Phenylacetylglycine, a putative biomarker of phospholipidosis: Its origins and relevance to phospholipid accumulation using amiodarone treated rats as a model

Biomarkers

Volumn 9, Issue 3, 2004, Pages 271-290

  Delaney, Jane ^a   Neville, William A ^a   Swain, Aubrey ^a   Miles, Adam ^a   Leonard, Michael S ^b   Waterfield, Catherine J ^a,c  

^a GLAXOSMITHKLINE   (United Kingdom)

^b GLAXOSMITHKLINE   (United States)

^c JEALOTT S HILL INTERNATIONAL RESEARCH CENTRE   (United Kingdom)

Author keywords

Amiodarone; Biomarker; PAG; Phenylacetylglycine; Phospholipidosis; Validation

Indexed keywords

AMIODARONE; BIOLOGICAL MARKER; GLYCINE DERIVATIVE; PENTOXYRESORUFIN DEALKYLASE; PHENOBARBITAL; PHENYLACETIC ACID; PHENYLACETYLGLYCINE; PHENYLALANINE; PHENYLALANINE 4 MONOOXYGENASE; PHOSPHOLIPID; TYROSINE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CHOLESTEROL BLOOD LEVEL; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; CORRELATION ANALYSIS; DRUG BLOOD LEVEL; DRUG TISSUE LEVEL; ENZYME ACTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INTESTINE ABSORPTION; LIPID BLOOD LEVEL; LIPID STORAGE; LIPIDOSIS; MALE; MASS SPECTROMETRY; NONHUMAN; RAT; URINARY EXCRETION;

AMIODARONE; ANIMALS; BIOLOGICAL MARKERS; BODY WEIGHT; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GLYCINE; LIPIDOSES; LIPIDS; LIVER; LYMPHOCYTES; MALE; ORGAN SIZE; PHENOBARBITAL; PHOSPHOLIPIDS; RATS; RATS, SPRAGUE-DAWLEY; TIME FACTORS; TISSUE DISTRIBUTION;

ANIMALIA;

EID: 11844289653     PISSN: 1354750X     EISSN: None     Source Type: Journal    
DOI: 10.1080/13547500400018570     Document Type: Article

References (69)

