Skip to main content
Biochemical Journal logoLink to Biochemical Journal
. 1985 Apr 15;227(2):537–544. doi: 10.1042/bj2270537

Effect of tryptophan metabolites on the activities of rat liver pyridoxal kinase and pyridoxamine 5-phosphate oxidase in vitro.

F Takeuchi, R Tsubouchi, Y Shibata
PMCID: PMC1144873  PMID: 2988502

Abstract

Pyridoxal kinase was purified 4760-fold from rat liver. The Km values for pyridoxine and pyridoxal were 120 and 190 microM respectively, and pyridoxine showed substrate inhibition at above 200 microM. Pyridoxamine 5-phosphate oxidase was also purified 2030-fold from rat liver, and its Km values for pyridoxine 5-phosphate and pyridoxamine 5-phosphate were 0.92 and 1.0 microM respectively. Pyridoxine 5-phosphate gave a maximum velocity that was 5.6-fold greater than with pyridoxamine 5-phosphate and showed strong substrate inhibition at above 6 microM. Among the tryptophan metabolites, picolinate, xanthurenate, quinolinate, tryptamine and 5-hydroxytryptamine inhibited pyridoxal kinase. However, pyridoxamine 5-phosphate oxidase could not be inhibited by tryptophan metabolites, and on the contrary it was activated by 3-hydroxykynurenine and 3-hydroxyanthranilate. Regarding the metabolism of vitamin B-6 in the liver, the effects of tryptophan metabolites that were accumulated in vitamin B-6-deficient rats after tryptophan injection were discussed.

