Merging pyridine(s) with porphyrins and analogues: An overview of synthetic approaches

Vallejo, Mariana Costa da Silva; Reis, Melani J.A.; Pereira, Ana; Serra, Vanda Vaz; Cavaleiro, José A. S.; Moura, Nuno M. M.; Neves, Maria G. P. M. S.

doi:10.1016/j.dyepig.2021.109298

Cited by 18 publications

(9 citation statements)

References 215 publications

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“…Meso -substituted porphyrins, bearing positively charged groups have shown remarkable photodynamic activity against both, Gram-(−) and Gram-(+) bacteria [ 66 , 81 , 160 ]. Positive charges are able to induce a strong electrostatic interaction with the external negatively charged structures of the bacterial cells, thus facilitating their interaction with the bacteria [ 161 , 162 ].…”

Section: Synthetic Access To Cellulose-based Photosensitizersmentioning

confidence: 99%

Porphyrin Photosensitizers Grafted in Cellulose Supports: A Review

Monteiro

Neves

Nativi

et al. 2023

IJMS

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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.

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Section: Synthetic Access To Cellulose-based Photosensitizersmentioning

confidence: 99%

Porphyrin Photosensitizers Grafted in Cellulose Supports: A Review

Monteiro

Neves

Nativi

et al. 2023

IJMS

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“…The structure of tetrapyrrolic macrocycles like porphyrins can be changed in the periphery, at the meso or β-pyrrolic positions, with several types of substituents or at the porphyrin inner core by metal coordination, affording stable metallo-based ligands [61,62].…”

Section: Porphyrins and Metalloporphyrins As Interactive G-quadruplex Ligandsmentioning

confidence: 99%

The Interactions of H2TMPyP, Analogues and Its Metal Complexes with DNA G-Quadruplexes—An Overview

et al. 2021

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The evidence that telomerase is overexpressed in almost 90% of human cancers justifies the proposal of this enzyme as a potential target for anticancer drug design. The inhibition of telomerase by quadruplex stabilizing ligands is being considered a useful approach in anticancer drug design proposals. Several aromatic ligands, including porphyrins, were exploited for telomerase inhibition by adduct formation with G-Quadruplex (GQ). 5,10,15,20-Tetrakis(N-methyl-4-pyridinium)porphyrin (H2TMPyP) is one of the most studied porphyrins in this field, and although reported as presenting high affinity to GQ, its poor selectivity for GQ over duplex structures is recognized. To increase the desired selectivity, porphyrin modifications either at the peripheral positions or at the inner core through the coordination with different metals have been handled. Herein, studies involving the interactions of TMPyP and analogs with different DNA sequences able to form GQ and duplex structures using different experimental conditions and approaches are reviewed. Some considerations concerning the structural diversity and recognition modes of G-Quadruplexes will be presented first to facilitate the comprehension of the studies reviewed. Additionally, considering the diversity of experimental conditions reported, we decided to complement this review with a screening where the behavior of H2TMPyP and of some of the reviewed metal complexes were evaluated under the same experimental conditions and using the same DNA sequences. In this comparison under unified conditions, we also evaluated, for the first time, the behavior of the AgII complex of H2TMPyP. In general, all derivatives showed good affinity for GQ DNA structures with binding constants in the range of 106–107 M−1 and ligand-GQ stoichiometric ratios of 3:1 and 4:1. A promising pattern of selectivity was also identified for the new AgII derivative.

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“…The use of the inner core of the porphyrin and analogues framework to coordinate iridium(III) was considered in different studies, affording Ir(III) porphyrinoids, which have emerged as new sources of metal catalysts [ 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 ], and also as complexes with distinct photoluminescent properties [ 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 ]. Alternatively, the functionalization of the porphyrin periphery with adequate metal binding groups (e.g., pyridines, terpyridines) affording assemblies with an external active metal center has also attracted a high interest from the scientific community [ 49 , 50 , 51 ]. In most of these studies the focus has been on the use of metals like Ru, Re, Ir, and Pt [ 49 , 52 , 53 , 54 , 55 , 56 ], but no report concerning the use of iridium as the external metal was considered at β-pyrrolic positions.…”

Section: Introductionmentioning

confidence: 99%

“…Alternatively, the functionalization of the porphyrin periphery with adequate metal binding groups (e.g., pyridines, terpyridines) affording assemblies with an external active metal center has also attracted a high interest from the scientific community [ 49 , 50 , 51 ]. In most of these studies the focus has been on the use of metals like Ru, Re, Ir, and Pt [ 49 , 52 , 53 , 54 , 55 , 56 ], but no report concerning the use of iridium as the external metal was considered at β-pyrrolic positions.…”

Section: Introductionmentioning

confidence: 99%

New Bis-Cyclometalated Iridium(III) Complexes with β-Substituted Porphyrin-Arylbipyridine as the Ancillary Ligand: Electrochemical and Photophysical Insights

Moura

Serra

Bastos

et al. 2022

IJMS

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An efficient synthetic access to new cationic porphyrin-bipyridine iridium(III) bis-cyclometalated complexes was developed. These porphyrins bearing arylbipyridine moieties at β-pyrrolic positions coordinated with iridium(III), and the corresponding Zn(II) porphyrin complexes were spectroscopically, electrochemically, and electronically characterized. The features displayed by the new cyclometalated porphyrin-bipyridine iridium(III) complexes, namely photoinduced electron transfer process (PET), and a remarkable efficiency to generate 1O2, allowing us to envisage new challenges and opportunities for their applications in several fields, such as photo(catalysis) and photodynamic therapies.

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Merging pyridine(s) with porphyrins and analogues: An overview of synthetic approaches

Cited by 18 publications

References 215 publications

Porphyrin Photosensitizers Grafted in Cellulose Supports: A Review

Porphyrin Photosensitizers Grafted in Cellulose Supports: A Review

The Interactions of H2TMPyP, Analogues and Its Metal Complexes with DNA G-Quadruplexes—An Overview

New Bis-Cyclometalated Iridium(III) Complexes with β-Substituted Porphyrin-Arylbipyridine as the Ancillary Ligand: Electrochemical and Photophysical Insights

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