1. Alvarez, D. L., Campistol, P. J., Ribes, R. A. and Riverola de Vecina, A. T. 1992, Phenylalanine metabolites in hyperphenylalaninaemic children. Anales Espanoles de Pediatria, 36, 371-374.
2. Asaoka, K. 1991, Enzymes that metabolize acyl-coenzyme A in the monkey - their distribution, properties and roles in an alternative pathway for the excretion of nitrogen. International Journal of Biochemistry, 23, 429-434.
3. Ayling, J., Pirson, R., Pirson, W. and Boehm, G. 1973, A specific kinetic assay for phenylalanine hydroxylase. Analytical Biochemistry, 51, 80-90.
4. Bargal, R. and Bach, G. 1988, Phospholipids accumulation in mucolipidosis IV cultured fibroblasts. Journal of Inherited Metabolic Disease, 11, 144-150.
5. Berdeaux, A., Roche, A., Labaille, T., Giroux, B., Edouard, A. and Guidicelli, J. F. 1984, Tissue extraction of amiodarone and N-desethylamiodarone in man after a single oral dose. British Journal of Clinical Pharmacology, 18, 759-763.
6. Burke, M. D., Thompson, S., Weaver, R. J., Wolf, C. R. and Mayer, R. T. 1994, Cytochrome P450 specificities of alkoxyresorufin O-dealkylation in human and rat liver. Biochemical Pharmacology, 48, 923-936.
7. Chitwood, K. K., Abdul-Haqq, A. J. and Heim-Duthoy, K. L. 1993, Cyclosporine-amiodarone interaction. Annals of Pharmacotherapy 27, 569-571.
8. Cochran, F. R., Roddick, V. L., Connor, J. R., Thornburg, J. T. and Waite, M. 1987, Regulation of arachadonic acid metabolism in resident and BCG-activated alveolar macrophages: role of lyso(bis phosphatidic acid. Journal of Immunology, 138, 1877-1883.
9. Cummings, J. H., Pomare, E. W., Branch, W. J., Naylor, C. P. E. and McFarlane, G. T. 1987, Short chain fatty acids in the human large intestine, portal, hepatic and venous blood. Gut, 28, 1221-1227.
10. Cummings, J. H. 1995, Short chain fatty acids. In Human Colonic Bacteria: Role in Nutrition, Physiology and Pathology, edited by G. R. Gibson and G. T. MacFarlane (Boca Raton: CRC Press), pp. 101-130.
11. Dake, M. D., Madison, J. M., Montgomery, C. K., Shellito, J. E., Hinchcliffe, W. A., Winkler, M. L. and Bainton, D. F. 1985, Electron microscopic demonstration of lysosomal inclusion bodies in lung, liver, lymph nodes and blood leukocytes of patients with amiodarone pulmonary toxicity. American Journal of Medicine, 78, 506-512.
12. Elleder, M. 1989, Niemann-Pick disease. Pathology, Research and Practice, 185, 293-328.
13. Erlandsen, H. and Stevens, R. C. 1999, The structural basis of phenylketonuria. Molecular Genetics and Metabolism, 68, 103-125.
14. Espina, J. R., Shockcor, J. P., Herron, W. J., Car, B. D., Contel, N. R., Ciaccio, P. J., Lindon, J. C., Holmes, E. and Nicholson, J. K. 2001, Net action of in vivo biomarkers of phospholipidosis using NMR-based metabonomic approaches. Magnetic Resonance in Chemistry, 39, 559-565.
15. Fowler, S. D., Brown, W. J., Warfel, J. and Greenspan, P. 1987, Use of Nile red for the rapid in situ quantitation of lipids on thin-layer chromatograms. Journal of Lipid Research, 28, 1225-1232.
16. Fredman, P., Klinghardt, G. W., Nilsson, O. and Svennerholm, L. 1982, Lipid accumulation in liver, spleen, lungs and kidneys of miniature-pigs after chloroquine treatment. Biochemical Journal, 201, 581-588.
17. Fruncillo, R. J., Bernhard, R., Swanson, B. N., Vlasses, P. H. and Ferguson, R. K. 1985, Effect of phenobarbitone on the pharmacokinetics and tissue levels of amiodarone in the rat. Journal of Pharmacy and Pharmacology, 37, 729-731.
