title: Oxyluciferin Derivatives: A Toolbox of Environment-Sensitive Fluorescence Probes for Molecular and Cellular Applications.
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 OxyLH2and its derivatives can be used as fluorescence reporters for monitoring biomolecular interactions.
authors.affiliation: Laboratoire de Biophotonique et Pharmacologie, UMR 7213 du CNRS, Faculté de Pharmacie, Université de Strasbourg , 74, Route du Rhin, 67401 Illkirch Cedex, France.
authors.forename: Avisek
authors.initials: A
authors.lastname: Ghose
authors.affiliation: Department Chemie, Technische Universität München , Lichtenbergstr. 4, 85748 Garching bei München, Germany.
authors.forename: Oleg V
authors.initials: OV
authors.lastname: Maltsev
authors.affiliation: Laboratoire de Biophotonique et Pharmacologie, UMR 7213 du CNRS, Faculté de Pharmacie, Université de Strasbourg , 74, Route du Rhin, 67401 Illkirch Cedex, France.
authors.forename: Nicolas
authors.initials: N
authors.lastname: Humbert
authors.affiliation: Department Chemie, Technische Universität München , Lichtenbergstr. 4, 85748 Garching bei München, Germany.
authors.forename: Lukas
authors.initials: L
authors.lastname: Hintermann
authors.affiliation: Laboratoire de Biophotonique et Pharmacologie, UMR 7213 du CNRS, Faculté de Pharmacie, Université de Strasbourg , 74, Route du Rhin, 67401 Illkirch Cedex, France.
authors.forename: Youri
authors.initials: Y
authors.lastname: Arntz
authors.affiliation: New York University Abu Dhabi , P.O. Box 129188, Abu Dhabi, United Arab Emirates.
authors.forename: Panče
authors.identifier: 0000-0003-2416-6569
authors.initials: P
authors.lastname: Naumov
authors.affiliation: Laboratoire de Biophotonique et Pharmacologie, UMR 7213 du CNRS, Faculté de Pharmacie, Université de Strasbourg , 74, Route du Rhin, 67401 Illkirch Cedex, France.
authors.forename: Yves
authors.identifier: 0000-0001-7328-8269
authors.initials: Y
authors.lastname: Mély
authors.affiliation: Laboratoire de Biophotonique et Pharmacologie, UMR 7213 du CNRS, Faculté de Pharmacie, Université de Strasbourg , 74, Route du Rhin, 67401 Illkirch Cedex, France.
authors.forename: Pascal
authors.identifier: 0000-0003-2850-9186
authors.initials: P
authors.lastname: Didier
mesh_terms: D000818:Animals; D048888:Fireflies; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D015497:HIV-1; D006367:HeLa Cells; D006801:Humans; D006863:Hydrogen-Ion Concentration; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D009838:Oligodeoxyribonucleotides / Q000737:chemistry / Q000378:metabolism*; D010196:Pancreatic Elastase / Q000737:chemistry / Q000378:metabolism; D011485:Protein Binding; D011719:Pyrazines / Q000138:chemical synthesis / Q000737:chemistry*; D013552:Swine; D000515:alpha 1-Antitrypsin / Q000737:chemistry / Q000378:metabolism; D054301:gag Gene Products, Human Immunodeficiency Virus / Q000737:chemistry / Q000378:metabolism*; D054322:tat Gene Products, Human Immunodeficiency Virus / Q000737:chemistry / Q000378:metabolism*
chemical_list: D005456:Fluorescent Dyes; D007211:Indoles; C071884:NCP7 protein, Human immunodeficiency virus 1; D009838:Oligodeoxyribonucleotides; D011719:Pyrazines; C043392:SERPINA1 protein, human; D000515:alpha 1-Antitrypsin; D054301:gag Gene Products, Human Immunodeficiency Virus; D054322:tat Gene Products, Human Immunodeficiency Virus; C014730:oxyluciferin; D010196:Pancreatic Elastase