Bioinspired Molecular Lantern: Tuning the Firefly Oxyluciferin Emission with Host-Guest Chemistry

Na'Il Saleh, Abdul Rahman Ba Suwaid, Ahmad Alhalabi, Ahmed Z.A. Abuibaid, Oleg V. Maltsev, Lukas Hintermann, Panče Naumov

Research output: Contribution to journalArticlepeer-review

Abstract

Fireflies generate flashes of visible light via luciferase-catalyzed chemiexcitation of the substrate (luciferin) to the first excited state of the emitter (oxyluciferin). Microenvironment effects are often invoked to explain the effects of the luciferase active pocket on the emission; however, the exceedingly complex spectrochemistry and synthetic burdens have precluded elucidation of the nature of these interactions. To decipher the effects of microenvironment on the light emission, here the hydrophobic interior of cucurbit[7]uril (CB7) is used to mimic the nonpolar active pocket of luciferase. The hydrophobic interior of CB7 induces shifts of the ground-state pKas by 1.9-2.5 units to higher values. Upon sequestration, the emission maxima of neutral firefly oxyluciferin and its conjugate monodeprotonated base are blue-shifted by 40 and 39 nm, respectively, resulting in visual color changes of the emitted light.

Original languageEnglish (US)
Pages (from-to)7671-7680
Number of pages10
JournalJournal of Physical Chemistry B
Volume120
Issue number31
DOIs
StatePublished - Aug 11 2016

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Surfaces, Coatings and Films
  • Materials Chemistry

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