Artículo

Afonso, S.C.; Enríquez De Salamanca, R.; Del C. Batlle, A.M. "The photodynamic and non-photodynamic actions of porphyrins" (1999) Brazilian Journal of Medical and Biological Research. 32(3):255-266
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Abstract:

Porphyrias are a family of inherited diseases, each associated with a partial defect in one of the enzymes of the heme biosynthetic pathway. In six of the eight porphyrias described, the main clinical manifestation is skin photosensitivity brought about by the action of light on porphyrins, which are deposited in the upper epidermal layer of the skin. Porphyrins absorb light energy intensively in the UV region, and to a lesser extent in the long visible bands, resulting in transitions to excited electronic states. The excited porphyrin may react directly with biological structures (type J reactions) or with molecular oxygen, generating excited singlet oxygen (type II reactions). Besides this well-known photodynamic action of porphyrins, a novel light-independent effect of porphyrins has been described. Irradiation of enzymes in the presence of porphyrins mainly induces type I reactions, although type II reactions could also occur, further increasing the direct non-photodynamic effect of porphyrins on proteins and macromolecules. Conformational changes of protein structure are induced by porphyrins in the dark or under UV light, resulting in reduced enzyme activity and increased proteolytic susceptibility. The effect of porphyrins depends not only on their physico-chemical properties but also on the specific site on the protein on which they act. Porphyrin action alters the functionality of the enzymes of the heme biosynthetic pathway exacerbating the metabolic deficiencies in porphyrias. Light energy absorption by porphyrins results in the generation of oxygen reactive species, overcoming the protective cellular mechanisms and leading to molecular, cell and tissue damage, thus amplifying the porphyric picture.

Registro:

Documento: Artículo
Título:The photodynamic and non-photodynamic actions of porphyrins
Autor:Afonso, S.C.; Enríquez De Salamanca, R.; Del C. Batlle, A.M.
Filiación:Centra Invest. Sobre Porfirinas P., Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina
Unidad de Porfirias, Hospital Universitario 12 de Octubre, Madrid, Spain
Viamonte, 1881, 10o A, 1056 Buenos Aires, Argentina
Palabras clave:Photodynamic; Porphyrias; Porphyrins; Protein alterations; enzyme; heme; hemoprotein; photosensitizing agent; porphyrin; protoporphyrin; reactive oxygen metabolite; uroporphyrin; chemically induced disorder; darkness; human; light; metabolism; porphyria; radiation exposure; review; skin disease; ultraviolet radiation; Darkness; Enzymes; Heme; Hemeproteins; Humans; Light; Photosensitizing Agents; Porphyrias; Porphyrins; Protoporphyrins; Reactive Oxygen Species; Skin Diseases; Ultraviolet Rays; Uroporphyrins
Año:1999
Volumen:32
Número:3
Página de inicio:255
Página de fin:266
DOI: http://dx.doi.org/10.1590/S0100-879X1999000300002
Título revista:Brazilian Journal of Medical and Biological Research
Título revista abreviado:Braz. J. Med. Biol. Res.
ISSN:0100879X
CODEN:RBPMB
CAS:Enzymes; Heme, 14875-96-8; Hemeproteins; Photosensitizing Agents; Porphyrins; Protoporphyrins; Reactive Oxygen Species; Uroporphyrins
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0100879X_v32_n3_p255_Afonso

Referencias:

