A turn-on fluorescent pyrene-based chemosensor for Cu(<scp>ii</scp>) with live cell application

Venkatesan, Parthiban; Wu, Shu-Pao

doi:10.1039/c5ra05440k

Cited by 45 publications

(23 citation statements)

References 31 publications

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“…Pyrenes are considered to be excellent organic fluorophores and they are applied as environmental probes with distinct morphology and tunable emission in various micro environments due to their polarity dependent vibronic emission, high charge carrier mobility, fluorescence lifetime and chemical stability [3][4][5][6]. Up to now, numerous pyrene derivatives with good fluorescence properties have been reported.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of (E)-3-(pyren-1-yl)-1-(pyridin-4-yl)prop-2-en-1-one, C₂₄H₁₅NO

Huang

Wang

Ren

et al. 2017

Zeitschrift Für Kristallographie - New Crystal Structures

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C 24 H 15 NO, monoclinic, P2 1 /n (no. 14), a = 10.3161 ( CCDC no.: 1579090The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters. Source of material1-Pyrenecarboxaldehyde (230 mg, 1.0 mmol) and methanol (30 mL) were placed in a round-bottom flask and stirred at room temperature for 10 min. Then 4-acetylpyridine (145 mg, 1.2 mmol) and NaOH (5 mol/L, 10 mL) were added. The resulting reaction mixture was stirred at room temperature for 30 min. The mixture was extracted with CH 2 Cl 2 . The solvent was removed under reduced pressure to give the crude product, which was purified by column chromatog- raphy (petroleum ether:ethyl acetate = 1:4) to give the title compound as a red solid (isolated yield 50%). The isolated product was crystallized from CHCl 3 to give red single crystals. Experimental detailsAll hydrogen H atoms were positioned geometrically and refined using a riding model, with d(C-H) = 0.93 Å and U iso (H) = 1.2 U eq (C). DiscussionPyrenes are considered to be excellent organic fluorophores and they are applied as environmental probes with distinct morphology and tunable emission in various micro environments due to their polarity dependent vibronic emission, high charge carrier mobility, fluorescence lifetime and chemical stability [3][4][5][6]. Up to now, numerous pyrene derivatives with good fluorescence properties have been reported. For example, (2-pyrene-1-yl-vinyl)pyridine has reversible luminescence and nonlinear optical properties [7], 4-((pyren-1-yl)methyleneamino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one exhibits notable aggregation induced emission (AIE) phenomena in both solution and solid state [5]. 1-Methyl benzoate-pyrene displays pure blue monomer photoluminescence and electrogenerated chemiluminescence emissions in non-aqueous media [8]. In order to search for more pyrene-based compounds, in this paper we report a new one.There is one molecule in the asymmetric unit (cf. the figure). Bond lengths and angles are all in the expected ranges [9]. The non-H atoms of the pyrene ring and pyridine ring are nearly planar, respectively. But the pyrene unit is not coplanar

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Section: Discussionmentioning

confidence: 99%

Crystal structure of (E)-3-(pyren-1-yl)-1-(pyridin-4-yl)prop-2-en-1-one, C₂₄H₁₅NO

Huang

Wang

Ren

et al. 2017

Zeitschrift Für Kristallographie - New Crystal Structures

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“…The chemosensors binding with the metal ion block the PET mechanism resulting in significant fluorescence enhancement. 21 Furthermore, Wu et al have developed a highly selective turn-on fluorescence sensor for Cu 2+ detection in living cells, in which the picolinohydrazide act as a chelator and can bind to Cu 2+ through two functional groups, namely the amide nitrogen atom and the pyridine nitrogen atom. 22 On the basis of the above, we have focused our interest on designing molecules which can serve as receptors to recognize cations based on a fluorescence 'off-on' mechanism.…”

Section: Introductionmentioning

confidence: 99%

Fluorescent turn-on sensors based on pyrene-containing Schiff base derivatives for Cu2+ recognition: spectroscopic and DFT computational studies

et al. 2016

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“…As one of the most abundant trace metal elements in the human body, Cu 2+ plays a crucial role in metabolic homeostasis, protein regulation, and the development of living organisms . Therefore, selective and sensitive detection of Hg 2+ and Cu 2+ is needed due to fundamental application in environmental and biomedical sciences …”

