Artículo

Cochón, A.C.; Aldonatti, C.; San Martín De Viale, L.C.; De Calmanovici, R.W. "Evaluation of the porphyrinogenic risk of antineoplastics" (1997) Journal of Applied Toxicology. 17(3):171-177
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Abstract:

The use of antineoplastics is common in cancer therapy, and some of them have been associated with the development of porphyria in patients with cancer. However, knowledge of their effects on the haeme metabolic pathway is at present scarce and unclear. So, the present study evaluates the porphyrinogenic ability of nine antineoplastics (both alkylating and non-alkylating). These were tested either alone or in conjunction with 3,5-diethoxycarbonyl-1,4-dihydrocollidine (latent porphyria model) in chick embryos and in mice. The results obtained suggest that the use of cyclophosphamide, azathioprine, 5-fluorouracil, busulphan, procarbazine and hexamethylmelamine be avoided in the treatment of porphyric patients. On the other hand, dacarbazine, chlorambucil and melphalan are non-porphyrinogenic. We also provide evidence showing that neither the presence of the mustard group in the structure of the antineoplastic nor alterations in ferrochelatase or protoporphyrinogen oxidase activities are responsible for the porphyrinogenic ability of cyclophosphamide.

Registro:

Documento: Artículo
Título:Evaluation of the porphyrinogenic risk of antineoplastics
Autor:Cochón, A.C.; Aldonatti, C.; San Martín De Viale, L.C.; De Calmanovici, R.W.
Filiación:Depto. de Quim. Biológica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Nuñez, 1428 Buenos Aires, Argentina
Palabras clave:δ-Aminolaevulinic acid synthase; Antineoplastics; Ferrochelatase; Porphyria; Porphyrins; Protoporphyrinogen oxidase; 5 aminolevulinate synthase; alkylating agent; altretamine; antineoplastic agent; azathioprine; busulfan; chlorambucil; cyclophosphamide; dacarbazine; ferrochelatase; fluorouracil; melphalan; porphyrin; procarbazine; protoporphyrinogen oxidase; animal experiment; animal tissue; article; cancer chemotherapy; chick embryo; controlled study; drug mechanism; embryo; enzyme activity; female; intraperitoneal drug administration; liver; male; mouse; nonhuman; porphyria; priority journal; species difference; structure activity relation; Alkylating Agents; Altretamine; Animals; Antineoplastic Agents; Azathioprine; Busulfan; Chick Embryo; Cyclophosphamide; Dacarbazine; Dicarbethoxydihydrocollidine; Female; Ferrochelatase; Flavoproteins; Fluorouracil; Liver; Male; Mice; Mice, Inbred BALB C; Mitochondrial Proteins; Oxidoreductases; Oxidoreductases Acting on CH-CH Group Donors; Porphyrias; Porphyrins; Procarbazine; Protoporphyrinogen Oxidase; Structure-Activity Relationship; Animalia
Año:1997
Volumen:17
Número:3
Página de inicio:171
Página de fin:177
DOI: http://dx.doi.org/10.1002/(SICI)1099-1263(199705)17:3<171::AID-JAT419>3.0.CO;2-A
Título revista:Journal of Applied Toxicology
Título revista abreviado:J. APPL. TOXICOL.
ISSN:0260437X
CODEN:JJATD
CAS:Alkylating Agents; Altretamine, 645-05-6; Antineoplastic Agents; Azathioprine, 446-86-6; Busulfan, 55-98-1; Cyclophosphamide, 50-18-0; Dacarbazine, 4342-03-4; Dicarbethoxydihydrocollidine, 632-93-9; Ferrochelatase, EC 4.99.1.1; Flavoproteins; Fluorouracil, 51-21-8; Mitochondrial Proteins; Oxidoreductases Acting on CH-CH Group Donors, EC 1.3.-; Oxidoreductases, EC 1.-; Porphyrins; Ppox protein, mouse, EC 1.3.3.4; Procarbazine, 671-16-9; Protoporphyrinogen Oxidase, EC 1.3.3.4
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0260437X_v17_n3_p171_Cochon

Referencias:

