Reaction-Based, Fluorescent Film Deposition from Dopamine and a Diamine-Tethered, Bis–Resorcinol Coupler

Alfieri, Maria Laura; Iacomino, Mariagrazia; Napolitano, Alessandra; d’Ischia, Marco

doi:10.3390/ijms20184532

Cited by 3 publications

(3 citation statements)

References 34 publications

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“…[16] On the other hand, in the last decade coatings inspired to the same chemistry, but using different starting materials have been explored and their potential assessed for different applications. [17][18][19][20][21][22][23][24][25] The versatile chemistry of catechols make different mode of interaction with amine components possible ranging from covalent-type via Michael-type addition or Schiff-base formation to non-covalent electrostatic and cation-π ones.…”

Section: Introduction: Functional Coatingsmentioning

confidence: 99%

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Multifunctional coatings hinging on the catechol/amine interplay

Alfieri,

Panzella,

Napolitano

2023

Eur J Org Chem

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Design and implementation of functional coatings is a topic of active research in a variety of health‐related applications, most of which require wet adhesion. The powerful wet adhesion of mussel byssus proteins rich in DOPA and lysine residues provided a clue to realize that the combination of a catechol and an amine component has a specific role in the interfacial adhesion. From this natural model, polydopamine (PDA)‐based coatings have been developed that result from the oxidative polymerization of dopamine combining the catechol and amine functionalities in the same molecule. Covalent interactions resulting from Michael‐type addition or Schiff‐base formation of the polymeric products from dopamine oxidation as well as non‐covalent π‐stacking and cation‐π interactions exemplify the diverse mode of catechol/amine interplay that have been identified as responsible of the adhesion and cohesion properties of PDA. In the last decade coatings inspired to the same chemistry but using different starting materials have been explored particularly catechols of natural origin and different amine components, while mechanistic studies with model compounds have allowed to rationalize the structural requirements for adhesion and to expand the potential of these functional coatings.

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Section: Introduction: Functional Coatingsmentioning

confidence: 99%

“…On the other hand, in the last decade coatings inspired to the same chemistry, but using different starting materials have been explored and their potential assessed for different applications [17–25] …”

Section: Introduction: Functional Coatingsmentioning

confidence: 99%

Multifunctional coatings hinging on the catechol/amine interplay

Alfieri,

Panzella,

Napolitano

2023

Eur J Org Chem

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“…As tyrosinase can convert monophenolamine into dopamine, this strategy can also be used for the detection of tyrosinase or alkaline phosphatase [44][45][46][47][48]. Furthermore, the quantum yield of Aza is closely related to pH, allowing it to be used for the detection of acidic or alkaline gases [49]. Additionally, the internal filtering effect of quantum dots or Cr 6+ ions on Aza can be utilized in the development of sensing platforms for the detection of biothiols [50], chromium ions, or ascorbic acid [51].…”

Section: Introductionmentioning

confidence: 99%

A Novel Fluorescence Probe Based on Azamonardine for Detecting and Imaging Cysteine in Cells and Zebrafish with High Selectivity and Sensitivity

Zhao,

Wang,

Abdulkhaleq

et al. 2023

Molecules

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A novel fluorescent probe based on azamonardine (Aza) fluorophore was designed and synthesized for the highly selective detection of cysteine (Cys) in vivo and in vitro. After reacting with acryloyl chloride, the fluorescence of Aza is effectively quenched, resulting in the formation of the Aza-acryl probe. Upon the addition of Cys, the ester bond of Aza-acryl is cleaved, releasing a new compound (Compound 1) with strong fluorescence, thereby achieving fluorescence turn-on detection of Cys. The structure of Aza-acryl was characterized using X-ray crystallography and NMR spectroscopy. Additionally, density functional theory was employed to elucidate the quenching mechanism of the acyl group on the Aza. Aza-acryl exhibits high selectivity towards Cys and distinguishes it from other biothiols such as homocysteine (Hcy) and glutathione (GSH). The mechanism of Aza-acryl for detecting Cys was investigated through HPLC, NMR spectroscopy, high-resolution mass spectrometry, and reaction kinetics experiments. Aza-acryl demonstrates excellent imaging capabilities for Cys in cells and zebrafish, providing a reliable and selectable tool for the detection and imaging of Cys in biological systems.

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Nature‐Inspired Functional Chromophores from Biomimetic o‐Quinone Chemistry

et al. 2021

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Dedicated to Professor Franco Cozzi on the occasion of his 70th birthday.A concise highlight of the main types of chromophoric systems obtained in the authors' and other laboratories through biomimetic chemistry or synthetic manipulation of natureinspired o-quinones is the primary focus of this Minireview. Following oxidative conversion of a variety of natural catechol substrates like DOPA, dopamine, 5-S-cysteinyldopa and caffeic acid, in the presence of suitable additives, a remarkable variety of chromophoric systems can be produced, which display specific optical and electronic properties, e. g. acidichromism, solvatochromism or strong emission upon excitation. Such properties can be tailored for specific applications through rational synthetic manipulations and/or fine-tuning through non-covalent and supramolecular interactions. Practical access routes to the reported o-quinone-derived chromophoric systems are illustrated along with the main prospective applications.

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Reaction-Based, Fluorescent Film Deposition from Dopamine and a Diamine-Tethered, Bis–Resorcinol Coupler

Cited by 3 publications

References 34 publications

Multifunctional coatings hinging on the catechol/amine interplay

Multifunctional coatings hinging on the catechol/amine interplay

A Novel Fluorescence Probe Based on Azamonardine for Detecting and Imaging Cysteine in Cells and Zebrafish with High Selectivity and Sensitivity

Nature‐Inspired Functional Chromophores from Biomimetic o‐Quinone Chemistry

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