Controlling the aggregation of 5,10,15,20-tetrakis-(4-sulfonatophenyl)-porphyrin by the use of polycations derived from polyketones bearing charged aromatic groups

Toncelli, Claudio; Pino-Pinto, Juan Pablo; Sano, Naoki; Picchioni, Francesco; Broekhuis, Antonius; Nishide, Hiroyuki; Moreno‐Villoslada, Ignacio

doi:10.1016/j.dyepig.2013.01.008

Cited by 37 publications

(64 citation statements)

References 59 publications

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“…Enquanto a maior intensidade da banda J em relação à banda H observada é característica de agregados do tipo oblique head-to-tail. 29 Adicionalmente, em porcentagens de água acima de 65% verificou-se o desaparecimento das bandas adicionais observadas entre 45 e 60% água/etanol (448 e 388 nm) e o aparecimento de outra banda em 424 nm (Figura 3C). Essa banda adicional apresentou um deslocamento para comprimentos de onda de menor energia em relação à molar e à concentração das espécies absorventes no meio, o sinal de RLS é proporcional ao volume do agregado e sua concentração.…”

Section: Autoagregação Da Tmpp Em Misturas áGua/etanolunclassified

“…As intensidades relativas das bandas nesses agregados dependem do ângulo entre os momentos de transição das unidades monoméricas no agregado (α). Para o agregado twisted sandwich-like a banda H é mais intensa do que a banda J, enquanto para o oblique head-to-tail a banda J é mais intensa do que a banda H. 29 Logo, neste trabalho investigaram-se as propriedades espectroscópicas da 5,10,15,20-tetrakis(4-metoxifenil)porfirina (TMPPFigura 1) em meio homogêneo constituído de solventes de diferentes polaridades, bem como as características espectroscópicas associadas a estratégias estatísticas para caracterização das espécies autoagregadas do FS em misturas água/etanol. …”

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Self-Aggregation of 5,10,15,20-Tetrakis(4-Methoxyphenyl)porphyrin (Tmpp): Spectroscopic Studies and Multivariate Analyzes

Braga¹,

Aparicio²,

Vilsinski³

et al. 2014

Química Nova

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SELF-AGGREGATION OF 5,10,15,20-TETRAKIS(4-METHOXYPHENYL)PORPHYRIN (TMPP): SPECTROSCOPIC STUDIES AND MULTIVARIATE ANALYZES. In this work, the spectroscopic properties of 5,10,15,20-tetrakis(4-methoxyphenyl)porphyrin (TMPP) in solvents of different polarities and water/ethanol mixtures were studied by electronic absorption spectroscopy and resonance light scattering associated with statistical analysis. The molar absorption coefficient and emission maximum of TMPP were dependent on solvent polarity. In the water/ethanol mixture, TMPP remained monomeric up to 25% of water, when it reaches its critical aggregation percentage. Oblique head-to-tail aggregate was found at intermediate water content (35 -55%), while formation of a J-type aggregate was observed at higher water content (> 60%).Keywords: photodynamic therapy; 5,10,15,20-tetrakis(4-methoxyphenyl)porphyrin; self-aggregation. INTRODUÇÃOAs porfirinas e macrociclos análogos são moléculas biologicamente importantes, apresentando funções fundamentais no metabolismo de seres vivos. Atuam como sítios ativos em diversos processos biológicos, como na ligação e transporte de oxigênio (mioglobina e hemoglobina), 1-3 captura de luz no processo de fotossíntese (clorofila), 4,5 transferência de elétrons (citocromo c) 6,7 e reações de metil-transferases (coenzima cobalamina -vitamina B 12 ), 8,9 além de atuarem como eficientes fotossensibilizadores (FS) em processos catalíticos e fotodinâmicos. 10As porfirinas são FS potenciais para aplicação em Terapia Fotodinâmica (TFD) 11 devido às suas características, como: afinidade e seletividade por células neoplásicas, alto rendimento do estado excitado triplete (Φ T ), alto tempo de vida do estado triplete (τ T ) e, alto rendimento quântico de oxigênio singlete (Φ ∆ ).12-15 O estado de agregação de moléculas fotoativas 16 é fundamental na eficácia fotodinâmica do fármaco in vitro e in vivo, devido ao decréscimo de biodisponibilidade e limitação na capacidade de absorver luz de moléculas agregadas. Além do que, estudos realizados mostraram que as porfirinas monoméricas foram mais fotoativas em relação às espécies autoagregadas, com maior τ T e maior Φ ∆ . 17,18 Estudos de agregação de porfirinas e compostos análogos em diferentes solventes e misturas água/solvente são realizados com frequên-cia, para melhor compreensão do estado de agregação e propriedades das espécies autoassociadas em sistemas modelo simples de diferentes polaridades.19 A extensão da formação de monômeros é dependente da constante dielétrica do meio, como exemplo a adição de álcool a sistemas aquosos favorece a formação de monômeros pela diminuição da polaridade da mistura e aumento da constante dielétrica. 20A formação de espécies agregadas pode ser caracterizada por téc-nicas espectroscópicas, como espectroscopia de absorção eletrônica e espalhamento de luz ressonante (RLS). A utilização da espectroscopia de absorção eletrônica deve-se ao fato de que a autoagregação leva a modificações drásticas no perfil espectral, como diminuição da intensidade de absorção...