  • Kyle, R.A., Dameshek, W., Porphyria cutanea tarda associated with chronic granulocytic leukemia treated with busulfan (1961) Blood, 23, pp. 776-785
  • Manzione, N.C., Wolkoff, A.W., Sassa, S., Development of porphyria cutanea tarda after treatment with cyclophosphamide (1988) Gastroenterology, 95, pp. 1119-1122
  • Arbus, M.H., Relationship between porphyria and the use of antineoplastics (1981) Am. J. Hosp. Pharm., 38, p. 631
  • Palma-Carlos, A.G., Palma-Carlos, M.L., Lourenco, M.G., Martins-Silva, J.A., Effect of alkylating agents on haem metabolism (1971) S. Afr J. Lab Clin. Med, 45, pp. 81-84
  • Rizzardini, M., Ferraroli, A., Dal Fiume, D., Cantoni, L., Cyclophosphamide-impaired regulation of hepatic heme metabolism (1984) Experientia, 40, pp. 1390-1392
  • El-Azhary, R.A., Ahmed, A.E., Effect of melphalan on δ-aminolevulinic acid synthetase in the spleen, bone marrow and liver of rats (1982) J. Pharmacol Exp. Ther., 223, pp. 457-461
  • El-Azhary, R.A., Ahmed, A.E., Heme metabolism in liver and spleen of 1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea (CCNU)-treated rats (1984) Biochem. Pharmacol., 33, pp. 3171-3175
  • Rifkind, A.B., Drug-induced exacerbations of porphyria (1976) Primary Care, 3, pp. 665-685
  • Moore, M.R., Biochemistry of porphyria (1993) Int J Biochem, 25, pp. 1353-1368
  • De Matteis, F., Disturbances of liver porphyrin metabolism caused by drugs (1967) Pharmacol Rev, 19, pp. 523-557
  • De Matteis, F., Drug interactions in experimental hepatic porphyria. A model for the exacerbation by drugs of human variegate porphyria (1973) Enzyme, 16, pp. 266-275
  • Anderson, K.E., Effects of antihypertensive drugs on hepatic heme biosynthesis and evaluation of ferrochelatase inhibitors to simplify testing of drugs for heme pathway induction (1978) Biochem. Biophys. Acta, 543, pp. 313-327
  • Deybach, J.C., Da Silva, V., Phung, L.N., Levy, J.C., Nordmann, Y., Le risque medicamenteux des porphyries hepatiques. Mise en place d'un modöle animal expérimental (1987) Presse Med., 16, pp. 68-71
  • Morgan, C.J., Badawy, A.A.-B., Effects of acute carbamazepine administration on haem metabolism in rat liver (1992) Biochem. Pharmacol., 43, pp. 1473-1477
  • Wainstok De Calmanovici, R., San Martin De Viale, L.C., Effect of some antineoplastics on metabolic heme pathway (1988) Int. J. Biochem, 20, pp. 1015-1020
  • Cochón, A.C., San Martin De Viale, L.C., Wainstok De Calmanovici, R., Cyclophosphamide and its metabolite acrolein. Some studies on their porphyrinogenic action in 17 day old chick embryo (1992) Comp Biochem. Physiol, 102 C, pp. 143-148
  • San Martin De Viale, L.C., Rios De Molina, M.D.C., Wainstok De Calmanovici, R., Tomio, J.M., Porphyrins and porphyrinogen carboxy-lyase in hexachlorobenzene-induced porphyria (1977) Biochem. J., 168, pp. 393-400
  • Doss, M., Analytical and preparative thinlayer chromatography of porphyrin methyl esters (1970) Z Klin. Chem. Klin. Biochem., 8, pp. 197-207
  • Marver, H.S., Tschudy, D.P., Perlroth, M.G., Collins, A., δ-Aminolevulinic acid synthetase I. Studies in liver homogenates (1966) J. Biol. Chem., 241, pp. 2803-2809
  • Brenner, D.A., Bloomer, J.R., A fluorometric assay for measurement of protoporphyrmogen oxidase activity in mammalian tissue (1980) Clin. Chim. Acta, 100, pp. 259-266
  • Cole, S.P.C., Vavasour, E.J., Marks, G.S., Drug-induced porphyrin biosynthesis-XIX. Potentiation of the porphyrin-inducing effects of SKF 525-A in the chick embryo liver by 3,5-diethoxycarbonyl-1,4-dihydro-2,4,6-trimethylpyridine, an inhibitor of ferrochelatase (1979) Biochem. Pharmacol., 28, pp. 3533-3538
  • Porra, R.J., Jones, O.T.G., Studies on ferrochelatase. 1 Assay and properties of ferrochelatase from a pig-liver mitochondnal extract (1963) Biochem. J., 87, pp. 181-185
  • Lowry, O.H., Rosenbrough, N.J., Farr, A.L., Randall, R.J., Protein measurement with the Folin phenol reagent (1951) J. Biol. Chem., 193, pp. 265-275
  • Racz, W.J., Marks, G.S., Drug-induced porphyrin biosynthesis-II. Simple procedure for screening drugs for porphyria-inducing activity (1969) Biochem. Pharmacol., 18, pp. 2009-2018
  • Taub, H., Krupa, V., Marks, G.S., Drug-induced porphyrin biosynthesis-Xl. Effect of SKF 525-A on the activity of porphyrin-inducing drugs in chick embryos, chickens and rats (1976) Biochem. Pharmacol., 25, pp. 511-516
  • Brady, A.M., Hasmall, R.L., Elcombe, B.M., Comparison of the effects of griseofulvin and dihydropyridines on ferrochelatase activity and porphyrin accumulation in primary cultures of mouse and rat hepatocytes (1993) Toxicol. in Vitro, 7, pp. 587-593
  • Frater, Y., Brady, A., Lock, E.A., De Matteis, F., Formation of N-methyl protoporphyrin in chemically-induced protoporphyria. Studies with a novel porphyrogenic agent (1993) Arch Toxicol., 67, pp. 179-185
  • Moore, M.R., McColl, K.E.L., Fitzsimons, E.J., Goldberg, A., The porphyrias (1990) Blood Rev., 4, pp. 88-96
  • Muhlbauer, J.E., Pathak, M.A., Tishler, P.V., Fitzpatrick, T.B., Variegate porphyria in New England (1982) JAMA, 247, pp. 3095-3102
  • Melero, M.J., Mattar, D.E., Stengel, F.M., Politi, A.J., Idiarte, L.B., Bacque, M.C., Porfiria cutanea tarda en dos pacientes con transplante renal (1993) Mediana, 53, pp. 232-234

