Relationship between porphyrin aggregation and formation of porphyrin ring structures in poly(n-alkyl methacrylate)/porphyrin blends

Tozoni, José Roberto; Neto, N.M. Barbosa; Ribeiro, Carlos; Pazin, Wallance Moreira; Ito, Amando Siuiti; Borissevitch, Iouri; Marletta, Alexandre

doi:10.1016/j.polymer.2016.09.009

Cited by 12 publications

(3 citation statements)

References 22 publications

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“…At a charge ratio of 1:2, the decay components are 8.2 ns and 10.3 ns and the average decay time is 9.25 ns. The shortening of decay time of TCPP aggregates from TCPP–dimer unambiguously confirms the H-type aggregation of the TCPP molecules [ 47 ]. As the charge ratio reaches 1:5, the decay components are 9.25 ns and 10.2 ns and the average decay time is 9.72 ns.…”

Section: Resultsmentioning

confidence: 78%

Transformation of H-Aggregates and J-Dimers of Water-Soluble Tetrakis (4-carboxyphenyl) Porphyrin in Polyion Complex Micelles

Liu

Wei

et al. 2018

Polymers

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Tetrakis (4-carboxyphenyl) porphyrin (TCPP) and polyelectrolyte poly(N-methyl-2-vinylpyridinium iodide)-b-poly(ethylene oxide) (PMVP41-b-PEO205) can self-aggregate into polyion complex (PIC) micelles in alkaline aqueous solution. UV-vis spectroscopy, fluorescence spectroscopy, transmission electron microscope, and dynamic light scattering were carried out to study PIC micelles. Density functional theory (DFT) calculation method was applied to study the interaction of TCPP and PMVP41-b-PEO205. We found that the H-aggregates and J-dimers of anionic TCPP transformed in PIC micelles. H-aggregates of TCPP formed at the charge ratio of TCPP/PMVP41-b-PEO205 1:2 and J-dimer species at the charge ratio above 1:4, respectively. It is worth noting that the transformation from H-aggregates to J-dimer species of TCPP occurred just by adjusting the ratio of polymer and TCPP rather than by changing other factors such as pH, temperature, and ions.

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Section: Resultsmentioning

confidence: 78%

Transformation of H-Aggregates and J-Dimers of Water-Soluble Tetrakis (4-carboxyphenyl) Porphyrin in Polyion Complex Micelles

Liu

Wei

et al. 2018

Polymers

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“…Porphyrin macrocycles have demonstrated the tendency to aggregate in aqueous solutions due to the hydrophobic effect in combination with hydrogen and Van-der-Waals interactions [ 54 , 55 , 56 , 57 ]. Triblock copolymers, such as Pluronic, have been shown to reduce the self-aggregation of molecules and increase the solubility of porphyrins in aqueous media [ 58 , 59 , 60 ].…”

Section: Resultsmentioning

confidence: 99%

Novel Cationic Meso-Arylporphyrins and Their Antiviral Activity against HSV-1

et al. 2021

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This work is devoted to the search for new antiherpes simplex virus type 1 (HSV-1) drugs among synthetic tetrapyrroles and to an investigation of their antiviral properties under nonphotodynamic conditions. In this study, novel amphiphilic 5,10,15,20-tetrakis(4-(3-pyridyl-n-propanoyl)oxyphenyl)porphyrin tetrabromide (3a), 5,10,15,20-tetrakis(4-(6-pyridyl-n-hexanoyl)oxyphenyl)porphyrin tetrabromide (3b) and known 5,10,15,20-tetrakis(1-methyl-4-pyridinio)porphyrin tetraiodide (TMePyP) were synthesized, and their dark antiviral activity in vitro against HSV-1 was studied. The influence of porphyrin’s nanosized delivery vehicles based on Pluronic F127 on anti-HSV-1 activity was estimated. All the received compounds 3a, 3b and TMePyP showed virucidal efficiency and had an effect on viral replication stages. The new compound 3b showed the highest antiviral activity, close to 100%, with the lowest concentration, while the maximum TMePyP activity was observed with a high concentration; porphyrin 3a was the least active. The inclusion of the synthesized compounds in Pluronic F-127 polymeric micelles had a noticeable effect on antiviral activity only at higher porphyrin concentrations. Action of the received compounds differs by influence on the early or later reproduction stages. While 3a and TMePyP acted on all stages of the viral replication cycle, porphyrin 3b inhibited viral replication during the early stages of infection. The resulting compounds are promising for the development of utilitarian antiviral agents and, possibly, medical antiviral drugs.

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“…The driving forces behind the aggregation of porphyrins are the cooperative formation of hydrogen bonds, van-der-Waals forces and the hydrophobic effects. [9][10][11] Pluronic micelles reduce self-aggregation and increase solubility of porphyrins in aqueous media. [9,12] The porphyrins employed in this work are: metal free 5-(4-carboxyphenyl)-10,15,20-tris(phenyl)porphyrin (1-H 2 ) and its ClGa derivative (complex 1-ClGa) as well as metal free 5-(4-(4-carboxyphenoxy)phenyl)-10,15,20-tris(phenyl) porphyrin (2-H 2 ) and its ClGa, Zn and Cl 2 Si derivatives (2-ClGa, 2-Zn, and 2-Cl 2 Si, respectively), Figure 1.…”

Section: Introductionmentioning

confidence: 99%

Porphyrins Encapsulated into Pluronic F127 Micelles: Evaluating the Effect of the Central Metal and Substituents on the Photophysicochemical Properties in Water

Managa¹,

Nyokong²

2017

MHC

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Relationship between porphyrin aggregation and formation of porphyrin ring structures in poly(n-alkyl methacrylate)/porphyrin blends

Cited by 12 publications

References 22 publications

Transformation of H-Aggregates and J-Dimers of Water-Soluble Tetrakis (4-carboxyphenyl) Porphyrin in Polyion Complex Micelles

Transformation of H-Aggregates and J-Dimers of Water-Soluble Tetrakis (4-carboxyphenyl) Porphyrin in Polyion Complex Micelles

Novel Cationic Meso-Arylporphyrins and Their Antiviral Activity against HSV-1

Porphyrins Encapsulated into Pluronic F127 Micelles: Evaluating the Effect of the Central Metal and Substituents on the Photophysicochemical Properties in Water

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