Synthesis and biological evaluation of methoxyphenyl porphyrin derivatives as potential photodynamic agents

Milanesio, M. Elisa; Morán, Flavia; Yslas, Edith Inés; Alvarez, M. Gabriela; Rivarola, Viviana; Durantini, Edgardo N.

doi:10.1016/s0968-0896(01)00138-9

Cited by 38 publications

(19 citation statements)

References 32 publications

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“…A similar tendency was also observed for meso-tetraphenylporphyrin dimer derivatives (37). Recently, a novel meso-2,4,6-trimethoxyphenylporphyrin covalently linked to a trifluoromethylphenyl derivative was evaluated as a photosensitizer (38). An attractive photobiological feature is its ability to inactivate cultured tumor cells with high efficiency by apoptotic or necrotic modes, depending on the light dose.…”

Section: Discussionsupporting

confidence: 62%

Possible in vivo mechanisms involved in photodynamic therapy using tetrapyrrolic macrocycles

Filip

Clichici

Daicoviciu

et al. 2011

Braz J Med Biol Res

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Section: Discussionsupporting

confidence: 62%

Possible in vivo mechanisms involved in photodynamic therapy using tetrapyrrolic macrocycles

Filip

Clichici

Daicoviciu

et al. 2011

Braz J Med Biol Res

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“…The two bands are characteristic of similar porphyrins such as THPPH 2 , 9 and they have been assigned to Q(0,0) and Q(0,1) transitions. 10 …”

Section: Synthesismentioning

confidence: 99%

Synthesis, spectroscopy and photosensitizing properties of hydroxynitrophenylporphyrins

Maestrin¹,

Tedesco²,

Neri³

et al. 2004

J. Braz. Chem. Soc.

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As hidroxinitrofenilporfirinas, 5,10,15,20-tetrakis(2-hidroxi-5-nitrofenil)porfirina e 5-mono(carboxifenil)-10,15,20-tris(2-hidroxi-5-nitrofenil)porfirina, estudadas neste trabalho, foram preparadas pelo método de Adler e caracterizadas por 1 H RMN e por espectroscopia de absorção e emissão na região espectral visível. A formação de 1 O 2 foi constatada através do teste do ácido úrico (AU), o qual consiste na observação do decréscimo na absorbância da banda do AU em 293 nm, após irradiação da solução, com laser, contendo o fotossenssibilizador e o AU. Os resultado obtidos indicaram que as hidroxinitrofenilporfirinas podem ser consideradas potenciais fotossensibilizadores para terapia fotodinâmica.The hydroxynitrophenylporphyrins, 5,10,15,20-tetrakis(2-hydroxy-5-nitrophenyl)porphyrin and 5-mono(carboxyphenyl)-10,15,20-tris(2-hydroxy-5-nitrophenyl)porphyrin described in this work were prepared through Adler's method. These compounds were characterized by 1 H NMR and light absorption and emission spectroscopy in the visible region. In order to demonstrate the involvement of 1 O 2 production, the uric (UA) acid test was carried out, which considers the decrease in the absorbance of UA at 293 nm following laser light irradiation of a solution containing UA and a photosensitizer. The results obtained demonstrate that these hydroxynitrophenylporphyrins can be considered as promising photosensitizers in PDT.

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“…In this case, a higher cellular incorporation is also accompanied by a higher photocytotoxic activity on Hep‐2 cells. On the other hand, a porphyrin derivative substituted by a trifluoromethyl group was evaluated on Hep‐2 and HeLa cell lines as interesting photosensitizer (19–21). An attractive photobiological feature is its ability to inactivate cultured tumor cells with high efficiency by apoptotic or necrotic modes depending on the light dose (20,2).…”

Section: Introductionmentioning

confidence: 99%

Photodynamic Studies and Photoinactivation of Escherichia coli Using meso‐Substituted Cationic Porphyrin Derivatives with Asymmetric Charge Distribution^¶

