Artículo

Estamos trabajando para incorporar este artículo al repositorio
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

This work investigated the modulation by melatonin (Mel) of the effects of the porphyrinogenic drugs 2-allyl-2-isopropylacetamide (AIA) and 3,5-diethoxycarbonyl-1,4-dihydro-2,4,6-collidine (DDC) on oxidative environment, glucose biosynthesis and heme pathway parameters. Administration of Mel before rat intoxication with AIA/DDC showed a clear beneficial effect in all cases. Mel induced decreases of 42% and 35% in the excretion of the hemeprecursors 5-aminolevulinic acid (ALA) and porphobilinogen (PBG), respectively, and a 33% decrease in the induction of the heme regulatory enzyme 5-aminolevulinic acid-synthase (ALA-S). The activity of the glucose metabolism enzyme phosphoenolpyruvate carboxykinase (PEPCK), which had been diminished by the porphyrinogenic treatment, was restored by 45% when animals were pre-treated with Mel. Mel abolished the modest decrease in glucose 6-phospatase (G6Pase) activity caused by AIA/DDC treatment. The oxidative status of lipids was attenuated by Mel treatment in homogenates by 47%, whereas no statistically significant AIA/DDC-induced increase in thiobarbituric acid reactive substances (TBARS) was observed in microsomes after Mel pre-treatment. We hypothesize that Mel may be scavenging reactive species of oxygen (ROS) that could be damaging lipids, PEPCK, G6Pase and ferrochelatase (FQ). Additionally, Mel administration resulted in the repression of the key enzyme ALA-S, and this could be due to an increase in glucose levels, which is known to inhibit ALA-S induction. The consequent decrease in levels of the heme precursors ALA and PBG had a beneficial effect on the drug-induced porphyria. The results obtained open the possibility of further research on the use of melatonin as a co-treatment option in acute porphyria. © 2016 The Authors.

Registro:

Documento: Artículo
Título:Melatonin modulates drug-induced acute porphyria
Autor:Lelli, S.M.; Mazzetti, M.B.; San Martín de Viale, L.C.
Filiación:Laboratorio de Disturbios Metabólicos por Xenobióticos, Salud Humana y Medio Ambiente, IQUIBICEN, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Departamento de Química Biológica, Ciudad Universitaria, Pab. II, 4to Piso, Ciudad Autónoma de Buenos Aires, C1428EGA, Argentina
Palabras clave:Acute porphyria; Glucose synthesis; Heme pathway; Melatonin; Oxidative stress; 1,4 dihydro 2,4,6 trimethyl 3,5 pyridinedicarboxylic acid diethyl ester; allylisopropylacetamide; aminolevulinic acid; ferrochelatase; glucose; glucose 6 phosphatase; heme; melatonin; phosphoenolpyruvate carboxykinase (GTP); reactive oxygen metabolite; thiobarbituric acid reactive substance; acute intermittent porphyria; animal model; animal tissue; Article; controlled study; enzyme activity; female; gluconeogenesis; glucose metabolism; intoxication; lipid peroxidation; microsome; nonhuman; oxidative stress; protein analysis; rat
Año:2016
Volumen:3
Página de inicio:141
Página de fin:147
DOI: http://dx.doi.org/10.1016/j.toxrep.2015.12.010
Título revista:Toxicology Reports
Título revista abreviado:Toxicol. Rep.
ISSN:22147500
CAS:1,4 dihydro 2,4,6 trimethyl 3,5 pyridinedicarboxylic acid diethyl ester, 12772-36-0, 632-93-9; allylisopropylacetamide, 299-78-5; aminolevulinic acid, 106-60-5; ferrochelatase, 9012-93-5; glucose, 50-99-7, 84778-64-3; glucose 6 phosphatase, 9001-39-2; heme, 14875-96-8; melatonin, 73-31-4; phosphoenolpyruvate carboxykinase (GTP), 9013-08-5
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_22147500_v3_n_p141_Lelli

