Dog bites man or man bites dog? the enigma of the amino acid conjugations

Biochemical Pharmacology

Volumn 83, Issue 10, 2012, Pages 1331-1339

  Beyolu, Diren ^a   Smith, Robert L ^b   Idle, Jeffrey R ^a  

^a UNIVERSITY OF BERN   (Switzerland)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

Amino acid conjugation; Amino acid scavenging; Hippuric acid; Neuroregulation; Phenacetylglutamine

Indexed keywords

AROMATIC CARBOXYLIC ACID; BENZOIC ACID; GLUTAMIC ACID; GLYCINE; HIPPURIC ACID; NEUROTRANSMITTER; NITROGEN; PHENYLACETIC ACID; UREA;

AMINO ACID ANALYSIS; AMINO ACID BLOOD LEVEL; AMINO ACID METABOLISM; AUTISM; BLOOD BRAIN BARRIER; BRAIN FUNCTION; CHEMICAL STRUCTURE; CONJUGATION; DETOXIFICATION; HUMAN; INBORN ERROR OF METABOLISM; LIVER MITOCHONDRION; MENTAL DISEASE; NEUROTOXICITY; NONHUMAN; PRIORITY JOURNAL; PROTEIN SECRETION; PROTEIN TRANSPORT; PSYCHOMOTOR ACTIVITY; REVIEW;

EID: 84862776600     PISSN: 00062952     EISSN: 18732968     Source Type: Journal    
DOI: 10.1016/j.bcp.2011.12.031     Document Type: Note

References (73)

