title: A Reduction-Based Sensor for Acrolein Conjugates with the Inexpensive Nitrobenzene as an Alternative to Monoclonal Antibody.
abstract: Acrolein, a highly toxic α, β-unsaturated aldehyde, has been a longstanding key biomarker associated with a range of disorders related to oxidative stresses. One of the most promising methods for detecting acrolein involves the use of antibodies that can recognize the acrolein-lysine conjugate, 3-formyl-3, 4-dehydropiperidines (FDP), within oxidatively stressed cells and tissues from various disease states. We have uncovered here that FDP could reduce nitroarenes in high yields at 100 °C in the presence of excess CaCl2as a Lewis acid promoter. This unique transformation allowed for the development of a de novo method for detecting levels of FDPs generated from proteins in urine or blood serum samples. Thus we successfully converted a non-fluorescent and inexpensive 4-nitrophthalonitrile probe to the corresponding fluorescent aniline, thereby constituting the concept of fluorescent switching. Its sensitivity level (0.84 nmol/mL) is more than that of ELISA assays (3.13 nmol/mL) and is already equally reliable and reproducible at this early stage of development. More importantly, this method is cost effective and simple to operate, requiring only mixing of samples with a kit solution. Our method thus possesses potential as a future alternative to the more costly and operatively encumbered conventional antibody-based methods.
authors: Biofunctional Synthetic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.|Department of Chemistry Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan.
authors: Masayuki
authors: M
authors: Takamatsu
authors: Department of Chemistry Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan.
authors: Koichi
authors: K
authors: Fukase
authors: Disease Glycomics Team, Global Research Cluster, RIKEN-Max Planck Joint Research Center for Systems Chemical Biology, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
authors: Ritsuko
authors: R
authors: Oka
authors: Disease Glycomics Team, Global Research Cluster, RIKEN-Max Planck Joint Research Center for Systems Chemical Biology, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
authors: Shinobu
authors: S
authors: Kitazume
authors: Disease Glycomics Team, Global Research Cluster, RIKEN-Max Planck Joint Research Center for Systems Chemical Biology, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
authors: Naoyuki
authors: N
authors: Taniguchi
authors: Biofunctional Synthetic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.|Biofunctional Chemistry Laboratory, A. Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlyovskaya street, Kazan 420008, Russia.|Japan Science and Technology Agency-PRESTO, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
authors: Katsunori
authors: K
authors: Tanaka
mesh_terms: D000171:Acrolein / Q000032:analysis* / Q000737:chemistry / Q000276:immunology; D000814:Aniline Compounds / Q000737:chemistry; D000818:Animals; D000911:Antibodies, Monoclonal; D015415:Biomarkers / Q000032:analysis / Q000737:chemistry; D005456:Fluorescent Dyes / Q000737:chemistry; D006801:Humans; D008239:Lysine / Q000737:chemistry; D051379:Mice; D015394:Molecular Structure; D009578:Nitrobenzenes; D010084:Oxidation-Reduction; D018384:Oxidative Stress
chemical_list: D000814:Aniline Compounds; D000911:Antibodies, Monoclonal; D015415:Biomarkers; D005456:Fluorescent Dyes; D009578:Nitrobenzenes; D000171:Acrolein; D008239:Lysine