18. Ha, H. R., Bigler, L., Binder, M., Kozlic, P., Stieger, B., Hesse, M., Altorfer, H. R. and Follath, F. 2001, Metabolism of amiodarone (Part I): Identification of a new hydroxylated metabolite of amiodarone. Drug Metabolism and Disposition, 29, 152-158.
19. Ha, H. R., Candinas, R., Stieger, B., Meyer, U. A. and Follath, F. 1996, Interaction between amiodarone and lidocaine. Journal of Cardiovascular Pharmacology, 28, 533-539.
20. Hanley, W. B., Lee, A. W., Hanley, A. J., Lehotay, D. C., Austin, V. J., Schoonheyt, W. E., Platt, B. A. and Clarke, J. T. 2000, 'Hypotyrosinaemia' in phenylketonuria. Molecular Genetics and Metabolism, 69, 286-294.
21. Harris, L., Hind, C. R. K., McKenna, W. J., Savage, C., Krikler, S. J., Storey, G. C. A. and Holt, D. W. 1983, Renal elimination of amiodarone and its desethyl metabolite. Postgraduate Medical Journal, 59, 440-442.
22. Holt, D. W., Tucker, G. T., Jackson, P. R. and Storey, G. C. A. 1983, Amiodarone pharmacokinetics. American Heart Journal, 106, 840-847.
23. Hook, G. E. 1991, Alveolar proteinosis and phospholipidoses of the lungs. Toxicologic Pathology, 19, 482-513.
24. James, M. O. and Bend, J. R. 1978, A radiochemical assay for glycine N-acyltransferase activity. Some properties of the enzyme in rat and rabbit. Biochemical Journal, 172, 285-291.
25. James, M. O., Smith, R. L., Williams, R. T. and Reidenberg, M. 1972, The conjugation of phenylacetic acid in man, sub-human primates and some non-primate species. Proceedings of the Royal Society London B, 182, 25-35.
26. 2+ ATPase in end-stage renal failure. Journal of the American Society of Nephrology 9, 1249-1257.
27. Jones, C. R., Guengerich, F. P., Rice, J. M. and Lubet R. A. 1992, Induction of various cytochromes CYP2B, CYP2C and CYP3A by phenobarbitone in non-human primates. Pharmacogenetics, 2, 160-172.
28. Khan, R. I., Onodera, R., Amin, M. R. and Mohammed, N. 1999, Production of tyrosine and other aromatic compounds from phenylalanine by rumen microorganisms. Amino Acids, 17, 335-346.
29. Kodovanti, U. P. and Mehendale, H. M. 1990, Cationic amphiphilic drugs and phospholipid storage disorder. Pharmacological Reviews, 42, 327-354.
30. Kozlic, P., Ha, H. R., Stieger, B., Bigler, L and Follath, F. 2001, Metabolism of amiodarone (Part III): Identification of rabbit cytochrome P450 isoforms involved in the hydroxylation of mono-N-desethylamiodarone. Xenobiotica, 31, 239-248.
31. Libersa, C. C., Brique, S. A., Motte, K. B., Caron, J. F., Guedon-Moreau, L. M., Humbert, L., Vincent, A., Devos, P. and Lhermitte, M. A. 2000, Dramatic inhibition of amiodarone metabolism induced by grapefruit juice. British Journal of Clinical Pharmacology, 49 373-378.
32. Marcus, F. I. 1983, Drug interactions with amiodarone. American Heart Journal, 106, 924-930.
33. Martin-Algarra, R. V., Pascual-Costa, R. M., Merino, M. and Casabo, V. G. 1994, Effects of surfactants on amiodarone intestinal absorption. I. Sodium laurylsulphate. Pharmaceutical Research, 11, 1042-1047.
34. Martin-Algarra, R. V., Pascual-Costa, R. M., Merino, M. and Casabo, V. G. 1995, Effects of polysorbate 80 on amiodarone intestinal absorption in the rat. International Journal of Pharmaceutics, 122, 1-8.
35. Mazue, G., Vic, P., Gouy, D., Remandet, B., Lacheretz, F., Berthe, J., Barchewitz, G. and Gagnol, J. P. 1984, Recovery from amiodarone-induced lipidosis in laboratory animals: a toxicological study. Fundamental and Applied Toxicology, 4, 992-999.
36. Michals, K. and Matalon, R. 1985, Phenylalanine metabolites, attention span and hyperactivity. American Journal of Clinical Nutrition, 42, 361-365.
