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Scientific Reports Apr 2018The study of organic/inorganic molecules with activity against intracellular fungi of the phylum Microsporidia is of critical importance. Here, for the first time, the...
The study of organic/inorganic molecules with activity against intracellular fungi of the phylum Microsporidia is of critical importance. Here, for the first time, the inactivation of these parasitic fungi by porphyrins is reported. The biological effects of porphyrins (10 µM and 100 µM) on the microsporidian Nosema ceranae was investigated in honeybee hosts using cage experiments. A significant reduction in the number of spores (from 2.6 to 5 fold) was observed in Nosema-infected honeybees with a sucrose-protoporphyrin amide [PP(Asp)] syrup diet compared to the control honeybees. PP(Asp) and the other porphyrin examined in vitro, TMePyP, had a direct impact on the microsporidia. Notably, neither porphyrin requires light excitation to be active against microsporidia. Moreover, microsporidia preincubated with these porphyrins exhibited decreased ability to infect honeybees. In particular, PP(Asp), possessing amphiphilic characteristics, exhibited significant inactivation of microsporidia, preventing the development of the microsporidia and diminishing the mortality of infected honeybees. In addition, the porphyrin-treated spores examined by scanning electron microscopy (SEM) showed morphological changes in their exosporium layers, which were distinctly deformed. Thus, we postulate that the mechanism of action of porphyrins on microsporidia is not based on photodynamic inactivation but on the destruction of the cell walls of the spores.
Topics: Animals; Bees; Dose-Response Relationship, Drug; Microbial Viability; Nosema; Porphyrins; Spores, Fungal
PubMed: 29615690
DOI: 10.1038/s41598-018-23678-8 -
Biomaterials Science May 2024Covalent organic frameworks (COFs) constitute a class of highly functional porous materials composed of lightweight elements interconnected by covalent bonds,... (Review)
Review
Covalent organic frameworks (COFs) constitute a class of highly functional porous materials composed of lightweight elements interconnected by covalent bonds, characterized by structural order, high crystallinity, and large specific surface area. The integration of naturally occurring porphyrin molecules, renowned for their inherent rigidity and conjugate planarity, as building blocks in COFs has garnered significant attention. This strategic incorporation addresses the limitations associated with free-standing porphyrins, resulting in the creation of well-organized porous crystal structures with molecular-level directional arrangements. The unique optical, electrical, and biochemical properties inherent to porphyrin molecules endow these COFs with diversified applications, particularly in the realm of biology. This review comprehensively explores the synthesis and modulation strategies employed in the development of porphyrin-based COFs and delves into their multifaceted applications in biological contexts. A chronological depiction of the evolution from design to application is presented, accompanied by an analysis of the existing challenges. Furthermore, this review offers directional guidance for the structural design of porphyrin-based COFs and underscores their promising prospects in the field of biology.
Topics: Porphyrins; Metal-Organic Frameworks; Humans; Porosity; Animals
PubMed: 38717456
DOI: 10.1039/d4bm00214h -
ChemMedChem Oct 2020Porphyrin photosensitizers are widely used in photodynamic therapy (PDT) because of their unique diagnostic and therapeutic functions. However, many factors such as poor... (Review)
Review
Porphyrin photosensitizers are widely used in photodynamic therapy (PDT) because of their unique diagnostic and therapeutic functions. However, many factors such as poor water solubility and instability of porphyrin compounds have limited their clinical application. Metal-organic frameworks (MOFs) have the beneficial characteristics of versatility, high porosity, and excellent biocompatibility. Porphyrin-MOF nanomaterials have attracted the attention of researchers because MOFs can effectively suppress the quenching caused by the self-aggregation of porphyrin compounds and promote drug delivery. This article reviews the latest applications of porphyrin-MOF nanomedicine in type II photodynamic therapy by increasing tumour cell oxygen concentration, depleting tumour cell functional molecules and releasing signal molecules. Current potential limitations and future applications are also emphasized and discussed herein.
Topics: Antineoplastic Agents; Biocompatible Materials; Cell Proliferation; Humans; Metal-Organic Frameworks; Nanomedicine; Neoplasms; Photochemotherapy; Photosensitizing Agents; Porphyrins
PubMed: 32715651
DOI: 10.1002/cmdc.202000353 -
Molecules (Basel, Switzerland) Nov 2021Colorectal cancer (CRC) is a leading cause of cancer-related death. The demand for new therapeutic approaches has increased attention paid toward therapies with high... (Review)
Review
Colorectal cancer (CRC) is a leading cause of cancer-related death. The demand for new therapeutic approaches has increased attention paid toward therapies with high targeting efficiency, improved selectivity and few side effects. Porphyrins are powerful molecules with exceptional properties and multifunctional uses, and their special affinity to cancer cells makes them the ligands par excellence for anticancer drugs. Porphyrin derivatives are used as the most important photosensitizers (PSs) for photodynamic therapy (PDT), which is a promising approach for anticancer treatment. Nevertheless, the lack of solubility and selectivity of the large majority of these macrocycles led to the development of different photosensitizer complexes. In addition, targeting agents or nanoparticles were used to increase the efficiency of these macrocycles for PDT applications. On the other hand, gold tetrapyrrolic macrocycles alone showed very interesting chemotherapeutic activity without PDT. In this review, we discuss the most important porphyrin derivatives, alone or associated with other drugs, which have been found effective against CRC, as we describe their modifications and developments through substitutions and delivery systems.
