Pyrene Functionalized Luminescent Phenylalanine for Selective Detection of Copper (II) Ions in Aqueous Media

Abstract

A novel pyrene-based uorescent chemosensor 1 (pyren-1ylmethyl)-L-phenylalanine was designed and synthesized by combining 1-pyrenecarboxyaldehyde and L-phenylalanine. 1 was characterized by several analytical methods and used as a uorescent chemosensor for the selective and sensitive detection of Cu 2+ ions through "turn-off" mechanism with a detection limit of 2 x 10 − 8 M. 1 can also be used to detect Cu 2+ ions in a natural water sample and exhibits gelation properties with high thermal stability.

New Amino Acid-Based Thiosemicarbazones and Hydrazones: Synthesis and Evaluation as Fluorimetric Chemosensors in Aqueous Mixtures

“…These features allow for higher detection sensitivity and lower detection and quantification limits, and their intrinsic biological nature also allows for prospective use in fluorescence-based biological assays, such as targeting peptides for molecular imaging; enzyme activity; or site-specific protein labelling for the in vivo tracking of protein localization, dynamics and concentration [4][5][6][7][8]. From a survey of the most recent literature, examples of amino acids and peptides involved in solution-or material-based fluorescent sensing were found to be highly varied and included a tryptophan-quinoline conjugate for the turn-off detection of Fe 2+ [9]; dipeptide receptors with aggregation-induced emission properties for the recognition of methylmercury and Hg 2+ [10]; cellulose nanofibers modified with L-histidine for the detection of Cr 6+ and Hg 2+ [11]; gold-silver bimetallic nanoclusters capped with tryptophan for the detection of histamine [12]; a near-infrared fluorophore based on a methionine attached to a chromenylium-cyanine for the analysis of Hg 2+ in the environment and living cells [13]; a phenylalanine-based dual-channel probe for the detection of Fe 3+ ; Cu 2+ and F − [14]; pyrene-phenylalanine conjugates for Cu 2+ analysis [15]; a derivative of tyrosine as a turn-off fluorescent sensor for Hg 2+ [16]; carbon quantum dots functionalized with different amino acids (glutamine, histidine, arginine, lysine and proline), capable of monitoring multiple metal ions in water [17]; and a series of pentapetides bearing tyrosine for the detection of Cu 2+ at the nanomolar level [18]. These are only a few examples that confirm the growing interest in and application of amino acids/peptides as bio-inspired systems for sensing.…”

Copper-guided tuning of supramolecular nano-assembly in pseudopeptide-based soft bioinspired materials

“…[3][4][5] Therefore, the detection or recognition of many ionic or neutral species occurs through a non-covalent interaction between the probe and the guest unit. 6,7 It provides an excellent tool for creating supramolecular assembly to detect various biologically and environmentally crucial metal ions. 8 Working on the natural system is, again, a difficult task because of its high complexity and understanding of the biological process at the molecular level.…”