1. R.T. Williams Detoxication mechanisms 1959 John Wiley & Sons Inc. New York
2. W. Keller On the conversion of benzoic acid into hippuric acid Prov Med J Retrosp Med Sci 4 1842 256 257
3. G. Bunge, and O. Schmiedeberg Ueber die Bildung der Hippursäure On the formation of hippuric acid Arch Exp Pathol Pharmakol vi 1877 233 255
4. E. Lackner, A. Levinson, and W. Morse The role of the liver in hippuric acid synthesis Biochem J 12 1918 184 189
5. A.W. Bryan Clinical and experimental studies on sodium benzoate: the value of the sodium benzoate test of renal function, and the effect of injury of the liver on hippuric acid synthesis J Clin Invest 2 1925 1 33
6. A.J. Quick Clinical value of the test for hippuric acid in cases of disease of the liver Arch Int Med 57 1936 544 556
7. H.W. Griffith, and H.B. Lewis 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 administration of benzoate J Biol Chem 57 1923 1 24
8. W.H. Griffith, and H.B. Lewis Studies in the synthesis of hippuric acid in the animal organism. VI. The influence of the protein of the diet on the synthesis and rate of elimination of hippuric acid after administration of benzoates J Biol Chem 57 1923 697 707
9. J.W. Bridges, M.R. French, R.L. Smith, and R.T. Williams The fate of benzoic acid in various species Biochem J 118 1970 47 51
10. M.O. James, R.L. Smith, R.T. Williams, and M. Reidenberg The conjugation of phenylacetic acid in man, sub-human primates and some non-primate species Proc R Soc Lond B Biol Sci 182 1972 25 35
11. J.R. Idle, P. Millburn, and R.T. Williams Taurine conjugates as metabolites of arylacetic acids in the ferret Xenobiotica 8 1978 253 264 (Pubitemid 8317782)
12. E.A. Bababunmi, R.L. Smith, and R.T. Williams The absence of hippuric acid synthesis in the Indian fruit bat Life Sci II 12 1973 317 326
13. G.O. Emerole, M.R. French, and R.T. Williams Effect of p-nitro-substitution on the metabolism of benzoic acid in the Indian fruit bat Biochem Exp Biol 13 1977 385 390 (Pubitemid 9108690)
14. J.R. Idle, P. Millburn, and R.T. Williams Benzoylglutamic acid, a metabolite of benzoic acid in Indian fruit bats FEBS Lett 59 1975 234 236
15. B.L. Goodwin, C.R. Ruthven, and M. Sandler Gut flora and the origin of some urinary aromatic phenolic compounds Biochem Pharmacol 47 1994 2294 2297 (Pubitemid 24216408)
16. http://www.hmdb.ca/ [accessed September 27, 2011]
17. D. Yang, M. Beylot, K.C. Agarwal, M.V. Soloviev, and H. Brunengraber Assay of the human liver citric acid cycle probe phenylacetylglutamine and of phenylacetate in plasma by gas chromatography-mass spectrometry Anal Biochem 212 1993 277 282 (Pubitemid 23219485)
18. G.M. Pacifici, S. Mogavero, L. Giuliani, and A. Rane Conjugation of benzoic acid with glycine in the human fetal and adult liver and kidney Dev Pharmacol Ther 17 1991 52 62
19. www.chemspider.com [accessed September 27, 2011]
20. P.I. Mackenzie, K.W. Bock, B. Burchell, C. Guillemette, S. Ikushiro, and T. Iyanagi Nomenclature update for the mammalian UDP glycosyltransferase (UGT) gene superfamily Pharmacogenet Genomics 15 2005 677 685 (Pubitemid 41345319)
21. I. Mano, S. Straud, and M. Driscoll Caenorhabditis elegans glutamate transporters influence synaptic function and behavior at sites distant from the synapse J Biol Chem 282 2007 34412 34419 (Pubitemid 350159466)
22. W. Meyer, and H.M. Poehling Regional distribution of putative amino acid neurotransmitters in the CNS of spiders (Arachnida: Araneida) Neurochem Int 11 1987 241 246 (Pubitemid 17125815)
23. P.A. Anderson, and H.G. Trapido-Rosenthal Physiological and chemical analysis of neurotransmitter candidates at a fast excitatory synapse in the jellyfish Cyanea capillata (Cnidaria, Scyphozoa) Invert Neurosci 9 2009 167 173
24. R.A. Hawkins The blood-brain barrier and glutamate Am J Clin Nutr 90 2009 867S 874S
25. J.B. Kuzmiski, and J.S. Bains Metabotropic glutamate receptors: gatekeepers of homeostasis J Neuroendocrinol 22 2010 785 792
26. J.W. Johnson, and P. Ascher Glycine potentiates the NMDA response in cultured mouse brain neurons Nature 325 1987 529 531 (Pubitemid 17056733)
