Meso‐Tetraphenylporphyrin Dimer Derivative as a Potential Photosensitizer in Photodynamic Therapy

Faustino, Maria A. F.; Neves, Maria G. P. M. S.; Vicente, M. Graça H.; Cavaleiro, José A. S.; Neumann, Marcus A.; Brauer, Hans-D.; Jori, Giulio

doi:10.1111/j.1751-1097.1997.tb03165.x

Cited by 33 publications

(31 citation statements)

References 33 publications

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“…Facing the PDT significance of the dimers and of those amide-substituted porphyrins, a program was started to synthesize and biologically assess new dimeric compounds, these were obtained by coupling meso-tetraarylporphyrin derivatives containing acid and amine substituents (5).…”

Section: Introductionmentioning

confidence: 99%

“…In a recent publication the synthesis of dimer D1 and the evaluation of its photophysical, pharmacokinetic and PDT properties were described (5). This compound showed a high selectivity for tumor localization; a significant delay in the growth of PDT-treated tumors was observed.…”

Section: Introductionmentioning

confidence: 99%

“…It is then possible to examine the biological and photophysical properties exhibited by these new synthesized dimers and to compare their behavior with the corresponding data previously found for dimer D1. (5)…”

Section: Introductionmentioning

confidence: 99%

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Part 2. meso-Tetraphenylporphyrin Dimer Derivatives as Potential Photosensitizers in Photodynamic Therapy¶

Faustino

Neves

Cavaleiro

et al. 2007

Photochemistry and Photobiology

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Studies on the synthesis, singlet oxygen and fluorescence yields and pharmacokinetic properties of three different dimeric porphyrins with an amide linkage (D2-D4) are described and compared with the results recently reported for a dimeric porphyrin (D1). The pharmacokinetic behavior of all dimers were examined in Balb/c mice bearing MS-2 fibrosarcomas. The maximal efficiency and selectivity of photosensitizer accumulation in each tumor tissue takes place at 24 h after drug administration of 1.0 mg kg Ϫ1 into DL-␣-dipalmitoylphosphatidylcholine liposomes by intravenous injection. Since the dimeric porphyrins exhibit high quantum yields of singlet oxygen generation, long triplet lifetimes and high photostability, the results obtained suggest that the evaluated dimeric structures may be promising candidates for further use in PDT experiments. The results also allow the possibility to establish a correlation between the chemical structure of the dyes and the efficiency/selectivity of the tumor accumulation and can be used for building up optimal photosensitizing agents for tumors.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Part 2. meso-Tetraphenylporphyrin Dimer Derivatives as Potential Photosensitizers in Photodynamic Therapy¶

Faustino

Neves

Cavaleiro

et al. 2007

Photochemistry and Photobiology

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“…In previous studies, we have investigated the photodynamic activity of porphyrin derivatives substituted by methoxy groups in different biomimetic and biological media (14,15). The presence of methoxy groups in the sensitizer appears to be beneficial from the standpoint of tumor localization (16,17). Also, a novel meso-2,4,6trimethoxyphenyl porphyrin covalently linked to a trifluoromethylphenyl derivative was evaluated as an interesting photosensitizer (18,19).…”

Section: Introductionmentioning

confidence: 99%

Porphyrin-fullerene C60 dyads with high ability to form photoinduced charge-separated state as novel sensitizers for photodynamic therapy

