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Porphyrinoids and Their Derivatives as Photosensitizers
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Porphyrinoids and Their Derivatives as Photosensitizers

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (31 March 2022) | Viewed by 19868

Special Issue Editor

Dr. Łukasz Sobotta

E-Mail Website
Guest Editor
Department of Inorganic and Analytical Chemistry, Poznan University of Medical Sciences, Grunwaldzka 6, 60-780 Poznan, Poland
Interests: porphyrinoids; singlet oxygen; photochemistry; photodynamic therapy; photodynamic antimicrobial chemotherapy
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Photodynamic therapy (PDT) is a modality of treatment of mainly cancers, and infections. PDT gives excellent treatment results, especially for skin cancers. In comparison to other methods, PDT does not induce scar formation. On the other hand, PDT offers an excellent tool to combat antibiotic-resistant bacteria. Bacteria can quickly adapt to adverse conditions, including the development of antibiotic resistance. Moreover, microbes can produce enzymes that neutralize free radicals. In the photodynamic process, free radicals are formed in an amount that the bacteria defense system is unable to neutralize. Most importantly, the leading agent in the photodynamic process is singlet oxygen (1O2). To the best of our knowledge, bacteria cannot neutralize 1O2. This makes PDT a perfect antibacterial tool against cutaneous and mucosa infections. The PDT mechanism of action both against cancer and bacteria is based on the interaction of three key agents—molecular oxygen, light, and photosensitizer. In the photodynamic process, ROS are formed—mainly singlet oxygen. Porphyrinoids present versatile properties needed for photosensitizer. Despite their excellent characteristics, they have some disadvantages (e.g., limited solubility). Therefore, new strategies are being developed to provide an ideal photosensitizer, i.e., new delivery systems, chemical modifications, and the introduction of additional agents (nanoparticles, radical sources).

Dr. Łukasz Sobotta
Guest Editor

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Keywords

  • Photodynamic therapy–PDT
  • Photodynamic antimicrobial chemotherapy–PACT
  • Porphyrinoid chemical modifications for photodynamic methods
  • Porphyrinoid–nanoparticle photosensitizers
  • Porphyrinoid delivery systems for phototherapy and imaging
  • Porphyrinoids and drugs for effective cancer and infection treatment

Published Papers (7 papers)

