Photodynamic Generation of Hydroxyl Radicals by Hematoporphyrin Derivative and Light

Steveninck, J. Van; Tijssen, Karmi; Boegheim, J. P. J.; Zee, Jolanda Van der; Dubbelman, T. M. A. R.

doi:10.1111/j.1751-1097.1986.tb05528.x

Cited by 38 publications

(9 citation statements)

References 17 publications

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“…The defect in ferrochelatase results in accumulation of protoporphyrin (Bottomley et al, 1975;Cox, 1997;Lim and Cohen, 1999), which may be produced in immature red blood cells, released into the plasma, and accumulate in the cell membranes of endothelial cells due to its hydrophobicity (Brun and Sandberg, 1991). Numerous in vitro studies have shown the generation of reactive oxygen species (ROS), such as singlet oxygen ( 1 O 2 ), hydroxyl radicals ( OH), and superoxide anion radicals (O 2 À ), during photodynamic reactions with various porphyrins (Buettner and Oberley, 1980;Torinuki and Miura, 1983;Blum and Grossweiner, 1985;Van Steveninck et al, 1986;Carraro and Pathak, 1988;Haseloff et al, 1989;Herrmann et al, 1996). Various cytotoxic effects of these ROS have been shown with endothelial cells in vitro (Sacks et al, 1978;Kvietys et al, 1989;Knepler et al, 2001;Kwon et al, 2001).…”

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confidence: 98%

In Vivo Oxygen Radical Generation in the Skin of the Protoporphyria Model Mouse with Visible Light Exposure: An L-Band ESR Study

Takeshita

Takajo

Hirata

et al. 2004

Journal of Investigative Dermatology

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Although oxygen radicals are thought to play a key role in the skin injury that is caused by protoporphyria, there is no direct evidence of generation of these radicals in vivo. This study measured the generation of oxygen radicals caused by visible light non-invasively in the skin of griseofulvin-induced protoporphyria model mice, using an in vivo electron spin resonance spectrometer equipped with a surface-coil-type resonator that could detect radicals within about 0.5 mm of the skin surface. A durable nitroxyl radical was administered intravenously as a probe. Light irradiation enhanced the decay of the nitroxyl signal in griseofulvin-treated mice, whereas light irradiation did not enhance the signal decay in control mice. The enhanced signal decay was completely suppressed by intravenous administration of hydroxyl radical scavengers, superoxide dismutase or catalase, or the intraperitoneal administration of desferrioxamine. The enhanced signal decay with illumination was reversible, and quickly responded to turning the light on and off. These observations suggest that the hydroxyl radical is generated via an iron-catalyzed reaction in the skin. This paper demonstrates, for the first time, the specific generation of oxygen radicals in response to light irradiation of the skin of protoporphyria model mice.

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confidence: 98%

In Vivo Oxygen Radical Generation in the Skin of the Protoporphyria Model Mouse with Visible Light Exposure: An L-Band ESR Study

Takeshita

Takajo

Hirata

et al. 2004

Journal of Investigative Dermatology

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“…Light activation of the localized porphyrin induces damage to mitochondria, cellular organelles, membranes, DNA, and specific proteins by singlet oxygen, produced under aerobic conditions and possibly by hydroxyl radicals (Reviewed by Moan, 1986;& Van Steveninck et al, 1986). Photodynamic therapy is based on administration of an HPD solution to the cancer patient and later on, illumination of the tumour by a 630nm laser light beam.…”

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confidence: 99%

Destruction of erythroleukaemic cells by photoactivation of endogenous porphyrins

