Synthesis of new metalloporphyrin derivatives from [5,10,15,20-tetrakis (pentafluorophenyl)porphyrin] and 4-mercaptobenzoic acid for homogeneous and heterogeneous catalysis

Castro, Kelly A.D. de F.; Simões, Mário M. Q.; Neves, Maria da Graça; Cavaleiro, José A. S.; Ribeiro, Ronny R.; Wypych, Fernando; Nakagaki, Shirley

doi:10.1016/j.apcata.2014.12.048

Cited by 30 publications

(2 citation statements)

References 66 publications

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“…The following aromatic nucleophilic substitution took place with 3- or 4-mercaptobenzoic acid in the presence of pyridine and DMF at room temperature. The required porphyrins P3 and P4 have been obtained with 90% and 93% yield, respectively [28,57,58]. The structures of the obtained products were confirmed by spectroscopic techniques (Figures S1–S15).…”

Section: Resultsmentioning

confidence: 80%

New Materials Based on Cationic Porphyrins Conjugated to Chitosan or Titanium Dioxide: Synthesis, Characterization and Antimicrobial Efficacy

Castro

Moura

Figueira

et al. 2019

IJMS

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The post-functionalization of 5,10,15-tris(1-methylpyridinium-4-yl)-20-(pentafluorophenyl)porphyrin tri-iodide, known as a highly efficient photosensitizer (PS) for antimicrobial photodynamic therapy (aPDT), in the presence of 3- or 4-mercaptobenzoic acid, afforded two new tricationic porphyrins with adequate carboxylic pending groups to be immobilized on chitosan or titanium oxide. The structural characterization of the newly obtained materials confirmed the success of the porphyrin immobilization on the solid supports. The photophysical properties and the antimicrobial photodynamic efficacy of the non-immobilized porphyrins and of the new conjugates were evaluated. The results showed that the position of the carboxyl group in the mercapto units or the absence of these substituents in the porphyrin core could modulate the action of the photosensitizer towards the bioluminescent Gram-negative Escherichia coli bacterium. The antimicrobial activity was also influenced by the interaction between the photosensitizer and the type of support (chitosan or titanium dioxide). The new cationic porphyrins and some of the materials were shown to be very stable in PBS and effective in the photoinactivation of E. coli bacterium. The physicochemical properties of TiO2 allowed the interaction of the PS with its surface, increasing the absorption profile of TiO2, which enables the use of visible light, inactivating the bacteria more efficiently than the corresponding PS immobilized on chitosan.

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Section: Resultsmentioning

confidence: 80%

New Materials Based on Cationic Porphyrins Conjugated to Chitosan or Titanium Dioxide: Synthesis, Characterization and Antimicrobial Efficacy

Castro

Moura

Figueira

et al. 2019

IJMS

Self Cite

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“…(1) The precursor 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin [H 2 (TPFPP)] was synthesized by condensation of pyrrole with pentafluorobenzaldehyde in the presence of acetic acid and nitrobenzene under reflux conditions. (2) The tetrasubstituted porphyrin 5,10,15,20-tetrakis[(4-carboxyphenyl) thio-2,3,5,6-tetrafluorophenyl] (simplified by P) was obtained by structural modification of [H 2 (TPFPP)] in the presence of the nucleophile 4-mercaptobenzoic acid and pyridine, using DMF as solvent at room temperature for 24 h (Castro et al, 2015). The compound P was characterized by 1 H and 19 F NMR (Bruker Avance 300 spectrometer at 300.13 and 282.38 MHz), UV-Vis (Agilent 8453 spectrophotometer), and fluorescence (F4500 -Hitachi spectrofluorometer) spectroscopies.…”

Section: Porphyrin Synthesis and Quantum Yields Of Singlet Oxygen Determinationmentioning

confidence: 99%

Hybrid Nanoparticles as an Efficient Porphyrin Delivery System for Cancer Cells to Enhance Photodynamic Therapy

Silva

Castro

Botteon

et al. 2021

Front. Bioeng. Biotechnol.

