A one step method for the functional and property modification of DOPA based nanocoatings

Lyu, Qinghua; Zhang, Jieyu; Neoh, K. G.; Chai, Christina L. L.

doi:10.1039/c7nr05293f

Cited by 20 publications

(21 citation statements)

References 34 publications

(47 reference statements)

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“…Stimuli responsive groups, like disulfide can be introduced into the binucleophilic linker allowing triggered cleavage of the polymer chain by an external stimulus, e.g. glutathione …”

Section: Resultsmentioning

confidence: 99%

“…glutathione. [94] Scheme 22. Oxidative copolymerization of N-acetyl dopa methyl ester with binucleophiles (top) and assumed monomer units (bottom).…”

Section: Oxidative Polymerization Of Analogues Of Damentioning

confidence: 99%

“…Oxidative copolymerization of N-acetyl dopa methyl ester with binucleophiles (top) and assumed monomer units (bottom). [94] Air oxidation of N-lactosylated dopamine in ethanol/ammonia resulted in a copolymer with dopamine (Scheme 23). Obviously, a part of the lactosylated dopamine underwent hydrolytic cleavage to lactosylacid and dopamine in the course of the reaction.…”

Section: Oxidative Polymerization Of Analogues Of Damentioning

confidence: 99%

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Chemistry of Polydopamine – Scope, Variation, and Limitation

2019

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Polydopamine (PDA) is a polymer easily obtained by oxidation of dopamine. It is composed of indole and dopamine units in various oxidation states and to a lesser extent of pyrroles. It adheres to all type of surfaces even under water due to its abundant catechol moieties assisted by amino groups. This property together with a widespread reactivity to nucleophiles and electrophiles allowing linkage of a variety of entities renders PDA extremely interesting for various applications in biology, biomedicine, membranes, catalysis, materials and water purification. The field of PDA is violently developing. The present review gives an overview about the chemistry and properties of PDA and its analogues with the focus on recent publications. Their widespread applications are occasionally touched. Analogues are obtained by two strategies: post‐modification of PDA and oxidative polymerization of dopamine analogues. Scope and limitations of these strategies are worked out giving impulses for future research in the field.

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“…Stimuli responsive groups, like disulfide can be introduced into the binucleophilic linker allowing triggered cleavage of the polymer chain by an external stimulus, e.g. glutathione …”

Section: Resultsmentioning

confidence: 99%

“…glutathione. [94] Scheme 22. Oxidative copolymerization of N-acetyl dopa methyl ester with binucleophiles (top) and assumed monomer units (bottom).…”

Section: Oxidative Polymerization Of Analogues Of Damentioning

confidence: 99%

Section: Oxidative Polymerization Of Analogues Of Damentioning

confidence: 99%

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Chemistry of Polydopamine – Scope, Variation, and Limitation

2019

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“…HMDA, regarded as a lysine mimic in mussel-inspired adhesive systems [27], has been shown to enable the deposition of adhesive films from gallic acid, caffeic acid, 5,6-dihydroxyindole [26], N -protected DOPA [28], and other catechol-containing polymers [29,30,31]. This versatile strategy provides an entry to the design of a variety of functional films and coatings, including, e.g., antioxidant properties via binding to melanin-related metabolites [32].…”

Section: Introductionmentioning

confidence: 99%

“…This versatile strategy provides an entry to the design of a variety of functional films and coatings, including, e.g., antioxidant properties via binding to melanin-related metabolites [32]. Different from the coupling of HMDA to catechol and catecholamines, which may occur via Michael addition or condensation reactions at the o -quinone intermediates [25,28], the chemistry leading to the fluorescent methanobenzofuroazocinone system from dopamine and resorcinol relies on the high nucleophilic reactivity of the carbon position of resorcinol, which efficiently competes with the primary amino group of the catecholamine, inhibiting the cyclization pathway.…”

