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Metabolism and Biology of Tryptophan

Some Clinical Implications

  • Chapter
Recent Advances in Tryptophan Research

Part of the book series: Advances in Experimental Medicine and Biology ((AEMB,volume 398))

Abstract

The age of 21 years is usually considered the age at which a person becomes an adult. So it is that the International Study Group for Tryptophan Research (ISTRY), which is now 21 years old becomes a mature organization. The first meeting was held 21 years ago here in beautiful and historic Padua organized by Professor L. Musajo and his able assistants Professors G. Allegri C. Costa and A. De Antoni. Intervening triennial meetings were held in Madison, Kyoto, Martinsried, Cardiff, Baltimore, and Nagoya. It is appropriate that this meeting again be in Padua to celebrate the maturity of ISTRY, and we are grateful to Professors Allegri-Filippini and Costa for hosting this conference.

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Reference

  • Aune, T.M., and Pogue, S.L. 1989. Inhibition of tumor cell growth by interferon-gamma is mediated by two distinct mechanisms dependent upon oxygen tension:induction of tryptophan degradation and depletion of intracellular nicotinamide adenine dinucleotide. J. Clin. Invest.84:863.

    Article  CAS  Google Scholar 

  • Baubichon-Cortay, H., Baggetto, L.G., Dayan, G. et al. 1994. 1994. Overexpression and purification of the carboxyl-terminal nucleotide-binding domain of mouse P-glycoprotein:Strategic location of a tryptophan residue. J. Biol. Chem. 269:22983

    Google Scholar 

  • Blakesley, V.A., Kato, H., Roberts, C.T. Jr., et al., 1995. Mutation of a conserved amino acid residue (tryptophan 1173) in the tyrosine domain of the IGF-I receptor abolishes autophosphorylation but does not eliminate biologic function. J. Biol Chem.270:2764.

    Article  CAS  Google Scholar 

  • Brown, R.R., Lee, C.M., Kohler, P.C., et al. 1989. Altered tryptophan metabolism in cancer patients treated with recombinant interleukin 2. Cancer Res. 49:4911.

    Google Scholar 

  • Brown, R.R., Ozaki, Y., Datta, S.P., et al. 1991. Implications of interferon-induced tryptophan catabolism in cancer, autoimmune diseases and AIDS. Adv. Expt. Med. Biol.294:425.

    CAS  Google Scholar 

  • Burke, F., Knowles, R.G., East, N., et al. 1995. The role of indoleamine 2,3-dioxygenase in the anti-tumor activity of human interferon-gamma in vivo. Int. J. Cancer60:115.

    Article  CAS  Google Scholar 

  • Byrne, G.I., Lehmann, L.K., Kirschbaum, J.G., et al. 1986. Induction of tryptophan degradation in vitroand in vivo, a gamma-interferon stimulated activity. J. Interferon Res.6:389.

    Article  CAS  Google Scholar 

  • Carlin, J.M., Ozaki, Y., Byrne, G.I., et al. 1989. Interferons and indoleamine 2,3-dioxygenase:role in antimicrobial and antitumor effects. Experientia45:535.

    Article  CAS  Google Scholar 

  • Carson, D.A., Seto, S., Wasson D.B., et al., 1986. DNA strand breaks, NAD metabolism and programmed cell death. Exp. Cell Res.164:273.

    Article  CAS  Google Scholar 

  • Christen, S., Thomas, S.R., Garner, B., et al. 1994. Inhibition by interferon-gamma of human mononuclear cell-mediated low density lipoprotein oxidation. Participation of tryptophan metabolism along the kynurenine pathway. J. Clin. Invest.93:2149.

    Article  CAS  Google Scholar 

  • Chu, M.C., Melish, M.E., and James, J.F. 1985. Tryptophan auxotypy associated with Staphylococcus aureus that produce toxic-shock-syndrome toxin. J. Infectious Dis.151:1157

    Article  CAS  Google Scholar 

  • Clackson, T., and Wells, J.A. 1995. A hot spot of binding energy in a hormone-receptor interface. Science267:383

    Article  CAS  Google Scholar 

  • Cady, S.G., and Sono, M. 1991.1-Methyl-DL-tryptophan, B-(3-benzofuranyl)-DL-alanine (the oxygen analog of tryptophan), and B-[3-benzo(b)thienyl]-DL-alanine are competitive inhibitors for indoleamine 2,3-dioxygenase. Arch. Biochem. Biophys. 291:326.

