The glycine deportation system and its pharmacological consequences

Pharmacology and Therapeutics

Volumn 135, Issue 2, 2012, Pages 151-167

  Beyoǧlu, Diren ^a   Idle, Jeffrey R ^a  

^a UNIVERSITY OF BERN   (Switzerland)

Author keywords

Benzoic acid; Catabolism; Deportation; Glycine; Hippuric acid; Homeostasis; Ifosfamide encephalopathy; Neuroregulation

Indexed keywords

BENZOIC ACID; GLYCINE; HIPPURIC ACID; IFOSFAMIDE; NICOTINIC ACID; SALICYLIC ACID; VALPROIC ACID;

AMINO ACID METABOLISM; AMINO ACID SYNTHESIS; AMINO ACID TRANSPORT; BRAIN DISEASE; DRUG METABOLISM; DRUG SYNTHESIS; GLYCINE DEPORTATION SYSTEM; HOMEOSTASIS; HUMAN; HYPERGLYCINEMIA; INBORN ERROR OF METABOLISM; LIVER FUNCTION TEST; NONHUMAN; PRIORITY JOURNAL; PROTEIN DEGRADATION; REVIEW; URINARY EXCRETION;

AMINO ACID OXIDOREDUCTASES; ANIMALS; BENZOIC ACID; CARRIER PROTEINS; GLYCINE; HOMEOSTASIS; HUMANS; MULTIENZYME COMPLEXES; TRANSFERASES;

EID: 84862659904     PISSN: 01637258     EISSN: 1879016X     Source Type: Journal    
DOI: 10.1016/j.pharmthera.2012.05.003     Document Type: Review

References (171)

1. Abbott, F. S., Kassam, J., Orr, J. M., & Farrell, K. (1986). The effect of aspirin on valproic acid metabolism. Clinical Pharmacology and Therapeutics 40, 94-100.
2. Adamson, R. H., Bridges, J. W., Evans, M. E., & Williams, R. T. (1970). Species differences in the aromatization of quinic acid in vivo and the role of gut bacteria. The Biochemical Journal 116, 437-443.
3. Alarcon, R. A., Meienhofer, J., & Atherton, E. (1972). Isophosphamide as a new acrolein-producing antineoplastic isomer of cyclophosphamide. Cancer Research 32, 2519-2523.
4. Altschul, R., Hoffer, A., & Stephen, J. D. (1955). Influence of nicotinic acid on serum cholesterol in man. Archives of Biochemistry and Biophysics 54, 558-559.
5. Ames, B., Lewis, L. D., Chaffee, S., Kim, J., & Morse, R. (2010). Ifosfamide-induced encephalopathy and movement disorder. Pediatric Blood & Cancer 54, 624-626.
6. Amsel, L. P., & Levy, G. (1969). Drug biotransformation interactions in man. II. A pharmacokinetic study of the simultaneous conjugation of benzoic and salicylic acids with glycine. Journal of Pharmaceutical Sciences 58, 321-326.
7. Applegarth, D. A., & Toone, J. R. (2006). Glycine encephalopathy (nonketotic hyperglycinemia): comments and speculations. American Journal of Medical Genetics. Part A 140, 186-188.
8. Arnold, H., Bourseaux, F., & Brock, N. (1958). Chemotherapeutic action of a cyclic nitrogen mustard phosphamide ester (B 518-ASTA) in experimental tumours of the rat. Nature 181, 931.
9. Arnold, H., Bourseaux, F., & Brock, N. (1961). On the relation between the chemical composition and the cancerotoxic effect in a series of phosphamide esters of bis-(beta-chloroethyl)-a mine. Arzneimittel-Forschung 11, 143-158.
10. Arnstein, H. R., & Neuberger, A. (1951). Hippuric acid synthesis in the rat. The Biochemical Journal 50, 154-162.
11. Banner, M. R., & Rosalki, S. B. (1967). Glyoxylate as a substrate for lactate dehydrogenase. Nature 213, 726-727.
12. Batshaw, M. L., & Brusilow, S. W. (1980). Treatment of hyperammonemic coma caused by inborn errors of urea synthesis. The Journal of Pediatrics 97, 893-900.
13. Batshaw, M. L., & Brusilow, S. W. (1981). Evidence of lack of toxicity of sodium phenylacetate and sodium benzoate in treating urea cycle enzymopathies. Journal of Inherited Metabolic Disease 4, 231.
14. Battistin, L., Grynbaum, A., & Lajtha, A. (1971). The uptake of various amino acids by the mouse brain in vivo. Brain Research 29, 85-99.
15. Benavides, J., Garcia, M. L., Lopez-Lahoya, J., Ugarte, M., & Valdivieso, F. (1980). Glycine transport in rat brain and liver mitochondria. Biochimica et Biophysica Acta 598, 588-594.
16. Betz, H., Gomeza, J., Armsen, W., Scholze, P., & Eulenburg, V. (2006). Glycine transporters: essential regulators of synaptic transmission. Biochemical Society Transactions 34, 55-58.
17. Betz, H., & Laube, B. (2006). Glycine receptors: recent insights into their structural organization and functional diversity. Journal of Neurochemistry 97, 1600-1610.
