title: Design, Synthesis, and Photophysical Properties of Pyrroloquinoline-Based Compounds Showing Strong Blue Fluorescence as Potential Dyes for Biomedical Applications.
abstract: A small library of 3-ethylpyrrolo[3,2-f]quinoline derivatives was synthesized to identify a novel class of dyes for use in biological studies. According to the spectroscopic analyses performed to evaluate the fluorimetric parameters of quantum yield and brightness, 7-methyl- and 6,7-dimethylpyrroloquinolin(9)one derivatives were found to be the best blue luminescent dyes for biological applications. To enhance the luminescence profiles and to obtain probes that could be conjugated to functional groups of supramolecular drug delivery systems, these compounds were further modified at position 3 to obtain 3-heptanoic acid and 3-aminohexylpyrroloquinolin(9)one methylated derivatives. The most brilliant 6,7-dimethyl-3-aminohexylpyrroloquinolinone hydrochloride was conjugated to pullulan, a biocompatible polysaccharide used to produce colloidal systems for drug delivery. Comparative studies showed that this compound can be properly exploited as a blue fluorescent label in biological investigations, namely cell trafficking and pharmacokinetics/biodistribution studies. These molecules possess higher fluorescence efficiency than commercial dyes in biological media, making them suitable alternatives to commercially available products in current use.
authors.affiliation: Department of Pharmaceutical and Pharmacological Sciences, University of Padova, 35131, Padova, Italy.
authors.forename: Davide
authors.initials: D
authors.lastname: Carta
authors.affiliation: Department of Pharmaceutical and Pharmacological Sciences, University of Padova, 35131, Padova, Italy.
authors.forename: Anna
authors.initials: A
authors.lastname: Balasso
authors.affiliation: Department of Pharmaceutical and Pharmacological Sciences, University of Padova, 35131, Padova, Italy.
authors.forename: Paolo
authors.initials: P
authors.lastname: Caliceti
authors.affiliation: Department of Pharmaceutical and Pharmacological Sciences, University of Padova, 35131, Padova, Italy. mariagrazia.ferlin@unipd.it.
authors.forename: Maria Grazia
authors.initials: MG
authors.lastname: Ferlin
mesh_terms: D002470:Cell Survival / Q000187:drug effects; D058948:Cell Tracking; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D061986:MCF-7 Cells; D015394:Molecular Structure; D055668:Photochemical Processes; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D005456:Fluorescent Dyes; D011758:Pyrroles; D011804:Quinolines; C410406:pyrroloquinoline
keywords: drug delivery; fluorescence; fluorescent labeling; pullulan; pyrroloquinolines