TY - JOUR
T1 - Oxyluciferin Derivatives
T2 - A Toolbox of Environment-Sensitive Fluorescence Probes for Molecular and Cellular Applications
AU - Ghose, Avisek
AU - Maltsev, Oleg V.
AU - Humbert, Nicolas
AU - Hintermann, Lukas
AU - Arntz, Youri
AU - Naumov, Panče
AU - Mély, Yves
AU - Didier, Pascal
N1 - Funding Information:
This work and A.G. were supported by the Human Frontier Science Program (project RGY0081/2011, Excited-State Structure of the Emitter and Color-Tuning Mechanism of the Firefly Bioluminescence). Authors thank Christian Boudier for providing unlabeled ?1-AT and PPE, Julien Godet, Hugues de Rocquigny for fruitful discussion and Salahedin Elmeshri for help in cell culture.
Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/2/23
Y1 - 2017/2/23
N2 - 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.
AB - 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.
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U2 - 10.1021/acs.jpcb.6b12616
DO - 10.1021/acs.jpcb.6b12616
M3 - Article
C2 - 28118001
AN - SCOPUS:85027250080
SN - 1520-6106
VL - 121
SP - 1566
EP - 1575
JO - Journal of Physical Chemistry B
JF - Journal of Physical Chemistry B
IS - 7
ER -