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Expedient Synthesis and Characterization of π-Extended Luciferins.

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|December 14, 2023
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Researchers developed a new two-step synthesis for bioluminescent imaging probes, improving access to far-red and near-infrared emitters. A novel naphthalene derivative shows comparable performance to existing probes, enhancing cell tracking and biological process visualization.

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Area of Science:

  • Biochemistry
  • Organic Chemistry
  • Biomedical Imaging

Background:

  • Bioluminescence imaging offers sensitive cell tracking and biological process visualization in vivo.
  • Far-red and near-infrared bioluminescent probes reduce tissue absorption and enable multiplexing.
  • Current syntheses for extended π-system luciferins are often multistep and complex.

Purpose of the Study:

  • To develop an efficient synthetic strategy for long-wavelength bioluminescent probes.
  • To synthesize and characterize novel AkaLumine analogues and coumarin/naphthalene-derived luciferins.
  • To identify new bioluminescent probes with high photon emission for imaging applications.

Main Methods:

  • A two-step synthesis involving Horner-Wadsworth-Emmons reaction and cysteine condensation was employed.
  • Improved synthesis of AkaLumine and its homologues (Tri- and Tetra-AkaLumine) were achieved.
  • Coumarin- and naphthalene-based luciferins were synthesized and tested with various luciferases.

Main Results:

  • An efficient two-step synthesis was established for π-extended luciferins.
  • Novel AkaLumine analogues and coumarin/naphthalene derivatives were successfully prepared.
  • A naphthalene derivative demonstrated photon emission comparable to the AkaLumine/Akaluc pair.

Conclusions:

  • The developed chemistry provides efficient access to valuable bioluminescent probes.
  • The new naphthalene-based luciferin is a promising tool for bioluminescence imaging.
  • This work expands the toolkit for advanced in vivo imaging applications.