    Google Scholar 

  • Dimicoli, J-L., and Helene, C. 1974. Interactions of aromatic residues of proteins with nucleic acids. I. Proton magnetic resonance studies of the binding of tryptophan-containing peptides of poly(adenylic acid) and deoxynucleic acid. Biochemistry, 13:714.

    Article  CAS  Google Scholar 

  • Dua, R.K., Taylor, E.W., and Phillips, R.S. 1993. S-aryl-L-cysteine S,S-dioxides:Design, synthesis and evaluation of a new class of inhibitors of kynureninase. J. Am. Chem. Soc.115:1264

    Article  CAS  Google Scholar 

  • Esposito, A., L., Poirier, W.J., Clarck, C.A., et al., 1989. The release of neutrophil chemoattractant activity by bronchoalveolar macrophages from adult and senescent mice. J. Gerontology:Biological Sciences, 44:B93

    CAS  Google Scholar 

  • Faurobert, E., Otto-Bruc, A., Chardin, P., et al. 1993. Tryptophan W207 in transducin tais the fluorescence sensor of the G protein activation switch and is involved in the effector binding. EMBO J. 12:4191.

    CAS  Google Scholar 

  • Feng, G., and Taylor, M.W. 1989. Interferon-gamma-resistant mutants are defective in the induction of indoleamine 2,3-dioxygenase. Proc. Nat. Acad. Sci., U.S.A.86:7144.

    Article  CAS  Google Scholar 

  • Gisslen, M., Larsson, M., Norkrans, G., et al. 1994. Tryptophan concentrations increase in cerebrospinal fluid and blood after Zidovudine treatment in patients with HIV type 1 infection. AIDS Res. Human Retroviruses.10:947.

    Article  CAS  Google Scholar 

  • Govindaraj, S., Eisenstein, E., Jones, L.H., et al. 1994. Aromatic amine dehydrogenase, a second tryptophan tryptophylquinone enzyme. J. Bacteriol.176:2922.

    CAS  Google Scholar 

  • Guillot, D., Lavergne, J-P., and Reboud, J-R 1993. Trp-221 is involved in the protective effect of elongation factor eEF-2 on the ricin/a-sarcin site of the ribosome. J. Biol. Chem.268:26082.

    CAS  Google Scholar 

  • Guillot, D., Penin, F., Di Pietro, A., et al. 1993a. GTP binding to elongation factor eEF-2 unmasks a tryptophan residue required for biological activity. J. Biol. Chem.268:20911.

    CAS  Google Scholar 

  • Helene, C., and Dimicoli, J-L. 1972. Interactions of oligopeptides containing aromatic amino acids with nucleic acids. Fluorescence and proton magnetic resonance studies. FEBS Letters. 26:6.

    Article  CAS  Google Scholar 

  • Heyes, M.P., Brew, B.J., Saito, S., et al., 1992. Inter-relationships between quinolinic acid, neuroactive kynurenines, neopterin and B2-microglobulin in cerebrospinal fluid and serum of HIV-1 infected patients. J. Neuroimmunol.40:71

    Article  CAS  Google Scholar 

  • Heyes, M.P., Saito, K., Major, E.O., et al. 1993. A mechanism of quinolinic acid formation by brain in inflammatory neurological disease. Attenuation of synthesis from L-tryptophan by 6-chlorotrypto- phan and 4-chloro-3-hydroxyanthranilate. Brain116:1425.

    Google Scholar 

  • Holmes, E.W., Russell, P.M., Kinzler, G.J., et al. 1994. Inflammation-associated changes in the cellular availability of tryptophan and kynurenine in renal transplant recipients. Clin. Chim. Acta227:1.

    Article  CAS  Google Scholar 

  • Hortin, G.L., Landt, M., and Powderly, W.G. 1994. Changes in plasma amino acid concentrations in response to HIV-1 infection. Clin. Chem.40:785.

    CAS  Google Scholar 

  • Intracel. 1995. Intracel retroviral products catalog. Intracel Corp., 359 Allston St., Cambridge MA 02139, pp. 13 - 23.

    Google Scholar 

  • Jaenike, L. 1994. Biological activity of blepharismone derivatives. In:Progress in Tryptophan and Serotonin Research, Eds. Schlossberger, H.G., Kochen, W., Linzen, B., and Steinhart, H., W. de Gruyter, Publ. Berlin, 1994, pp. 815 - 826.

