title: Determination of the isomeric forms proportion of fluorogenic naphthalene-2,3-dicarboxaldehyde in a binary mixture of water:methanol using electrochemical methods.
abstract: The electrochemical response of the fluorogenic label naphthalene-2,3-dicarboxyaldehyde (NDA) in a binary mixture of water/methanol was characterized with cyclic voltammetry (CV) and differential pulse voltammetry (DPV) electrochemical techniques. Naphthalene-2,3-dicarboxyaldehyde does exist in three isomeric forms in aqueous solution: the unhydrated dialdehyde (DA), the acyclic monohydrated (MA) and the cyclic hemiacetal (HAC). The study underlines that the proportion of each of them varies according to the working pH. At low and high pH, the dialdehyde form is in larger proportion than the acyclic monohydrated form. Conversely at intermediate pH, the concentration of the acyclic form is in greater proportion than the dialdehyde form. These results allowed us to determine the optimal pH of 9 for which the labeling of biomolecules could be more efficient due to the base catalyzed regeneration of the unhydrated form. At this pH, the data processing from the analysis of measured currents and estimation of diffusion coefficients of each form according to the semi-empirical models of Wilke-Chang, Scheibel, Reddy-Doraiswamy and Lusis-Ratcliff allowed us to obtain the concentration of dialdehyde (0.28 mM), acyclic monohydrated (0.57 mM) and cyclic hemiacetal monohydrated (0.15 mM) forms starting from 1mM naphthalene-2,3-dicarboxyaldehyde.
authors.affiliation: Sorbonne Universités, UPMC Univ Paris 06, CNRS, Laboratoire Interfaces et Systèmes Electrochimiques, 4 place Jussieu, F-75005 Paris, France.
authors.forename: Mathilde
authors.initials: M
authors.lastname: Faure
authors.affiliation: CNRS, Institut Galien Paris-Sud, UMR 8612, F-92290 Châtenay-Malabry, France; Université Paris-Sud, Faculté de Pharmacie, 5 rue Jean-Baptiste Clément, 92290 Châtenay-Malabry, France.
authors.forename: Isabelle
authors.initials: I
authors.lastname: Le Potier
authors.affiliation: CNRS, Laboratoire de Photonique et de Nanostructures, UPR20, Marcoussis 91460, France; Université Paris-Sud, Faculté de Pharmacie, 5 rue Jean-Baptiste Clément, 92290 Châtenay-Malabry, France.
authors.forename: Antoine
authors.initials: A
authors.lastname: Pallandre
authors.affiliation: Sorbonne Universités, UPMC Univ Paris 06, CNRS, Laboratoire Interfaces et Systèmes Electrochimiques, 4 place Jussieu, F-75005 Paris, France.
authors.forename: Syrine
authors.initials: S
authors.lastname: Chebil
authors.affiliation: CNRS, Laboratoire de Photonique et de Nanostructures, UPR20, Marcoussis 91460, France.
authors.forename: Anne-Marie
authors.initials: AM
authors.lastname: Haghiri-Gosnet
authors.affiliation: Sorbonne Universités, UPMC Univ Paris 06, CNRS, Laboratoire Interfaces et Systèmes Electrochimiques, 4 place Jussieu, F-75005 Paris, France.
authors.forename: Claude
authors.initials: C
authors.lastname: Deslouis
authors.affiliation: Sorbonne Universités, UPMC Univ Paris 06, CNRS, Laboratoire Interfaces et Systèmes Electrochimiques, 4 place Jussieu, F-75005 Paris, France.
authors.forename: Emmanuel
authors.initials: E
authors.lastname: Maisonhaute
authors.affiliation: Sorbonne Universités, UPMC Univ Paris 06, CNRS, Laboratoire Interfaces et Systèmes Electrochimiques, 4 place Jussieu, F-75005 Paris, France. Electronic address: jean.gamby@upmc.fr.
authors.forename: Jean
authors.initials: J
authors.lastname: Gamby
mesh_terms: D055664:Electrochemical Techniques / Q000379:methods*; D005456:Fluorescent Dyes / Q000032:analysis* / Q000737:chemistry; D007536:Isomerism; D000432:Methanol / Q000737:chemistry*; D009281:Naphthalenes / Q000032:analysis* / Q000737:chemistry; D014867:Water / Q000737:chemistry*
chemical_list: D005456:Fluorescent Dyes; D009281:Naphthalenes; D014867:Water; C027717:2,3-naphthalenedicarboxaldehyde; D000432:Methanol
keywords: Acyclic monohydrated; Cyclic hemiacetal; Cyclic voltammetry; Dialdehyde; Differential pulse voltammetry; Naphthalene-2,3-dicarboxaldehyde