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Photodynamic therapy (PDT) is a potential non-invasive approach for application in oncological diseases, based on the activation of a photosensitizer (PS) by light at a specific wavelength in the presence of molecular oxygen to produce reactive oxygen species (ROS) that trigger the death tumor cells. In this context, porphyrins are interesting PS because they are robust, have high chemical, photo, thermal, and oxidative stability, and can generate singlet oxygen (1O2). However, porphyrins exhibit low solubility and a strong tendency to aggregate in a biological environment which limits their clinical application. To overcome these challenges, we developed hybrid nanostructures to immobilize 5,10,15,20-tetrakis[(4-carboxyphenyl) thio-2,3,5,6-tetrafluorophenyl] (P), a new third-generation PS. The biological effect of this system was evaluated against bladder cancer (BC) cells with or without light exposition. The nanostructure composed of lipid carriers coated by porphyrin-chitosan (P-HNP), presented a size of ca. 130 nm and low polydispersity (ca. 0.25). The presence of the porphyrin-chitosan (P-chitosan) on lipid nanoparticle surfaces increased the nanoparticle size, changed the zeta potential to positive, decreased the recrystallization index, and increased the thermal stability of nanoparticles. Furthermore, P-chitosan incorporation on nanoparticles increased the stability and enhanced the self-organization of the system and the formation of spherical structures, as observed by small-angle X-ray scattering (SAXS) analysis. Furthermore, the immobilization process maintained the P photoactivity and improved the photophysical properties of PS, minimizing its aggregation in the cell culture medium. In the photoinduction assays, the P-HNP displayed high phototoxicity with IC50 3.2-folds lower than free porphyrin. This higher cytotoxic effect can be correlated to the high cellular uptake of porphyrin immobilized, as observed by confocal images. Moreover, the coated nanoparticles showed mucoadhesive properties interesting to its application in vivo. Therefore, the physical and chemical properties of nanoparticles may be relevant to improve the porphyrin photodynamic activity in BC cells.

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Recent progress in organometallic porphyrin‐based molecular materials for optical sensing, light conversion, and magnetic cooling

Ломова

2021

Applied Organom Chemis

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We present the review of fundamental parameters and properties of metalloporphyrins/phthalocyanines with axial covalent M-O/M-N bonds (M is a metal atom in the oxidation degree more than 2+) for use in the development of the chemistry of molecular materials. The porphyrin complexes covalently bonded along the axial axis are differed by the high oxidation state of a metal atom and related heightened axial reactivity compared with the corresponding derivatives of two charged metal cations, applications of which in both scientific studies and practical areas are most widely reflected in publications. The selection of chemical structures of the 3d, 4d, 5d, and 4f metal derivatives of porphyrins/phthalocyanines and study of their properties promising in the detection of bioactive organic bases, optoelectronics (active components of allsmall molecular organic solar cells), and spintronics (room-temperature magnetocaloric materials) are detailed in the article. The results of the first critical analysis of this topic in the review and the insight into chemical structure effects in the function of MPXs/MPcXs as molecular materials will contribute to further development of their organometallic chemistry.

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Synthesis of new metalloporphyrin derivatives from [5,10,15,20-tetrakis (pentafluorophenyl)porphyrin] and 4-mercaptobenzoic acid for homogeneous and heterogeneous catalysis

Cited by 30 publications

References 66 publications

New Materials Based on Cationic Porphyrins Conjugated to Chitosan or Titanium Dioxide: Synthesis, Characterization and Antimicrobial Efficacy

New Materials Based on Cationic Porphyrins Conjugated to Chitosan or Titanium Dioxide: Synthesis, Characterization and Antimicrobial Efficacy

Hybrid Nanoparticles as an Efficient Porphyrin Delivery System for Cancer Cells to Enhance Photodynamic Therapy

Recent progress in organometallic porphyrin‐based molecular materials for optical sensing, light conversion, and magnetic cooling

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