    Google Scholar 

  • Launay, J-M., Copel, L., Callebert, J., et al. 1988. Decreased whole blood 5-hydroxytryptamine(serotonin) in AIDS patients. J. Acquired Immune Def. Syndromes.1:324.

    CAS  Google Scholar 

  • Liu, J., Chen, C-M., and Walsh C.T. 1991. Human and Escherichia coli cyclophylins:Sensitivity to inhibition by the immunosuppressant cyclosporin A correlates with a specific tryptophan residue. Biochemistry30:2306.

    Article  CAS  Google Scholar 

  • Maenaka, K., Kawai, G., Watanabe, K., et al., 1994. Functional and structural role of a tryptophan generally observed in protein-carbohydrate interaction:Trp-62 of hen egg white lysozyme. J. Biol Chem.269:7070.

    CAS  Google Scholar 

  • Mclntire, W.S. 1994. Quinoproteins. FASEBJ. 8:513.

    Google Scholar 

  • Meers, P., and Mealy, T. 1994. Phospholipid determinants for annexin V binding sites and the role of tryptophan 187. Biochemistry33:5829.

    Article  CAS  Google Scholar 

  • Myake, A. 1994. Blepharismone:A conjugation-inducing tryptophan derivative in the ciliate Blepharisma. In:Progress in Tryptophan and Serotonin Research, Eds. Schlossberger, H.G., Kochen, W., Linzen, B., and Steinhart, H., W. de Gruyter, Publ. Berlin, 1994, pp 807 - 813.

    Google Scholar 

  • Ozaki, Y., Edelstein, M., and Duch, D. 1987. The actions of interferon and antiinflammatory agents on induction of indoleamine 2,3-dioxygenase in human peripheral blood monocytes. Biochem. Biophys. Res. Commun.144:1147

    Article  CAS  Google Scholar 

  • Ozaki, Y., Edelstein, M., and Duch, D. 1988. Induction of indoleamine dioxygenase:a mechanism of the antitumor activity of interferon-gamma. Proc. Nat. Acad. Sci. U.S. A.85:1242.

    Article  CAS  Google Scholar 

  • Page, M.D., and Jones, S.J., 1993. Mutants of Methylobacterium extorquensand Paracoccus denitrificansdeficient in c-type cytochrome biogenesis synthesize the methylamine-dehydrogenase polypeptides but cannot assemble the tryptophan-tryptophylquinone group. Eur. J. Biochem.218:711.

    Article  CAS  Google Scholar 

  • Pellicciari, R., Natalini, B., Constantino, G., et al., 1994. Modulation of the kynurenine pathway in search for new neuroprotective agents. Synthesis and preliminary evaluation of (m-nitrobenzoyl)alanine, a potent inhibitor of kynurenine-3-hydroxylase. J. Med. Chem.37:647.

    Article  CAS  Google Scholar 

  • Peterson A.C., La Loggia, A.J., Hamaker, L.K., 1993. Evaluation of substituted B-carbolines as noncompetitive indoleamine 2,3-dioxygenase inhibitors. Med. Chem. Res.3:473.

    Google Scholar 

  • Peterson, A.C., Migawa, M.T., La Loggia, A.J., et al. 1994. Evaluation of functionalized tryptophan derivatives and related compounds as competitive inhibitors of indoleamine 2,3-dioxygenase. Med. Chem. Res.3:531.

    CAS  Google Scholar 

  • Raszka, M., and Mandel, M. 1971. Interaction of aromatic amino acids with neutral polyadenylic acid. Proc. Nat. Acad. Sci. U.S.A.68:1190.

    Article  CAS  Google Scholar 

  • Saito, K., Markey, S.P. and Heyes M.P. 1994. 6-Chloro-D,L-tryptophan, 4-chloro-3-hydroxyanthranilate and dexamethasone attenuate quinolinic acid accumulation in brain and blood following systemic immune activation. Neurosci. Letters. 178:211.

    Google Scholar 

  • Salter, M., Beams, R.M., Critchley, M.A.E., et al., 1991. Effects of tryptophan 2,3-dioxygenase inhibitors in the rat. Adv. Expt. Med. Biol.294:281.

    CAS  Google Scholar 

  • Shimizu, T., Nomiyama, S. Hirata, F., et al. Indoleamine 2,3-dioxygenase. Purification and some properties. J. Biol. Chem. 253:4700.