  • McDonagh, A.F., Bissell, D.M., Porphyria and porphyrinology - The past fifteen years (1998) Seminars in Liver Disease, 18, pp. 3-15
  • Moore, M.R., McColl, K.E.L., Rimington, C., Goldberg, A., (1987) Disorders of Porphyrin Metabolism, pp. 21-116. , Plenum Medical Book Co., New York & London
  • Van Steveninck, J., Dubbelman, T.M.A.R., Verweij, H., Photodynamic membrane damage (1983) Porphyrin Photosensitization, pp. 227-240. , Kessel D & Dougherty TV (Editors). Plenum Press, New York
  • Del C Batlle, A.M., Porphyrins, porphyrias, cancer and photodynamic therapy. A model for carcinogenesis (1993) Journal of Photochemistry and Photobiology. B, Biology, 20, pp. 5-22
  • Sandberg, S., Romslo, I., Hovding, G., Bjorndal, T., Porphyrin-induced photodamage as related to the subcellular localization of the porphyrins (1982) Acta Dermato-Venereologica, 100 (SUPPL.), pp. 75-80
  • Verweij, H., Van Steveninck, J., Model studies on photodynamic cross-linking (1982) Photochemistry and Photobiology, 35, pp. 265-267
  • Vincent, S.H., Holeman, B., Cully, B.C., Müller-Eberhard, U., Porphyrin-induced photodynamic cross-linking of hepatic heme-binding proteins (1986) Life Sciences, 38, pp. 365-372
  • Sandberg, S., Brun, A., Light-induced protoporphyrin release from erythrocytes in erythropoietic protoporphyria (1982) Journal of Clinical Investigation, 70, pp. 693-698
  • Girotti, A.W., Deziel, M.R., Photodynamic action of protoporphyrin on resealed erythrocyte membranes: Mechanisms of release of trapped markers (1983) Advances in Experimental Medicine and Biology, 60, pp. 213-225
  • Firey, P.A., Rodgers, M.J.A., Photochemical properties of erythrocyte ghosts containing porphyrin (1988) Photochemistry and Photobiology, 47, pp. 615-619
  • De Goeij, A.F.P.M., Ververgaert, P.H.J.T., Van Steveninck, J., Photodynamic effects of protoporphyrin on the architecture of erythrocyte membranes in protoporphyria and in normal red blood cells (1975) Clinica Chimica Acta, 62, pp. 287-292
  • Girotti, A.W., Photodynamic action of protoporphyrin IX on human erythrocytes: Cross-linking of membrane proteins (1976) Biochemical and Biophysical Research Communications, 72, pp. 1367-1374
  • Brun, A., Sandberg, S., Photodynamic release of protoporphyrin from intact erythrocytes in erythropoietic protoporphyria: The effect of small repetitive light doses (1985) Photochemistry and Photobiology, 41, pp. 535-541
  • Sandberg, S., Romslo, I., Porphyrin-induced photodamage at the cellular and subcellular level as related to the solubility of the porphyrins (1981) Clinica Chimica Acta, 28, pp. 13-23
  • Jon, G., Reddi, E., Cozzani, I., Tomio, L., Controlled targeting of different subcellular sites by porphyrins in tumourbearing mice (1986) British Journal of Cancer, 53, pp. 615-621
  • Sandberg, S., Glette, J., Hopen, G., Solberg, C., Romslo, I., Porphyrin-induced photodamage to isolated human neutrophils (1981) Photochemistry and Photobiology, 34, pp. 471-475
  • Christensen, T., Moan, J., Brown, J., Waksvik, H., Stigum, H., Studies on HPD: Chemical composition and in vitro photosensitization (1983) Advances in Experimental Medicine and Biology, 60, pp. 151-164
  • Lim, H.W., Gigli, I., Wasserman, S.I., Differential effects of protoporphyrin and uroporphyrin on murine mast cells (1987) Journal of Investigative Dermatology, 88, pp. 281-286
  • Konrad, K., Hönigsmann, H., Gschnait, F., Wolff, K., Mouse model for protoporphyria II. Cellular and subcellular events in the photosensitivity flare of the skin (1975) Journal of Investigative Dermatology, 65, pp. 300-310
  • Gomer, C.J., Razum, N.J., Acute skin response in albino mice following porphyrin sensitization under oxic and anoxic conditions (1984) Photochemistry and Photobiology, 40, pp. 435-439
  • Dubertret, L., Santus, R., Bazin, M., De Sa E Melo, T., Photochemistry in human epidermis. A quantitative approach (1982) Photochemistry and Photobiology, 35, pp. 103-107
  • Parrish, J.A., Rosen, C.F., Gange, R.W., Therapeutic uses of light (1985) Annals of the New York Academy of Sciences, 454, pp. 354-364
  • Kohn, K., Kessel, D., On the mode of cytotoxic action of photoactivated porphyrins (1979) Biochemical Pharmacology, 28, pp. 2465-2470
  • Sandberg, S., Romslo, I., Porphyrin-sensitized photodynamic damage of isolated rat liver mitochondria (1980) Biochimica et Biophysics Acta, 593, pp. 187-195
  • Moan, J., Rognan, S.E., Evensen, J.F., Malik, Z., Cell photosensitization by porphyrins (1987) Photochemistry and Photobiology, 46 (SUPPL.), pp. 385-395
  • Lamola, A.A., Asher, I., Müller-Eberhardt, U., Poh-Fitzpatrick, M.B., Fluorometric study of the binding of protoporphyrin to naemopexin and albumin (1981) Biochemical Journal, 196, pp. 693-698
  • Poh-Fitzpatrick, M.B., Porphyrin-sensitized cutaneous photosensitivity (1985) Clinics in Dermatology, 3, pp. 41-82
  • Vazquez, E.S., Buzaleh, A.M., Navone, N.M., Polo, C.F., Schoua, E.A., Del C Batlle, A.M., The effect of griseofulvin on the heme pathway studies on tissue explant cultures (1987) Toxicology, 46, pp. 73-82
  • Rimington, C., Lockwood, W.H., Belcher, R.V., The excretion of porphyrin-peptide conjugates in variegate porphyria (1968) Clinical Sciences, 35, pp. 211-247
  • Eales, L., Day, R.S., Blekkenhorst, G.H., The clinical ana biochemical features of variegate porphyria (1980) International Journal of Biochemistry, 12, pp. 837-854
