Oxyluciferin Derivatives: A Toolbox of Environment-Sensitive Fluorescence Probes for Molecular and Cellular Applications

Avisek Ghose, Oleg V. Maltsev, Nicolas Humbert, Lukas Hintermann, Youri Arntz, Pance Naumov, Yves Mély, Pascal Didier

Research output: Contribution to journalArticle

Abstract

In this work, we used firefly oxyluciferin (OxyLH2) and its polarity-dependent fluorescence mechanism as a sensitive tool to monitor biomolecular interactions. The chromophores, OxyLH2, and its two analogues, 4-MeOxyLH and 4,6′-DMeOxyL, were modified trough carboxylic functionalization and then coupled to the N-terminus part of Tat and NCp7 peptides of human immunodeficiency virus type-1 (HIV-1). The photophysical properties of the labeled peptides were studied in live cells as well as in complex with different oligonucleotides in solution. By monitoring the emission properties of these derivatives we were able, for the first time, to study in vitro biomolecular interactions using oxyluciferin as a sensor. As an additional application, cyclopropyl-oxyluciferin (5,5-Cpr-OxyLH) was site-specifically conjugated to the thiol group (Cys-232) of the human protein α-1 antytripsin to investigate its interaction with porcine pancreatic elastase. Our data demonstrate that OxyLH2 and its derivatives can be used as fluorescence reporters for monitoring biomolecular interactions.

Original languageEnglish (US)
Pages (from-to)1566-1575
Number of pages10
JournalJournal of Physical Chemistry B
Volume121
Issue number7
DOIs
StatePublished - Feb 23 2017

Fingerprint

Molecular Probes
Peptides
Fluorescence
Derivatives
fluorescence
Monitoring
probes
Oligonucleotides
Chromophores
Viruses
peptides
Pancreatic Elastase
fireflies
interactions
Proteins
Sulfhydryl Compounds
human immunodeficiency virus
oligonucleotides
Sensors
troughs

ASJC Scopus subject areas

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

Cite this

Oxyluciferin Derivatives : A Toolbox of Environment-Sensitive Fluorescence Probes for Molecular and Cellular Applications. / Ghose, Avisek; Maltsev, Oleg V.; Humbert, Nicolas; Hintermann, Lukas; Arntz, Youri; Naumov, Pance; Mély, Yves; Didier, Pascal.

In: Journal of Physical Chemistry B, Vol. 121, No. 7, 23.02.2017, p. 1566-1575.

Research output: Contribution to journalArticle

Ghose, Avisek ; Maltsev, Oleg V. ; Humbert, Nicolas ; Hintermann, Lukas ; Arntz, Youri ; Naumov, Pance ; Mély, Yves ; Didier, Pascal. / Oxyluciferin Derivatives : A Toolbox of Environment-Sensitive Fluorescence Probes for Molecular and Cellular Applications. In: Journal of Physical Chemistry B. 2017 ; Vol. 121, No. 7. pp. 1566-1575.
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