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Research

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17 pages, 3812 KiB  
Article
Assessing the In Vitro Activity of Selected Porphyrins in Human Colorectal Cancer Cells
by Maciej Piotr Frant, Mariusz Trytek and Roman Paduch
Molecules 2022, 27(6), 2006; https://doi.org/10.3390/molecules27062006 - 21 Mar 2022
Cited by 4 | Viewed by 2222
Abstract
Standard in vitro analyses determining the activity of different compounds included in the chemotherapy of colon cancer are currently insufficient. New ideas, such as photodynamic therapy (PDT), may bring tangible benefits. The aim of this study was to show that the biological activity [...] Read more.
Standard in vitro analyses determining the activity of different compounds included in the chemotherapy of colon cancer are currently insufficient. New ideas, such as photodynamic therapy (PDT), may bring tangible benefits. The aim of this study was to show that the biological activity of selected free-base and manganese (III) metallated porphyrins differs in the limitation of colon cancer cell growth in vitro. White light irradiation was also hypothesized to initiate a photodynamic effect on tested porphyrins. Manganese porphyrin (>1 μM) significantly decreased the viability of the colon tumor and normal colon epithelial cells, both in light/lack of light conditions, while decreasing a free-base porphyrin after only 3 min of white light irradiation. Both porphyrins interacted with cytostatics in an antagonistic manner. The manganese porphyrin mainly induced apoptosis and necrosis in the tumor, and apoptosis in the normal cells, regardless of light exposure conditions. The free-base porphyrin conducted mainly apoptosis and autophagy. Normal and tumor cells released low levels of IL-1β and IL-10. Tumor cells released a low level of IL-6. Light conditions and porphyrins were influenced at the cytokine level. Tested manganese (III) metallated and free-base porphyrins differ in their activity against human colon cancer cells. The first showed no photodynamic, but a toxic activity, whereas the second expressed high photodynamic action. White light use may induce a photodynamic effect associated with porphyrins. Full article
(This article belongs to the Special Issue Porphyrinoids and Their Derivatives as Photosensitizers)
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18 pages, 1671 KiB  
Article
Tuning Photodynamic Properties of BODIPY Dyes, Porphyrins’ Little Sisters
by Wojciech Krzemien, Monika Rohlickova, Miloslav Machacek, Veronika Novakova, Jaroslaw Piskorz and Petr Zimcik
Molecules 2021, 26(14), 4194; https://doi.org/10.3390/molecules26144194 - 10 Jul 2021
Cited by 7 | Viewed by 2684
Abstract
The photodynamic properties of a series of non-halogenated, dibrominated and diiodinated BODIPYs with a phthalimido or amino end modification on the phenoxypentyl and phenoxyoctyl linker in the meso position were investigated. Halogen substitution substantially increased the singlet oxygen production based on the heavy [...] Read more.
The photodynamic properties of a series of non-halogenated, dibrominated and diiodinated BODIPYs with a phthalimido or amino end modification on the phenoxypentyl and phenoxyoctyl linker in the meso position were investigated. Halogen substitution substantially increased the singlet oxygen production based on the heavy atom effect. This increase was accompanied by a higher photodynamic activity against skin melanoma cancer cells SK-MEL-28, with the best compound reaching an EC50 = 0.052 ± 0.01 µM upon light activation. The dark toxicity (toxicity without light activation) of all studied dyes was not detected up to the solubility limit in cell culture medium (10 µM). All studied BODIPY derivatives were predominantly found in adiposomes (lipid droplets) with further lower signals colocalized in either endolysosomal vesicles or the endoplasmic reticulum. A detailed investigation of cell death indicated that the compounds act primarily through the induction of apoptosis. In conclusion, halogenation in the 2,6 position of BODIPY dyes is crucial for the efficient photodynamic activity of these photosensitizers. Full article
(This article belongs to the Special Issue Porphyrinoids and Their Derivatives as Photosensitizers)
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19 pages, 5808 KiB  
Article
A Transcriptomic Approach to the Metabolism of Tetrapyrrolic Photosensitizers in a Marine Annelid
by Maria Leonor Santos, Mariaelena D’Ambrosio, Ana P. Rodrigo, A. Jorge Parola and Pedro M. Costa
Molecules 2021, 26(13), 3924; https://doi.org/10.3390/molecules26133924 - 27 Jun 2021
Cited by 5 | Viewed by 2586
Abstract
The past decade has seen growing interest in marine natural pigments for biotechnological applications. One of the most abundant classes of biological pigments is the tetrapyrroles, which are prized targets due their photodynamic properties; porphyrins are the best known examples of this group. [...] Read more.
The past decade has seen growing interest in marine natural pigments for biotechnological applications. One of the most abundant classes of biological pigments is the tetrapyrroles, which are prized targets due their photodynamic properties; porphyrins are the best known examples of this group. Many animal porphyrinoids and other tetrapyrroles are produced through heme metabolic pathways, the best known of which are the bile pigments biliverdin and bilirubin. Eulalia is a marine Polychaeta characterized by its bright green coloration resulting from a remarkably wide range of greenish and yellowish tetrapyrroles, some of which have promising photodynamic properties. The present study combined metabolomics based on HPLC-DAD with RNA-seq transcriptomics to investigate the molecular pathways of porphyrinoid metabolism by comparing the worm’s proboscis and epidermis, which display distinct pigmentation patterns. The results showed that pigments are endogenous and seemingly heme-derived. The worm possesses homologs in both organs for genes encoding enzymes involved in heme metabolism such as ALAD, FECH, UROS, and PPOX. However, the findings also indicate that variants of the canonical enzymes of the heme biosynthesis pathway can be species- and organ-specific. These differences between molecular networks contribute to explain not only the differential pigmentation patterns between organs, but also the worm’s variety of novel endogenous tetrapyrrolic compounds. Full article
