Photosensitization with Derivatives of Haematoporphyrin

Kessel, David

doi:10.1080/09553008514553131

Cited by 56 publications

(16 citation statements)

References 39 publications

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“…In contrast, b-1,3-glucan-complexed 1-3 showed toxicityt hat increased in ad ose-dependent manner upon photoirradiation (> 610 nm). [28,29] Consequently,t he photody-namic activities of b-1,3-glucan-complexed 1, 2,a nd 3 were approx.6 4, 20, and 137 times higher, respectively,t han that of Photofrin. 0.035, 0.087,a nd 0.027 mm,r espectively ( Figure 6).…”

Section: Intracellular Uptake Of B-13-glucan-complexed Diazaporphyrinsmentioning

confidence: 96%

Improved Stability and Photodynamic Activity of Water‐Soluble 5,15‐Diazaporphyrins Incorporated in β‐(1,3‐1,6)‐d‐Glucan with On‐Off Switch

Hino

Satake

Shinmori

et al. 2019

Chemistry An Asian Journal

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5,15-Diazaporphyrins, which have al arge absorption at wavelengths over 600 nm, were dissolved in water by complexf ormation with b-(1,3-1,6)-d-glucans. Aqueous solutions of these complexes were relativelys table compared with their trimethyl-b-cyclodextrin-complexed analogues. b-Glucan-complexed diazaporphyrins showed quenched fluorescencea nd had low singlet-oxygen-genera-tion abilities owing to random self-aggregation.H owever, external stimuli, such as the presenceo fl iposomes or intracellularu ptake, restored the fluorescence and singletoxygen-generation abilities of b-glucan-complexed diazaporphyrins. Consequently, b-glucan-complexed diazaporphyrins showedv ery high photodynamic activities toward HeLa cells.

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Section: Intracellular Uptake Of B-13-glucan-complexed Diazaporphyrinsmentioning

confidence: 96%

Improved Stability and Photodynamic Activity of Water‐Soluble 5,15‐Diazaporphyrins Incorporated in β‐(1,3‐1,6)‐d‐Glucan with On‐Off Switch

Hino

Satake

Shinmori

et al. 2019

Chemistry An Asian Journal

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“…Hematoporphyrin derivative or Photofrin was the first PS to be studied in detail. However, it proved highly frustrating for scientists who attempted to determine its chemical structure and to identify its components [11,[16][17][18][19]. There was significant variation between batches and attempts to fractionate it into its individual component molecules frequently yielded mixtures as complicated as the starting material [20,21].…”

Section: Photosensitizersmentioning

confidence: 99%

Mechanisms in photodynamic therapy: part one—photosensitizers, photochemistry and cellular localization

Castaño

Demidova

Hamblin

2004

Photodiagnosis and Photodynamic Therapy

1,800

1,335

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SummaryThe use of non-toxic dyes or photosensitizers (PS) in combination with harmless visible light that is known as photodynamic therapy (PDT) has been known for over a hundred years, but is only now becoming widely used. Originally developed as a tumor therapy, some of its most successful applications are for non-malignant disease. In a series of three reviews we will discuss the mechanisms that operate in the field of PDT. Part one discusses the recent explosion in discovery and chemical synthesis of new PS. Some guidelines on how to choose an ideal PS for a particular application are presented. The photochemistry and photophysics of PS and the two pathways known as Type I (radicals and reactive oxygen species) and Type II (singlet oxygen) photochemical processes are discussed. To carry out PDT effectively in vivo, it is necessary to ensure sufficient light reaches all the diseased tissue. This involves understanding how light travels within various tissues and the relative effects of absorption and scattering. The fact that most of the PS are also fluorescent allows various optical imaging and monitoring strategies to be combined with PDT. The most important factor governing the outcome of PDT is how the PS interacts with cells in the target tissue or tumor, and the key aspect of this interaction is the subcellular localization of the PS. Examples of PS that localize in mitochondria, lysosomes, endoplasmic reticulum, Golgi apparatus and plasma membranes are given. Finally the use of 5-aminolevulinic acid as a natural precursor of the heme biosynthetic pathway, stimulates accumulation of the PS protoporphyrin IX is described.

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“…The porphyrins most widely used for PDT are hematoporphyrin derivative (HPD), also known as Photofrin-I, and its active tumorlocalizing component, dihematoporphyrin ether (DHE), also known as Photofrin-II (3,4), both of which are complex mixtures of porphyrins and their aggregated ether or ester products. Both DHE and HPD mediate their phototoxic effects through oxygen-mediated membrane damage (5,6).…”

Section: Introductionmentioning

confidence: 99%

A novel mechanism for the generation of superoxide anions in hematoporphyrin derivative-mediated cutaneous photosensitization. Activation of the xanthine oxidase pathway.

Athar¹,

Elmets²,

Bickers³

et al. 1989

J. Clin. Invest.

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Prior studies, both in vitro and in vivo, have suggested that cutaneous porphyrin photosensitization requires the generation of superoxide anion 2O-) and various other reactive oxygen metabolites. No unifying concept has emerged, however, that unequivocally demonstrates the source of generation of these species. Since xanthine oxidase is known to generate *02 in reperfused ischemic tissue and in certain inflammatory disorders, we attempted to assess its role in porphyrin photosensitization. C3H mice were rendered photosensitive by the intraperitoneal administration of dihematoporphyrin ether (DHE) (5 mg/kg) followed by irradiation with visible light. Murine ear swelling was used as a marker of the acute photosensitization response and involvement of oxygen radicals was evaluated using electron spin resonance (ESR) spectroscopy. The administration of allopurinol, a potent inhibitor of xanthine oxidase, afforded 90% protection against DHE-mediated acute photosensitivity in vivo. Furthermore, xanthine oxidase activity was twofold higher in the skin of photosensitized mice than in unirradiated animals. ESR spectra of 5,5-dimethyl-1-pyrroline N-oxide-trapped radicals from the skin of photosensitized mice verified the presence of O2 and 'OH, while neither of these species was detected in the skin of control mice or mice receiving allopurinol. The administration of a soybean trypsin inhibitor or verapamil before irradiation also partially blocked the photosensitivity response, suggesting that calcium-dependent proteases play a role in the activation of xanthine oxidase in this photodynamic process. These data provide in vivo evidence for the involvement of O0 in DHE-mediated cutaneous photosensitization and suggest that these radicals are generated through the activation of the xanthine oxidase pathway. The administration of allopurinol and calcium channel blockers may thus offer new approaches for the treatment of cutaneous porphyrin photosensitization.

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Photosensitization with Derivatives of Haematoporphyrin

Abstract: This review describes recent progress in delineation of the structure of the active component(s) in the tumour-localizing photosensitizer HPD (haematoporphyrin derivative), along with suggestions concerning the likely determinants of accumulation of this product by different tissues.

Cited by 56 publications

References 39 publications

Improved Stability and Photodynamic Activity of Water‐Soluble 5,15‐Diazaporphyrins Incorporated in β‐(1,3‐1,6)‐d‐Glucan with On‐Off Switch

Improved Stability and Photodynamic Activity of Water‐Soluble 5,15‐Diazaporphyrins Incorporated in β‐(1,3‐1,6)‐d‐Glucan with On‐Off Switch

Mechanisms in photodynamic therapy: part one—photosensitizers, photochemistry and cellular localization

A novel mechanism for the generation of superoxide anions in hematoporphyrin derivative-mediated cutaneous photosensitization. Activation of the xanthine oxidase pathway.

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