Referencias:

  • Ayes, B.N., Assay of inorganic phosphate, total phosphate and phosphatases (1966) Carbohydrate Metabolism, Part E: Methods in Enzymology, 8, pp. 115-118. , Academic Press, New York
  • Baginski, E.S., Foa, P.P., Zak, B., Glucose-6-phosphatase (1974) Method of Enzymatic Analysis, 1, pp. 876-880. , Verlag Chemie/Academic Press, New York
  • Besur, S., Hou, W., Schmeltzer, P., Bonkovsky, H.L., Clinically important features of porphyrin and heme metabolism and the porphyrias (2014) Metabolites, 4, pp. 977-1006. , Review. PMID:25372274. [PubMed] PMCID: PMC4279155
  • Dalle-Donne, I., Rossi, R., Giustarini, D., Milzani, A., Colombo, R., Protein carbonyl groups as biomarkers of oxidative stress (2003) Clin. Chim. Acta, 329, pp. 23-38. , PMID:12589963[PubMed-indexed for MEDLINE]
  • De Matteis, F., Abbritti, G., Gibbs, A.H., Decreased liver activity of porphyrin-metal chelatase in hepatic porphyria caused by 3,5-diethoxycarbonyl-1,4-dihydrocollidine. Studies in rats and mice (1973) Biochem. J., 134, pp. 717-727. , PMID:4749272[PubMed - indexed for MEDLINE] PMCID:PMC1177868
  • Faut, M., Paiz, A., San Martín de Viale, L.C., Mazzetti, M.B., Alterations of the redox state, pentose pathway and glutathione metabolism in an acute porphyria model. Their impact on heme pathway (2013) Exp. Biol. Med. (Maywood), 238, pp. 133-143. , Epub 2013 Feb 6. PMID:23390166
  • Franco, R., Ma, J.G., Lu, Y., Ferreira, G.C., Shelnutt, J.A., Porphyrin interactions with wild-type and mutant mouse ferrochelatase (2000) Biochemistry, 39, pp. 2517-2529. , PMID:10704201[PubMed-indexed for MEDLINE]
  • García, J.J., López-Pingarrón, L., Almeida-Souza, P., Tres, A., Escudero, P., García-Gil, F.A., Tan, D.X., Bernal-Pérez, M., Protective effects of melatonin in reducing oxidative stress and in preserving the fluidity of biological membranes: a review (2014) Pineal Res., 56, pp. 225-237. , PMID:24571249 [PubMed-indexed for MEDLINE]
  • Ghosh, A., Shieh, J.J., Pan, C.J., Sun, M.S., Chou, J.Y., The catalytic center of glucose-6-phosphatase. HIS176 is the nucleophile forming the phosphohistidine-enzyme intermediate during catalysis (2002) J. Biol. Chem., 277, pp. 32837-32842. , PMID:12093795 [PubMed-indexed for MEDLINE]
  • Ghosh, A., Shieh, J.J., Pan, C.J., Chou, J.Y., Histidine 167 is the phosphate acceptor in glucose-6-phosphatase-beta forming a phosphohistidine enzyme intermediate during catalysis (2004) J. Biol. Chem., 279, pp. 12479-12483. , PMID:14718531 [PubMed - indexed for MEDLINE]
  • Karbownik, M., Tan, D., Manchester, L.C., Reiter, R.J., Renal toxicity of the carcinogen delta-aminolevulinic acid: antioxidant effects of melatonin (2000) Cancer Lett., 161, pp. 1-7. , http://dx.doi.org/10.1016/S0304-3835(00)00568-1PMID:11078907, [PubMed - indexed for MEDLINE]
  • Karbownik, M., Reiter, R.J., Garcia, J.J., Tan, D.X., Qi, W., Manchester, L.C., Melatonin reduces rat hepatic macromolecular damage due to oxidative stress caused by delta-aminolevulinic acid (2000) Biochim. Biophys. Acta, 1523, pp. 140-146. , PMID:11042377 [PubMed-indexed for MEDLINE]