    Google Scholar 

  • Sigel, H., and Naumann, C.F. 1976. Ternary complexes in solution XXIV. Metal ion bridging of stacked purine-indole adducts. The mixed-ligand complexes of adenosine 5’-triphosphate, tryptophan, and manganese(II), copper (II),or zinc (II). J. Am. Chem. Soc.98:730.

    Article  CAS  Google Scholar 

  • Silverman, G., 1994. Superantigens and the spectrum of unconventional B-cell antigens. The Immunologist2:51.

    CAS  Google Scholar 

  • Stahl, N., and Prusiner, S.B. 1991. Prions and prion proteins. FASEB J. 5:2799.

    CAS  Google Scholar 

  • Swamy, N., Brisson, M., and Ray, R. 1995. Trp-145 is essential for the binding of 25-hydroxyvitamin D3 to human serum vitamin D-binding protein. J. Biol. Chem.270:2636.

    Article  CAS  Google Scholar 

  • Takikawa, O., Kuroiwa, T., Yamazaki, F., et al. 1988. Mechanism of interferon-gamma action. J. Biol. Chem.263:2041.

    CAS  Google Scholar 

  • Takikawa, O., Habara-Ohkubo, A., and Yoshida, R. 1990. IFN-gamma is the inducer of indoleamine 2,3-di-oxygenase in allografted tumor cells undergoing rejection. J. Immunol.145:1246.

    CAS  Google Scholar 

  • Taub, D.D., and Blank, K.J. 1993. Superantigens and microbial pathogenesis. Annals of Internal Med. 119:89.

    CAS  Google Scholar 

  • Taylor, M.W. and Feng G. 1991. Relationship between interferon-gamma, indoleamine 2,3-dioxygenase, and tryptophan catabolism. FASEB J. 5:2516

    CAS  Google Scholar 

  • Toulme, J-J., Charlier, M., and Helene, C. 1974. Specific recognition of single-stranded regions in ultraviolet- irradiated and heat-denatured DNA by tryptophan-containing peptides. Proc. Nat. Acad. Sci., U.S.A. 71:3185.

    Article  CAS  Google Scholar 

  • Truswell, A.S., Hansen J.D.L., and Wannenburg, P. 1968. Plasma tryptophan and other amino acids in pellagra. Am. J. Clin.Nutr.21:1314.

    CAS  Google Scholar 

  • Werner, E.R., Werner-Felmayer, G., Fuchs, D., et al. 1989. Parallel induction of tetrahydrobiopterin biosyn¬thesis and indoleamine 2,3-dioxygenase activity in human cells and cell lines by interferon-gamma. Biochem. J.262:861.

    CAS  Google Scholar 

  • Wilson, B.A., Blanke, S.R., Reich, K.A.. et al., 1994. Active-site mutations of diphtheria toxin:Tryptophan 50 is a major determinant of NAD affinity. J. Biol Chem.269:23296.

    CAS  Google Scholar 

  • Yamazaki, F., Kuroiwa, T., Takikawa, O., et al. 1985. Human indolylamine 2,3-dioxygenase. its tissue distribution and characterization of the placental enzyme. Biochem J. 230:635.

    CAS  Google Scholar 

  • Yoshida, R., Imanishi, J., Oku, K.T, et al. 1981. Induction of pulmonary indoleamine 2,3-dioxygenase by interferon. Proc. Nat. Acad. Sci., U.S.A.78:129.

    Article  CAS  Google Scholar 

  • Yoshida, R., Urade, Y., Tokuda, M., et al., 1979. Induction of indoleamine 2,3-dioxygenase in mouse lung during virus infection. Proc. Nat. Acad. Sci. U.S.A.76:4084

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Human Oncology, University of Wisconsin Medical School, Madison, Wisconsin, 53792, USA

    R. R. Brown (Professor Emeritus)

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  1. R. R. Brown
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Editors and Affiliations

  1. University Of Padova, Padova, Italy

    Graziella Allegri Filippini , Carlo V. L. Costa  & Antonella Bertazzo ,  & 

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© 1996 Plenum Press, New York

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Brown, R.R. (1996). Metabolism and Biology of Tryptophan. In: Filippini, G.A., Costa, C.V.L., Bertazzo, A. (eds) Recent Advances in Tryptophan Research. Advances in Experimental Medicine and Biology, vol 398. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-0381-7_2

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  • DOI: https://doi.org/10.1007/978-1-4613-0381-7_2

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4613-8026-9

  • Online ISBN: 978-1-4613-0381-7

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