Topics: Colorectal Neoplasms; Humans; Nanoparticles; Photochemotherapy; Photosensitizing Agents; Porphyrins
PubMed: 34885849
DOI: 10.3390/molecules26237268 -
Molecules (Basel, Switzerland) Jul 2017Phthalocyanine and porphyrin were among the first organic compounds investigated by means of electronic spectroscopy in superfluid helium nanodroplets. Superfluid helium... (Review)
Review
Phthalocyanine and porphyrin were among the first organic compounds investigated by means of electronic spectroscopy in superfluid helium nanodroplets. Superfluid helium nanodroplets serve as a very gentle host system for preparing cold and isolated molecules. The uniqueness of helium nanodroplets is with respect to the superfluid phase which warrants the vanishing viscosity and, thus, minimal perturbation of the dopant species at a temperature as low as 0.37 K. These are ideal conditions for the study of molecular spectra in order to analyze structures as well as dynamic processes. Besides the investigation of the dopant species itself, molecular spectroscopy in helium droplets provides information on the helium droplet and in particular on microsolvation. This article, as part of a special issue on phthalocyanines and porphyrins, reviews electronic spectroscopy of phthalocyanine and porphyrin compounds in superfluid helium nanodroplets. In addition to the wide variety of medical as well as technical and synthetical aspects, this article discusses electronic spectroscopy of phthalocyanines and porphyrins in helium droplets in order to learn about both the dopant and the helium environment.
Topics: Helium; Indoles; Isoindoles; Nanoparticles; Photoelectron Spectroscopy; Porphyrins
PubMed: 28757568
DOI: 10.3390/molecules22081244 -
Biometals : An International Journal on... Feb 2022In this report 5 compounds were synthesized and structural and their photophysical characterization was performed (Φ and Φ). Furthermore, in this in vitro study, their...
Photophysical characterization and in vitro anti-leishmanial effect of 5,10,15,20-tetrakis(4-fluorophenyl) porphyrin and the metal (Zn(II), Sn(IV), Mn(III) and V(IV)) derivatives.
In this report 5 compounds were synthesized and structural and their photophysical characterization was performed (Φ and Φ). Furthermore, in this in vitro study, their biological activity against Leishmania panamensis was evaluated. The photophysical behavior of these compounds was measured and high Φ and low Φ was observed. Besides, DFT quantum calculations on the electronic structures were performed. Finally, the biological activity was determined by means of the compounds capacity to inhibit the viability of parasites using the MTT assay. The inclusion of the metal ions substantially modified the photophysical and biological properties in comparison with the free metal porphyrin (1). In fact, Zn porphyrin derivative (2) showed a marked decrease of Φ and increase of Φ. In this sense, using TDDFT approaches, a luminescent process for Sn derivative (3) was described, where emissive states involve the ML-LCT transition. So, this led to a decrease in the singlet oxygen production (0.82-0.67). Biological results showed that all compounds inhibit the viability of L. panamensis with high efficiency; the decrease in the viability was greater as the concentration of exposure increased. Finally, under light irradiation the IC of L. panamensis against the Zn(II)-porphyrin (2) and V(IV)-porphyrin (5) was lower than the IC of the Glucantime control (IC = 2.2 and 6.95 μM Vs IC = 12.7 μM, respectively). We showed that the use of porphyrin and metalloporphyrin-type photosensitizers with exceptional photophysical properties can be successful in photodynamic therapy (PDT) against L. panamensis, being the diamagnetic ion Zn a candidate for the preparation of metalloporphyrins with high singlet oxygen production.