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Section: Autoagregação Da Tmpp Em Misturas áGua/etanolunclassified

unclassified

Self-Aggregation of 5,10,15,20-Tetrakis(4-Methoxyphenyl)porphyrin (Tmpp): Spectroscopic Studies and Multivariate Analyzes

Braga¹,

Aparicio²,

Vilsinski³

et al. 2014

Química Nova

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“…From among a large number of works concerning free porphyrins [38][39][40][41][42][43], attention is paid here to those able to produce the singlet oxygen. The process involves conversion of ground-state O 2 into 1 O 2 by porphyrins serving as photosensitizers.…”

Section: Free-base Porphyrins Generating Singlet Oxygenmentioning

confidence: 99%

Porphyrins functionalized by quaternary pyridinium units

Girek

Śliwa

2013

J. Porphyrins Phthalocyanines

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In this review, free-base and metalloporphyrins, functionalized on meso-positions by quaternary pyridinium units, also referred to as cationic porphyrins, are presented. The article consists of five parts. In the first part free-base porphyrins are described, especially taking account on generation of singlet oxygen; next parts concern metalloporphyrins. The second and third parts deal with zinc and manganese porphyrins, respectively; in the fourth part copper, palladium, and platinum porphyrins are presented. In the fifth part, describing porphyrins with various metal ions an attention is paid to porphyrin metal-organic frameworks (MOFs) and metal-organic materials (MOMs) in which metalloporphyrins are immobilized; syntheses and characterization of obtained products are shown.

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“…[12][13][14][15][16] Copolymers based on acrylic acid and methyl methacrylate have been tested as coatings of pharmaceutical products for oral administration due to their pH-sensitive properties. [22][23][24][25] The aggregation of polyelectrolyte chains by means of these secondary interactions may result in structures with defined features, such as shape, size, and zeta potential. 18 .…”

Section: Introductionmentioning

confidence: 99%

“…27 Perfectly alternating copolymers of carbon monoxide and unsaturated hydrocarbon monomers (such as propylene and ethylene) can be easily obtained using palladium derivatives as catalysts. 23 An excess of this aromatic cationic polymer has been proved to bind and disperse an aromatic, anionic water-soluble dye such as 5,10,15,20-tetrakis-(4-sulfonatophenyl)-porphyrin whereas aliphatic, cationic polymers induce the dye selfaggregation, indicating the role of hydrophobic and aromaticaromatic interactions on the binding properties observed. Upon this reaction, 1,4-dicarbonyl groups in the polyketones are transformed into N-substituted pyrrole groups.…”

Section: Introductionmentioning

confidence: 99%

Novel polyketones with pendant imidazolium groups as nanodispersants of hydrophobic antibiotics

Araya-Hermosilla

Orellana

Toncelli

et al. 2015

J of Applied Polymer Sci

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In this work, we present a new method to nanodisperse the pH-sensitive antibiotics oxolinic acid and flumequine by the use of a pH-sensitive synthetic polyketone derivative with amphiphilic characteristics. The pH-sensitive polymer bears imidazolium residues on pendant groups as weak acids, and its solvophobic properties can be tuned by changing the pH. While the antibiotics are soluble in water at pHs higher than 7.0 for flumequine and 8.4 for oxolinic acid, and the polymer is soluble in water at pHs lower than 5.5, nanoprecipitates presenting hydrodynamic radius of 35-100 nm and positive zeta potential containing both the polymer and any of the antibiotics are formed at pH 6.8 by mixing stock solutions whose pH has been adjusted to 5.4 for the polymer and higher than 10 for the antibiotics. The out-of-equilibrium process occurring upon mixing both solutions produces pH changing, molecular arrangement, and a controlled collapse of the system in the form of nano-and submicron particles. The driving forces for the arrangements are found among hydrophobic forces, long-range electrostatic interactions, and short range aromatic-aromatic interactions.

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Controlling the aggregation of 5,10,15,20-tetrakis-(4-sulfonatophenyl)-porphyrin by the use of polycations derived from polyketones bearing charged aromatic groups

Cited by 37 publications

References 59 publications

Self-Aggregation of 5,10,15,20-Tetrakis(4-Methoxyphenyl)porphyrin (Tmpp): Spectroscopic Studies and Multivariate Analyzes

Self-Aggregation of 5,10,15,20-Tetrakis(4-Methoxyphenyl)porphyrin (Tmpp): Spectroscopic Studies and Multivariate Analyzes

Porphyrins functionalized by quaternary pyridinium units

Novel polyketones with pendant imidazolium groups as nanodispersants of hydrophobic antibiotics

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