27. H. Betz, and B. Laube Glycine receptors: recent insights into their structural organization and functional diversity J Neurochem 97 2006 1600 1610 (Pubitemid 43873655)
28. V. Schmieden, G. Grenningloh, P.R. Schofield, and H. Betz Functional expression in Xenopus oocytes of the strychnine binding 48 kD subunit of the glycine receptor EMBO J 8 1989 695 700 (Pubitemid 19273239)
29. D. Langosch, C.M. Becker, and H. Betz The inhibitory glycine receptor: a ligand-gated chloride channel of the central nervous system Eur J Biochem 194 1990 1 8
30. M. Takahashi, B. Billups, D. Rossi, M. Sarantis, M. Hamann, and D. Attwell The role of glutamate transporters in glutamate homeostasis in the brain J Exp Biol 200 1997 401 409 (Pubitemid 27126472)
31. N. Kawai, M. Bannai, S. Seki, T. Koizumi, K. Shinkai, and K. Nagao Pharmacokinetics and cerebral distribution of glycine administered to rats Amino Acids 2011 10.1007/s00726-011-0950-y
32. E.N. Busanello, A.P. Moura, C.M. Viegas, A. Zanatta, G. da Costa Ferreira, and P.F. Schuck Neurochemical evidence that glycine induces bioenergetical dysfunction Neurochem Int 56 2010 948 954
33. H. Huang, L. Barakat, D. Wang, and A. Bordey Bergmann glial GlyT1 mediates glycine uptake and release in mouse cerebellar slices J Physiol 560 2004 721 736 (Pubitemid 39530113)
34. J.H. Quastel Biochemistry and mental disorder Lancet 220 1932 1417 1419
35. M.R. Lockwood, and D.R. Davies Blood-urea changes in abnormal mental states after the administration of amino-acid Biochem J 26 1932 745 752
36. A.J. Quick The conjugation of benzoic acid in man J Biol Chem 92 1931 65 85
37. J.H. Quastel, and W.T. Wales Faulty detoxication in schizophrenia Lancet 232 1938 301 305
38. R. Strom-Olsen, G.D. Greville, and R.W. Lennon Hippuric acid synthesis in schizophrenia Lancet 232 1938 995 996
39. D.R. Davies, and T.P.E. Hughes Faulty detoxication in mental disorder Lancet 235 1940 403 405
40. G.D. Greville The hippuric acid excretion test in schizophrenia Proc R Soc Med 38 1945 671 674
41. Y.T. Wong The hippuric acid liver function test in schizophrenia J Nerv Ment Dis 102 1945 183 184
42. P.E. Koersner Some observations on the hippuric acid test in schizophrenia Acta Psychiatr Scand 22 Suppl. 47 1947 145 155
43. K. Stern, J.S. Tyhurst, and B.A. Askonas Note on hippuric acid synthesis in senility Am J Med Sci 212 1946 302 305
44. G.C. Cook Impairment of glycine absorption by glucose and galactose in man J Physiol 217 1971 61 70
45. H. Persky, R.R. Grinker, and I.A. Mirsky The excretion of hippuric acid in subjects with free anxiety J Clin Invest 29 1950 110 114
46. W. Fabisch, and C. Fellner Excretion of hippuric acid in schizophrenic and depressive patients after E.C.T. Psychosom Med 19 1957 320 325
47. H. Betz, J. Gomeza, W. Armsen, P. Scholze, and V. Eulenburg Glycine transporters: essential regulators of synaptic transmission Biochem Soc Trans 34 2006 55 58 (Pubitemid 43235533)
48. J.R. Field, A.G. Walker, and P.J. Conn Targeting glutamate synapses in schizophrenia Trends Mol Med 17 2011 689 698
49. C.H. Lin, H.Y. Lane, and G.E. Tsai Glutamate signaling in the pathophysiology and therapy of schizophrenia Pharmacol Biochem Behav 2011 10.1016/j.pbb.2011.03.023
50. N. Dolu Dose-related anxiogenic effect of glycine in the elevated plus maze and in electrodermal activity J Basic Clin Physiol Pharmacol 18 2007 141 147 (Pubitemid 47208445)
51. A.W. Lis, I. McLaughlin, R.K. Mpclaughlin, E.W. Lis, and E.G. Stubbs Profiles of ultraviolet-absorbing components of urine from autistic children, as obtained by high-resolution ion-exchange chromatography Clin Chem 22 1976 1528 1532
52. G. Arribas-Lorenzo, and F.J. Morales Estimation of dietary intake of 5-hydroxymethylfurfural and related substances from coffee to Spanish population Food Chem Toxicol 48 2010 644 649
53. I.K. Yap, M. Angley, K.A. Veselkov, E. Holmes, J.C. Lindon, and J.K. Nicholson Urinary metabolic phenotyping differentiates children with autism from their unaffected siblings and age-matched controls J Proteome Res 9 2010 2996 3004