18. Beyoǧlu, D., Smith, R. L., & Idle, J. R. (2011). Dog bites man or man bites dog? The enigma of the amino acid conjugations. Biochemical Pharmacology 83, 1331-1339.
19. Blatherwick, N. R., & Long, M. L. (1923). Studies on urinary acidity. II. The increased acidity produced by eating prunes and cranberries. The Journal of Biological Chemistry 57, 815-818.
20. Bloch, K., & Rittenberg, D. (1945). An estimation of acetic acid formation in the rat. The Journal of Biological Chemistry 159, 45-58.
21. Boddy, A. V., Proctor, M., Simmonds, D., Lind, M. J., & Idle, J. R. (1995). Pharmacokinetics, metabolism and clinical effect of ifosfamide in breast cancer patients. European Journal of Cancer 31A, 69-76.
22. Borroni, E., Zhou, Y., Ostrowitzki, S., Alberati, D., Kumar, A., Hainzl, D., et al. (2011). Preclinical characterization of [(11)C]R05013853 as a novel radiotracer for imaging of the glycine transporter type 1 by positron emission tomography. NeuroImage, http://dx.doi.org/10.1016/j.neuroimage.2011.11.090.
23. Bremer, J. (1956). Species differences in the conjugation of free bile acids with taurine and glycine. The Biochemical Journal 63, 507-513.
24. Bremer, J., & Gloor, U. (1955). Studies on the conjugation of cholic acid with taurine in cell subfractions. Bile acids and steroids 23. Acta Chemica Scandinavica 9, 689-698.
25. Briggs, R., Ertem, G., Ferris, J. P., Greenberg, J. M., McCain, P. J., Mendoza-Gomez, C. X., et al. (1992). Comet Halley as an aggregate of interstellar dust and further evidence for the photochemical formation of organics in the interstellar medium. Origins of Life and Evolution of the Biosphere 22, 287-307.
26. Brock, N., & Hohorst, H. J. (1967). Metabolism of cyclophosphamide. Cancer 20, 900-904.
27. Brock, N., Pohl, J., & Stekar, J. (1981). Detoxification of urotoxic oxazaphosphorines by sulfhydryl compounds. Journal of Cancer Research and Clinical Oncology 100, 311-320.
28. Brock, N., Stekar, J., Pohl, J., Niemeyer, U., & Scheffler, G. (1979). Acrolein, the causative factor of urotoxic side-effects of cyclophosphamide, ifosfamide, trofosfamide and sufosfamide. Arzneimittel- Forschung 29, 659-661.
29. Brusilow, S. W., Danney, M., Waber, L. J., Batshaw, M., Burton, B., Levitsky, L., et al. (1984). Treatment of episodic hyperammonemia in children with inborn errors of urea synthesis. The New England Journal of Medicine 310, 1630-1634.
30. Brusilow, S. W., Valle, D. L., & Batshaw, M. (1979). New pathways of nitrogen excretion in inborn errors of urea synthesis. Lancet 2, 452-454.
31. Caner, V., Cokal, Y., Cetin, C., Sen, A., & Karagenc, N. (2008). The detection of hipO gene by real-time PCR in thermophilic Campylobacter spp. with very weak and negative reaction of hippurate hydrolysis. Antonie Van Leeuwenhoek 94, 527-532.
32. Cantwell, B.M., & Harris, A. L. (1985). Ifosfamide/mesa and encephalopathy. Lancet 1, 752.
33. Chatton, J. Y., Idle, J. R., Vagbo, C. B., & Magistretti, P. J. (2001). Insights into the mechanisms of ifosfamide encephalopathy: drug metabolites have agonistic effects on alpha-amino-3-hydroxy-5-methyl-4- isoxazolepropionic acid (AMPA)/kainate receptors and induce cellular acidification in mouse cortical neurons. The Journal of Pharmacology and Experimental Therapeutics 299, 1161-1168.
34. Chen, P., & Abramson, F. P. (1998). Measuring DNA synthesis rates with [1-13C]glycine. Analytical Chemistry 70, 1664-1669.
35. Choi, C., Ganji, S. K., DeBerardinis, R. J., Dimitrov, I. E., Pascual, J. M., Bachoo, R., et al. (2011). Measurement of glycine in the human brain in vivo by 1H-MRS at 3 T: application in brain tumors. Magnetic Resonance in Medicine 66, 609-618.
36. Cotran, R., Kendrick, M. I., & Kass, E. H. (1960). Role of intestinal bacteria in aromatization of quinic acid in man and guinea pig. Proceedings of the Society for Experimental Biology and Medicine 104, 424-426.
37. Creider, J. C., Hegele, R. A., & Joy, T. R. (2012). Niacin: another look at an underutilized lipid-lowering medication. Nature Reviews. Endocrinology, http://dx.doi.org/10.1038/nrendo.2012.22.
38. Csonka, F. A. (1924). On the administration of various proteins with benzoic acid to a pig. The Journal of Biological Chemistry 60, 545-582.
39. Cubelos, B., Gimenez, C., & Zafra, F. (2005). Localization of the GLYT1 glycine transporter at glutamatergic synapses in the rat brain. Cerebral Cortex 15, 448-459.
40. Dannhardt, G., & Kohl, B. K. (1998). The glycine site on the NMDA receptor: structure-activity relationships and possible therapeutic applications. Current Medicinal Chemistry 5, 253-263.