Lazzeri

Rovera

Pascual

et al. 2004

Photochem & Photobiology

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The photodynamic activities of novel asymmetrically meso substituted cationic porphyrins, 5,10‐di(4‐methylphenyl)‐ 15,20‐di(4‐trimethylammoniumphenyl)porphyrin iodide 1 and 5‐(4‐trifluorophenyl)‐10,15,20‐tris(4‐trimethylammoniumphenyl)porphyrin iodide 2 and its metal complex with Pd(II) 3, have been investigated in both homogeneous medium bearing photooxidizable substrates and in vitro on a typical gram‐negative bacterium Escherichia coli. The amphiphilic character of porphyrin 2 was increased by the presence of a high‐lipophilic trifluoromethyl group and its photophysical properties changed by forming a complex with Pd(II). Absorption and fluorescence spectroscopic studies were compared in different media. Fluorescence quantum yields (øF) of 0.16 for 1 in tetrahydrofuran and 0.08 for 2 in N, N‐dimethylformamide (DMF) were calculated, whereas no significant emission was detected for Pd(II) porphyrin 3. The singlet molecular oxygen, O2(1Δ(g), production was evaluated using 9,10‐dimethylanthracene in DMF yielding relative values of 1, 0.55 and 0.47 for porphyrins 3, 2 and 1, respectively. A faster decomposition of L‐tryptophan was obtained using Pd(II) porphyrin 3 as sensitizer with respect to the free‐base porphyrins 1 and 2. In biological medium, the behavior of cationic porphyrins 1‐3 were compared with that of 5‐(4‐carboxyphenyl)‐10,15,20‐tris(4‐methylphenyl)porphyrin 4, which was used as a noncationic sensitizer. These porphyrins are rapidly bound to E. coli cells in 5 min and the amount of cell‐bound sensitizer is not appreciably changed incubating the cultures for longer times. The recovered porphyrin 2 after one washing step reaches a value of ∼2.9 nmol/106 cells and this amount remains high even after three washes, indicating that this sensitizer is tightly bound to cells. Photosensitized inactivation of E. coli was analyzed using cells without and with one washing step. In both cases, a higher photoinactivation of cells was found for tricationic porphyrin 2 and 3, causing a ‐5.5 log (99.999%) decrease of cell survival, when treated with 10 μM of sensitizer. Under these conditions, a lower effect was found for porphyrin 1 (‐4 log) whereas sensitizer 4 did not produce appreciable photodamage. The results were also confirmed by growth delay experiments. These studies show that the amphiphilic tricationic porphyrin 2 and 3 bearing a trifluoromethyl group can be a promising model for phototherapeutic agents with potential applications in inactivation of bacteria by photodynamic therapy.

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Synthesis and biological evaluation of methoxyphenyl porphyrin derivatives as potential photodynamic agents

Cited by 38 publications

References 32 publications

Possible in vivo mechanisms involved in photodynamic therapy using tetrapyrrolic macrocycles

Possible in vivo mechanisms involved in photodynamic therapy using tetrapyrrolic macrocycles

Synthesis, spectroscopy and photosensitizing properties of hydroxynitrophenylporphyrins

Photodynamic Studies and Photoinactivation of Escherichia coli Using meso‐Substituted Cationic Porphyrin Derivatives with Asymmetric Charge Distribution^¶

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Synthesis and biological evaluation of methoxyphenyl porphyrin derivatives as potential photodynamic agents

Cited by 38 publications

References 32 publications

Possible in vivo mechanisms involved in photodynamic therapy using tetrapyrrolic macrocycles

Possible in vivo mechanisms involved in photodynamic therapy using tetrapyrrolic macrocycles

Synthesis, spectroscopy and photosensitizing properties of hydroxynitrophenylporphyrins

Photodynamic Studies and Photoinactivation of Escherichia coli Using meso‐Substituted Cationic Porphyrin Derivatives with Asymmetric Charge Distribution¶

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Photodynamic Studies and Photoinactivation of Escherichia coli Using meso‐Substituted Cationic Porphyrin Derivatives with Asymmetric Charge Distribution^¶