Chemically Modified Dansyl Probes: A Fluorescent Diagnostic for Ion and Proton Detection in Solution and in Polymers

O’Connor, Naphtali; Sakata, S. T.; Zhu, Huide; Shea, Kenneth J.

doi:10.1021/ol060130y

Cited by 34 publications

(17 citation statements)

References 37 publications

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“…The influence of pH on the fluorescence detection of D‐P5 to Hg 2+ and Cu 2+ was measured, as shown in Figure . Results indicated that D‐P5, D‐P5‐Hg and D‐P5‐Cu showed a weak fluorescence intensity in acidic solution (pH < 4) that could be attributed to charge transfer between the dimethylamino group and napthyl moiety and was prevented by the protonated dimethylamino group (pK a ~4) of fluorophore dansyl chloride . However, a weakly alkaline environment had less influence on these fluorescence peaks.…”

Section: Resultsmentioning

confidence: 96%

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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Section: Resultsmentioning

confidence: 96%

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

et al. 2019

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“…The unusual four-membered coordination ring motif proposed for the mono-Cd 2 þ complex has been identified in an X-ray crystal structure of a 1,8-naphthyridine -Ir(III) complex (107). However, the acyclic, mono-or dinuclear complexes (see below) of various transition metals (Ru (108), Cu, Ni, Zn, Co (114)(115)(116) reduced the rate of PET. Upon coordinating the first Cd 2 þ to form the proposed mononuclear complex, the HOMO of the fluorophore is lowered to afford a more efficient PET process, which results in fluorescence quenching.…”

Section: Group 2: Ligands Capable Of Forming Both Monoand Dinuclear Cmentioning

confidence: 96%

Mini review: Fluorescent heteroditopic ligands of metal ions

Zhu

Zhang

Younes

2009

Supramolecular Chemistry

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The recent advances in the development of fluorescent heteroditopic ligands of metal ions are reviewed. The scientific endeavour in this area is fuelled partly by the need for sensing technologies that are (1) targeting substances over large concentration ranges and (2) capable of analysing multiple analytes simultaneously. These objectives are largely not attainable using monotopic coordination platforms. The investigations of the fluorescent heteroditopic ligands of metal ions have revealed surprisingly intricate interplays between metal coordination at two different sites and the photophysical states that are accessible through those systems. The chemical complexity of fluorescent heteroditopic ligands of metal ions warrants further investigations on the fundamental science front in order to fully acquire their potential for meeting our practical needs.

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“…This can be described by considering that a classical on-off probe (from acidic to neutral-basic pH) has been converted to an off-on probe for the same pH modification. 25 The fluorescence emission maximum of the dansyl chromophore of 3 in an aqueous solution (Fig. S12 † for pH titration).…”

Section: Acid-base Titration Of Compoundmentioning

confidence: 99%

The synthesis of new fluorescent bichromophoric compounds as ratiometric pH probes for intracellular measurements

et al. 2015

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Registro de acceso restringido Este recurso no está disponible en acceso abierto por política de la editorial. No obstante, se puede acceder al texto completo desde la Universitat Jaume I o si el usuario cuenta con suscripción. Registre d'accés restringit Aquest recurs no està disponible en accés obert per política de l'editorial. No obstant això, es pot accedir al text complet des de la Universitat Jaume I o si l'usuari compta amb subscripció. Restricted access item This item isn't open access because of publisher's policy. The full--text version is only available from Jaume I University or if the user has a running suscription to the publisher's contents.

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Chemically Modified Dansyl Probes: A Fluorescent Diagnostic for Ion and Proton Detection in Solution and in Polymers

Cited by 34 publications

References 37 publications

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

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

Mini review: Fluorescent heteroditopic ligands of metal ions

The synthesis of new fluorescent bichromophoric compounds as ratiometric pH probes for intracellular measurements

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Chemically Modified Dansyl Probes: A Fluorescent Diagnostic for Ion and Proton Detection in Solution and in Polymers

Cited by 34 publications

References 37 publications

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

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

Mini review: Fluorescent heteroditopic ligands of metal ions

The synthesis of new fluorescent bichromophoric compounds as ratiometric pH probes for intracellular measurements

Contact Info

Product

Resources

About

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

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