41. de Vries, A., Alexander, B., & Quamo, Y. (1948). Studies on amino acid metabolism. III. Plasma glycine concentration and hippuric acid formation following the ingestion of benzoate. The Journal of Clinical Investigation 27, 665-668.
42. Deguchi, T., Takemoto, M., Uehara, N., Lindup, W. E., Suenaga, A., & Otagiri, M. (2005). Renal clearance of endogenous hippurate correlates with expression levels of renal organic anion transporters in uremic rats. The Journal of Pharmacology and Experimental Therapeutics 314, 932-938.
43. Dennis, C., Gardner, B., Patti, J., & Chenouda, M. (1975). The effect of sodium benzoate and taurocholic acid feeding on human bile composition. Proceedings of the Society for Experimental Biology and Medicine 148, 601-605.
44. Dhamija, R., Gavrilova, R. H., & Wirrell, E. C. (2011). Valproate-induced worsening of seizures: clue to underlying diagnosis. Journal of Child Neurology 26, 1319-1321.
45. Di Cataldo, A., Astuto, M., Rizzo, G., Bertuna, G., Russo, G., & Incorpora, G. (2009). Neurotoxicity during ifosfamide treatment in children. Medical Science Monitor 15, CS22-CS25.
46. Ding, R. W., Kolbe, K., Merz, B., de Vries, J., Weber, E., & Benet, L. Z. (1989). Pharmacokinetics of nicotinic acid-salicylic acid interaction. Clinical Pharmacology and Therapeutics 46, 642-647.
47. Douce, R., Bourguignon, J., Neuburger, M., & Rebeille, F. (2001). The glycine decarboxylase system: a fascinating complex. Trends in Plant Science 6, 167-176.
48. Druckrey, H., & Raabe, S. (1952). Specific chemotherapy of carcinoma of the prostate. Klinische Wochenschrift 30, 882-884.
49. D'Souza, D. C., Gil, R., Cassello, K., Morrissey, K., Abi-Saab, D., White, J., et al. (2000). IV glycine and oral D-cycloserine effects on plasma and CSF amino acids in healthy humans. Biological Psychiatry 47, 450-462.
50. Esterbauer, H., Zollner, H., & Scholz, N. (1975). Reaction of glutathione with conjugated carbonyls. Zeitschrift für Naturforschung. C, Journal of Biosciences 30, 466-473.
51. Fellers, C. R., Redmon, B. C., & Parrott, E. M. (1933). Effect of cranberries on urinary acidity and blood alkali reserve. The Journal of Nutrition 6, 455-463.
52. Femia, F. J., Maresca, K. P., Hillier, S. M., Zimmerman, C. N., Joyal, J. L., Barrett, J. A., et al. (2008). Synthesis and evaluation of a series of 99mTc(CO)3+ lisinopril complexes for in vivo imaging of angiotensin-converting enzyme expression. Journal of Nuclear Medicine 49, 970-977.
53. Forman, W. B., Davidson, E. D., & Webster, L. T., Jr. (1971). Enzymatic conversion of salicylate to salicylurate. Molecular Pharmacology 7, 247-259.
54. Foxall, P. J., Lenz, E. M., Lindon, J. C., Neild, G. H., Wilson, I. D., & Nicholson, J. K. (1996). Nuclear magnetic resonance and high-performance liquid chromatographynuclear magnetic resonance studies on the toxicity and metabolism of ifosfamide. Therapeutic Drug Monitoring 18, 498-505.
55. Foxall, P. J., Singer, J. M., Hartley, J. M., Neild, G. H., Lapsley, M., Nicholson, J. K., et al. (1997). Urinary proton magnetic resonance studies of early ifosfamide-induced nephrotoxicity and encephalopathy. Clinical Cancer Research 3, 1507-1518.
56. Gatley, S. J., & Sherratt, H. S. A. (1976). The localization of hippurate synthesis in the matrix of rat liver mitochondria. Biochemical Society Transactions 4, 525-526.
57. Gatley, S. J., & Sherratt, H. S. A. (1977). The synthesis of hippurate from benzoate and glycine by rat liver mitochondria. Submitochondrial localization and kinetics. The Biochemical Journal 166, 39-47.
58. Geng,W.,& Pang, K. S. (1999). Differences in excretion of hippurate, as ametabolite of benzoate and as an administered species, in the single-pass isolated perfused rat kidney explained. The Journal of Pharmacology and Experimental Therapeutics 288, 597-606.
59. Goldman, N., Reed, E. J., Fried, L. E., William Kuo, I. F., & Maiti, A. (2010). Synthesis of glycine-containing complexes in impacts of comets on early Earth. Nature Chemistry 2, 949-954.
60. Gonthier, M. P., Verny, M. A., Besson, C., Remesy, C., & Scalbert, A. (2003). Chlorogenic acid bioavailability largely depends on its metabolism by the gut microflora in rats. The Journal of Nutrition 133, 1853-1859.
61. Goodwin, B. L., Ruthven, C. R., & Sandler, M. (1994). Gut flora and the origin of some urinary aromatic phenolic compounds. Biochemical Pharmacology 47, 2294-2297.
