Examination of tryptamine-squaraine complexes as both colorimetric and fluorometric stains in gel electrophoresis

D. E. Lynch, Martin J. Cox, Patrick M. King, G. Smith

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A water-soluble dual pendent squaraine with tryptaminium cations has been mixed with mono-nitroaromatics in solution to create ternary complexes with the aim of creating indole-nitroaromatic charge-transfer pairs. Examination of the X-ray crystal structures of two tryptamine-nitroaromatic complexes, without the squaraine moiety, revealed that neither demonstrated charge-transfer pair or stacking associations between the indole and nitroaromatic rings. Examination of the fluorescence performance upon illumination with 300 nm light of each ternary squaraine complex, particularly in the presence of an equimolar amount of protein, showed that the levels across the series were no more than that observed for the base bis-tryptaminium squaraine, as was observed in a previous study. However, electrophoresis gels stained with the base bis-tryptaminium squaraine, whose X-ray crystal structure is also reported, were found to fluorescence; the only other squaraine dye of this type to do so in addition to the bis-piperidinium squaraine of previous studies.
NOTICE: this is the author’s version of a work that was accepted for publication in Journal of Photochemistry and Photobiology A: Chemistry . Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Journal of Photochemistry and Photobiology A: Chemistry, [VOL 324, 2016 DOI: 10.1016/j.jphotochem.2016.03.017

© 2016, Elsevier. Licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/
Original languageEnglish
Pages (from-to)87–95
JournalJournal of Photochemistry and Photobiology A: Chemistry
Publication statusPublished - 26 Mar 2016


  • Squaraine dyes
  • X-ray crystal structure
  • Gel electrophoresis
  • Tryptaminium salts
  • Protein detection
  • Fluorescence


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