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Molecules (Basel, Switzerland) Oct 2020Molecular recognition is a specific non-covalent and frequently reversible interaction between two or more systems based on synthetically predefined character of the... (Review)
Review
Molecular recognition is a specific non-covalent and frequently reversible interaction between two or more systems based on synthetically predefined character of the receptor. This phenomenon has been extensively studied over past few decades, being of particular interest to researchers due to its widespread occurrence in biological systems. In fact, a straightforward inspiration by biological systems present in living matter and based on, e.g., hydrogen bonding is easily noticeable in construction of molecular probes. A separate aspect also incorporated into the molecular recognition relies on the direct interaction between host and guest with a covalent bonding. To date, various artificial systems exhibiting molecular recognition and based on both types of interactions have been reported. Owing to their rich optoelectronic properties, chromophores constitute a broad and powerful class of receptors for a diverse range of substrates. This review focuses on BODIPY and porphyrin chromophores as probes for molecular recognition and chiral discrimination of amino acids and their derivatives.
Topics: Amino Acids; Boron Compounds; Ions; Models, Molecular; Molecular Probes; Porphyrins
PubMed: 33023164
DOI: 10.3390/molecules25194523 -
Chemosphere Mar 2019Porphyrin-based chemistry has reached an unprecedented period of rapid development after decades of study. Due to attractive multifunctional properties, porphyrins and... (Review)
Review
Porphyrin-based chemistry has reached an unprecedented period of rapid development after decades of study. Due to attractive multifunctional properties, porphyrins and their analogues have emerged as multifunctional organometals for environmental and energy purposes. In particular, pioneer works have been conducted to explore their application in pollution abatement, energy conversion and storage and molecule recognition. This review summarizes recent advances of porphyrins chemistry, focusing on elucidating the nature of catalytic process. The Fenton-like redox chemistry and photo-excitability of porphyrins and their analogues are discussed, highlighting the generation of high-valent iron oxo porphyrin species. Finally, challenges in current research are identified and perspectives for future development in this area are presented.
Topics: Catalysis; Energy-Generating Resources; Environmental Pollution; Metalloporphyrins; Oxidation-Reduction; Porphyrins; Research
PubMed: 30554049
DOI: 10.1016/j.chemosphere.2018.12.024 -
Chemical Communications (Cambridge,... Dec 2019The association of hydrophobic cavities with porphyrin derivatives has been used to mimic haemoprotein structures. The most employed cavity in this field is... (Review)
Review
The association of hydrophobic cavities with porphyrin derivatives has been used to mimic haemoprotein structures. The most employed cavity in this field is β-cyclodextrin (β-CD), and scaffolds combining β-CDs and porphyrins are expected to inspire the combination of porphyrins and cucurbiturils in the near future. Aside from providing water solubility to various porphyrinic structures, the β-CD framework can also modulate and control the reactivity of the metal core of the porphyrin. After a general introduction of the challenges faced in the field of haemoprotein models and the binding behavior of β-CDs, this article will discuss covalent and non-covalent association of porphyrins with β-CDs. In each approach, the role of the CD differs according to the relative position of the concave CD host, either directly controlling the binding and transformation of a substrate on the metalloporphyrin or playing a dual role of controlling the water solubility and selecting the axial ligand of the metal core. The discussion will be of interest to the cucurbituril community as well as to the cavitand community, as the information provided should be useful for the design of haemoprotein mimics using cucurbiturils.
Topics: Cyclodextrins; Hemeproteins; Hydrophobic and Hydrophilic Interactions; Ligands; Models, Molecular; Molecular Structure; Porphyrins; Solubility; Water
PubMed: 31748764
DOI: 10.1039/c9cc07545c -
International Journal of Molecular... Feb 2023Cellulose is the most abundant natural biopolymer and owing to its compatibility with biological tissues, it is considered a versatile starting material for developing... (Review)
Review
Cellulose is the most abundant natural biopolymer and owing to its compatibility with biological tissues, it is considered a versatile starting material for developing new and sustainable materials from renewable resources. With the advent of drug-resistance among pathogenic microorganisms, recent strategies have focused on the development of novel treatment options and alternative antimicrobial therapies, such as antimicrobial photodynamic therapy (aPDT). This approach encompasses the combination of photoactive dyes and harmless visible light, in the presence of dioxygen, to produce reactive oxygen species that can selectively kill microorganisms. Photosensitizers for aPDT can be adsorbed, entrapped, or linked to cellulose-like supports, providing an increase in the surface area, with improved mechanical strength, barrier, and antimicrobial properties, paving the way to new applications, such as wound disinfection, sterilization of medical materials and surfaces in different contexts (industrial, household and hospital), or prevention of microbial contamination in packaged food. This review will report the development of porphyrinic photosensitizers supported on cellulose/cellulose derivative materials to achieve effective photoinactivation. A brief overview of the efficiency of cellulose based photoactive dyes for cancer, using photodynamic therapy (PDT), will be also discussed. Particular attention will be devoted to the synthetic routes behind the preparation of the photosensitizer-cellulose functional materials.