  • Longas, M.O., Poh-Fitzpatrick, M.B., A tightly bound protein-porphyrin complex isolated from the plasma of a patient with variegate porphyria (1982) Clinica Chimica Acta, 118, pp. 219-228
  • Varigos, G., Schiltz, J.R., Bickers, D.R., Uroporphyrin I stimulation of collagen biosynthesis in human skin fibroblasts (1982) Journal of Clinical Investigation, 69, pp. 129-135
  • Ignarro, L.J., Wood, K.S., Wolin, M.S., Activation of purified soluble guanylate cyclase by protoporphyrin. IX (1982) Proceedings of the National Academy of Sciences, USA, 70, pp. 2870-2873
  • Khanum, F., Jain, V., Effects of hematoporphyrin derivative on the cellular energy metabolism in the absence and presence of light (1989) Photochemistry and Photobiology, 50, pp. 647-651
  • Bodaness, S.R., The nonphotosensitized potentiation by the photosensitizer hematoporphyrin of the horseradish peroxidase-catalyzed hydrogen peroxide-mediated oxidation of NADPH to NADP+ (1984) Biochemical and Biophysical Research Communications, 118, pp. 191-197
  • Van Steveninck, J., Boegheim, J.P.J., Dubbelman, T.M.A.R., Van Der Zee, J., The influence of porphyrins on iron-catalyzed generation of hydroxyl radicals (1988) Biochemical Journal, 250, pp. 197-201
  • Köningsberger, J.C., Rademakers, L.H.P.M., Van Hattum, J., Baart De La Faille, H., Wiegman, L.J.J.M., Italiaander, E., Van Berge Henegouwen, G.P., Marx, J.J.M., Exogenous protoporphyrin inhibits hep g2 proliferation, increases the intracellular hydrogen peroxide concentration and causes ultrastructural alterations (1995) Journal of Hepatology, 22, pp. 57-65
  • Afonso, S., Chinarro, S., Muñoz, J., Salamanca, R.E., Batlle, A., Light-dependent and light-independent inactivation of red cell porphobilinogenase and deaminase by type I and III porphyrins (1987) Bollettino dell'lstituto Dermatologico San Gallicano, 13, pp. 35-40
  • Afonso, S., Chinarro, S., Salamanca, R., Batlle, A., Further evidence on the photodynamic and the novel non-photodynamic inactivation of uroporphyrinogen decarboxylase by uroporphyrin I (1991) Journal of Enzyme Inhibition, 5, pp. 225-233
  • Afonso, S.G., Chinarro, S., Salamanca, R., Batlle, A., δ-aminolevulinic acid dehydratase inactivation by uroporphyin I in light and darkness (1994) International Journal of Biochemistry, 26, pp. 255-258
  • Afonso, S.G., Salamanca, R., Batlle, A., Cytosolic and mitochondrial enzymes inactivation by uroporphyrin in light and darkness (1996) Journal of Enzyme Inhibition, 10, pp. 141-146
  • Afonso, S.G., Chinarro, S., Muñoz, J., Salamanca, R.E., Batlle, A., Photodynamic and non-photodynamic action of several porphyrins on the activity of some heme-enzymes (1990) Journal of Enzyme Inhibition, 3, pp. 303-310
  • Afonso, S.G., Chinarro, S., Enriquez De Salamanca, R., Del C Batlle, A.M., How the atmosphere and the presence of substrate affect the photo and non-photo inactivation of heme enzymes by uroporphyrin I (1994) International Journal of Biochemistry, 26, pp. 259-262
  • Afonso, S.G., Polo, C.F., Enriquez De Salamanca, R., Batlle, A., Mechanistic studies on URO I-induced enzyme photoinactivation (1996) International Journal of Biochemistry and Cellular Biology, 38, pp. 415-420
  • Bachowsky, G.J., Morehouse, K.M., Girotti, A.W., Porphyrin-sensitized photoreactions in the presence of ascorbate. Oxidation of cell membrane lipids and hydroxyl radical traps (1988) Photochemistry and Photobiology, 47, pp. 635-645
  • Van Steveninck, J., Boegheim, J.P.J., Dubbelman, T.M.A.R., Van Der Zee, J., The influence of porphyrins on iron-catalized generation of hydroxyl radicals (1988) Biochemical Journal, 250, pp. 197-201
  • Buettner, G.R., Hall, R.D., Superoxide, hydrogen peroxide, and singlet oxygen in hematoporphyrin derivative, cysteine. NADPH and light systems (1987) Biochimica et Biophysica Acta, 923, pp. 501-507
  • Mauzerall, D., Fehrer, G., A study of the photoinduced porphyrin free radical by electron spin resonance (1964) Biochimica et Biophysica Acta, 79, pp. 430-432
  • Girotti, A.W., Protoporphyrin-sensitized photodamage in isolated membranes of human erythrocytes (1979) Biochemistry, 18, pp. 4403-4411
  • Afonso, S.G., Enriquez De Salamanca, R., Batlle, A., Porphyrin induced protein structural alterations of heme enzymes (1997) International Journal of Biochemistry and Cellular Biology, 29, pp. 1113-1121
  • Afonso, S.G., Enriquez De Salamanca, R., Batlle, A., Porphyrin induced protein structural alterations of heme enzymes. II. Protection of ALA-D and PBG-D from the photodynamic and non-photodynamic effects of URO and PROTO (1998) International Journal of Biochemistry and Cellular Biology, 30, pp. 535-543
  • Davies, K.J., Protein damage and degradation by oxygen radicals I. General aspects (1987) Journal of Biological Chemistry, 262, pp. 9895-9901
  • Afonso, S.G., Enriquez De Salamanca, R., Del C Batlle, A.M., Folding and unfolding of δ-aminolevulinic acid dehydratase and porphobilinogen deaminase induced by URO and PROTO porphyrin (1997) International Journal of Biochemistry and Cellular Biology, 29, pp. 493-503
  • Dean, R.T., A mechanism for accelerated degradation of intracellular proteins after limited damage by free radicals (1987) FEBS Letters, 220, pp. 278-282
  • Davies, K.J., Lin, S.W., Pacifici, R.E., Protein damage and degradation by oxygen radicals. IV. Modification of denatured protein (1987) Journal of Biological Chemistry, 262, pp. 9914-9920
  • Kehrer, J.P., Free radical as mediators of tissue iniury and disease (1993) Critical Reviews in Toxicology, 23, pp. 21-48

