High Ionic Strength Formation of DOPA‐Melanin Coating for Loading and Release of Cationic Antimicrobial Compounds

Kuang, Jinghao; Guo, Jason L; Messersmith, Phillip B.

doi:10.1002/admi.201400145

Cited by 53 publications

(49 citation statements)

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“…Increased structural information of pigments may also inform the design of tailored techniques for solution processing of NatMel and SynMel into exfoliated structures or device‐quality electronically active thin films. Facile processing of melanin pigments could expand the use of redox active biologically derived materials for many applications including protective coatings, functional membranes, bioelectronics interfaces, or energy‐storage materials . For example, aqueous electrolytes coupled with biologically derived cathode materials with large positive potentials for sodium ion insertion may be used to power ingestible electronics, medical implants, or compostable devices for use in environmentally sensitive environments and beyond …”

mentioning

confidence: 99%

Evidence of Porphyrin‐Like Structures in Natural Melanin Pigments Using Electrochemical Fingerprinting

Kim

Khetan

et al. 2016

Advanced Materials

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Eumelanins are extended heterogeneous biopolymers composed of molecular subunits with ambiguous macromolecular topology. Here, an electrochemical fingerprinting technique is described, which suggests that natural eumelanin pigments contain indole-based tetramers that are arranged into porphyrin-like domains. Spectroscopy and density functional theory calculations suggest that sodium ions undergo occupancy-dependent stepwise insertion into the core of porphyrin-like tetramers in natural eumelanins at discrete potentials.

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confidence: 99%

Evidence of Porphyrin‐Like Structures in Natural Melanin Pigments Using Electrochemical Fingerprinting

Kim

Khetan

et al. 2016

Advanced Materials

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“…In contrast to the well-established dopamine surface polymerization, l-DOPA provides an additional carboxylic group and poly(l-DOPA) coatings exhibit higher hydrophilicity than polydopamine. [20,21] We anticipate that poly(l-DOPA) would show a greater potential in enhancing the aqueous stability of fNDs. In our experimental setup, 100 µg fNDs were dispersed in MilliQ water under sonication.…”

Section: Preparation and Characterization Of L-dopa-coated Nanodiamondsmentioning

confidence: 99%

Transferrin‐Coated Nanodiamond–Drug Conjugates for Milliwatt Photothermal Applications

Harvey

Raabe

Ermakova

et al. 2019

Advanced Therapeutics

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Fluorescent nanodiamonds (fNDs) are unique carbon-based nanomaterials due to their outstanding optical and magnetic properties. However, realization of the full potential of fNDs is often limited by their processability because fNDs aggregate strongly in both organic and aqueous solutions. Therefore, robust and potentially universal coating strategies are urgently needed to address these limitations. Derived from mussel foot proteins, the polymerization of l-3,4-dihydroxyphenylalanine (l-DOPA) provides important surface functional groups including amines, carboxylic acid, alcohols, and conjugated Michael acceptors. Herein, l-DOPA is polymerized on fNDs with a high control over the shell thickness. Photoluminescence and optically detected magnetic resonance studies reveal that the unique photophysical properties of fNDs are preserved after thin poly(l-DOPA) film coating. Subsequently, conjugation of transferrin, a heme protein that provides efficient receptor-specific cellular transport, improves the colloidal stability and cellular uptake of the poly(l-DOPA)-coated fNDs. The loading of FDA-approved indocyanine green as a photothermal agent yields an integrated biohybrid material exhibiting an amplified photothermal effect in cells at very low energy intake (≈90 mW cm −2 ).

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“…† The original dip-and-coat method pioneered by Messersmith et al 3,4 was employed in coating studies with NADOPAMe as monomer using silicon wafer as substrate. In contrast to studies with L-DOPA as monomer, 4 no coating was formed on the silicon wafer when NADOPAMe was used ( Fig. S2a †).…”

Section: Coatings From Copolymerization Of Nadopame and Various Diffementioning

confidence: 99%

“…3 Other related catecholamines such as L-3,4dihydroxyphenylalanine (L-DOPA) and norepinephrine can also undergo similar oxidative self-polymerization reactions (Scheme 1a). [4][5][6] Despite the many reported applications of such poly(catecholamines), the deposition mechanism and structures of poly(catecholamines) have yet to be unambiguously determined. 7 This is true for even the most well-studied poly(catecholamine), i.e.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2017

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Biomimetic poly(catecholamine) coatings have gained much attention in recent years due to their versatility as functional materials. Despite this, only limited methods are available to modify the function and property of poly(catecholamine) coatings, primarily through post-modification methods. Our approach reported herein provides a simple approach to the fabrication of novel functionalized poly(catecholamine) coatings. The strategy employs the copolymerization of N-Ac-3,4-dihydroxyphenylalanine methyl ester (NADOPAMe) with nucleophilic additives, giving rise to nano-coatings on various surfaces including plastic, metal, glass and polymers. With the appropriate choice of nucleophilic additives, coatings with desired properties can be achieved. This is demonstrated through the fabrication of a redox responsive coating based on NADOPAMe with cysteamine as additive, which shows a concentration-dependent glutathione (GSH) responsive behavior. The ability to utilize this as a controlled release system is also demonstrated.

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High Ionic Strength Formation of DOPA‐Melanin Coating for Loading and Release of Cationic Antimicrobial Compounds

Cited by 53 publications

References 50 publications

Evidence of Porphyrin‐Like Structures in Natural Melanin Pigments Using Electrochemical Fingerprinting

Evidence of Porphyrin‐Like Structures in Natural Melanin Pigments Using Electrochemical Fingerprinting

Transferrin‐Coated Nanodiamond–Drug Conjugates for Milliwatt Photothermal Applications

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

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