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Chimeric GFP-uracil based molecular rotor fluorophores.

Mria Chowdhury1, Julia A Turner1, Daniela Cappello1

  • 1Department of Chemistry, The University of Western Ontario, London, Ontario, Canada N6A 5B7. rhhudson@uwo.

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|November 24, 2023
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This summary is machine-generated.

Researchers developed novel uracil-based fluorescent molecules inspired by green fluorescent protein (GFP). These nucleobase-chromophores show environmental sensitivity and can be integrated into peptide nucleic acid (PNA) for DNA detection.

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Area of Science:

  • Organic Chemistry
  • Biophysical Chemistry
  • Molecular Biology

Background:

  • Green fluorescent protein (GFP) is a widely used biological marker.
  • Nucleobase modifications offer opportunities for novel fluorescent probes.
  • Understanding microenvironmental effects on fluorescence is crucial for probe design.

Purpose of the Study:

  • To synthesize and characterize novel uracil-derived nucleobase-chromophores.
  • To investigate the photophysical properties and environmental sensitivity of these analogues.
  • To incorporate these probes into peptide nucleic acid (PNA) for DNA sensing applications.

Main Methods:

  • Erlenmeyer azlactone synthesis followed by amination using hexamethyl disilazane (HMDS).
  • Spectroscopic analysis (emission, solvatochromism) to determine photophysical properties.
  • Incorporation into PNA strands and evaluation of fluorescence response upon DNA hybridization.

Main Results:

  • A library of uracil analogues emitting in the green spectrum was synthesized.
  • Analogues exhibited solvatochromism and viscosity-dependent fluorescence enhancement.
  • Solid-state quantum yields reached approximately 0.2 with emission >500 nm.
  • PNA-incorporated probes showed fluorescence turn-off with mismatches and turn-on (>3-fold) with complementary DNA.

Conclusions:

  • Novel nucleobase-chromophores with tunable fluorescence properties were created.
  • These probes are sensitive to their microenvironment.
  • The developed PNA-DNA systems demonstrate potential for sensitive and selective nucleic acid detection.