Melanin‐Inspired Chromophoric Microparticles Composed of Polymeric Peptide Pigments

Lampel, Ayala; McPhee, Scott A.; Kassem, Salma; Sementa, Deborah; Massarano, Tlalit; Aramini, James M.; He, Ye; Ulijn, Rein V.

doi:10.1002/anie.202015170

Cited by 29 publications

(43 citation statements)

References 44 publications

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“…Lampel et al performed the enzymatic oxidation of Y on a selfassembling KYF tripeptide to obtain melanin-like chromophoric microparticles with unique optical properties. 310 The work shows that the preorganization of Y on self-assembled KYF was crucial during enzymatic oxidation to form green emitting nanostructures (λ em = 533 nm). Detailed chemical analysis revealed the formation of new catechol and quinone units, which further polymerize to form stable assemblies.…”

Section: Photonic Electronic Protonic and Ionic Conduction And Commun...mentioning

confidence: 99%

Peptide-Based Supramolecular Systems Chemistry

et al. 2021

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Peptide-based supramolecular systems chemistry seeks to mimic the ability of life forms to use conserved sets of building blocks and chemical reactions to achieve a bewildering array of functions. Building on the design principles for short peptide-based nanomaterials with properties, such as self-assembly, recognition, catalysis, and actuation, are increasingly available. Peptide-based supramolecular systems chemistry is starting to address the far greater challenge of systems-level design to access complex functions that emerge when multiple reactions and interactions are coordinated and integrated. We discuss key features relevant to systems-level design, including regulating supramolecular order and disorder, development of active and adaptive systems by considering kinetic and thermodynamic design aspects and combinatorial dynamic covalent and noncovalent interactions. Finally, we discuss how structural and dynamic design concepts, including preorganization and induced fit, are critical to the ability to develop adaptive materials with adaptive and tunable photonic, electronic, and catalytic properties. Finally, we highlight examples where multiple features are combined, resulting in chemical systems and materials that display adaptive properties that cannot be achieved without this level of integration.

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Section: Photonic Electronic Protonic and Ionic Conduction And Commun...mentioning

confidence: 99%

Peptide-Based Supramolecular Systems Chemistry

et al. 2021

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“…[68] Additionally, Lampel et al developed new melanin-inspired pigments with an enhanced range of color, UV absorbance, and fluorescent emission spectrum compared to natural melanin. [69] Finally, Vasileiou and Summerer were bioinspired by the mechanism melanized fungi protection against ionizing radiation in order to apply it for the protection of astronauts. [70] Novel bioinspired and biomimetic skin-adhesives and flexible electronics were developed based on the suction cups of various organisms.…”

Section: Transdermal Drug Deliverymentioning

confidence: 99%

Bioengineered Biomimetic and Bioinspired Noninvasive Drug Delivery Systems

Rahamim

Azagury

2021

Adv Funct Materials

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The main purpose herein is to provide an up-to-date review on noninvasive biomimetic, bioinspired, and bioengineered drug delivery system (DDS). Noninvasive DDS is an ever-growing field critical for the applicability of drugs. It offers noninvasive administration routes with improved controlled, targeted, and triggered drug delivery. Noninvasive DDS employ many approaches and strategies, such as, nano-and microparticles, lipid-based systems, sonophoresis, electrophoresis and iontophoresis, penetration enhancers, microneedles, and gels. The last decade seen a surge in research papers employing the paradigms of biomimicry, bioinspiration, and bioengineering. However, since the use of these terms in noninvasive DDS field is often inconsistent and unclear, some generalized perspectives are provided on the possible usage of these terms in future publications. Additionally, a critical discussion on the novelty and origins of these paradigms is provided. The advantages and disadvantages of each of the noninvasive routes and their current main limitations are summarized. The main aspects of indicated fields are discussed: The unique physiology of the related tissues, the main hurdles for mass transport, the various DDS tested, and materials selection. Finally, the basic concepts and therapeutic effects of these DDS are discussed and future venues for noninvasive biomimetic, bioinspired, and bioengineered DDS research are proposed.

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“…[14,15] Inspired by these biological phenomena, we hypothesized that synthetic tyrosine derivatives may also function as substrates for tyrosinase, which can initiate their melanogenesis-like cascade reaction, thereby generating functional films. This postulation was based on a recent report that commercially available noncatechol amines, including tannic acid, [16] protocatechuic aldehyde, [17] tyrosine, [18] and exquisitely designed peptide/(conjugates), [19][20][21][22] can form functional films, [16][17][18][19][20] adhesives, [21] or chromophoric microparticles [22] solely in the presence of enzymes that catalyze the oxidative polymerization of noncatechol amines. In particular, tyrosine-based azido derivative (TBAD) can generate universal "clickable" films that can be further conjugated with external alkyne ligands through Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC).…”

Section: Introductionmentioning

confidence: 99%

Development of Universal and Clickable Film by Mimicking Melanogenesis: On‐Demand Oxidation of Tyrosine‐Based Azido Derivative by Tyrosinase

Bisht

Jeong

Hong

et al. 2022

Macromol. Rapid Commun.

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A tyrosine‐based azido derivative (TBAD) that permits both substrate‐independent surface coating and clickable film functionalization by mimicking natural melanogenesis is synthesized here. In contrast to catechol derivatives, which are generally susceptible to oxidation by air under ambient conditions, the monophenol‐based TBAD remains stable under alkaline and neutral conditions and is activated to oxidized quinone in situ by tyrosinase to initiate melanin‐like polymerization. The resulting poly(TBAD) film can be formed on various substrates including noble metals, metal oxides, and synthetic polymers, which can undergo click reaction with terminal alkyne moieties on the entire surface or a specific region through Cu(I)‐catalyzed azide‐alkyne cycloaddition. The enzyme‐mediated coating can rapidly form thin films (≈10 nm) and produce a uniform film morphology, which are important aspects in surface chemistry. This on‐demand, clickable coating may become a significant tool for bioconjugation, soft lithography, and labeling techniques.

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Melanin‐Inspired Chromophoric Microparticles Composed of Polymeric Peptide Pigments

Cited by 29 publications

References 44 publications

Peptide-Based Supramolecular Systems Chemistry

Peptide-Based Supramolecular Systems Chemistry

Bioengineered Biomimetic and Bioinspired Noninvasive Drug Delivery Systems

Development of Universal and Clickable Film by Mimicking Melanogenesis: On‐Demand Oxidation of Tyrosine‐Based Azido Derivative by Tyrosinase

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