Topics: Photosensitizing Agents; Porphyrins; Cellulose; Photochemotherapy; Anti-Infective Agents
PubMed: 36834886
DOI: 10.3390/ijms24043475 -
Journal of Photochemistry and... Nov 2023This comprehensive review provides the current trends and recent developments of porphyrin-based photosensitizers. We discuss their evolution from first-generation to... (Review)
Review
This comprehensive review provides the current trends and recent developments of porphyrin-based photosensitizers. We discuss their evolution from first-generation to third-generation compounds, including cutting-edge nanoparticle-integrated derivatives, and explores their pivotal role in advancing photodynamic therapy (PDT) for enhanced cancer treatment. Integrating porphyrins with nanoparticles represents a promising avenue, offering improved selectivity, reduced toxicity, and heightened biocompatibility. By elucidating recent breakthroughs, innovative methodologies, and emerging applications, this review provides a panoramic snapshot of the dynamic field, addressing challenges and charting prospects. With a focus on harnessing reactive oxygen species (ROS) through light activation, PDT serves as a minimally invasive therapeutic approach. This article offers a valuable resource for researchers, clinicians, and PDT enthusiasts, highlighting the potential of porphyrin photosensitizers to improve the future of cancer therapy.
Topics: Photosensitizing Agents; Photochemotherapy; Porphyrins; Singlet Oxygen; Reactive Oxygen Species
PubMed: 37804542
DOI: 10.1016/j.jphotobiol.2023.112796 -
Chembiochem : a European Journal of... Jul 2020Advances in porphyrin chemistry have provided novel materials and exciting technologies for bioanalysis such as colorimetric sensor array (CSA), photo-electrochemical... (Review)
Review
Advances in porphyrin chemistry have provided novel materials and exciting technologies for bioanalysis such as colorimetric sensor array (CSA), photo-electrochemical (PEC) biosensing, and nanocomposites as peroxidase mimetics for glucose detection. This review highlights selected recent advances in the construction of supramolecular assemblies based on the porphyrin macrocycle that provide recognition of various biologically important entities through the unique porphyrin properties associated with colorimetry, spectrophotometry, and photo-electrochemistry.
Topics: Biosensing Techniques; Colorimetry; Electrochemical Techniques; Light; Nanocomposites; Peroxidases; Porphyrins
PubMed: 32187831
DOI: 10.1002/cbic.202000067 -
Accounts of Chemical Research Apr 2017DNA is well-known as bearer of the genetic code. Since its structure elucidation nearly seven decades ago by Watson, Crick, Wilkins, and Franklin, much has been learned... (Review)
Review
DNA is well-known as bearer of the genetic code. Since its structure elucidation nearly seven decades ago by Watson, Crick, Wilkins, and Franklin, much has been learned about its detailed structure, function, and genetic coding. The development of automated solid-phase synthesis, and with it the availability of synthetic DNA with any desired sequence in lengths of up to hundreds of bases in the best case, has contributed much to the advancement of the field of DNA research. In addition, classic organic synthesis has allowed introduction of a very large number of modifications in the DNA in a sequence specific manner, which have initially been targeted at altering the biological function of DNA. However, in recent years DNA has become a very attractive scaffold in supramolecular chemistry, where DNA is taken out of its biological role and serves as both stick and glue molecule to assemble novel functional structures with nanometer precision. The attachment of functionalities to DNA has led to the creation of supramolecular systems with applications in light harvesting, energy and electron transfer, sensing, and catalysis. Functional DNA is clearly having a significant impact in the field of bioinspired nanosystems. Of particular interest is the use of porphyrins in supramolecular chemistry and bionanotechnology, because they are excellent functional groups due to their electronic properties that can be tailored through chemical modifications of the aromatic core or through insertion of almost any metal of the periodic table into the central cavity. The porphyrins can be attached either to the nucleobase, to the phosphate group, or to the ribose moiety. Additionally, noncovalent templating through Watson-Crick base pairing forms an alternative and attractive approach. With this, the combination of two seemingly simple molecules gives rise to a highly complex system with unprecedented possibilities for modulation of function, and with it applications, particularly when combined with other functional groups. Here, an overview is given on the developments of using porphyrin modified DNA for the construction of functional assemblies. Strategies for the synthesis and characterization are presented alongside selected applications where the porphyrin modification has proven to be particularly useful and superior to other modifiers but also has revealed its limitations. We also discuss implications on properties and behavior of the porphyrin-DNA, where similar issues could arise when using other hydrophobic and bulky substituents on DNA. This includes particularly problems regarding synthesis of the building blocks, DNA synthesis, yields, solubility, and intermolecular interactions.
Topics: DNA; Nanotechnology; Porphyrins
PubMed: 28272871
DOI: 10.1021/acs.accounts.6b00583 -
Journal of Materials Chemistry. B Nov 2023Covalent organic frameworks (COFs) have promising applications in enhanced phototherapy. However, COFs that can sustainably play a role in phototherapy without...