62. Gopaul, V. S., Tang, W., Farrell, K., & Abbott, F. S. (2003). Amino acid conjugates: metabolites of 2-propylpentanoic acid (valproic acid) in epileptic patients. Drug Metabolism and Disposition 31, 114-121.
63. Goren, M. P., Wright, R. K., Pratt, C. B., & Pell, F. E. (1986). Dechloroethylation of ifosfamide and neurotoxicity. Lancet 2, 1219-1220.
64. Gottlieb, M., Wang, Y., & Teichberg, V. I. (2003). Blood-mediated scavenging of cerebrospinal fluid glutamate. Journal of Neurochemistry 87, 119-126.
65. Gregus, Z., Fekete, T., Halaszi, E., & Klaassen, C. D. (1996). Does hepatic ATP depletion impair glycine conjugation in vivo? Drug Metabolism and Disposition 24, 1347-1354.
66. Gregus, Z., Fekete, T., Varga, F., & Klaassen, C. D. (1993). Dependence of glycine conjugation on availability of glycine: role of the glycine cleavage system. Xenobiotica 23, 141-153.
67. Gregus, Z., Fekete, T., Varga, F., & Klaassen, C. D. (1993). Effect of valproic acid on glycine conjugation of benzoic acid. The Journal of Pharmacology and Experimental Therapeutics 267, 1068-1075.
68. Griffith, W. H. (1925). Benzoylated amino acids in the animal organism. I. The behavior of hippuric acid following its oral administration. The Journal of Biological Chemistry 66, 671-681.
69. Griffith, W. H., & Lewis, H. B. (1923). Studies in the synthesis of hippuric acid in the animal organism. V. The influence of amino acids and related substances on the synthesis and rate of elimination of hippuric acid after the administration of benzoate. The Journal of Biological Chemistry 57, 1-24.
70. Hall, D. A., & Ringel, S. P. (2004). Adult nonketotic hyperglycinemia (NKH) crisis presenting as severe chorea and encephalopathy. Movement Disorders 19, 485-486.
71. Hamosh, A., McDonald, J. W., Valle, D., Francomano, C. A., Niedermeyer, E., & Johnston, M. V. (1992). Dextromethorphan and high-dose benzoate therapy for nonketotic hyperglycinemia in an infant. The Journal of Pediatrics 121, 131-135.
72. Hampson, R. K., Barron, L. L., & Olson, M. S. (1983). Regulation of the glycine cleavage system in isolated rat liver mitochondria. The Journal of Biological Chemistry 258, 2993-2999.
73. Hampson, R. K., Taylor, M. K., & Olson, M. S. (1984). Regulation of the glycine cleavage system in the isolated perfused rat liver. The Journal of Biological Chemistry 259, 1180-1185.
74. Hardy, R. W., Gaylor, J. L., & Baumann, C. A. (1960). Biosynthesis of sterols and fatty acids as affected by nicotinic acid and related compounds. The Journal of Nutrition 71, 159-167.
75. Haslewood, G. A., & Sjovall, J. (1954). Comparative studies of bile salts. 8. Preliminary examination of bile salts by paper chromatography. The Biochemical Journal 57, 126-130.
76. Hempel, J., Kaiser, R., & Jornvall, H. (1985). Mitochondrial aldehyde dehydrogenase from human liver. Primary structure, differences in relation to the cytosolic enzyme, and functional correlations. European Journal of Biochemistry 153, 13-28.
77. Huang, H., Barakat, L., Wang, D., & Bordey, A. (2004). Bergmann glial GlyT1 mediates glycine uptake and release in mouse cerebellar slices. The Journal of Physiology 560, 721-736.
78. Iijima, K., Takase, S., Tsumuraya, K., Endo, M., & Itahara, K. (1978). Changes in free amino acids of cerebrospinal fluid and plasma in various neurological diseases. The Tohoku Journal of Experimental Medicine 126, 133-150.
79. Inagawa, K., Hiraoka, T., Kohda, T., Yamadera, W., & Takahashi, M. (2006). Subjective effects of glycine ingestion before bedtime on sleep quality. Sleep and Biological Rhythms 4, 75-77.
80. IOM (1998). Dietary Reference Intakes for Thiamin, Riboflavin, Niacin, Vitamin B6, Folate, Vitamin B12, Pantothenic Acid, Biotin, and Choline. Washington, D.C.: National Academy Press.
81. Jafarian-Tehrani, M., Listwak, S., Barrientos, R. M., Michaud, A., Corvol, P., & Sternberg, E. M. (2000). Exclusion of angiotensin I-converting enzyme as a candidate gene involved in exudative inflammatory resistance in F344/N rats. Molecular Medicine 6, 319-331.
82. Jia, L., Liu, Z., Sun, L., Miller, S. S., Ames, B. N., Cotman, C. W., et al. (2007). Acrolein, a toxicant in cigarette smoke, causes oxidative damage and mitochondrial dysfunction in RPE cells: protection by (R)-alpha-lipoic acid. Investigative Ophthalmology & Visual Science 48, 339-348.
83. Jois, M., Hall, B., & Brosnan, J. T. (1990). Stimulation of glycine catabolism in isolated perfused rat liver by calcium mobilizing hormones and in isolated rat liver mitochondria by submicromolar concentrations of calcium. The Journal of Biological Chemistry 265, 1246-1248.
