Porphyrinoid biohybrid materials as an emerging toolbox for biomedical light management

Almeida-Marrero, Verónica; Winckel, Eveline van de; Anaya‐Plaza, Eduardo; Torres, Tomás; Escosura, Andrés de la

doi:10.1039/c7cs00554g

Cited by 175 publications

(142 citation statements)

References 304 publications

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“…In fact, these ABAB‐type ZnPcs constitute a new paradigm for PDT photosensitizers . Moreover, the geometry of these derivatives and the presence of amino, carboxylic acid, vinyl or ethynyl moieties permits to build third‐generation photosensitizers, where the ZnPc can be covalently conjugated to two site‐specific delivery agents affording solubility in physiological media and selective accumulation within the targeted tissue . Therefore, it appears of interest to establish the singlet oxygen generation capabilities of this family of compounds.…”

Section: Introductionmentioning

confidence: 99%

Crosswise Phthalocyanines with Collinear Functionalization: New Paradigmatic Derivatives for Efficient Singlet Oxygen Photosensitization

et al. 2019

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We describe here the preparation of a series of trans‐ABAB Zn(II) phthalocyanines (ZnPcs, which combine several interesting features. First, these compounds present high solubility and hindered aggregation, due to the functionalization of two facing isoindole constituents (B) of the ZnPc with bis(trifluoromethylphenyl) units. Second, the other two isoindoles (A) bear extra‐annulated phthalimide units containing different substituents in the nitrogen positions, this feature results in a collinear arrangement of a variety of functional groups. Some of these collinearly functionalized ZnPcs are interesting building blocks for constructing either homo‐ or heteroarrays containing ZnPc units. Furthermore, the amphiphilic nature of some members of the series renders them interesting candidates for photosensitization of singlet oxygen. Photophysical studies on a model compound of the series have shown that these molecules are efficient singlet oxygen photosensitizers in both polar and apolar media, with 1O2 quantum yields (φΔ) as high as 0.74.

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Section: Introductionmentioning

confidence: 99%

Crosswise Phthalocyanines with Collinear Functionalization: New Paradigmatic Derivatives for Efficient Singlet Oxygen Photosensitization

et al. 2019

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“…In particular, molecular oxygen as oxidation source has gained focused attention, as it is considered as an environmental‐friendly approach . In this direction, organic chromophores such as porphyrinoids have been employed to convert nonreactive O 2 into reactive oxygen species (ROS) at room temperature, with wide application in nanomedicine and catalysis . Dye‐containing heterogeneous catalysts can be easily separated from the reaction medium, offering advantages for scale‐up and continuous‐flow processes.…”

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confidence: 99%

Phthalocyanine–Virus Nanofibers as Heterogeneous Catalysts for Continuous‐Flow Photo‐Oxidation Processes

et al. 2019

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The generation of highly reactive oxygen species (ROS) at room temperature for application in organic synthesis and wastewater treatment represents a great challenge of the current chemical industry. In fact, the development of biodegradable scaffolds to support ROS‐generating active sites is an important prerequisite for the production of environmentally benign catalysts. Herein, the electrostatic cocrystallization of a cationic phthalocyanine (Pc) and negatively charged tobacco mosaic virus (TMV) is described, together with the capacity of the resulting crystals to photogenerate ROS. To this end, a novel peripherally crowded zinc Pc (1) is synthesized. With 16 positive charges, this photosensitizer shows no aqueous aggregation, and is able to act as a molecular glue in the unidimensional assembly of TMV. A step‐wise decrease of ionic strength in mixtures of both components results in exceptionally long fibers, constituted by hexagonally bundled viruses thoroughly characterized by electron and confocal microscopy. The fibers are able to produce ROS in a proof‐of‐concept microfluidic device, where they are immobilized and irradiated in several cycles, showing a resilient performance. The bottom‐up approach also enables the light‐triggered disassembly of fibers after use. This work represents an important example of a biohybrid material with projected application in light‐mediated heterogeneous catalysis.

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“…However, taking into account the accessibility, selectivity and immune responseserum albumin is an easily accessible candidate for coating. Serum albumin is the most abundant blood protein, and has long serum half-life and widely used in clinically approved applications in drug delivery [37,38]. The thiol-maleimide chemistry is frequently used for specific conjugation utilizing cysteine residue in serum albumin [39][40][41][42].…”

Section: Introductionmentioning

confidence: 99%

Development of albumin macroinitiator for polymers to use in DNA origami coating

Bilir¹,

Emul²,

Sağlam³

2020

Turk J Med Sci

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Background/aim: DNA nanostructures have many advantages over polymers and lipid based drug delivery agents such as biodegradability and biocompatibility. However their transfection rates and stability still limit their widely use in nanomedicine. In this study highly versatile and straightforward albumin coating preparation method is showed for DNA nanostructures. Materials and methods: N-methylolmaleimide was esterified with a-bromoisobutyrl bromide (BiBB) to achive bromine functional structure. Then it was attached to bovine serum albumin (BSA) via cysteine-maleimide bond further to use as macroinitiator for atom transfer radical polymerization (ATRP). Cationic polymers can be synthesized from this end further to use as binding domain for fabricated 60 Helix bundle DNA origami. Results: Proton nuclear magnetic resonance (1 H NMR) analysis used for characterization. Methyelene group hydrogens' peak in 5.0 ppm and strong peak in 1.5-2.0 ppm range showed proper methylolation of maleimide and bromine functional formation, respectively. Then BSA-macroinitiator formation is verified by 1780 Da peak shift in MALDI-TOF (Matrix-assisted laser desorption/ionizationtime of flight) spectrum. Moreover electrophoretic mobility shift assay (EMSA) showed successful dense 60 Helix bundle formation. Conclusion: In this study, a facile method is developed to synthesize protein conjugated-ATRP initiator further can be used in polymerization and coating DNA nanostructures. It is feasible for any protein containing cysteine amino acid.

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Porphyrinoid biohybrid materials as an emerging toolbox for biomedical light management

Cited by 175 publications

References 304 publications

Crosswise Phthalocyanines with Collinear Functionalization: New Paradigmatic Derivatives for Efficient Singlet Oxygen Photosensitization

Crosswise Phthalocyanines with Collinear Functionalization: New Paradigmatic Derivatives for Efficient Singlet Oxygen Photosensitization

Phthalocyanine–Virus Nanofibers as Heterogeneous Catalysts for Continuous‐Flow Photo‐Oxidation Processes

Development of albumin macroinitiator for polymers to use in DNA origami coating

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