(This article belongs to the Special Issue Porphyrinoids and Their Derivatives as Photosensitizers)
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15 pages, 1908 KiB  
Article
Solar Driven Photocatalytic Activity of Porphyrin Sensitized TiO2: Experimental and Computational Studies
by Sebastian Otieno, Anabel E. Lanterna, John Mack, Solomon Derese, Edith K. Amuhaya, Tebello Nyokong and Juan C. Scaiano
Molecules 2021, 26(11), 3131; https://doi.org/10.3390/molecules26113131 - 24 May 2021
Cited by 9 | Viewed by 3176
Abstract
The absence of a secure long-term sustainable energy supply is recognized as a major worldwide technological challenge. The generation of H2 through photocatalysis is an environmentally friendly alternative that can help solve the energy problem. Thus, the development of semiconductor materials that [...] Read more.
The absence of a secure long-term sustainable energy supply is recognized as a major worldwide technological challenge. The generation of H2 through photocatalysis is an environmentally friendly alternative that can help solve the energy problem. Thus, the development of semiconductor materials that can absorb solar light is an attractive approach. TiO2 has a wide bandgap that suffers from no activity in the visible spectrum, limiting its use of solar radiation. In this research, the semiconductor absorption profile was extended into the visible region of the solar spectrum by preparing porphyrin-TiO2 (P-TiO2) composites of meso-tetra(4-bromophenyl)porphyrin (PP1) and meso-tetra(5-bromo-2-thienyl)porphyrin (PP2) and their In(III), Zn(II) and Ga(III) metal complexes. Density functional theory (DFT) and time-dependent density functional theory (TD-DFT) calculations were performed on the porphyrins to gain insight into their electron injection capability. The results demonstrate that P-TiO2 systems merit further in-depth study for applications that require efficient photocatalytic H2 generation. Full article
(This article belongs to the Special Issue Porphyrinoids and Their Derivatives as Photosensitizers)
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20 pages, 9838 KiB  
Article
Nipagin-Functionalized Porphyrazine and Phthalocyanine—Synthesis, Physicochemical Characterization and Toxicity Study after Deposition on Titanium Dioxide Nanoparticles P25
by Dariusz T. Mlynarczyk, Daniel Ziental, Emil Kolasinski, Lukasz Sobotta, Tomasz Koczorowski, Jadwiga Mielcarek and Tomasz Goslinski
Molecules 2021, 26(9), 2657; https://doi.org/10.3390/molecules26092657 - 1 May 2021
Cited by 6 | Viewed by 2664
Abstract
Aza-porphyrinoids exhibit distinct spectral properties in UV-Vis, and they are studied in applications such as photosensitizers in medicine and catalysts in technology. The use of appropriate peripheral substituents allows the modulation of their physicochemical properties. Phthalocyanine and sulfanyl porphyrazine octa-substituted with 4-(butoxycarbonyl)phenyloxy moieties [...] Read more.
Aza-porphyrinoids exhibit distinct spectral properties in UV-Vis, and they are studied in applications such as photosensitizers in medicine and catalysts in technology. The use of appropriate peripheral substituents allows the modulation of their physicochemical properties. Phthalocyanine and sulfanyl porphyrazine octa-substituted with 4-(butoxycarbonyl)phenyloxy moieties were synthesized and characterized using UV-Vis and NMR spectroscopy, as well as mass spectrometry. A comparison of porphyrazine with phthalocyanine aza-porphyrinoids revealed that phthalocyanine macrocycle exhibits higher singlet oxygen generation quantum yields, reaching the value of 0.29 in DMF. After both macrocycles had been deposited on titanium dioxide nanoparticles P25, the cytotoxicities and photocytotoxicities of the prepared materials were studied using a Microtox® acute toxicity test. The highest cytotoxicity occurred after irradiation with a red light for the material composed of phthalocyanine deposited on titania nanoparticles. Full article
(This article belongs to the Special Issue Porphyrinoids and Their Derivatives as Photosensitizers)
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21 pages, 7894 KiB  
Article
Photophysical and Bactericidal Properties of Pyridinium and Imidazolium Porphyrins for Photodynamic Antimicrobial Chemotherapy
by Florent Le Guern, Tan-Sothéa Ouk, Issabayev Yerzhan, Yesmurzayeva Nurlykyz, Philippe Arnoux, Céline Frochot, Stéphanie Leroy-Lhez and Vincent Sol
Molecules 2021, 26(4), 1122; https://doi.org/10.3390/molecules26041122 - 20 Feb 2021
Cited by 19 | Viewed by 2850
Abstract
Despite advances achieved over the last decade, infections caused by multi-drug-resistant bacterial strains are increasingly becoming important societal issues that need to be addressed. New approaches have already been developed in order to overcome this problem. Photodynamic antimicrobial chemotherapy (PACT) could provide an [...] Read more.
Despite advances achieved over the last decade, infections caused by multi-drug-resistant bacterial strains are increasingly becoming important societal issues that need to be addressed. New approaches have already been developed in order to overcome this problem. Photodynamic antimicrobial chemotherapy (PACT) could provide an alternative to fight infectious bacteria. Many studies have highlighted the value of cationic photosensitizers in order to improve this approach. This study reports the synthesis and the characterization of cationic porphyrins derived from methylimidazolium and phenylimidazolium porphyrins, along with a comparison of their photophysical properties with the well-known N-methylpyridyl (pyridinium) porphyrin family. PACT tests conducted with the tetracationic porphyrins of these three families showed that these new photosensitizers may offer a good alternative to the classical pyridinium porphyrins, especially against S.aureus and E.coli. In addition, they pave the way to new cationic photosensitizers by the means of derivatization through amide bond formation. Full article
(This article belongs to the Special Issue Porphyrinoids and Their Derivatives as Photosensitizers)
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Review