84. Juge, N., Hiasa, M., Omoto, H., & Moriyama, Y. (2009). Vesicular inhibitory amino acid transporter is a Cl-/gamma-aminobutyrate co-transporter. The Journal of Biological Chemistry 284, 35073-35078.
85. Kanai, Y., & Hediger, M. A. (2004). The glutamate/neutral amino acid transporter family SLC1: molecular, physiological and pharmacological aspects. Pflügers Archiv 447, 469-479.
86. Kasuya, F., Tatsuki, T., Ohta, M., Kawai, Y., & Igarashi, K. (2006). Purification, characterization, and mass spectrometric sequencing of a medium chain acyl-CoA synthetase from mouse liver mitochondria and comparisons with the homologues of rat and bovine. Protein Expression and Purification 47, 405-414.
87. Kasuya, F., Yamaoka, Y., Osawa, E., Igarashi, K., & Fukui, M. (2000). Difference of the liver and kidney in glycine conjugation of ortho-substituted benzoic acids. Chemico-Biological Interactions 125, 39-50.
88. Kaufman, M. J., Prescot, A. P., Ongur, D., Evins, A. E., Barros, T. L., Medeiros, C. L., et al. (2009). Oral glycine administration increases brain glycine/creatine ratios in men: a proton magnetic resonance spectroscopy study. Psychiatry Research 173, 143-149.
89. Kelley, M., & Vessey, D. A. (1993). Isolation and characterization of mitochondrial acyl- CoA: glycine N-acyltransferases from kidney. Journal of Biochemical Toxicology 8, 63-69.
90. Kerdudo, C., Orbach, D., Sarradet, J. L., & Doz, F. (2006). Ifosfamide neurotoxicity: an atypical presentation with psychiatric manifestations. Pediatric Blood & Cancer 47, 100-102.
91. Kikuchi, G., Motokawa, Y., Yoshida, T., & Hiraga, K. (2008). Glycine cleavage system: reaction mechanism, physiological significance, and hyperglycinemia. Proceedings of the Japan Academy. Series B, Physical and Biological Sciences 84, 246-263.
92. Kochi, H., Hayasaka, K., Hiraga, K., & Kikuchi, G. (1979). Reduction of the level of the glycine cleavage system in the rat liver resulting from administration of dipropylacetic acid: an experimental approach to hyperglycinemia. Archives of Biochemistry and Biophysics 198, 589-597.
93. Koeller, D. M., DiGiulio, K. A., Angeloni, S. V., Dowler, L. L., Frerman, F. E., White, R. A., et al. (1995). Cloning, structure, and chromosome localization of the mouse glutaryl-CoA dehydrogenase gene. Genomics 28, 508-512.
94. Korman, S. H., Wexler, I. D., Gutman, A., Rolland, M. O., Kanno, J., & Kure, S. (2006). Treatment from birth of nonketotic hyperglycinemia due to a novel GLDC mutation. Annals of Neurology 59, 411-415.
95. Kotler, J. M., Hinman, N. W., Yan, B., Stoner, D. L., & Scott, J. R. (2008). Glycine identification in natural jarosites using laser desorption Fourier transform mass spectrometry: implications for the search for life on Mars. Astrobiology 8, 253-266.
96. Kreis, H., Frese, K., & Wilmes, G. (1967). Physiological and histological changes in rats fed benzoic acid. Food and Cosmetics Toxicology 5, 505-511.
97. Küpfer, A., Aeschlimann, C., Wermuth, B., & Cerny, T. (1994). Prophylaxis and reversal of ifosfamide encephalopathy with methylene-blue. Lancet 343, 763-764.
98. Kure, S., Kojima, K., Kudo, T., Kanno, K., Aoki, Y., Suzuki, Y., et al. (2001). Chromosomal localization, structure, single-nucleotide polymorphisms, and expression of the human H-protein gene of the glycine cleavage system (GCSH), a candidate gene for nonketotic hyperglycinemia. Journal of Human Genetics 46, 378-384.
99. Kure, S., Koyata, H., Kume, A., Ishiguro, Y., & Hiraga, K. (1991). The glycine cleavage system. The coupled expression of the glycine decarboxylase gene and the H-protein gene in the chicken. The Journal of Biological Chemistry 266, 3330-3334.
100. Labrude, P., & Becq, C. (2003). Pharmacist and chemist Henri Braconnot. Revue d'Histoire de la Pharmacie 51, 61-78.
101. Lauterburg, B. H., Nguyen, T., Hartmann, B., Junker, E., Kupfer, A., & Cerny, T. (1994). Depletion of total cysteine, glutathione, and homocysteine in plasma by ifosfamide/mesna therapy. Cancer Chemotherapy and Pharmacology 35, 132-136.
102. Lautermann, E. (1863). XXV. Ueber die Reduction der Chinasäure zu Benzoësäure und die Verwandlung derselben in Hippursäure im thierischen Organismus. European Journal of Organic Chemistry 125, 9-13.
103. Lawson, M., Vasilaras, A., De Vries, A., Mactaggart, P., & Nicol, D. (2008). Urological implications of cyclophosphamide and ifosfamide. Scandinavian Journal of Urology and Nephrology 42, 309-317.