Malik

Lugaci²

1987

Br J Cancer

281

114

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Cancer therapy ideally should be based on high selectivity of the therapeutic agent for the transformed cells, low specificity for normal tissues and high cytotoxic efficiency to the target tumour. These requirements are partially fulfilled by haematoporphyrin derivative (HPD) phototherapy.The method is based on the capability of porphyrins to be selectively localized in malignant tumours. Light activation of the localized porphyrin induces damage to mitochondria, cellular organelles, membranes, DNA, and specific proteins by singlet oxygen, produced under aerobic conditions and possibly by hydroxyl radicals (Reviewed by Moan, 1986;& Van Steveninck et al., 1986). Photodynamic therapy is based on administration of an HPD solution to the cancer patient and later on, illumination of the tumour by a 630nm laser light beam. The treated area undergoes necrosis, with minimal changes in the surrounding tissues (Dougherty, 1984; Land, 1984;Berenbaum et al., 1982).Although HPD is quite an effective tumour localizer, the trend is to synthesize new porphyrin-compounds with higher tumour localizing capacities, and being chemically well defined, to overcome the main problem of HPD viz. its complex porphyrin composition and aggregation state (Kessel & Chou, 1985;Evensen et al., 1984). Recently, a variety of new molecules with good tumour localization and sensitization properties were introduced into experimental systems, like haematoporphyrin di-ethers (Rimington et al., 1987) and chlorin-porphyrin ester . Uroporphyrin I was reevaluated mainly for diagnostic applications (El-Far & Pimstone, 1986). On the other hand, it is well known that the natural protoporphyrin is an excellent photosensitizer, inducing haemolysis and light sensitivity of the skin in porphyric patients (Meyer & Schmid, 1978). It is a poor tumour localizer despite its high photo-activity potential on in vitro incubated cells (Malik & Djaldetti, 1980). In addition, protoporphyrin is biosynthesized in low amounts, by all tumour cells, as well as non-transformed tissues, while in specific transformed cells such as erythroleukaemia, it can be produced more efficiently (Marks & Rifkind, 1978). In their proerythroblastic phase the enzymatic activity of porphyrin biosynthesis was found to be constitutive, except for the first enzyme, the ALA-synthase which is the rate limiting step of the pathway and is inducible (Sassa, 1976), and iron uptake from transferrin (Lasky et al., 1986). Therefore, in order to induce porphyrin synthesis by erythroblasts, exogenous 5-ALA must be supplied to circumvent the first limiting enzyme .Mice injected with 5-ALA showed porphyrin production in the skin, an effect similar to that of 5-ALA in cultured Friend erythroleukaemic cells (Pottier et al., 1986). From both these systems it can be concluded that the cellular concentration of porphyrin can be increased by exogenous addition of the precursor for porphyrins.The purpose of the present study was to determine whether endogenous porphyrins produced from 5-ALA erythroleukaemic cells ca...

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“…Increasing evidence indicates that cytotoxicity induced by PDT is mediated through the photochemical generation of singlet oxygen via a Type II reaction (Spikes). In addition, a number of studies have documented that various other reactive species -including hydroxyl radicals, hydrogen peroxide and superoxide anion -can be produced by porphyrin photosensitization (12). The main purpose of the present study was to test the effectiveness of liposomal delivered protoporphyrindisodiumsalt for photodynamic therapy.…”

Section: Discussionmentioning

confidence: 98%

Photodynamic therapy of human bladder carcinoma cells in vitro with liposomes as a carrier for protoporphyrindisodiumsalt

Schmidt

Wenderoth

Reich

et al. 1995

Proceedings of SPIE

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In vitro experiments were performed on human bladder carcinoma cells to evaluate the efficiency of photodynamic activity of protoporphyrindisodiumsalt encapsulated within liposomes. The bladder carcinoma cell line EJ 28, (Tumorbank Heidelberg) was grown on DMEM + 10 % FCS + 2 % Glutamine + 1 % Penicillin 1 Streptomycin as a monolayer culture.In the log phase, cells were trypsinized, counted and inoculated into 35 mmdiameter multiwells at i05 cells/well and allowed to grow for 24 h. The cells were incubated for 1 h with 5, 10, 20 ug/mI protoporphyrindisodiumsalt in liposomes. (DPPC/Cholesterol 7:3). After incubation cells were refed with complete medium and irradiated with 3 and 6 J/cm2. After irradiation, the cells were incubated for 2 days at 37° C, then fixed, stained, counted and compared to the control group. Mean survival rates of 7,21 %, 2,99 %, 1 ,33 % after irradiation with 3 J/cm2 and 4,3 %, 1,48 % and 0,88 % after irradiation with 6 J/cm2 were found. By using a fluorescence microscope, we evaluated the intracellular uptake of protoporphyrindisodiumsalt in liposomes. The vesicular fluorescence pattern exhibited concentration of photosensitizer in the nuclear membrane and adjacent parts of cytoplasm as well as in the plasma membrane. By transmission electron microscopy marked changes were observed at the mitochondria with dissolution of the cristae and development of vacuols.

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Photodynamic Generation of Hydroxyl Radicals by Hematoporphyrin Derivative and Light

Cited by 38 publications

References 17 publications

In Vivo Oxygen Radical Generation in the Skin of the Protoporphyria Model Mouse with Visible Light Exposure: An L-Band ESR Study

In Vivo Oxygen Radical Generation in the Skin of the Protoporphyria Model Mouse with Visible Light Exposure: An L-Band ESR Study

Destruction of erythroleukaemic cells by photoactivation of endogenous porphyrins

Photodynamic therapy of human bladder carcinoma cells in vitro with liposomes as a carrier for protoporphyrindisodiumsalt

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