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Chemical Compound Review

Monoiodotyrosine     (2S)-3-(4-hydroxyphenyl)-2...

Synonyms: AC1MHUUB, AG-E-96456, CTK0J9830, 29592-76-5
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Disease relevance of IODOTYROSINE

  • Since adequate clinical and chemical control of hyperthyroidism with antithyroid drugs and iodine was attained in the 8 Group I subjects without a decrease in the % T4I or T3I below that of normal thyroids, it suggests that inhibition of iodotyrosine coupling is not required for this effect [1].

High impact information on IODOTYROSINE


Biological context of IODOTYROSINE


Anatomical context of IODOTYROSINE

  • Radiolabeled material in both types of endosomes is comprised of high molecular weight, insulin-sized, and low molecular weight components, with B chain-labeled small molecular weight material in two peaks, one corresponding to iodotyrosine and one to small peptides (Mr less than 1500) [9].
  • This suggestion was strengthened by the finding that only the cytosol of the RBC, not its membranes, rapidly degraded Tyr-MIF-1 to free iodine and iodotyrosine [10].
  • Iodotyrosine release showed a biphasic Arrhenius plot with an activation energy of 17 kcal/mol above but 27 kcal/mol below 20 degrees C. These results indicate that cell membrane polypeptides require a temperature-limiting event as well as passage through an ion-sensitive compartment prior to their complete degradation to constituent amino acids [11].
  • At 37 degrees C, 125I-insulin bound to adipocytes was rapidly degraded into small fragments or iodotyrosine [12].
  • Serotonin concentration was significantly reduced (P less than 0.025) in the median eminence but not in the hypothalamus after iodotyrosine administration [13].

Associations of IODOTYROSINE with other chemical compounds


Gene context of IODOTYROSINE


Analytical, diagnostic and therapeutic context of IODOTYROSINE

  • A major disadvantage of (131)iodine (I)-labeled monoclonal antibodies (MAbs) for radioimmunotherapy has been the rapid diffusion of iodotyrosine from target cells after internalization and catabolism of the radioiodinated MAbs [23].
  • Gel exclusion chromatography of tryptic peptides and microsequenator analysis of tryptic glycopeptides showed that iodotyrosine was present at each of the only readily accessible residues in intact hormone: alpha Tyr21, alpha Tyr92, and alpha Tyr93 [24].
  • In an attempt to improve the separation of the T4-containing peptides in thyroglobulin tryptic digests from the much more abundant iodotyrosine-containing ones, which are present as contaminants, we have used a very simple and fast step prior to the HPLC fractionation as it is a self-packed ion-exchange column chromatography [25].
  • Gastric peroxidase activity is specifically stimulated by adrenalectomy and is inhibited by glucocorticoids which also inhibit iodotyrosine formation in stomach [26].
  • At steady state about half of the label dissociated from the cells as iodoinsulin and about half as iodotyrosine, as judged by gel filtration and paper chromatography in two solvent systems [27].