Covalent organic frameworks (COFs) have promising applications in enhanced phototherapy. However, COFs that can sustainably play a role in phototherapy without continuous irradiation are extremely scarce. Herein, we report the fabrication of porphyrin-anthracene multifunctional COFs (Por-DPA) for sustainable photosterilization and bacterial-infected wound healing. A porphyrin photosensitizer, as one of the monomers, was used to provide photothermal and photodynamic activities under irradiation. An anthracene derivative, a good chemical source of singlet oxygen (O), was selected as another monomer to capture O and release it continuously cycloreversion in the dark. The prepared Por-DPA COF prevents the self-aggregation quenching of the photosensitizer and thermal damage caused by continuous exposure to external light sources. Besides, Por-DPA exhibits good photothermal conversion performance and efficient O production capacity through dual pathways of photosensitization and cycloreversion. The developed sustainable photosterilization platform not only has good bactericidal effects on and , but also promotes wound healing without obvious side effects, and is expected to be a novel efficient bactericide.
Topics: Photosensitizing Agents; Metal-Organic Frameworks; Porphyrins; Phototherapy; Singlet Oxygen
PubMed: 37987617
DOI: 10.1039/d3tb02017g -
Skin Research and Technology : Official... May 2016Many ingredients used in cosmetics evoke a comedogenic response. Rabbit ear model (REM) is a useful method that can replace human in examining materials and products in... (Clinical Trial)
Clinical Trial
BACKGROUND/PURPOSE
Many ingredients used in cosmetics evoke a comedogenic response. Rabbit ear model (REM) is a useful method that can replace human in examining materials and products in early developmental stage. However, a number of studies pointed out its disadvantage that it overreacts to comedogenic materials. The purpose of this study was to find the most appropriate region for evaluating comedogenicity in human skin.
METHODS
Sixty-six female subjects (age 32.48 ± 10 years; range 20-52 years) with mild to moderate facial acne lesions were included in this study. The whole face, upper chest, and back of volunteers were photographed. Lesion (closed and open comedones) counting, instrumentation of sebum secretion level, and analysis of porphyrin number were performed. The entire study was performed under environmental conditions of specific relative temperature and humidity, controlled and maintained identically for each volunteer.
RESULTS
In case of closed comedone, forehead showed a significant correlation with frontal cheek, lateral cheek, chin, and upper back. Meanwhile, significant correlations were observed between frontal cheek and chin as well as lateral cheek and chest. As for open comedone, forehead showed a significant correlation with chin site. A significant correlation was also observed between front cheek and lateral cheek as well as between upper chest and back. Analyzing the correlation between the occurrence of comedones and sebum in each region, a significant correlation between closed comedone and sebum was observed in frontal and lateral cheek. Analyzing the correlation between the occurrence of comedones and porphyrine in each region, a significant correlation between open comedone and porphyrin was observed in chin.
CONCLUSION
When evaluating the comedogenicity of cosmetics ingredients or products, this study recommends using both of the methods of testing on back and directly testing on face according to the characteristics of the materials. In case of mild potent ingredients or products in particular, verification through usability test that the directly test on face will help securing reliability.
Topics: Acne Vulgaris; Adult; Biological Assay; Cosmetics; Face; Female; Humans; Middle Aged; Porphyrins; Reproducibility of Results; Sebum; Sensitivity and Specificity; Skin; Young Adult
PubMed: 26094640
DOI: 10.1111/srt.12244 -
Chemical Reviews May 2022The replacement of one or more pyrrolic building block(s) of a porphyrin by a nonpyrrolic heterocycle leads to the formation of so-called pyrrole-modified porphyrins... (Review)
Review
The replacement of one or more pyrrolic building block(s) of a porphyrin by a nonpyrrolic heterocycle leads to the formation of so-called pyrrole-modified porphyrins (PMPs), porphyrinoids of broad structural variability. The wide range of coordination environments (type, number, charge, and architecture of the donor atoms) that the pyrrole-modified frameworks provide to the central metal ions, the frequent presence of donor atoms at their periphery, and their often observed nonplanarity or conformational flexibility distinguish the complexes of the PMPs clearly from those of the traditional square-planar, dianionic, N-coordinating (hydro)porphyrins. Their different coordination properties suggest their utilization in areas beyond which regular metalloporphyrins are suitable. Following a general introduction to the synthetic methodologies available to generate pyrrole-modified porphyrins, their general structure, history, coordination chemistry, and optical properties, this Review highlights the chemical, electronic (optical), and structural differences of specific classes of metalloporphyrinoids containing nonpyrrolic heterocycles. The focus is on macrocycles with similar "tetrapyrrolic" architectures as porphyrins, thusly excluding the majority of expanded porphyrins. We highlight the relevance and application of these metal complexes in biological and technical fields as chemosensors, catalysts, photochemotherapeutics, or imaging agents. This Review provides an introduction to the field of metallo-PMPs as well as a comprehensive snapshot of the current state of the art of their synthesis, structures, and properties. It also aims to provide encouragement for the further study of these intriguing and structurally versatile metalloporphyrinoids.
Topics: Coordination Complexes; Metalloporphyrins; Molecular Conformation; Porphyrins; Pyrroles
PubMed: 35302354
DOI: 10.1021/acs.chemrev.1c00694