Milanesio

Alvarez

Rivarola

et al. 2005

Photochem Photobiol

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The photodynamic activities of a porphyrin-C60 dyad (P-C60) and its metal complex with Zn(II) (ZnP-C60) were compared with 5-(4-acetamidophenyl)-10,15,20-tris(4-methoxyphenyl)porphyrin (P), both in homogeneous medium-bearing photooxidizable substrates and in vitro on the Hep-2-human-larynx-carcinoma cell line. This study represents the first evaluation of dyads, with a high capacity to form a photoinduced charge-separated state, to act as agents to inactivate cells by photodynamic therapy (PDT). Absorption and fluorescence spectroscopic studies were performed in toluene and N,N-dimethylformamide (DMF). The emission of the porphyrin moiety in the dyads is strongly quenched by the attached fullerene C60 moiety. The singlet molecular oxygen, O2(1delta(g)), productions (phi(delta)) were determined using 9,10-dimethylanthracene (DMA). The values of phi(delta) were strongly dependent on the solvent's polarity. Comparable phi(delta) values were found for dyads and P in toluene, while O2(1delta(g)) production was significantly diminished for the dyads in DMF. In more polar solvent, the stabilization of charge-transfer state takes place, decreasing the efficiency of porphyrin triplet-state formation. Also, both dyads photosensitize the decomposition of L-tryptophan in DMF. In biological medium, no dark cytotoxicity was observed using sensitizer concentrations < or = 1 microM and 24 h of incubation. The uptake of sensitizers into Hep-2 was studied using 1 microM of sensitizer and different times of incubation. Under these conditions, a value of approximately 1.5 nmol/10(6) cells was found between 4 and 24 h of incubation. The cell survival after irradiation of the cells with visible light was dependent upon light-exposure level. A higher photocytotoxic effect was observed for P-C60, which inactivates 80% of cells after 15 min of irradiation. Moreover, both dyads keep a high photoactivity even under argon atmosphere. Thus, depending on the microenvironment where the sensitizer is localized, these compounds could produce biological photodamage through either an O2(1delta(g))-mediated photoreaction process or a free-radicals mechanism under low oxygen concentration. These results show that molecular dyads, which can form a photoinduced charge-separated state, are a promising model for phototherapeutic agents, with potential applications in cell inactivation by PDT.

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“…42, 43 Faustino et al 44,45 evaluated the meso-tetraphenylporphyrin dimer derivative as a potential photosensitizer in PDT. Recently, Pegaz et al 46 showed that TPP-loaded nanoparticles exhibited more photothrombic efficiency than free TPP.…”

Section: Trp and Bsa Photooxidations And Binding Of Sensitizers To Bsamentioning

confidence: 99%

Photodynamic activity of chloro(5,10,15,20-tetraphenylporphyrinato)indium(III)

Silva¹,

Pelegrino²,

Tedesco³

et al. 2008

J. Braz. Chem. Soc.

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A atividade fotodinâmica do cloro (5,10,15,20-tetrafenilporfirinato) de índio(III) (InTPP) in vitro foi investigado para possível uso em terapia fotodinâmica (PDT). O rendimento quântico de oxigênio singlete do InTPP (Φ ∆ = 0,72) em DMSO foi maior que da 5,10,15,20-tetrafenilporfirina (TPP) (Φ ∆ = 0,52). Os sítios de ligação entre os fotossensibilizadores e albumina bovina (BSA) são independentes e com células vermelhas de sangue humano (RBC) são cooperativos, com um e quatro sítios de ligação por molécula, respectivamente. As constantes de associação com BSA são (1,15 ± 0,07) × 10 5 e (2,6 ± 0,1) × 10 4 L mol -1 e com RBC são (2,40 ± 0,05) × 10 7 L mol -1 e (7,2 ± 0,2) × 10 4 L mol ) of photosensitizers were used. InTPP was 1.37-1.5 times more effective in the photooxidation of RBC than Photofrin®. Our results indicate that InTPP should be used in future studies of PDT.

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Meso‐Tetraphenylporphyrin Dimer Derivative as a Potential Photosensitizer in Photodynamic Therapy

Cited by 33 publications

References 33 publications

Part 2. meso-Tetraphenylporphyrin Dimer Derivatives as Potential Photosensitizers in Photodynamic Therapy¶

Part 2. meso-Tetraphenylporphyrin Dimer Derivatives as Potential Photosensitizers in Photodynamic Therapy¶

Porphyrin-fullerene C60 dyads with high ability to form photoinduced charge-separated state as novel sensitizers for photodynamic therapy

Photodynamic activity of chloro(5,10,15,20-tetraphenylporphyrinato)indium(III)

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