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, Pance Naumov

Research output: Contribution to journalArticle

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

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fireflies
Luciferases
Tuning
tuning
chemistry
Light emission
Excited states
Ground state
Color
light emission
flash
emitters
Substrates
color
ground state
shift
excitation
oxyluciferin
interactions

ASJC Scopus subject areas

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

Cite this

Saleh, NI., Suwaid, A. R. B., Alhalabi, A., Abuibaid, A. Z. A., Maltsev, O. V., Hintermann, L., & Naumov, P. (2016). Bioinspired Molecular Lantern: Tuning the Firefly Oxyluciferin Emission with Host-Guest Chemistry. Journal of Physical Chemistry B, 120(31), 7671-7680. https://doi.org/10.1021/acs.jpcb.6b06557

Bioinspired Molecular Lantern : Tuning the Firefly Oxyluciferin Emission with Host-Guest Chemistry. / Saleh, Na'Il; Suwaid, Abdul Rahman Ba; Alhalabi, Ahmad; Abuibaid, Ahmed Z.A.; Maltsev, Oleg V.; Hintermann, Lukas; Naumov, Pance.

In: Journal of Physical Chemistry B, Vol. 120, No. 31, 11.08.2016, p. 7671-7680.

Research output: Contribution to journalArticle

Saleh, NI, Suwaid, ARB, Alhalabi, A, Abuibaid, AZA, Maltsev, OV, Hintermann, L & Naumov, P 2016, 'Bioinspired Molecular Lantern: Tuning the Firefly Oxyluciferin Emission with Host-Guest Chemistry', Journal of Physical Chemistry B, vol. 120, no. 31, pp. 7671-7680. https://doi.org/10.1021/acs.jpcb.6b06557
Saleh NI, Suwaid ARB, Alhalabi A, Abuibaid AZA, Maltsev OV, Hintermann L et al. Bioinspired Molecular Lantern: Tuning the Firefly Oxyluciferin Emission with Host-Guest Chemistry. Journal of Physical Chemistry B. 2016 Aug 11;120(31):7671-7680. https://doi.org/10.1021/acs.jpcb.6b06557
Saleh, Na'Il ; Suwaid, Abdul Rahman Ba ; Alhalabi, Ahmad ; Abuibaid, Ahmed Z.A. ; Maltsev, Oleg V. ; Hintermann, Lukas ; Naumov, Pance. / Bioinspired Molecular Lantern : Tuning the Firefly Oxyluciferin Emission with Host-Guest Chemistry. In: Journal of Physical Chemistry B. 2016 ; Vol. 120, No. 31. pp. 7671-7680.
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