37. Moldave, K. and Meister, A. 1957, Synthesis of phenylacetylglutamine by human tissue. Journal of Biological Chemistry 229, 463-476.
38. Moss, D. W., Henderson, M. B. and Kachmar, J. F. 1987, Enzymes. In Fundamentals of Clinical Chemistry, edited by N. W, Tietz, 3rd edn (Philadelphia: W. B. Saunders), p. 12 (ch. 12).
39. Nakashima, S., Nagata, K., Banno, Y., Sakiyama, T., Kitagawa, T., Miyawaki, S. and Nozawa, Y. 1984, A mouse model for Niemann-Pick disease: phospholipid class and fatty acid composition of various tissues. Journal of Lipid Research, 25, 219-227.
40. Nicholls, A. W., Mortishire-Smith, R. J. and Nicholson, J. K. 2003, NMR spectroscopic-based metabonomic studies of urinary metabolite variation in acclimatising germ-free rats. Chemical Research in Toxicology, 16, 1395-1404.
41. Nicholls, A. W., Nicholson, J. K., Haselden, J. N. and Waterfield, C. J. 2000, A metabonomic approach to the investigation of drug-induced phospholipidosis: an NMR spectroscopy and pattern recognition study. Biomarkers, 5, 410-423.
42. Omura, T. and Sato, R. 1964, The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its haemoprotein nature. Journal of Biological Chemistry, 239, 2370-2378.
43. Pakuts, A. P., Parks, R. J., Paul, C. J., Bujaki, S. J. and Mueller, R. W. 1990, Ketoconazole-induced hepatic lysosomal phospholipidosis: the effect of concurrent barbiturate treatment. Research Communications in Chemical Pathology and Pharmacology, 67 55-62.
44. Petruschka, L., Rebrin, I., Grimm, U. and Herrmann, F. H. 1990, The immunological evidence for a phenylalanine hydroxylase like immunoreactive protein in different human cells and tissues. Clinica et Chimica Acta, 193, 65-78.
45. Phipps, A. N., Stewart, J., Wright, B. and Wilson, I. D. 1998, Effect of diet on the urinary excretion of hippuric acid and other dietary-derived aromatics in rat. A complex interaction between diet, gut microflora and substrate specificity. Xenobiotica, 28, 527-537.
46. Reasor, M. J. and Davis, M. E. 1985, Prevention of chlorphentermine-induced pulmonary phospholipidosis in rats by phenobarbital. Drug Metabolism and Disposition, 13, 192-196.
47. Reasor, M. J., McCloud, C. M., Beard, T. L., Ebert, D. C., Kacew, S., Gardner, M. F., Aldern, K. A. and Hostetler, K. Y. 1996, Comparative evaluation of amiodarone-induced phospholipidosis and drug accumulation in Fischer-344 and Sprague-Dawley rats. Toxicology, 106, 139-147.
48. Reasor, M. J., Ogle, C. L., Walker, E. R. and Kacew, S. 1988, Amiodarone-induced phospholipidosis in rat alveolar macrophages. American Review of Respiratory Disease, 137, 510-518.
49. Remesy, C. and Demigne, C. 1976, Partition and absorption of volatile fatty acids in the alimentary canal of the rat. Annales de Recherches Veterinaires, 7, 39-55.
50. 2+-ATPase activities and biogenic amine concentrations in phenylketonuria. Clinical Biochemistry, 35, 281-285.
51. Schulz, T. G., Thiel, R., Neubert, D., Brassil, P. J., Schulz-Utermoehl, T., Boobis, A. R. and Edwards, R. J. 2001, Assessment of P450 induction in the marmoset monkey using targeted anti-peptide antibodies. Biochimica et Biophysica Acta, 1546, 143-155.
52. Seakins, J. W. T. 1971, the determination of urinary phenylacetylglutamine as phenylacetic acid. Studies on its origins in normal subjects and children with cystic fibrosis. Clinica Chimica Acta, 35 b, 121-131.
53. Simenhoff, M., Saukkonen, J., Schaedler, R., Gordon, S. and Burke, J. 1974, Amine metabolism and the small intestinal flora in uraemia. Clinical Science and Molecular Medicine, 46, 23.
