valentin ; Levitus, Marcia ; Loncarek, Jadranka ; Sauer, Markus ; Schnermann, Martin J. / Cyanine Conformational Restraint in the Far-Red Range. In: Journal of the American Chemical Society. 2017 ; Vol. 139, No. 36. pp. 12406-12409.
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