Section: Introductionmentioning

confidence: 99%

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

Alfieri

Iacomino

Napolitano

et al. 2019

IJMS

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The reaction-based deposition on various surfaces of an all-organic fluorescent coating is reported here, involving autoxidation of 2 mM dopamine in carbonate buffer at pH 9.0, in the presence of a 1 mM diamine–resorcinol coupler (Bis–Res) prepared from 2,4-dihydroxybenzaldehyde and hexamethylenediamine (HMDA). Spectral analysis of the films coupled with an LC-MS investigation of the yellow fluorescent mixture was compatible with the formation and deposition of HMDA-linked methanobenzofuroazocinone fluorophores. Both the emission properties and hydrophobicity of the film were abated in a reversible manner following exposure to acid vapors. These results provide an entry to efficient and practical fluorescent coating methodologies based on in situ generation and the deposition of wet adhesive, as well as fluorescent materials combining a strongly emitting fluorophore with the film-forming properties of long chain diamines.

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Black Phosphorus: Degradation Mechanism, Passivation Method, and Application for In Situ Tissue Regeneration

Xie

Abbasi

Xiao

et al. 2020

Adv Materials Inter

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have been already applied for the restoration. [2] During the development of the treatments, the term "tissue engineering" was advanced in the 1980s, in which the biological and engineering principles are combined to fabricate functional replacements for regenerating injured tissues. [3] However, the classical tissue engineering strategy needs a lot of time and much laborious effort for extensive cell expansion steps. In the past few decades, a new idea, known as in situ tissue regeneration (ISTR), was introduced. ISTR means that the host endogenous stem cells or tissuespecific progenitor cells are guided to the location of trauma for tissue recovery in vivo by implanting specific biomaterials system without complicated in vitro manipulation. [4] Many biomaterials, including natural biomaterials, [5] synthetic biopolymers, [6] and bioceramics, [7] have been widely applied for ISTR. The degradation rate of materials is crucial to the successful ISTR, as a rapid degradation may influence the properties of implanted biomaterial composites, for example, causing a mechanical failure. From the other side, if the composite degrades too sluggishly, an inflammation might occur and impair the recovery of damaged tissue. [8] Along with the rapid development of nanomaterials, the 2D materials [9] have attracted ever-increasing interest in tissue regeneration, owing to their remarkable optical properties, biocompatibility, large specific surface area, and high payload of drugs and agents. However, the ISTR application area is limited by the poor biodegradability of conventional 2D nanomaterials. Attributed to the excellent biodegradation ability, 2D black phosphorus (BP) has stepped into people's horizon, which shows more promising potentials in organism restoration over other 2D materials. The bulk form of BP was first synthesized by Bridgman in 1914 from white phosphorus with a high-pressure synthesis method. [10] Nevertheless, the BP crystal did not gain much attention due to the small band gap and the difficulty of controlling the material quality, [11] until a monolayer (ML) of BP crystal was introduced by several research groups in 2014. [12] The 2D nanomaterial of BP, also known as phosphorene, has several different properties from other 2D materials, e.g., graphene. One different major point is that the lone pair electron makes phosphorus atom be an active chemical adsorption position for oxygen molecules. With the rapid increase of BP surface, phosphorene will chemically decompose very quickly Nanomaterials have attracted ever-increasing interest in tissue regeneration in the past few decades. As an emerging 2D layered nanomaterial, black phosphorus shows more promising potentials in organism restoration than other 2D materials, attributed to its extraordinary biodegradation ability, remarkable optical properties, and high payload of drugs and agents. The degradation products, i.e., phosphate, can be adsorbed by tissues for specific regeneration such as bone, yet the excessive degradation rate of black phosphorus wil...

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A one step method for the functional and property modification of DOPA based nanocoatings

Cited by 20 publications

References 34 publications

Chemistry of Polydopamine – Scope, Variation, and Limitation

Chemistry of Polydopamine – Scope, Variation, and Limitation

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

Black Phosphorus: Degradation Mechanism, Passivation Method, and Application for In Situ Tissue Regeneration

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