Pharmacokinetic and tumour-photosensitizing properties of methoxyphenyl porphyrin derivative

Alvarez, M. Gabriela; Morán, Flavia; Yslas, Edith Inés; Vittar, Natalia Belén Rumie; Bertuzzi, Mabel; Durantini, Edgardo N.; Rivarola, Viviana

doi:10.1016/s0753-3322(03)00030-1

Cited by 17 publications

(6 citation statements)

References 21 publications

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“…In previous studies, we have investigated the photodynamic activity of porphyrin derivatives in different biomimetic media and in vitro on the Hep-2 human larynx carcinoma cell line. [24][25][26][27] In particular, the presence of a cationic charge in the porphyrin structure produces an increase of about three times in the uptake of this porphyrin into Hep-2 cells with respect to a non-ionic porphyrin model. 28 In this case, a higher cellular incorporation is also accompanied by a higher photocytotoxic activity on Hep-2 cells.…”

Section: Introductionmentioning

confidence: 98%

Photodynamic activity of cationic and non-charged Zn(ii) tetrapyridinoporphyrazine derivatives: biological consequences in human erythrocytes and Escherichia coli

Dupouy

Lazzeri

Durantini

2004

Photochem Photobiol Sci

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The photodynamic activity of a cationic Zn(II) tetramethyltetrapyridinoporphyrazinium salt (ZnPc ) was compared with that of a non-charged Zn(II) tetrapyridinoporphyrazine (ZnPc 1), both in vitro using human red blood (HRB) cells and a typical Gram-negative bacterium Escherichia coli. Absorption and fluorescence spectroscopic studies were analyzed in different media. Fluorescence quantum yields (phi(F)) of 0.35 for ZnPc 1 and 0.30 for ZnPc 2 were calculated in N,N-dimethylformamide (DMF). The singlet molecular oxygen, O(2)((1)Delta(g)), production was evaluated using 9,10-dimethylanthracene (DMA) in DMF yielding values of Phi(Delta)= 0.56 for ZnPc 1 and 0.50 for ZnPc 2. In biological medium, the photodynamic effect was first evaluated in HRB cells. Both phthalocyanines produce similar photohemolysis of HRB cells, reaching values >90% of lysis after 5 min of irradiation with visible light. The photodynamic effect is accompanied by an increase in the membrane fluidity of HRB cells. However, these studies on E. coli cells showed that the cationic ZnPc 2 produces a higher photoinactivation of Gram-negative bacteria than ZnPc 1. Also, these results were established by stopped of growth curves for E. coli. Therefore the studies show that cationic ZnPc 2 is an efficient phototherapeutic agent with potential applications in tumor cell and Gram-negative bacteria inactivation by photodynamic therapy.

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Section: Introductionmentioning

confidence: 98%

Photodynamic activity of cationic and non-charged Zn(ii) tetrapyridinoporphyrazine derivatives: biological consequences in human erythrocytes and Escherichia coli

Dupouy

Lazzeri

Durantini

2004

Photochem Photobiol Sci

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“…Which pathway is induced depends on the different properties of the photosensitizer, the type of cells, the density of population, and the experimental method. Furthermore, the method itself varies by photosensitizing agent concentration, light dose, and incubation time (Blank et al, 2002;Alvarez et al, 2003). Which pathway the cell takes to PDT-induced death is organelle-dependent as well.…”

Section: Introductionmentioning

confidence: 99%

Cellular and Molecular Mechanisms of Photodynamic Hypericin Therapy for Nasopharyngeal Carcinoma Cells

Wang

Guo²,

Yang³

et al. 2010

J Pharmacol Exp Ther

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Hypericin-mediated photodynamic therapy (HY-PDT) has become a potential treatment for tumors and nonmalignant disorders. Some studies reported that HY-PDT could lead to apoptosis in some carcinoma cells. However, the molecular mechanism of HY-PDT remains unknown. In this study, we evaluated the molecular mechanisms of hypericin associated with light-emitting diode irradiation on the poorly differentiated human nasopharyngeal carcinoma cell line CNE-2 in vitro. To comprehensively understand the effects of HY-PDT on CNE-2 cells, we detected cell viability, cell cycle, apoptosis, intracellular glutathione content, and intracellular caspase (caspase-9, caspase-3, and caspase-8) activity. Furthermore, we performed genome-wide expression analysis via microarrays at different time points in response to HY-PDT, and we found that differentially expressed genes were highly enriched in the pathways related to reactive oxygen species generation, mitochondrial activity, DNA replication and repair, cell cycle/proliferation, and apoptosis. These results were consistent with our cytology test results and demonstrated that caspasedependent apoptosis occurred after HY-PDT. Taken together, both cellular and molecular data revealed that HY-PDT could inhibit the growth of CNE-2 cells and induce their apoptosis.

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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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Pharmacokinetic and tumour-photosensitizing properties of methoxyphenyl porphyrin derivative

Cited by 17 publications

References 21 publications

Photodynamic activity of cationic and non-charged Zn(ii) tetrapyridinoporphyrazine derivatives: biological consequences in human erythrocytes and Escherichia coli

Photodynamic activity of cationic and non-charged Zn(ii) tetrapyridinoporphyrazine derivatives: biological consequences in human erythrocytes and Escherichia coli

Cellular and Molecular Mechanisms of Photodynamic Hypericin Therapy for Nasopharyngeal Carcinoma Cells

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

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Pharmacokinetic and tumour-photosensitizing properties of methoxyphenyl porphyrin derivative

Cited by 17 publications

References 21 publications

Photodynamic activity of cationic and non-charged Zn(ii) tetrapyridinoporphyrazine derivatives: biological consequences in human erythrocytes and Escherichia coli

Photodynamic activity of cationic and non-charged Zn(ii) tetrapyridinoporphyrazine derivatives: biological consequences in human erythrocytes and Escherichia coli

Cellular and Molecular Mechanisms of Photodynamic Hypericin Therapy for Nasopharyngeal Carcinoma Cells

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^¶