Full text

PDF
537

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Abercrombie D. M., Martin D. L. Inhibition of pyridoxal kinase by the pyridoxal-gamma-aminobutyrate imine. J Biol Chem. 1980 Jan 10;255(1):79–84. [PubMed] [Google Scholar]
  2. Bosron W. F., Veitch R. L., Lumeng L., Li T. K. Subcellular localization and identification of pyridoxal 5'-phosphate-binding proteins in rat liver. J Biol Chem. 1978 Mar 10;253(5):1488–1492. [PubMed] [Google Scholar]
  3. Cash C. D., Maitre M., Rumigny J. F., Mandel P. Rapid purification by affinity chromatography of rat brain pyridoxal kinase and pyridoxamine-5-phosphate oxidase. Biochem Biophys Res Commun. 1980 Oct 31;96(4):1755–1760. doi: 10.1016/0006-291x(80)91377-7. [DOI] [PubMed] [Google Scholar]
  4. Chern C. J., Beutler E. Purification and characterization of human erythrocyte pyridoxine kinase. Clin Chim Acta. 1975 Jun 20;61(3):353–365. doi: 10.1016/0009-8981(75)90425-8. [DOI] [PubMed] [Google Scholar]
  5. Choi J. D., Bowers-Komro M., Davis M. D., Edmondson D. E., McCormick D. B. Kinetic properties of pyridoxamine (pyridoxine)-5'-phosphate oxidase from rabbit liver. J Biol Chem. 1983 Jan 25;258(2):840–845. [PubMed] [Google Scholar]
  6. Churchich J. E. Brain pyridoxine-5-phosphate oxidase. A dimeric enzyme containing one FMN site. Eur J Biochem. 1984 Jan 16;138(2):327–332. doi: 10.1111/j.1432-1033.1984.tb07918.x. [DOI] [PubMed] [Google Scholar]
  7. Churchich J. E., Wu C. Nucleoside phosphorothioates as probes of the nucleotide binding site of brain pyridoxal kinase. J Biol Chem. 1982 Oct 25;257(20):12136–12140. [PubMed] [Google Scholar]
  8. Coburn S. P., Mahuren J. D., Schaltenbrand W. E., Wostmann B. S., Madsen D. Effects of vitamin B-6 deficiency and 4'- deoxypyridoxine on pyridoxal phosphate concentrations, pyridoxine kinase and other aspects of metabolism in the rat. J Nutr. 1981 Feb;111(2):391–398. doi: 10.1093/jn/111.2.391. [DOI] [PubMed] [Google Scholar]
  9. Ebadi M., Govitrapong P. Biogenic amine-mediated alteration of pyridoxal phosphate formation in rat brain. J Neurochem. 1979 Mar;32(3):845–853. doi: 10.1111/j.1471-4159.1979.tb04569.x. [DOI] [PubMed] [Google Scholar]
  10. Evans G. W., Johnson P. E., Brushmiller J. G., Ames R. W. Detection of labile zinc-binding ligands in biological fluids by modified gel filtration chromatography. Anal Chem. 1979 Jun;51(7):839–843. doi: 10.1021/ac50043a016. [DOI] [PubMed] [Google Scholar]
  11. Gregory J. F., 3rd Effects of epsilon-pyridoxyllysine and related compounds on liver and brain pyridoxal kinase and liver pyridoxamine (pyridoxine) 5'-phosphate oxidase. J Biol Chem. 1980 Mar 25;255(6):2355–2359. [PubMed] [Google Scholar]
  12. Ikeda S., Kotake Y. Urinary excretion of xanthurenic acid and zinc in diabetes: 1) Separation of xanthurenic acid-Zn2+ complex by ion-exchange chromatography. Acta Vitaminol Enzymol. 1984;6(1):23–28. [PubMed] [Google Scholar]
  13. Johansson S., Lindstedt S., Tiselius H. G. Metabolic interconversions of different forms of vitamin B6. J Biol Chem. 1974 Oct 10;249(19):6040–6046. [PubMed] [Google Scholar]
  14. Karawya E., Fonda M. L. Physical and kinetic properties of sheep liver pyridoxine kinase. Arch Biochem Biophys. 1982 Jun;216(1):170–177. doi: 10.1016/0003-9861(82)90201-6. [DOI] [PubMed] [Google Scholar]
  15. Karawya E., Fonda M. L. Purification, assay, and kinetic properties of sheep liver pyridoxal kinase. Anal Biochem. 1978 Oct 15;90(2):525–533. doi: 10.1016/0003-2697(78)90146-x. [DOI] [PubMed] [Google Scholar]
  16. Karawya E., Mostafa M. H., Osman N. The kinetic mechanism of inhibition of liver pyridoxal kinase with tryptophan metabolites. Biochim Biophys Acta. 1981 Jan 15;657(1):153–158. doi: 10.1016/0005-2744(81)90138-8. [DOI] [PubMed] [Google Scholar]
  17. Kazarinoff M. N., McCormick D. B. Rabbit liver pyridoxamine (pyridoxine) 5'-phosphate oxidase. Purification and properties. J Biol Chem. 1975 May 10;250(9):3436–3442. [PubMed] [Google Scholar]
  18. Korytnyk W., Hakala M. T., Potti P. G., Angelino N., Chang S. C. On the inhibitory activity of 4-vinyl analogues of pyridoxal: enzyme and cell culture studies. Biochemistry. 1976 Dec 14;15(25):5458–5466. doi: 10.1021/bi00670a006. [DOI] [PubMed] [Google Scholar]
  19. Kozik A., McCormick D. B. Mechanism of pyridoxine uptake by isolated rat liver cells. Arch Biochem Biophys. 1984 Feb 15;229(1):187–193. doi: 10.1016/0003-9861(84)90143-7. [DOI] [PubMed] [Google Scholar]
  20. Kwok F., Churchich J. E. Brain pyridoxal kinase. Purification, substrate specificities, and sensitized photodestruction of an essential histidine. J Biol Chem. 1979 Jul 25;254(14):6489–6495. [PubMed] [Google Scholar]
