Azides and Porphyrinoids: Synthetic Approaches and Applications. Part 1—Azides, Porphyrins and Corroles

Araújo, Ana R. L.; Tomé, Augusto C.; Santos, Carla I. M.; Faustino, Maria A. F.; Neves, Maria G. P. M. S.; Simões, Mário M. Q.; Moura, Nuno M. M.; Abu‐Orabi, Sultan T.; Cavaleiro, José A. S.

doi:10.3390/molecules25071662

Cited by 11 publications

(7 citation statements)

References 130 publications

(193 reference statements)

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“…In general, these entities are introduced by making use of silicon reactants bearing hydrolysable groups (typically alkoxy, acyloxy, amine, or chlorine) that can react with hydroxyl groups on cellulose ( Figure 3 , path g). The non-hydrolysable unit typically holds a moiety that can react with a biologically active molecule [ 121 , 122 ].…”

Section: Functionalization Of Cellulose Supportsmentioning

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: Functionalization Of Cellulose Supportsmentioning

confidence: 99%

Porphyrin Photosensitizers Grafted in Cellulose Supports: A Review

Monteiro

Neves

Nativi

et al. 2023

IJMS

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“…Most recently, K. B. Sharpless shared the 2022 Nobel Prize in Chemistry with C. R. Bertozzi and M. Meldal for the development of click chemistry and bioorthogonal chemistry. Due to high product yields, quick reaction times, and excellent regioselectivity, the "click" cycloaddition reaction has enabled the synthesis of several compounds with a wide range of applications in a variety of sectors, including bioconjugation [ 5 – 6 ] drug development [ 7 – 8 ], glycoscience [ 9 – 10 ], porphyrin chemistry [ 11 ], nanoscience [ 12 ], and materials research [ 13 – 14 ].…”

Section: Introductionmentioning

confidence: 99%

CuAAC-inspired synthesis of 1,2,3-triazole-bridged porphyrin conjugates: an overview

Singh¹

2023

Beilstein J. Org. Chem.

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Among all the available approaches in organic synthesis, the “click chemistry” protocol is very common nowadays to covalently connect two diverse moieties in a single framework. Therefore, this review focuses on the synthesis and photophysical studies of β- and meso-substituted and 1,2,3-triazole-fused porphyrin conjugates. All of the porphyrin conjugates discussed here are synthesized via a copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction between an azide and a terminal alkyne, also popular as "click reaction" or CuAAC reaction. Moreover, the 1,2,3-triazole ring also serves as a spacer and an electron transfer bridge between the porphyrin and the attached chromophores. In order to provide a critical overview of the synthesis and properties of various porphyrin-triazole hybrids, this review will discuss some of the key reactions involved in the preparation of triazole-linked porphyrin conjugates.

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“…Corroles are aromatic contracted tetrapyrrolic macrocycles with unique physicochemical features to be used in different fields including oxidative catalysis, sensing, and therapeutic applications [1][2][3][4][5]. Under the context of medicinal applications, their optical properties such as high extinction molar coefficients, fluorescence quantum yield (Φ Flu ), and ability to generate singlet oxygen ( 1 O 2 ) make them obvious candidates to be exploited as therapeutic agents, namely for photodynamic therapy (PDT) for cancer [5][6][7][8][9][10][11][12][13][14] and antimicrobial photodynamic therapy (aPDT) approaches [15,16]. The principles of PDT for treating cancer cells and aPDT for eliminating microorganisms are the same; both approaches require the activation of a dye (the photosensitizer, PS) by an adequate visible light source in the presence of dioxygen ( 3 O 2 ) in order to produce reactive oxygen species (ROS, e.g., 1 O 2 , among others) responsible for selective killing.…”

Section: Introductionmentioning

confidence: 99%

Can Corrole Dimers Be Good Photosensitizers to Kill Bacteria?

et al. 2022

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Corroles possess key photophysical and photochemical properties to be exploited as therapeutic agents in antimicrobial photodynamic therapy (aPDT). Herein, we present for the first time the antimicrobial efficiency of three corrole dimers and of the corresponding precursor against the Gram(+) bacterium Staphylococcus aureus. Additionally, to explore future clinical applications, the cytotoxicity of the most promising derivatives towards Vero cells was evaluated. The aPDT assays performed under white light irradiation (50 mW/cm2; light dose 450 J/cm2) and at a corrole concentration of 15 µM showed that some dimers were able to reduce 99.9999% of S. aureus strain (decrease of 5 log10 CFU/mL) and their photodynamic efficiency was dependent on position, type of linkage, and aggregation behavior. Under the same light conditions, the corrole precursor 1 demonstrated notable photodynamic efficiency, achieving total photoinactivation (>8.0 log10 CFU/mL reduction) after the same period of irradiation (light dose 450 J/cm2). No cytotoxicity was observed when Vero cells were exposed to corrole 1 and dimer 3 for 24 h according to ISO guidelines (ISO 10993-5) for in vitro cytotoxicity of medical devices. The results show that corrole dimers, dependent on their structures, can be considered good photosensitizers to kill Staphylococcus aureus.

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Azides and Porphyrinoids: Synthetic Approaches and Applications. Part 1—Azides, Porphyrins and Corroles

Cited by 11 publications

References 130 publications

Porphyrin Photosensitizers Grafted in Cellulose Supports: A Review

Porphyrin Photosensitizers Grafted in Cellulose Supports: A Review

CuAAC-inspired synthesis of 1,2,3-triazole-bridged porphyrin conjugates: an overview

Can Corrole Dimers Be Good Photosensitizers to Kill Bacteria?

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