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Porphyrinoid Derivatives: Synthesis and Biological Applications
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Porphyrinoid Derivatives: Synthesis and Biological Applications

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

Deadline for manuscript submissions: closed (30 September 2020) | Viewed by 18981

Special Issue Editor

Prof. Dr. José A. S. Cavaleiro

E-Mail Website
Guest Editor
Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal
Interests: porphyrins; chlorins; Corroles; phthalocyanines; catalysis; PDT; PDI
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Porphyrinoid derivatives are being work-target macrocycles for many research groups; researchers from several areas (mainly from chemistry, physics, biology, pharmacy, and medicine) are looking for new derivatives with potentially significant applications.
The medicinal applications already demonstrated by some porphyrinic formulations in the detection and treatment of cancer (a procedure known as photodynamic therapy, PDT) point to the need of having better, more efficient compounds. Also, another significant application already under study is related to the photodynamic inactivation of microorganisms (PDI), mainly those that are antibiotic resistant.
The physical-chemistry properties of such macrocycles also explain the reason for their interaction with several chemical entities, mainly toxic species. Accordingly, such macrocycles can act as promising sensors (e.g., in water treatments, in food protection, etc).
Then there is a wide range of highly significant applications. This points to the need of having well established synthetic procedures leading to new derivatives, with their properties being well assessed.
Manuscripts describing studies pointing to such targets will be welcome in this Special Issue of Molecules.

Prof. Dr. José A. S. Cavaleiro
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • porphyrinoids
  • novel synthesis
  • PDT
  • PDI
  • sensor properties

Published Papers (5 papers)

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Research

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13 pages, 2472 KiB  
Communication
Synthesis of a Naphthalocyanine-Like Dye: The First Report on Zn(II)-1,6-methano[10]annulenecyanine
by Nicholas Roberto da Silva Gobo, Timothy John Brocksom and Kleber Thiago de Oliveira
Molecules 2020, 25(9), 2164; https://doi.org/10.3390/molecules25092164 - 5 May 2020
Viewed by 2635
Abstract
The synthesis of the new dye 1,6-methano[10]annulenecyanine is described. For this purpose, the 3,4-dicyano-1,6-methano[10]annulene and 3,4-carboxyimide-1,6-methano[10]annulene buildings blocks were synthesized in six to eight steps. In both cases, these building blocks were then cyclotetramerized to furnish a new Zn(II)-1,6-methano[10]annulenecyanine which presents a strong [...] Read more.
The synthesis of the new dye 1,6-methano[10]annulenecyanine is described. For this purpose, the 3,4-dicyano-1,6-methano[10]annulene and 3,4-carboxyimide-1,6-methano[10]annulene buildings blocks were synthesized in six to eight steps. In both cases, these building blocks were then cyclotetramerized to furnish a new Zn(II)-1,6-methano[10]annulenecyanine which presents a strong red-shifted absorption band at 800 nm and high solubility in common organic solvents. Full article
(This article belongs to the Special Issue Porphyrinoid Derivatives: Synthesis and Biological Applications)
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21 pages, 3940 KiB  
Article
Synthesis, Characterization and Photodynamic Activity against Bladder Cancer Cells of Novel Triazole-Porphyrin Derivatives
by Ana T. P. C. Gomes, Rosa Fernandes, Carlos F. Ribeiro, João P. C. Tomé, Maria G. P. M. S. Neves, Fernando de C. da Silva, Vítor F. Ferreira and José A. S. Cavaleiro
Molecules 2020, 25(7), 1607; https://doi.org/10.3390/molecules25071607 - 31 Mar 2020
Cited by 13 | Viewed by 3071
Abstract
Novel triazole-porphyrin derivatives (TZ-PORs) were synthesized through the Heck reaction and then incorporated into polyvinylpyrrolidone (PVP) micelles. After verifying that this incorporation did not compromise the photophysical and chemical features of TZ-PORs as photosensitizers, the phototoxicity of the formulations towards cancer cells was [...] Read more.
Novel triazole-porphyrin derivatives (TZ-PORs) were synthesized through the Heck reaction and then incorporated into polyvinylpyrrolidone (PVP) micelles. After verifying that this incorporation did not compromise the photophysical and chemical features of TZ-PORs as photosensitizers, the phototoxicity of the formulations towards cancer cells was screened. Biological studies show high photodynamic activity of all PVP-TZ-POR formulations against a bladder cancer cell line with a particular highlight to PVP-TZ-POR 7e and 7f that are able to significantly reduce HT-1376 cell viability, while they had no effect on control ARPE-19 cells. Full article
(This article belongs to the Special Issue Porphyrinoid Derivatives: Synthesis and Biological Applications)
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9 pages, 2071 KiB  
Communication
Synthesis and Characterization of a Binuclear Copper(II)-dipyriamethyrin Complex: [Cu2(dipyriamethyrin)(μ2-1,1-acetato)2]
by James T. Brewster II, Harrison D. Root, Hadiqa Zafar, Gregory D. Thiabaud, Adam C. Sedgwick, Jiaming He, Vincent M. Lynch and Jonathan L. Sessler
Molecules 2020, 25(6), 1446; https://doi.org/10.3390/molecules25061446 - 23 Mar 2020
Cited by 6 | Viewed by 3325
Abstract
The reaction between dipyriamethyrin and copper(II) acetate [Cu(OAc)2] afforded what is, to our knowledge, the first transition metal-dipyriamethyrin complex. Molecular and electronic characterization of this binuclear Cu(II) complex via EPR, UV-vis, and single crystal X-ray diffraction analysis revealed marked differences between [...] Read more.
The reaction between dipyriamethyrin and copper(II) acetate [Cu(OAc)2] afforded what is, to our knowledge, the first transition metal-dipyriamethyrin complex. Molecular and electronic characterization of this binuclear Cu(II) complex via EPR, UV-vis, and single crystal X-ray diffraction analysis revealed marked differences between the present constructs and previously reported binuclear copper(II) hexaphyrin species. UV-vis titration analyses provided evidence for a homotropic positive allosteric effect, wherein the binuclear species is formed without significant intermediacy of a monomeric complex. Full article
(This article belongs to the Special Issue Porphyrinoid Derivatives: Synthesis and Biological Applications)
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18 pages, 3058 KiB  
Article
Assessing Amphiphilic ABAB Zn(II) Phthalocyanines with Enhanced Photosensitization Abilities in In Vitro Photodynamic Therapy Studies Against Cancer
by Miguel Á. Revuelta-Maza, Marta Mascaraque, Patricia González-Jiménez, Arturo González-Camuñas, Santi Nonell, Ángeles Juarranz, Gema de la Torre and Tomás Torres
Molecules 2020, 25(1), 213; https://doi.org/10.3390/molecules25010213 - 4 Jan 2020
Cited by 11 | Viewed by 3283
Abstract
We have previously demonstrated that singlet oxygen photosensitization abilities of Zn(II) phthalocyanines (Zn(II)Pcs) are enhanced through α-functionalization with bulky fluorinated substituents (i.e., bis(trifluoromethyl)phenyl units) at facing positions of ABAB Zn(II)Pcs, where A and B refer to differently functionalized isoindoles. In this work, we [...] Read more.
We have previously demonstrated that singlet oxygen photosensitization abilities of Zn(II) phthalocyanines (Zn(II)Pcs) are enhanced through α-functionalization with bulky fluorinated substituents (i.e., bis(trifluoromethyl)phenyl units) at facing positions of ABAB Zn(II)Pcs, where A and B refer to differently functionalized isoindoles. In this work, we have prepared the Zn(II)Pc ABAB 1 endowed with hydrophilic triethylene glycol monomethyl ether (i.e., at the A isoindoles) to provide solubility in aqueous media, together with its A3B and A4 counterparts, and compared their ability to behave as photosensitizers for photodynamic therapy. All photophysical data, aggregation studies and preliminary in vitro biological assays in cell cultures of SCC-13 (squamous cell carcinoma) and HeLa (cervical cancer cells), have proved ABAB 1 as the best photosensitizer of the series. Full article
(This article belongs to the Special Issue Porphyrinoid Derivatives: Synthesis and Biological Applications)
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Review