Topics: Leishmania; Metalloporphyrins; Metals; Photochemotherapy; Photosensitizing Agents; Porphyrins; Singlet Oxygen; Zinc
PubMed: 34993713
DOI: 10.1007/s10534-021-00357-2 -
Molecules (Basel, Switzerland) Aug 2022The emergence of metal-organic frameworks (MOFs) in recent years has stimulated the interest of scientists working in this area as one of the most applicable archetypes... (Review)
Review
The emergence of metal-organic frameworks (MOFs) in recent years has stimulated the interest of scientists working in this area as one of the most applicable archetypes of three-dimensional structures that can be used as promising materials in several applications including but not limited to (photo-)catalysis, sensing, separation, adsorption, biological and electrochemical efficiencies and so on. Not only do MOFs have their own specific versatile structures, tunable cavities, and remarkably high surface areas, but they also present many alternative procedures to overcome emerging obstacles. Since the discovery of such highly effective materials, they have been employed for multiple uses; additionally, the efforts towards the synthesis of MOFs with specific properties based on planned (template) synthesis have led to the construction of several promising types of MOFs possessing large biological or bioinspired ligands. Specifically, metalloporphyrin-based MOFs have been created where the porphyrin moieties are either incorporated as struts within the framework to form porphyrinic MOFs or encapsulated inside the cavities to construct porphyrin@MOFs which can combine the peerless properties of porphyrins and porous MOFs simultaneously. In this context, the main aim of this review was to highlight their structure, characteristics, and some of their prominent present-day applications.
Topics: Adsorption; Catalysis; Metal-Organic Frameworks; Metalloporphyrins; Porphyrins
PubMed: 35956867
DOI: 10.3390/molecules27154917 -
Current Treatment Options in Oncology Sep 2023Photodynamic therapy (PDT) has garnered increasing attention in cancer treatment because of its advantages such as minimal invasiveness and selective destruction. With... (Review)
Review
Photodynamic therapy (PDT) has garnered increasing attention in cancer treatment because of its advantages such as minimal invasiveness and selective destruction. With the development of PDT, impressive progress has been made in the preparation of photosensitizers, particularly porphyrin photosensitizers. However, the limited tissue penetration of the activating light wavelengths and relatively low light energy capture efficiency of porphyrin photosensitizers are two major disadvantages in conventional photosensitizers. Therefore, tissue penetration needs to be enhanced and the light energy capture efficiency of porphyrin photosensitizers improved through structural modifications. The indirect excitation of porphyrin photosensitizers using fluorescent donors (fluorescence resonance energy transfer) has been successfully used to address these issues. In this review, the enhancement of the light energy capture efficiency of porphyrins is discussed.
Topics: Humans; Photosensitizing Agents; Porphyrins; Photochemotherapy
PubMed: 37407889
DOI: 10.1007/s11864-023-01120-0 -
Spectrochimica Acta. Part A, Molecular... Oct 2022This research on porphyrin-based photosensitizer system has a very important theoretical and practical significance in the photodynamic therapy (PDT) treatment of...
This research on porphyrin-based photosensitizer system has a very important theoretical and practical significance in the photodynamic therapy (PDT) treatment of cancer. Based on this, in this article, a series of porphyrin derivatives were first designed and synthesized, and a "push-pull" porphyrin photosensitizer with two symmetrical ethanethioate groups was finally constructed. Based on the characterization of their chemical structures (H andC NMR, MS, IR, and UV-Vis spectroscopy) and the use of the density functional theory (DFT) and time-dependent DFT (TDDFT) to address the nature of the excited states as well as the dark/phototoxicity, the results have indicated the relationship between the porphyrin structure and properties. The experimental and theoretical UV-Vis absorption properties of porphyrins were discussed. The four porphyrin compounds synthesized all demonstrated a high capacity to generate singlet oxygen under long-wavelength (590 nm) light and low dark toxicity. Compared with the conventional porphyrin photosensitizers, P4 with a CT band (from 580 to 750 nm) is beneficial to the penetration of the light, presenting the potential for applications in PDT.
Topics: Photochemotherapy; Photosensitizing Agents; Porphyrins; Singlet Oxygen
PubMed: 35689847
DOI: 10.1016/j.saa.2022.121447 -
Journal of Inorganic Biochemistry Oct 2022Cobalt(III) and rhodium(III) complexes containing the water-soluble porphyrin ligand meso-tri(4-sulfonatophenyl)mono(4-carboxyphenyl)porphine (CSTPP),...
Cobalt(III) and rhodium(III) complexes containing the water-soluble porphyrin ligand meso-tri(4-sulfonatophenyl)mono(4-carboxyphenyl)porphine (CSTPP), [Rh(CSTPP)]Na•nHO (1) and [Co(CSTPP)]Na•nHO (2) were prepared from the direct reaction of free porphyrin and metal chloride salts in refluxing MeOH/DMF or EtOH/HO. Compounds 1 and 2 were characterized using UV-vis and H NMR spectroscopies, and high-resolution mass spectrometry. Cell culture based assays of opioid receptor activation showed that while the rhodium complex reduced fentanyl opioid activity 113-fold to an IC50 value of 1.7 μM, the cobalt complex reduced fentanyl activity by 160-fold to an IC50 value of 2.4 μM. An oxidative mechanism for fentanyl breakdown is proposed.
Topics: Cobalt; Fentanyl; Ligands; Porphyrins; Rhodium
PubMed: 35932757
DOI: 10.1016/j.jinorgbio.2022.111935