Tetraphenylporphyrin as a protein label for triple detection analytical systems

Konopińska, Kamila; Pietrzak, Mariusz; Mazur, Radosław; Malinowska, Elżbieta

doi:10.1016/j.heliyon.2015.e00053

Cited by 3 publications

(3 citation statements)

References 45 publications

(45 reference statements)

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“…Further, Németh et al, in 1998 again used the same carbodiimide conjugation strategy to generate a-Thy-1-hematoporphyrin antibody targeting Thy-l antigen in T lymphocytes to show the selective killing of T lymphocytes by the phototoxic conjugate upon irradiation ( Berki and Németh, 1998 ). Other groups have also used similar carboxyl modified commercially available photosensitizers, and have performed amide coupling with antibodies for targeted tumor cell killing ( Roberts et al, 1987 ; Martsev et al, 1995 ; Linares et al, 2004 ; Deonarain et al, 2012 ; Konopińska et al, 2015 ). Various polymeric linkers (polyvinyl alcohol, polyglutamic acid, dextran, and polylysine) have also been incorporated to generate photoimmunoconjugates ( Bullous et al, 2011 ).…”

Section: Conjugation To Proteinsmentioning

confidence: 99%

Synthesis and Applications of Porphyrin-Biomacromolecule Conjugates

et al. 2021

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With potential applications in materials and especially in light-responsive biomedicine that targets cancer tissue selectively, much research has focused on developing covalent conjugation techniques to tether porphyrinoid units to various biomacromolecules. This review details the key synthetic approaches that have been employed in the recent decades to conjugate porphyrinoids with oligonucleotides and peptides/proteins. In addition, we provide succinct discussions on the subsequent applications of such hybrid systems and also give a brief overview of the rapidly progressing field of porphyrin-antibody conjugates. Since nucleic acid and peptide systems vary in structure, connectivity, functional group availability and placement, as well as stability and solubility, tailored synthetic approaches are needed for conjugating to each of these biomacromolecule types. In terms of tethering to ONs, porphyrins are typically attached by employing bioorthogonal chemistry (e.g., using phosphoramidites) that drive solid-phase ON synthesis or by conducting post-synthesis modifications and subsequent reactions (such as amide couplings, hydrazide-carbonyl reactions, and click chemistry). In contrast, peptides and proteins are typically conjugated to porphyrinoids using their native functional groups, especially the thiol and amine side chains. However, bioorthogonal reactions (e.g., Staudinger ligations, and copper or strain promoted alkyne-azide cycloadditions) that utilize de novo introduced functional groups onto peptides/proteins have seen vigorous development, especially for site-specific peptide-porphyrin tethering. While the ON-porphyrin conjugates have largely been explored for programmed nanostructure self-assembly and artificial light-harvesting applications, there are some reports of ON-porphyrin systems targeting clinically translational applications (e.g., antimicrobial biomaterials and site-specific nucleic acid cleavage). Conjugates of porphyrins with proteinaceous moieties, on the other hand, have been predominantly used for therapeutic and diagnostic applications (especially in photodynamic therapy, photodynamic antimicrobial chemotherapy, and photothermal therapy). The advancement of the field of porphyrinoid-bioconjugation chemistry from basic academic research to more clinically targeted applications require continuous fine-tuning in terms of synthetic strategies and hence there will continue to be much exciting work on porphyrinoid-biomacromolecule conjugation.

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Section: Conjugation To Proteinsmentioning

confidence: 99%

Synthesis and Applications of Porphyrin-Biomacromolecule Conjugates

et al. 2021

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“…Among the numerous dyes, porphyrin derivatives are widely used as photosensitizers due to their outstanding photophysical properties. The combination of the intense absorption in the visible spectral range and pronounced fluorescence and photochemical activity, resulting in the photoinduced generation of different reactive oxygen species, makes porphyrin derivatives efficient photovoltaic dyes [ 13 , 14 , 15 , 16 , 17 ], optical sensors, and fluorescent imaging agents [ 18 , 19 , 20 , 21 ], and efficient visible light photocatalysts [ 22 , 23 ] and photosensitizers in photodynamic therapy [ 24 , 25 , 26 , 27 , 28 ].…”