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17 pages, 3765 KiB  
Review
Application of TD-DFT Theory to Studying Porphyrinoid-Based Photosensitizers for Photodynamic Therapy: A Review
by Agnieszka Drzewiecka-Matuszek and Dorota Rutkowska-Zbik
Molecules 2021, 26(23), 7176; https://doi.org/10.3390/molecules26237176 - 26 Nov 2021
Cited by 6 | Viewed by 2753
Abstract
An important focus for innovation in photodynamic therapy (PDT) is theoretical investigations. They employ mostly methods based on Time-Dependent Density Functional Theory (TD-DFT) to study the photochemical properties of photosensitizers. In the current article we review the existing state-of-the-art TD-DFT methods (and beyond) [...] Read more.
An important focus for innovation in photodynamic therapy (PDT) is theoretical investigations. They employ mostly methods based on Time-Dependent Density Functional Theory (TD-DFT) to study the photochemical properties of photosensitizers. In the current article we review the existing state-of-the-art TD-DFT methods (and beyond) which are employed to study the properties of porphyrinoid-based systems. The review is organized in such a way that each paragraph is devoted to a separate aspect of the PDT mechanism, e.g., correct prediction of the absorption spectra, determination of the singlet–triplet intersystem crossing, and interaction with molecular oxygen. Aspects of the calculation schemes are discussed, such as the choice of the most suitable functional and inclusion of a solvent. Finally, quantitative structure–activity relationship (QSAR) methods used to explore the photochemistry of porphyrinoid-based systems are discussed. Full article
(This article belongs to the Special Issue Porphyrinoids and Their Derivatives as Photosensitizers)
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