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31 pages, 3804 KiB  
Review
Porphyrin Derivative Nanoformulations for Therapy and Antiparasitic Agents
by Daiana K. Deda, Bernardo A. Iglesias, Eduardo Alves, Koiti Araki and Celia R. S. Garcia
Molecules 2020, 25(9), 2080; https://doi.org/10.3390/molecules25092080 - 29 Apr 2020
Cited by 29 | Viewed by 6038
Abstract
Porphyrins and analogous macrocycles exhibit interesting photochemical, catalytic, and luminescence properties demonstrating high potential in the treatment of several diseases. Among them can be highlighted the possibility of application in photodynamic therapy and antimicrobial/antiparasitic PDT, for example, of malaria parasite. However, the low [...] Read more.
Porphyrins and analogous macrocycles exhibit interesting photochemical, catalytic, and luminescence properties demonstrating high potential in the treatment of several diseases. Among them can be highlighted the possibility of application in photodynamic therapy and antimicrobial/antiparasitic PDT, for example, of malaria parasite. However, the low efficiency generally associated with their low solubility in water and bioavailability have precluded biomedical applications. Nanotechnology can provide efficient strategies to enhance bioavailability and incorporate targeted delivery properties to conventional pharmaceuticals, enhancing the effectiveness and reducing the toxicity, thus improving the adhesion to the treatment. In this way, those limitations can be overcome by using two main strategies: (1) Incorporation of hydrophilic substituents into the macrocycle ring while controlling the interaction with biological systems and (2) by including them in nanocarriers and delivery nanosystems. This review will focus on antiparasitic drugs based on porphyrin derivatives developed according to these two strategies, considering their vast and increasing applications befitting the multiple roles of these compounds in nature. Full article
(This article belongs to the Special Issue Porphyrinoid Derivatives: Synthesis and Biological Applications)
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