Section: Introductionmentioning

confidence: 99%

Optical and Electrophysical Properties of Vinylidene Fluoride/Hexafluoropropylene Ferroelectric Copolymer Films: Effect of Doping with Porphyrin Derivatives

Kochervinskiĭ¹,

Gradova

Градов

et al. 2023

Nanomaterials

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Polymer films doped by different porphyrins, obtained by crystallization from the acetone solutions, differ in absorption and fluorescence spectra, which we attribute to the differences in the structuring and composition of the rotational isomers in the polymer chains. According to the infrared spectroscopy data, the crystallization of the films doped with tetraphenylporphyrin (TPP) proceeds in a mixture of α- and γ-phases with TGTG− and T3GT3G− conformations, respectively. Three bonds in the planar zigzag conformation ensures the contact of such segments with the active groups of the porphyrin macrocycle, significantly changing its electronic state. Structuring of the films in the presence of TPP leads to an increase in the low-voltage AC-conductivity and the registration of an intense Maxwell-Wagner polarization. An increased conductivity by an order of magnitude in TPP-doped films was also observed at high-voltage polarization. The introduction of TPP during the film formation promotes the displacement of the chemical attachment defects of “head-to-head” type in the monomeric units into the surface. This process is accompanied by a significant increase in the film surface roughness, which was registered by piezo-force microscopy. The latter method also revealed the appearance of hysteresis phenomena during the local piezoelectric coefficient d33 measurements.

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“…To date, porphyrins are widely used for the photodynamic therapy (PDT) of tumors and as labels for cancer detection . Moreover, there are several publications where porphyrin-based fluorophores were employed in peptide labeling. − However, to the best of our knowledge, there is only one report in the literature where porphyrin derivatives bearing NTA groups have been employed in the labeling of various peptides and proteins that possess the His 6 -tag . More specific, metallochelate coupling was applied to produce several oligopeptide- and polypeptide-based phosphorescent probes.…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Porphyrin–Nitrilotriacetic Acid Dyads with Potential Applications in Peptide Labeling through Metallochelate Coupling

et al. 2022

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The need to detect and monitor biomolecules, especially within cells, has led to the emerging growth of fluorescent probes. One of the most commonly used labeling techniques for this purpose is reversible metallochelate coupling via a nitrilotriacetic acid (NTA) moiety. In this study, we focus on the synthesis and characterization of three new porphyrin–NTA dyads, TPP-Lys-NTA, TPP-CC-Lys-NTA, and Py 3 P-Lys-NTA composed of a porphyrin derivative covalently connected with a modified nitrilotriacetic acid chelate ligand (NTA), for possible metallochelate coupling with Ni2+ ions and histidine sequences. Emission spectroscopy studies revealed that all of the probes are able to coordinate with Ni2+ ions and consequently can be applied as fluorophores in protein/peptide labeling applications. Using two different histidine-containing peptides as His6-tag mimic, we demonstrated that the porphyrin–NTA hybrids are able to coordinate efficiently with the peptides through the metallochelate coupling process. Moving one step forward, we examined the ability of these porphyrin–peptide complexes to penetrate and accumulate in cancer cells, exploring the potential utilization of our system as anticancer agents.

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Tetraphenylporphyrin as a protein label for triple detection analytical systems

Cited by 3 publications

References 45 publications

Synthesis and Applications of Porphyrin-Biomacromolecule Conjugates

Synthesis and Applications of Porphyrin-Biomacromolecule Conjugates

Optical and Electrophysical Properties of Vinylidene Fluoride/Hexafluoropropylene Ferroelectric Copolymer Films: Effect of Doping with Porphyrin Derivatives

Design and Synthesis of Porphyrin–Nitrilotriacetic Acid Dyads with Potential Applications in Peptide Labeling through Metallochelate Coupling

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