Section: Introductionmentioning

confidence: 99%

Multifunctional peptide‐based fluorescent chemosensor for detection of Hg²⁺, Cu²⁺ and S²⁻ ions

et al. 2019

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A novel multifunctional fluorescent peptide sensor based on pentapeptide dansyl-Gly-His-Gly-Gly-Trp-COOH (D-P5) was designed and synthesized efficiently using Fmoc solid-phase peptide synthesis (SPPS). This fluorescent peptide sensor shows selective and sensitive responses to Hg 2+ and Cu 2+ among 17 metal ions and six anions studied in N-2-hydroxyethylpiperazine-N-2-ethane sulfonic acid (HEPES) buffer solution. The peptide probe differentiates Hg 2+ and Cu 2+ ions by a 'turn-on' response to Hg 2+ and a 'turn-off' response to Cu 2+ . Upon addition of Hg 2+ or Cu 2+ ions, the sensor displayed an apparent color change that was visible under an ultraviolet lamp to the naked eye. The limits of detection (LOD) of DP-5 were 25.0 nM for Hg 2+ and 85.0 nM for Cu 2+ ; the detection limits for Cu 2+ were much lower than the drinking water maximum contaminant levels set out by the United States Environmental Protection Agency (USEPA). It is noteworthy that both D-P5-Hg and D-P5-Cu systems were also used to detect S 2− successfully based on the formation of ternary complexes. The LODs of D-P5-Hg and D-P5-Cu systems for S 2− were 217.0 nM and 380.0 nM, respectively. Furthermore, the binding stoichiometry, binding affinity and pH sensitivity of the probe for Hg 2+ and Cu 2+ were investigated. This study gives new possibilities for using a short fluorescent peptide sensor for multifunctional detection, especially for anions. KEYWORDS cupric ion, fluorescent sensor, mercury ion, peptide-based sensor, sulfide ion

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A turn-on fluorescent pyrene-based chemosensor for Cu(ii) with live cell application

Abstract: A pyrene-based fluorescent sensor (PHP) was synthesized for Cu(ii) detection.

Cited by 45 publications

References 31 publications

Crystal structure of (E)-3-(pyren-1-yl)-1-(pyridin-4-yl)prop-2-en-1-one, C₂₄H₁₅NO

Crystal structure of (E)-3-(pyren-1-yl)-1-(pyridin-4-yl)prop-2-en-1-one, C₂₄H₁₅NO

Fluorescent turn-on sensors based on pyrene-containing Schiff base derivatives for Cu2+ recognition: spectroscopic and DFT computational studies

Multifunctional peptide‐based fluorescent chemosensor for detection of Hg²⁺, Cu²⁺ and S²⁻ ions

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A turn-on fluorescent pyrene-based chemosensor for Cu(ii) with live cell application

Abstract: A pyrene-based fluorescent sensor (PHP) was synthesized for Cu(ii) detection.

Cited by 45 publications

References 31 publications

Crystal structure of (E)-3-(pyren-1-yl)-1-(pyridin-4-yl)prop-2-en-1-one, C24H15NO

Crystal structure of (E)-3-(pyren-1-yl)-1-(pyridin-4-yl)prop-2-en-1-one, C24H15NO

Fluorescent turn-on sensors based on pyrene-containing Schiff base derivatives for Cu2+ recognition: spectroscopic and DFT computational studies

Multifunctional peptide‐based fluorescent chemosensor for detection of Hg2+, Cu2+ and S2− ions

Contact Info

Product

Resources

About

Crystal structure of (E)-3-(pyren-1-yl)-1-(pyridin-4-yl)prop-2-en-1-one, C₂₄H₁₅NO

Crystal structure of (E)-3-(pyren-1-yl)-1-(pyridin-4-yl)prop-2-en-1-one, C₂₄H₁₅NO

Multifunctional peptide‐based fluorescent chemosensor for detection of Hg²⁺, Cu²⁺ and S²⁻ ions