104. Lees, K. R. (1997). Cerestat and other NMDA antagonists in ischemic stroke. Neurology 49, S66-S69.
105. Lerch, S., Kupfer, A., Idle, J. R., & Lauterburg, B. H. (2006). Cerebral formation in situ of Scarboxymethylcysteine after ifosfamide administration to mice: a further clue to the mechanism of ifosfamide encephalopathy. Toxicology Letters 161, 188-194.
106. Levy, G. (1965). Pharmacokinetics of salicylate elimination in man. Journal of Pharmaceutical Sciences 54, 959-967.
107. Li, F., Patterson, A. D., Hofer, C. C., Krausz, K. W., Gonzalez, F. J., & Idle, J. R. (2010). Comparative metabolism of cyclophosphamide and ifosfamide in the mouse using UPLC-ESI-QTOFMS-based metabolomics. Biochemical Pharmacology 80, 1063-1074.
108. Lin, J. Y., Chen, K. C., Hale, J., Totten, P. A., & Holmes, K. K. (1986). Two-dimensional thin-layer chromatography for the specific detection of hippurate hydrolysis by microorganisms. Journal of Clinical Microbiology 23, 118-123.
109. Lind, M. J., McGown, A. T., Hadfield, J. A., Thatcher, N., Crowther, D., & Fox, B. W. (1989). The effect of ifosfamide and its metabolites on intracellular glutathione levels in vitro and in vivo. Biochemical Pharmacology 38, 1835-1840.
110. Lind, M. J., Roberts, H. L., Thatcher, N., & Idle, J. R. (1990). The effect of route of administration and fractionation of dose on the metabolism of ifosfamide. Cancer Chemotherapy and Pharmacology 26, 105-111.
111. Liu, Y. L., Tsai, S. H., Chang, F. W., & Yu, M. H. (2010). Ifosfamide-induced encephalopathy in patients with uterine sarcoma. Taiwanese Journal of Obstetrics & Gynecology 49, 77-80.
112. Luis, P. B., Ruiter, J. P., Ofman, R., Ijlst, L., Moedas, M., Diogo, L., et al. (2011). Valproic acid utilizes the isoleucine breakdown pathway for its complete beta-oxidation. Biochemical Pharmacology 82, 1740-1746.
113. Madeira, C., Freitas, M. E., Vargas-Lopes, C., Wolosker, H., & Panizzutti, R. (2008). Increased brain D-amino acid oxidase (DAAO) activity in schizophrenia. Schizophrenia Research 101, 76-83.
114. Makarovsky, I., Markel, G., Hoffman, A., Schein, O., Brosh-Nissimov, T., Tashma, Z., et al. (2008). Strychnine - a killer from the past. The Israel Medical Association Journal 10, 142-145.
115. Marmet, D., Bornstein, N., & Fleurette, J. (1990). Detection of hippurate hydrolysis by Legionella spp. by using a rapid high-performance liquid chromatography method. Journal of Clinical Microbiology 28, 2828-2829.
116. Marsh, J. B., & Diffenderfer, M. R. (1991). Use of [15N]glycine in the measurement of apolipoprotein B synthesis in perfused rat liver. Journal of Lipid Research 32, 2019-2024.
117. Mas, N., Saiz, A., Leite, M. I., Waters, P., Baron, M., Castano, D., et al. (2011). Antiglycinereceptor encephalomyelitis with rigidity. Journal of Neurology, Neurosurgery, and Psychiatry 82, 1399-1401.
118. Mawal, Y. R., & Qureshi, I. A. (1994). Purification to homogeneity of mitochondrial acyl coa:glycine n-acyltransferase from human liver. Biochemical and Biophysical Research Communications 205, 1373-1379.
119. Mdluli, K., Booth, M. P., Brady, R. L., & Rumsby, G. (2005). A preliminary account of the properties of recombinant human Glyoxylate reductase (GRHPR), LDHA and LDHB with glyoxylate, and their potential roles in its metabolism. Biochimica et Biophysica Acta 1753, 209-216.
120. Meanwell, C. A., Blake, A. E., Kelly, K. A., Honigsberger, L., & Blackledge, G. (1986). Prediction of ifosfamide/mesna associated encephalopathy. European Journal of Cancer & Clinical Oncology 22, 815-819.
121. Meanwell, C. A., Blake, A. E., Latief, T. N., Blackledge, G., Mould, J. J., Blake, D. R., et al. (1985). Encephalopathy associated with ifosfamide/mesna therapy. Lancet i(8425), 406-407.
122. Merrill, J. M. (1958). Effect of nicotinic acid on the incorporation of radiocarbon into cholesterol. Circulation Research 6, 482-484.
123. Misiura, K. (2006). Ifosfamide. Metabolic studies, new therapeutic approaches and new analogs. Mini Reviews in Medicinal Chemistry 6, 395-400.
124. Mitchell, D. Y., & Petersen, D. R. (1989). Metabolism of the glutathione-acrolein adduct, S-(2-aldehydo-ethyl)glutathione, by rat liver alcohol and aldehyde dehydrogenase. The Journal of Pharmacology and Experimental Therapeutics 251, 193-198.