  21. Kwok F., Churchich J. E. Interaction between pyridoxal kinase and pyridoxine-5-P oxidase, two enzymes involved in the metabolism of vitamin B6. J Biol Chem. 1980 Feb 10;255(3):882–887. [PubMed] [Google Scholar]
  22. LOWRY O. H., ROSEBROUGH N. J., FARR A. L., RANDALL R. J. Protein measurement with the Folin phenol reagent. J Biol Chem. 1951 Nov;193(1):265–275. [PubMed] [Google Scholar]
  23. Li T. K., Lumeng L., Veitch R. L. Regulation of pyridoxal 5'-phosphate metabolism in liver. Biochem Biophys Res Commun. 1974 Nov 27;61(2):677–684. doi: 10.1016/0006-291x(74)91010-9. [DOI] [PubMed] [Google Scholar]
  24. MCCORMICK D. B., GREGORY M. E., SNELL E. E. Pyridoxal phosphokinases. I. Assay, distribution, I. Assay, distribution, purification, and properties. J Biol Chem. 1961 Jul;236:2076–2084. [PubMed] [Google Scholar]
  25. MCCORMICK D. B., SNELL E. E. Pyridoxal phosphokinases. II. Effects of inhibitors. J Biol Chem. 1961 Jul;236:2085–2088. [PubMed] [Google Scholar]
  26. Meisler N. T., Thanassi J. W. Pyridoxine kinase, pyridoxine phosphate phosphatase and pyridoxine phosphate oxidase activities in control and B-6-deficient rat liver and brain. J Nutr. 1980 Oct;110(10):1965–1975. doi: 10.1093/jn/110.10.1965. [DOI] [PubMed] [Google Scholar]
  27. Merrill A. H., Horiike K., McCormick D. B. Evidence for the regulation of pyridoxal 5-phosphate formation in liver by pyridoxamine (pyridoxine) 5 -phosphate oxidase. Biochem Biophys Res Commun. 1978 Aug 14;83(3):984–990. doi: 10.1016/0006-291x(78)91492-4. [DOI] [PubMed] [Google Scholar]
  28. Neary J. T., Diven W. F. Purification, properties, and a possible mechanism for pyridoxal kinase from bovine brain. J Biol Chem. 1970 Nov 10;245(21):5585–5593. [PubMed] [Google Scholar]
  29. Neary J. T., Meneely R. L., Grever M. R., Diven W. F. The interactions between biogenic amines and pyridoxal, pyridoxal phosphate, and pyridoxal kinase. Arch Biochem Biophys. 1972 Jul;151(1):42–47. doi: 10.1016/0003-9861(72)90470-5. [DOI] [PubMed] [Google Scholar]
  30. Nutter L. M., Meisler N. T., Thanassi J. W. Absence of pyridoxine- (pyridoxamine-) 5'-phosphate oxidase in Morris hepatoma 7777. Biochemistry. 1983 Mar 29;22(7):1599–1604. doi: 10.1021/bi00276a012. [DOI] [PubMed] [Google Scholar]
  31. Rasmussen K. M., Barsa P. M., McCormick D. B. Pyridoxamine (pyridoxine) 5'-phosphate oxidase activity in rat tissues during development of riboflavin or pyridoxine deficiency. Proc Soc Exp Biol Med. 1979 Sep;161(4):527–530. doi: 10.3181/00379727-161-40589. [DOI] [PubMed] [Google Scholar]
  32. Smith S. A., Carr F. P., Pogson C. I. The metabolism of L-tryptophan by isolated rat liver cells. Quantification of the relative importance of, and the effect of nutritional status on, the individual pathways of tryptophan metabolism. Biochem J. 1980 Nov 15;192(2):673–686. doi: 10.1042/bj1920673. [DOI] [PMC free article] [PubMed] [Google Scholar]
  33. Stock A., Ortanderl F., Pfleiderer G. Darstellung von radioaktiv markiertem Pyridoxal-5'-phosphat. Biochem Z. 1966 Jun 7;344(4):353–360. [PubMed] [Google Scholar]
  34. Takeuchi F., Shibata Y. Kynurenine metabolism in vitamin-B-6-deficient rat liver after tryptophan injection. Biochem J. 1984 Jun 15;220(3):693–699. doi: 10.1042/bj2200693. [DOI] [PMC free article] [PubMed] [Google Scholar]
  35. Tsubosaka M., Makino K. Study on the pyridoxal kinase of mouse brain. J Vitaminol (Kyoto) 1969 Jun 10;15(2):131–141. doi: 10.5925/jnsv1954.15.131. [DOI] [PubMed] [Google Scholar]
  36. Tsuge H., Itoh K., Akatsuka F., Okada T., Ohashi K. Activation of pyridoxamine 5'-phosphate oxidase by aliphatic primary amine. Biochem Int. 1983 Jun;6(6):743–749. [PubMed] [Google Scholar]
  37. WADA H., SNELL E. E. The enzymatic oxidation of pyridoxine and pyridoxamine phosphates. J Biol Chem. 1961 Jul;236:2089–2095. [PubMed] [Google Scholar]
  38. Yeh J. K., Brown R. R. Effects of vitamin B-6 deficiency and tryptophan loading on urinary excretion of tryptophan metabolites in mammals. J Nutr. 1977 Feb;107(2):261–271. doi: 10.1093/jn/107.2.261. [DOI] [PubMed] [Google Scholar]
  39. van den Berg H., Bogaards J. J., Sinkeldam E. J., Schreurs W. H. Effect of different levels of vitamin B6 in the diet of rats on the content of pyridoxamine-5'-phosphate and pyridoxal-5'-phosphate in the liver. Int J Vitam Nutr Res. 1982;52(4):407–416. [PubMed] [Google Scholar]

Articles from Biochemical Journal are provided here courtesy of The Biochemical Society

RESOURCES