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Area of Science:

  • Organic Synthesis
  • Biochemistry
  • Luminescence

Background:

  • Native coelenterazine (CTZ) is a bioluminescent substrate.
  • Analogs of CTZ are explored for modified luminescent properties.
  • Vinylene-bridged analogs offer potential for red-shifted emission.

Purpose of the Study:

  • To develop a novel and concise synthetic method for v-coelenterazine (v-CTZ).
  • To investigate the luminescence properties of a new trifluoromethyl-substituted v-CTZ analog.
  • To evaluate the performance of v-CTZ analogs with Renilla luciferases.

Main Methods:

  • Sequential cross-coupling reactions.
  • Ring-closing metathesis (RCM) for cyclization.
  • Synthesis of a C2-modified trifluoromethyl analog (cf3-v-CTZ).

Main Results:

  • A concise synthetic route to v-CTZ was established.
  • The cf3-v-CTZ analog exhibited luminescence properties.
  • cf3-v-CTZ showed slightly red-shifted luminescence compared to v-CTZ when used with Renilla luciferases.

Conclusions:

  • A practical synthesis for v-CTZ analogs is now available.
  • The C2-trifluoromethyl modification offers tunable luminescence.
  • These findings advance the development of novel bioluminescent probes.