125. Motrescu, E. R., Otto, A. M., Brischwein, M., Zahler, S., & Wolf, B. (2005). Dynamic analysis of metabolic effects of chloroacetaldehyde and cytochalasin B on tumor cells using bioelectronic sensor chips. Journal of Cancer Research and Clinical Oncology 131, 683-691.
126. Neeman, G., Blanaru, M., Bloch, B., Kremer, I., Ermilov, M., Javitt, D. C., et al. (2005). Relation of plasma glycine, serine, and homocysteine levels to schizophrenia symptoms and medication type. The American Journal of Psychiatry 162, 1738-1740.
127. Nelson, L. M. (1955). Fixed drug eruptions; a report of two cases, one caused by niacin, the other by cocaine. California Medicine 82, 127-128.
128. Nissim, I., Horyn, O., Daikhin, Y., Luhovyy, B., Phillips, P. C., & Yudkoff, M. (2006). Ifosfamide-induced nephrotoxicity: mechanism and prevention. Cancer Research 66, 7824-7831.
129. Norpoth, K. (1976). Studies on the metabolism of isophosphamide (NSC-109724) in man. Cancer Treatment Reports 60, 437-443.
130. Osborne, R. J., & Slevin, M. L. (1985). Ifosfamide, mesna, and encephalopathy. Lancet i(8442), 1398-1399.
131. Oz, M., Lorke, D. E., Hasan, M., & Petroianu, G. A. (2011). Cellular and molecular actions of Methylene Blue in the nervous system. Medicinal Research Reviews 31, 93-117.
132. Pacifici, G. M., Mogavero, S., Giuliani, L., & Rane, A. (1991). Conjugation of benzoic acid with glycine in the human fetal and adult liver and kidney. Developmental Pharmacology and Therapeutics 17, 52-62.
133. Palmieri, F. (2004). The mitochondrial transporter family (SLC25): physiological and pathological implications. Pflügers Archiv 447, 689-709.
134. Patel, D. K., Ogunbona, A., Notarianni, L. J., & Bennett, P. N. (1990). Depletion of plasma glycine and effect of glycine by mouth on salicylate metabolism during aspirin overdose. Human & Experimental Toxicology 9, 389-395.
135. Patton, A. R. (1937). A comparison of the glycine contents of the proteins of normal and chondrodystrophic chick embryos at different stages of development. The Journal of Nutrition 13, 123-126.
136. Pearlman, B. L., & Gambhir, R. (2009). Salicylate intoxication: a clinical review. Postgraduate Medicine 121, 162-168.
137. Pellicoro, A., van den Heuvel, F. A., Geuken, M., Moshage, H., Jansen, P. L., & Faber, K. N. (2007). Human and rat bile acid-CoA:amino acid N-acyltransferase are liverspecific peroxisomal enzymes: implications for intracellular bile salt transport. Hepatology 45, 340-348.
138. Pollay, M. (1976). Movement of glycine across the blood-brain barrier of the rabbit. Journal of Neurobiology 7, 123-128.
139. Pollegioni, L., Piubelli, L., Sacchi, S., Pilone, M. S., & Molla, G. (2007). Physiological functions of D-amino acid oxidases: from yeast to humans. Cellular and Molecular Life Sciences 64, 1373-1394.
140. Poon, K., & Pang, K. S. (1995). Benzoic acid glycine conjugation in the isolated perfused rat kidney. Drug Metabolism and Disposition 23, 255-260.
141. Porter, R. K. (2000). Mammalian mitochondrial inner membrane cationic and neutral amino acid carriers. Biochimica et Biophysica Acta 1459, 356-362.
142. Quick, A. J. (1931). The conjugation of benzoic acid in man. The Journal of Biological Chemistry 92, 65-85.
143. Quick, A. J. (1936). Clinical value of the test for hippuric acid in cases of disease of the liver. Archives of Internal Medicine 57, 544-556.
144. Ren, S., Kalhorn, T. F., & Slattery, J. T. (1999). Inhibition of human aldehyde dehydrogenase 1 by the 4-hydroxycyclophosphamide degradation product acrolein. Drug Metabolism and Disposition 27, 133-137.
145. Rossi, S., Daniele, I., Bastrenta, P., Mastrangelo, M., & Lista, G. (2009). Early myoclonic encephalopathy and nonketotic hyperglycinemia. Pediatric Neurology 41, 371-374.
146. Rousseau, F., Aubrey, K. R., & Supplisson, S. (2008). The glycine transporter GlyT2 controls the dynamics of synaptic vesicle refilling in inhibitory spinal cord neurons. The Journal of Neuroscience 28, 9755-9768.
147. Ryan, W. L., & Carver, M. J. (1966). Free amino acids of human foetal and adult liver. Nature 212, 292-293.
148. Ryan, C. W., Montag, A. G., Hosenpud, J. R., Samuels, B., Hayden, J. B., Hung, A. Y., et al. (2008). Histologic response of dose-intense chemotherapy with preoperative hypofractionated radiotherapy for patients with high-risk soft tissue sarcomas. Cancer 112, 2432-2439.
149. Savica, R., Rabinstein, A. A., & Josephs, K. A. (2011). Ifosfamide associated myoclonusencephalopathy syndrome. Journal of Neurology 258, 1729-1731.
150. Schachter, D., & Taggart, J. V. (1954). Glycine N-acylase: purification and properties. The Journal of Biological Chemistry 208, 263-275.