  • Karbownik, M., Lewinski, A., Reiter, R.J., Anticarcinogenic actions of melatonin which involve antioxidative processes: comparison with other antioxidants (2001) Int. J. Biochem. Cell Biol., 33, pp. 735-753. , 10.1016/S1357-2725(01)00059-0, Review. PMID: 11404179 [PubMed - indexed for MEDLINE]
  • Lelli, S.M., San Martin de Viale, L.C., Mazzetti, M.B., Response of glucose metabolism enzymes in an acute porphyria model. Role of reactive oxygen species (2005) Toxicology, 216, pp. 49-58. , PMID:16125296 [PubMed-indexed for MEDLINE
  • Levine, R.L., Williams, J.A., Stadtman, E.R., Shacter, E., Carbonyl assays for determination of oxidatively modified proteins (1994) Oxygen Radicals in Biological Systems. Methods in Enzymology, 233, pp. 346-357. , Academic Press, San Diego
  • Lowry, O., Rosebrough, N., Farr, A., Randall, R., Protein measurement with the folin-phenol reagent (1951) J. Biol. Chem., 193, pp. 265-275. , PMID:14907713[PubMed-indexed for MEDLINE]
  • Masters, A., Pandi-Perumal, S.R., Seixas, A., Girardin, J.L., McFarlane, S.I., Melatonin, the hormone of darkness: from sleep promotion to Ebola treatment (2014) Brain Disord. Ther., 4. , PMID:25705578 [PubMed] PMCID: PMC4334454
  • Marks, G.S., McCluskey, S.A., Mackie, J.E., Riddick, D.S., James, C.A., Disruption of hepatic heme biosynthesis after interaction of xenobiotics with cytochrome P-450 (1988) FASEB J., 2, pp. 2774-2783. , 0892-6638/88/0002-2774; PMID:3044903 [PubMed-indexed for MEDLINE]
  • Marver, H.S., Tschudy, D.P., Perlroth, M.G., Collins, A., Delta-aminolevulinic acid synthetase. I. Studies in liver homogenates (1966) J. Biol. Chem., 241, pp. 2803-2889. , PMID: 4957991 [PubMed-indexed for MEDLINE]
  • Matkovic, L.B., D'Andrea, F., Fornes, D., San Martín de Viale, L.C., Mazzetti, M.B., How porphyrinogenic drugs modeling acute porphyria impair the hormonal status that regulates glucose metabolism. Their relevance in the onset of this disease (2011) Toxicology, 290, pp. 22-30. , PMID:21889565PubMed-indexed for MEDLINE]
  • Mauzerall, D., Granick, S., The occurrence and determination of delta-amino-levulinic acid and porphobilinogen in urine (1956) J. Biol. Chem., 219, pp. 435-446. , PMID:13295297[PubMed-indexed for MEDLINE]
  • Mazzetti, M.B., Taira, M.C., Lelli, S.M., Dascal, E., Basabe, J.C., San Martín de Viale, L.C., Hexachlorobenzene impairs glucose metabolism in a rat model of porphyria cutaneatarda: a mechanistic approach (2004) Arch. Toxicol, 78, pp. 25-33. , PMID:12898129 [PubMed-indexed for MEDLINE]
  • Ohkawa, H., Ohishi, N., Yagi, K., Assay for lipid peroxides in animal tissues by thiobarbituric acid reaction (1979) Anal. Biochem., 95. , 351-358. PMID:36810 [PubMed-indexed for MEDLINE]
  • Petrescu, I., Bojan, O., Saied, M., Barzu, O., Schmidt, F., Kuhnle, H.F., Determination of phosphoenolpyruvate carboxykinase activity with deoxyguanosine 5'-diphosphate as nucleotide substrate (1979) Anal. Biochem., 96, pp. 279-281. , PMID:474956[PubMed - indexed for MEDLINE]