Citas:

---------- APA ----------
Afonso, S.C., Enríquez De Salamanca, R. & Del C. Batlle, A.M. (1999) . The photodynamic and non-photodynamic actions of porphyrins. Brazilian Journal of Medical and Biological Research, 32(3), 255-266.
http://dx.doi.org/10.1590/S0100-879X1999000300002
---------- CHICAGO ----------
Afonso, S.C., Enríquez De Salamanca, R., Del C. Batlle, A.M. "The photodynamic and non-photodynamic actions of porphyrins" . Brazilian Journal of Medical and Biological Research 32, no. 3 (1999) : 255-266.
http://dx.doi.org/10.1590/S0100-879X1999000300002
---------- MLA ----------
Afonso, S.C., Enríquez De Salamanca, R., Del C. Batlle, A.M. "The photodynamic and non-photodynamic actions of porphyrins" . Brazilian Journal of Medical and Biological Research, vol. 32, no. 3, 1999, pp. 255-266.
http://dx.doi.org/10.1590/S0100-879X1999000300002
---------- VANCOUVER ----------
Afonso, S.C., Enríquez De Salamanca, R., Del C. Batlle, A.M. The photodynamic and non-photodynamic actions of porphyrins. Braz. J. Med. Biol. Res. 1999;32(3):255-266.
http://dx.doi.org/10.1590/S0100-879X1999000300002