151. Schön, H. (1958). Effect of nicotinic acid on the cholesterol contents of rat-livers. Nature 182, 534.
152. Shemin, D., & Rittenberg, D. (1945). The utilization of glycine for the synthesis of a porphyrin. The Journal of Biological Chemistry 159, 567-568.
153. Shoolingin-Jordan, P. M., Al-Daihan, S., Alexeev, D., Baxter, R. L., Bottomley, S. S., Kahari, I. D., et al. (2003). 5-Aminolevulinic acid synthase: mechanism, mutations and medicine. Biochimica et Biophysica Acta 1647, 361-366.
154. Solaas, K., Ulvestad, A., Soreide, O., & Kase, B. F. (2000). Subcellular organization of bile acid amidation in human liver: a key issue in regulating the biosynthesis of bile salts. Journal of Lipid Research 41, 1154-1162.
155. Sood, C., & O'Brien, P. J. (1996). 2-Chloroacetaldehyde-induced cerebral glutathione depletion and neurotoxicity. The British Journal of Cancer. Supplement 27, S287-S293.
156. Stewart, M. J., Malek, K., & Crabb, D. W. (1996). Distribution of messenger RNAs for aldehyde dehydrogenase 1, aldehyde dehydrogenase 2, and aldehyde dehydrogenase 5 in human tissues. Journal of Investigative Medicine 44, 42-46.
157. Suzuki, Y., Kure, S., Oota, M., Hino, H., & Fukuda, M. (2010). Nonketotic hyperglycinemia: proposal of a diagnostic and treatment strategy. Pediatric Neurology 43, 221-224.
158. Tajino, T., Kikuchi, S., Yamada, H., Takeda, A., & Konno, S. (2010). Ifosfamide encephalopathy associated with chemotherapy for musculoskeletal sarcomas: incidence, severity, and risk factors. Journal of Orthopaedic Science 15, 104-111.
159. Toth, E., & Lajtha, A. (1981). Elevation of cerebral levels of nonessential amino acids in vivo by administration of large doses. Neurochemical Research 6, 1309-1317.
160. van der Rest, M., & Fietzek, P. P. (1982). A comprehensive approach to the study of collagen primary structure based on high-performance liquid chromatography. European Journal of Biochemistry 125, 491-496.
161. van der Westhuizen, F. H., Pretorius, P. J., & Erasmus, E. (2000). The utilization of alanine, glutamic acid, and serine as amino acid substrates for glycine Nacyltransferase. Journal of Biochemical and Molecular Toxicology 14, 102-109.
162. van Platerink, C. J., Janssen, H. G., & Haverkamp, J. (2007). Development of an at-line method for the identification of angiotensin-I inhibiting peptides in protein hydrolysates. Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences 846, 147-154.
163. Vandevijvere, S., Andjelkovic, M., De Wil, M., Vinkx, C., Huybrechts, I., Van Loco, J., et al. (2009). Estimate of intake of benzoic acid in the Belgian adult population. Food Additives & Contaminants. Part A, Chemistry, Analysis, Control, Exposure & Risk Assessment 26, 958-968.
164. Vessey, D. A., Kelley, M., & Warren, R. S. (1999). Characterization of the CoA ligases of human liver mitochondria catalyzing the activation of
165. Vessey, D. A., Lau, E., Kelley, M., & Warren, R. S. (2003). Isolation, sequencing, and expression of a cDNA for the HXM-A form of xenobiotic/medium-chain fatty acid: CoA ligase from human liver mitochondria. Journal of Biochemical and Molecular Toxicology 17, 1-6.
166. Visarius, T. M., Bahler, H., Kupfer, A., Cerny, T., & Lauterburg, B. H. (1998). Thiodiglycolic acid is excreted by humans receiving ifosfamide and inhibits mitochondrial function in rats. Drug Metabolism and Disposition 26, 193-196.
167. Vree, T. B., Hekster, Y. A., & Anderson, P. G. (1992). Contribution of the human kidney to the metabolic clearance of drugs. The Annals of Pharmacotherapy 26, 1421-1428.
168. Wong, D. F., Ostrowitzki, S., Zhou, Y., Raymont, V., Hofmann, C., Borroni, E., et al. (2012). Characterization of [(11)C]RO5013853, a novel PET tracer for the glycine transporter type 1 (GlyT1) in humans. NeuroImage, http://dx.doi.org/10.1016/j.neuroimage.2011.11.052.
169. Yamadera, W., Inagawa, K., Chiba, S., Bannai, M., Takahashi, M., & Nakayama, K. (2007). Glycine ingestion improves subjective sleep quality in human volunteers, correlating with polysomnographic changes. Sleep and Biological Rhythms 5, 126-131.
170. Yoshizumi, T., Gondolesi, G. E., Bodian, C. A., Jeon, H., Schwartz, M. E., Fishbein, T. M., et al. (2003). A simple new formula to assess liver weight. Transplantation Proceedings 35, 1415-1420.
171. Zitting, A., & Heinonen, T. (1980). Decrease of reduced glutathione in isolated rat hepatocytes caused by acrolein, acrylonitrile, and the thermal degradation products of styrene copolymers. Toxicology 17, 333-341.