  • Piper, W.N., Condie, L.W., Tephly, T.R., The role of substrates for glycine acyltransferase in the reversal of chemically induced porphyria in the rat (1973) Arch. Biochem. Biophys., 159, pp. 671-677. , Science direct
  • Porra, R.J., Jones, O.T., Studies on ferrochelatase. I. Assay and properties of ferrochelatase from a pig-liver mitochondrial extract (1963) Biochem. J., 87, pp. 181-185. , PMID: 13972328 [PubMed - indexed for MEDLINE] PMCID: PMC1276858
  • Reiter, R.J., Tan, D.X., Osuna, C., Gitto, E., Actions of melatonin in the reduction of oxidative stress. A review (2000) J. Biomed. Sci., 7, pp. 444-458. , PMID:11060493[PubMed-indexed for MEDLINE
  • Reiter, R.J., Tan, D.X., Maldonado, M.D., Melatonin as an antioxidant: physiology versus pharmacology (2005) J. Pineal Res., 39, pp. 215-216. , PMID:16098101 [PubMed-indexed for MEDLINE]
  • Reiter, R.J., Tan, D.X., Galano, A., Melatonin reduces lipid peroxidation and membrane viscosity (2014) Front. Physiol., 5, p. 377. , PMID:25339906 [PubMed] PMCID: PMC4186275
  • Ressmeyer, A.R., Mayo, J.C., Zelosko, V., Sáinz, R.M., Tan, D.X., Poeggeler, B., Antioxidant properties of the melatonin metabolite N1-acetyl-5-methoxykynuramine (AMK): scavenging of free radicals and prevention of protein destruction (2003) Redox Rep., 8, pp. 205-213. , http://dx.doi.org/10.1179/135100003225002709, PMID:14599344 [PubMed - indexed for MEDLINE]
  • Sellers, V.M., Johnson, M.K., Dailey, H.A., Function of the [2FE-2S] cluster in mammalian ferrochelatase: a possible role as a nitric oxide sensor (1996) Biochemistry, 35, pp. 2699-2704. , PMID:8611576 [PubMed-indexed for MEDLINE]
  • Tan, D.X., Reiter, R.J., Manchester, L.C., Yan, M.T., El-Sawi, M., Sainz, R.M., Chemical and physical properties and potential mechanisms: melatonin as a broad hspectrum antioxidant and free radical scavenger (2002) Curr. Top. Med. Chem., 2, pp. 181-197. , PMID:11899100 [PubMed-indexed for MEDLINE]
  • Tschudy, D.P., Welland, F.H., Collins, A., Hunter, G., The effect of carbohydrate feeding on the induction of delta-aminolevulinic acid synthetase (1964) Metabolism, 13, pp. 396-406. , PMID:14169218 [PubMed-indexed for MEDLINE]

Citas:

---------- APA ----------
Lelli, S.M., Mazzetti, M.B. & San Martín de Viale, L.C. (2016) . Melatonin modulates drug-induced acute porphyria. Toxicology Reports, 3, 141-147.
http://dx.doi.org/10.1016/j.toxrep.2015.12.010
---------- CHICAGO ----------
Lelli, S.M., Mazzetti, M.B., San Martín de Viale, L.C. "Melatonin modulates drug-induced acute porphyria" . Toxicology Reports 3 (2016) : 141-147.
http://dx.doi.org/10.1016/j.toxrep.2015.12.010
---------- MLA ----------
Lelli, S.M., Mazzetti, M.B., San Martín de Viale, L.C. "Melatonin modulates drug-induced acute porphyria" . Toxicology Reports, vol. 3, 2016, pp. 141-147.
http://dx.doi.org/10.1016/j.toxrep.2015.12.010
---------- VANCOUVER ----------
Lelli, S.M., Mazzetti, M.B., San Martín de Viale, L.C. Melatonin modulates drug-induced acute porphyria. Toxicol. Rep. 2016;3:141-147.
http://dx.doi.org/10.1016/j.toxrep.2015.12.010