54. R.J. Anderson, D.J. Bendell, I. Garnett, P.W. Groundwater, W.J. Lough, and M.J. Mills Identification of indolyl-3-acryloylglycine in the urine of people with autism J Pharm Pharmacol 54 2002 295 298 (Pubitemid 34150066)
55. S.G. Khan, H.L. Levy, R. Legerski, E. Quackenbush, J.T. Reardon, and S. Emmert Xeroderma pigmentosum group C splice mutation associated with autism and hypoglycinemia J Invest Dermatol 111 1998 791 796 (Pubitemid 28509320)
56. A. Shinohe, K. Hashimoto, K. Nakamura, M. Tsujii, Y. Iwata, and K.J. Tsuchiya Increased serum levels of glutamate in adult patients with autism Prog Neuropsychopharmacol Biol Psychiatry 30 2006 1472 1477 (Pubitemid 44634960)
57. A. Ghanizadeh Targeting of glycine site on NMDA receptor as a possible new strategy for autism treatment Neurochem Res 36 2011 922 923
58. H.B. Lewis Studies in the synthesis of hippuric acid in the animal organism. II. The synthesis and rate of elimination of hippuric acid after benzoate ingestion in man J Biol Chem 18 1914 225 231
59. G.T. Shiple, and C.P. Sherwin Synthesis of amino acids in animal organisms. I. Synthesis of glycocoll and glutamine in the human organism J Am Chem Soc 44 1922 618 624
60. S.W. Brusilow, D.L. Valle, and M. Batshaw New pathways of nitrogen excretion in inborn errors of urea synthesis Lancet 2 1979 452 454 (Pubitemid 9250407)
61. O. Simell, I. Sipila, J. Rajantie, D.L. Valle, and S.W. Brusilow Waste nitrogen excretion via amino acid acylation: benzoate and phenylacetate in lysinuric protein intolerance Pediatr Res 20 1986 1117 1121 (Pubitemid 16005719)
62. G. Sebastio, M.P. Sperandeo, and G. Andria Lysinuric protein intolerance: reviewing concepts on a multisystem disease Am J Med Genet C Semin Med Genet 157 2011 54 62
63. A.A. Jackson, A.V. Badaloo, T. Forrester, J.M. Hibbert, and C. Persaud Urinary excretion of 5-oxoproline (pyroglutamic aciduria) as an index of glycine insufficiency in normal man Br J Nutr 58 1987 207 214 (Pubitemid 18020751)
64. B. Lee, W. Rhead, G.A. Diaz, B.F. Scharschmidt, A. Mian, and O. Shchelochkov Phase 2 comparison of a novel ammonia scavenging agent with sodium phenylbutyrate in patients with urea cycle disorders: safety, pharmacokinetics and ammonia control Mol Genet Metab 100 2010 221 228
65. B.M. McGuire, I.A. Zupanets, M.E. Lowe, X. Xiao, V.A. Syplyviy, and J. Monteleone Pharmacology and safety of glycerol phenylbutyrate in healthy adults and adults with cirrhosis Hepatology 51 2010 2077 2085
66. A. Thibault, M.R. Cooper, W.D. Figg, D.J. Venzon, A.O. Sartor, and A.C. Tompkins A phase I and pharmacokinetic study of intravenous phenylacetate in patients with cancer Cancer Res 54 1994 1690 1694 (Pubitemid 24116171)
67. A. Thibault, D. Samid, M.R. Cooper, W.D. Figg, A.C. Tompkins, and N. Patronas Phase I study of phenylacetate administered twice daily to patients with cancer Cancer 75 1995 2932 2938
68. T.P. Mulder, A.G. Rietveld, and J.M. van Amelsvoort Consumption of both black tea and green tea results in an increase in the excretion of hippuric acid into urine Am J Clin Nutr 81 2005 256S 260S
69. V.I. Teichberg, K. Cohen-Kashi-Malina, I. Cooper, and A. Zlotnik Homeostasis of glutamate in brain fluids: an accelerated brain-to-blood efflux of excess glutamate is produced by blood glutamate scavenging and offers protection from neuropathologies Neuroscience 158 2009 301 308
70. M. Gottlieb, Y. Wang, and V.I. Teichberg Blood-mediated scavenging of cerebrospinal fluid glutamate J Neurochem 87 2003 119 126 (Pubitemid 37210646)
71. J.N. Smith Detoxications of aromatic acids with glutamic acid and arginine in spiders Nature 195 1962 399 400
72. L. Friedler, and J.N. Smith Comparative detoxication. 3. Hippuric acid formation in adult locusts Biochem J 57 1954 396 400
73. S.M. Rogers, T. Matheson, K. Sasaki, K. Kendrick, S.J. Simpson, and M. Burrows Substantial changes in central nervous system neurotransmitters and neuromodulators accompany phase change in the locust J Exp Biol 207 2004 3603 3617 (Pubitemid 39384815)