  1. Thyroidal triiodothyronine and thyroxine in Graves' disease: correlation with presurgical treatment, thyroid status, and iodine content. Larsen, P.R. J. Clin. Endocrinol. Metab. (1975) [Pubmed]
  2. Spatial requirement for coupling of iodotyrosine residues to form thyroid hormones. Cahnmann, H.J., Pommier, J., Nunez, J. Proc. Natl. Acad. Sci. U.S.A. (1977) [Pubmed]
  3. N-glycans modulate in vivo and in vitro thyroid hormone synthesis. Study at the N-terminal domain of thyroglobulin. Mallet, B., Lejeune, P.J., Baudry, N., Niccoli, P., Carayon, P., Franc, J.L. J. Biol. Chem. (1995) [Pubmed]
  4. Location of dehydroalanine residues in the amino acid sequence of bovine thyroglobulin. Identification of "donor" tyrosine sites for hormonogenesis in thyroglobulin. Ohmiya, Y., Hayashi, H., Kondo, T., Kondo, Y. J. Biol. Chem. (1990) [Pubmed]
  5. In vivo N-glycosylation and fate of Asn-X-Ser/Thr tripeptides. Geetha-Habib, M., Park, H.R., Lennarz, W.J. J. Biol. Chem. (1990) [Pubmed]
  6. Inactivation of transferrin iron binding capacity by the neutrophil myeloperoxidase system. Clark, R.A., Pearson, D.W. J. Biol. Chem. (1989) [Pubmed]
  7. Stimulation by thyroid hormone analogues of red blood cell Ca2+-ATPase activity in vitro. Correlations between hormone structure and biological activity in a human cell system. Davis, F.B., Cody, V., Davis, P.J., Borzynski, L.J., Blas, S.D. J. Biol. Chem. (1983) [Pubmed]
  8. Cloning and Characterization of a Novel Isoform of Iodotyrosine Dehalogenase 1 (DEHAL1) DEHAL1C from Human Thyroid: Comparisons with DEHAL1 and DEHAL1B. Gnidehou, S., Lacroix, L., Sezan, A., Ohayon, R., Noël-Hudson, M.S., Morand, S., Francon, J., Courtin, F., Virion, A., Dupuy, C. Thyroid (2006) [Pubmed]
  9. Isolation of insulin degradation products from endosomes derived from intact rat liver. Hamel, F.G., Posner, B.I., Bergeron, J.J., Frank, B.H., Duckworth, W.C. J. Biol. Chem. (1988) [Pubmed]
  10. Uptake of peptides containing Tyr-Pro by human and mouse erythrocytes. Banks, W.A., Kastin, A.J. Biochem. Pharmacol. (1990) [Pubmed]
  11. Degradation of surface-labeled hepatoma membrane polypeptides: effect of inhibitors. Hare, J.F., Huston, M. Arch. Biochem. Biophys. (1984) [Pubmed]
  12. Pathways of insulin degradation in isolated adipocytes: evaluation by gel filtration and differential precipitation. Kahn, C.R., Baird, K.L. Metab. Clin. Exp. (1985) [Pubmed]
  13. A simple procedure for the assay of brain biogenic amines by selected-ion monitoring: its application to the elucidation of the mechanism of prolactin release induced by 3-iodo-L-tyrosine. Smythe, G.A., Brandstater, J.F., Bradshaw, J.E., Lazarus, L. Aust. J. Biol. Sci. (1979) [Pubmed]
  14. Iodotyrosine deiodinase is the first mammalian member of the NADH oxidase/flavin reductase superfamily. Friedman, J.E., Watson, J.A., Lam, D.W., Rokita, S.E. J. Biol. Chem. (2006) [Pubmed]
  15. Mechanism for the anti-thyroid action of minocycline. Doerge, D.R., Divi, R.L., Deck, J., Taurog, A. Chem. Res. Toxicol. (1997) [Pubmed]
  16. Method for the quantitation of iodothyronines in body tissues and fluids using high-performance liquid chromatography. Hendrich, C.E., Berdecia-Rodriguez, J., Wiedmeier, V.T., Porterfield, S.P. J. Chromatogr. (1992) [Pubmed]
  17. Exogenous free iodotyrosine inhibits iodide transport through the sequential intracellular events. Nasu, M., Sugawara, M. Eur. J. Endocrinol. (1994) [Pubmed]
  18. Coupling of iodotyrosine catalyzed by human thyroid peroxidase in vitro. Sugawara, M. J. Clin. Endocrinol. Metab. (1985) [Pubmed]
  19. Improved assay method for activity of thyroid peroxidase-catalysed coupling of iodotyrosine residues of thyroglobulin utilizing h.p.l.c. for analysis of iodothyronines. Ohmori, T., Tarutani, O., Hosoya, T. Biochem. J. (1989) [Pubmed]
  20. Ferredoxin and ferredoxin reductase activities in bovine thyroid. Possible relationship to iodotyrosine deiodinase. Goswami, A., Rosenberg, I.N. J. Biol. Chem. (1981) [Pubmed]
  21. Carrier-mediated transport of vasopressin across the blood-brain barrier of the mouse. Banks, W.A., Kastin, A.J., Horvath, A., Michals, E.A. J. Neurosci. Res. (1987) [Pubmed]
  22. Iodotyrosine dehalogenase 1 (DEHAL1) is a transmembrane protein involved in the recycling of iodide close to the thyroglobulin iodination site. Gnidehou, S., Caillou, B., Talbot, M., Ohayon, R., Kaniewski, J., Noël-Hudson, M.S., Morand, S., Agnangji, D., Sezan, A., Courtin, F., Virion, A., Dupuy, C. FASEB J. (2004) [Pubmed]
  23. Improved iodine radiolabels for monoclonal antibody therapy. Stein, R., Govindan, S.V., Mattes, M.J., Chen, S., Reed, L., Newsome, G., McBride, B.J., Griffiths, G.L., Hansen, H.J., Goldenberg, D.M. Cancer Res. (2003) [Pubmed]
  24. Bovine luteinizing hormone iodinated at alpha Tyr21, alpha Tyr92, or alpha Tyr93 retains specific binding activity. Sharp, S.B., Hunkapiller, M.W. Endocrinology (1984) [Pubmed]
  25. Improvement in HPLC fractionation of thyroxine-containing thyroglobulin tryptic peptides by prior Accell ion-exchange column chromatography. Miguel, J., Asuncion, M., Marin, C., Seguido, A., Lamas, L., Mendez, E. FEBS Lett. (1988) [Pubmed]
  26. Endocrine control of extrathyroidal peroxidases and iodide metabolism. De, S.K., Ganguly, C.K., Chakraborty, T.K., Bose, A.K., Banerjee, R.K. Acta Endocrinol. (1985) [Pubmed]
  27. Receptor-bound insulin as a substrate for insulin degradation in adipocytes. Gliemann, J., Sonne, O. Prog. Clin. Biol. Res. (1979) [Pubmed]
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