54. Sirajudeen, K. N. S., Selvi, R. T., Babakrishan, Devaraj, H. and Devaraj, N. S. 2000, Effect of amiodarone on membrane bound enzymes of rat intestine. Drug and Chemical Toxicology, 23, 387-400.
55. Smith, E. A. and MacFarlane, G. T. 1996, Enumeration of human colonic bacteria producing phenolic and indolic compounds: effects of pH, carbohydrate availability and retention time on dissimilatory aromatic amino acid metabolism. Journal of Applied Bacteriology, 81, 288-302.
56. Smith, E. A. and MacFarlane, G. T. 1997, Formation of phenolic and indolic compounds by anaerobic bacteria in the human large intestine. Microbial Ecology, 33, 180-188.
57. Tjiong, H. B., Lepthin, J. and Debuch, H. 1978, Lysosomal phospholipids from rat liver after treatment with different drugs. Hoppe-Seylers Zeitschrift fur Physiologische Chemie, 359, 63-67.
58. Trivier, J.-M., Libersa, C., Belloc, C. and Lhermitte, M. 1993, Amiodarone N-deethylation in human liver microsomes: involvement of cytochrome P4503A enzymes (First report). Life Sciences 52, 91-96.
59. Van der Heiden, C., Wadman, S. K., Ketting, D. and de Bree, P. K. 1971a, Urinary and faecal excretion of metabolites of tyrosine and phenylalanine in a patient with cystic fibrosis and severely impaired amino acid absorption. Clinica Chimica Acta, 31, 133-141.
60. Van der Heiden, C., Wauters, E. A. K., Ketting, D., Duran, M. and Wadman, S. K. 1971b, Gas chromatographic analysis of urinary tyrosine and phenylalanine metabolites in patients with gastrointestinal disorders. Clinica Chimica Acta, 34, 289-296.
61. Wadman, S. K., Van der Heiden, C., Ketting, D. and Van Sprang, F. J. 1971, Abnormal tyrosine and phenylalanine metabolism in patients tyrosyluria and phenylketonuria: gas-liquid chromatographic analysis of urinary metabolites. Clinica et Chimica Acta, 34, 277-287.
62. Waters, P. J., Parniak, M. A., Nowacki, P. and Scriver, C. R. 1998, In vitro expression analysis of mutations in phenylalanine hydroxylase: linking genotype to phenotype and structure to function. Human Mutation, 11, 4-17.
63. Weaver, R. J., Thompson, S., Smith, G., Dickens, M., Elcombe, C. R., Mayer, R. T. and Burke, M. D. 1994, A comparative study of constitutive and induced alkoxyresorufin O-dealkylation and individual cytochrome P450 forms in cynomolgous monkey (Macaca fascicularis), human, mouse, rat and hamster liver microsomes. Biochemical Pharmacology, 47, 763-773.
64. Webster, L. T., Siddiqui, U. A., Lucas, S. V., Strong, J. M. and Mieyal. J. J. 1976, Identification of separate acyl-coA:glycine and acyl-coA:glutamine N-acyltransferase activities in mitochondrial fractions from liver of rhesus monkey and man. Journal Biological Chemistry, 251, 3352-3358.
65. Woolf, L. I. 1951, Excretion of conjugated phenylacetic acid in phenylketonuria. Biochemical Journal, 49, ix-x.
66. Yamamoto, A., Adachi, S., Kitani, T, Shinji, Y., Seki, K., Nasu, T. and Nishikawa, M. 1971, Drug-induced lipidosis in human cases and in animal experiments. Journal of Biochemistry, 69, 613-615.
67. Young, G. A. and Parsons, F. M. 1973, Impairment of phenylalanine hydroxylation in chronic renal insufficiency. Clinical Science, 45, 89-97.
68. Young, R. A. and Mehendale, H. M. 1987, Effect of cytochrome P-450 and flavin-containing monooxygenase modifying factors on the in vitro metabolism of amiodarone by rat and rabbit. Drug Metabolism and Disposition, 15, 511-517.
69. Zimmerman, L, Egestad, B., Jornvall, H. and Bergstrom, J. 1989, Identification and determination of phenylacetylglutamine, a major nitrogenous metabolite in plasma of uraemic patients. Clinical Nephrology, 32, 124-128.