Citas:

---------- APA ----------
Cochón, A.C., Aldonatti, C., San Martín De Viale, L.C. & De Calmanovici, R.W. (1997) . Evaluation of the porphyrinogenic risk of antineoplastics. Journal of Applied Toxicology, 17(3), 171-177.
http://dx.doi.org/10.1002/(SICI)1099-1263(199705)17:3<171::AID-JAT419>3.0.CO;2-A
---------- CHICAGO ----------
Cochón, A.C., Aldonatti, C., San Martín De Viale, L.C., De Calmanovici, R.W. "Evaluation of the porphyrinogenic risk of antineoplastics" . Journal of Applied Toxicology 17, no. 3 (1997) : 171-177.
http://dx.doi.org/10.1002/(SICI)1099-1263(199705)17:3<171::AID-JAT419>3.0.CO;2-A
---------- MLA ----------
Cochón, A.C., Aldonatti, C., San Martín De Viale, L.C., De Calmanovici, R.W. "Evaluation of the porphyrinogenic risk of antineoplastics" . Journal of Applied Toxicology, vol. 17, no. 3, 1997, pp. 171-177.
http://dx.doi.org/10.1002/(SICI)1099-1263(199705)17:3<171::AID-JAT419>3.0.CO;2-A
---------- VANCOUVER ----------
Cochón, A.C., Aldonatti, C., San Martín De Viale, L.C., De Calmanovici, R.W. Evaluation of the porphyrinogenic risk of antineoplastics. J. APPL. TOXICOL. 1997;17(3):171-177.
http://dx.doi.org/10.1002/(SICI)1099-1263(199705)17:3<171::AID-JAT419>3.0.CO;2-A