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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 -
Journal of Molecular Recognition : JMR Aug 2023The G-quadruplex planar-ligand complex is used to detect heavy metal cations such as Ag , Cu , Pb , Hg , organic molecules, nucleic acids, and proteins. The interaction...
The G-quadruplex planar-ligand complex is used to detect heavy metal cations such as Ag , Cu , Pb , Hg , organic molecules, nucleic acids, and proteins. The interaction of the three planar porphyrins (L1), 5,10,15,20-tetrakis (1-ethyl-1-λ -pyridine-4-yl) porphyrin (L2), and 5,10,15,20-tetrakis (1-methyl-1-λ -pyridine-4-yl) porphyrin (L3), coming from the porphyrin family, with G-quadruplex obtained from human DNA telomeres in the presence of lithium, sodium, potassium, rubidium, cesium, magnesium, and calcium ions was studied by molecular dynamics simulation. When G-quadruplex containing divalent ions of magnesium and calcium interacts with L1, L2, and L3 ligands, the hydrogen bonds of the lower G-quadruplex sheet are more affected by ligands and the distance between guanines in the lower tetrad increases. In the case of G-quadruplex interactions containing monovalent ions with ligands, the hydrogen bond between the sheets does not follow a specific trend. For example, in the presence of lithium ions, the upper and middle sheets are more affected by ligands, while they are less affected by ligands in the presence of sodium. The binding pocket and the binding energy of the three ligands to the G-quadruplex were also obtained in the various systems. The results show that ligands make the G-quadruplex more stable through the penetration between the sheets and the interaction with the loops. Among the ligands mentioned, the interaction level of the ligand L2 is greater than the others. Our calculations are consistent with the previous experimental observations so that it can help to understand the molecular mechanism of porphyrin interaction and its derivatives with the G-quadruplex.
Topics: Humans; Porphyrins; Ligands; Lithium; Calcium; Magnesium; G-Quadruplexes; Cations; Pyridines; Sodium
PubMed: 37025015
DOI: 10.1002/jmr.3017 -
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 -
Photochemical & Photobiological... Jul 2022Onychomycosis is the most common disease caused by fungal nail infections, and often caused by dermatophytes. This infection is very resistant to antifungal treatments,...
Onychomycosis is the most common disease caused by fungal nail infections, and often caused by dermatophytes. This infection is very resistant to antifungal treatments, and promising Photodynamic Therapy (PDT) mediated treatments has been presented as a multitarget tracking. Optimization of PDT guide for uptake time, concentration of photosensitizers (PS) and the light dose to inactivate Trichophyton mentagrophytes. Curcumin derivatives, porphyrin Chlorin e6 (CHL-E6) and Chlorin-P6-6-N-butylamide-7-methyl-ester (CHL-butyl) were evaluated. PS photobleaching was observed on the hyphae photosensitized over the time, correlating the PS concentration and light dose of antifungal PDT. Porphyrin, Curcumin, Chl-e6 and Chl-butyl concentrations of 2.5 µg/mL, 0.025 µg/mL, 10 µg/mL and 5 µg/mL respectively, under illumination of 10.5 J/cm were the best antifungal conditions found in the study. Curcumin, in low concentrations, and chlorin were the PSs with higher activity anti-T. mentagrophytes.
Topics: Antifungal Agents; Curcumin; Photochemotherapy; Photosensitizing Agents; Porphyrins; Trichophyton
PubMed: 35325444
DOI: 10.1007/s43630-022-00205-3 -
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 -
Chemical Reviews May 2022Confusion is a novel concept of isomerism in porphyrin chemistry, delivering a steady stream of new chemistry since the discovery of N-confused porphyrin, a porphyrin... (Review)
Review
Confusion is a novel concept of isomerism in porphyrin chemistry, delivering a steady stream of new chemistry since the discovery of N-confused porphyrin, a porphyrin mutant, in 1994. These days, the number of confused porphyrinoids is increasing, and confusion and associated fusion are found in various fields such as supramolecular chemistry, materials chemistry, biological chemistry, and catalysts. In this review, the birth and growth of confused porphyrinoids in the last three decades are described.
Topics: Isomerism; Porphyrins
PubMed: 35230807
DOI: 10.1021/acs.chemrev.1c00065 -
International Journal of Molecular... Mar 2023Chlorophyll and heme are essential molecules for photosynthesis and respiration, which are competing branches of the porphyrin metabolism pathway. Chlorophyll and heme...
Chlorophyll and heme are essential molecules for photosynthesis and respiration, which are competing branches of the porphyrin metabolism pathway. Chlorophyll and heme balance regulation is very important for the growth and development of plants. The chimeric leaves of var. were composed of central photosynthetic tissue (PT) and marginal albino tissue (AT), which were ideal materials for the study of porphyrin metabolism mechanisms. In this study, the regulatory function of ALA content on porphyrin metabolism (chlorophyll and heme balance) was revealed by comparing PT and AT, 5-Aminolevulinic Acid (ALA) exogenous supply, and interference of expression. The AT remained similar in porphyrin metabolism flow level to the PT by keeping an equal ALA content in both tissues, which was very important for the normal growth of the chimeric leaves. As the chlorophyll biosynthesis in AT was significantly inhibited, the porphyrin metabolism flow was directed more toward the heme branch. Both tissues had similar Mg contents; however, Fe content was significantly increased in the AT. The chlorophyll biosynthesis inhibition in the white tissue was not due to a lack of Mg and ALA. A 1.5-fold increase in ALA content inhibited chlorophyll biosynthesis while promoting heme biosynthesis and hemA expression. The doubling of ALA content boosted chlorophyll biosynthesis while decreasing expression and heme content. expression interference resulted in a higher ALA content and a lower chlorophyll content, while the heme content remained at a relatively low and stable level. Conclusively, a certain amount of ALA was important for the stability of porphyrin metabolism and the normal growth of plants. The ALA content appears to be able to regulate chlorophyll and heme content by bidirectionally regulating porphyrin metabolism branch direction.
Topics: Porphyrins; Aminolevulinic Acid; Ananas; Chlorophyll; Heme
PubMed: 36982348
DOI: 10.3390/ijms24065274 -
Molecules (Basel, Switzerland) Apr 2020Azides and porphyrinoids (such as porphyrin and corrole macrocycles) can give rise to new derivatives with significant biological properties and as new materials'... (Review)
Review
Azides and porphyrinoids (such as porphyrin and corrole macrocycles) can give rise to new derivatives with significant biological properties and as new materials' components. Significant synthetic approaches have been studied. A wide range of products (e.g., microporous organic networks, rotaxane and dendritic motifs, dendrimers as liquid crystals, as blood substitutes for transfusions and many others) can now be available and used for several medicinal and industrial purposes.
Topics: Azides; Molecular Structure; Porphyrins
PubMed: 32260294
DOI: 10.3390/molecules25071662