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Chemical Compound Review

DL-THYRONINE     2-amino-3-[4-(4- hydroxyphenoxy)phenyl]prop...

Synonyms: SureCN285216, ACMC-1BYLJ, AG-D-14181, CHEBI:30661, T1501_SIGMA, ...
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Disease relevance of thyronine

  • It primed T cells for thyroiditis transfer, but noniodinated peptide containing thyronine (T0) was not compared [1].
  • Circulating levels of thyroid hormones (T4, free T4, T3) and reverse tri-iodo thyronine (rT3) and thyroid-hormone binding globulin were related to the nutritional state of patients with cancer cachexia, patients with malnutrition due to other reasons and to well-nourished patients with acute illness [2].
  • Treatment of rats daily with T3 (8 mug/100 g BW) for 15 days resulted in an increase in heart weight to body weight ratio, which was ameliorated by antioxidants, melatonin (2 mg/100 g BW) or vitamin E (4 mg/100 g BW) [3].
  • In conclusion: (1) T3 effects on GH gene expression depend on the period of life in which the hyperthyroidism is set and on the length of T3 treatment in the NP and (2) transient neonatal hyperthyroidism leads to a lower GH mRNA expression in adult life accompanied by physiological repercussions indicative of GH deficiency [4].
  • OBJECTIVE: to assess the relative contributions of de novo protein synthesis and attenuated protein degradation to increased protein mass associated with cardiomyocyte hypertrophy elicited by IGF-1 and thyroid hormones (tri-iodo thyronine T3, and l-thyroxine T4), respectively [5].

High impact information on thyronine

  • Aortic constriction and T3 treatment predominantly increased the size of smaller myocytes [6].
  • An equivalent effect is not observed in mitochondria from T3-treated rats [7].
  • Evidence for the presence of two active forms of cytosolic 3,5,3'-triiodo-L-thyronine (T3)-binding protein (CTBP) in rat kidney. Specialized functions of two CTBPs in intracellular T3 translocation [8].
  • Thus, under defined conditions, T3 is able to regulate MHC gene expression at a pretranslational level without the need for other exogenous factors [9].
  • Addition of 3,5,3'-triiodo-L-thyronine (T3) caused a rapid induction of alpha-MHC mRNA and decreased beta-MHC mRNA levels without affecting the skeletal muscle MHC mRNAs [9].

Chemical compound and disease context of thyronine

  • To clarify whether serum free fatty acid (FFA) is an inhibitor of extrathyroidal conversion (IEC) of thyroxine (T4) to thyronine (T3), we measured the concentration of FFA, IEC activity and thyroid hormones in normal subjects, acute ketotic children and children with low T3 syndrome due to nonthyroidal illness (NTI) [10].

Biological context of thyronine

  • Using a selected monoclonal antibody, we were able to identify a binding site on thyroglobulin containing iodinated thyronine [11].
  • However, thyronine did not inhibit collagen-induced platelet aggregation [12].
  • By mutagenesis studies we showed that this coded for selenocysteine, consistent with the previously described requirement for selenium for hepatic and renal thyronine deiodination [13].
  • 3'-isopropyl-3,5-diiodo-L-thyronine: a potent synthetic thyromimetic thyronine analog. Studies of its kinetics and biological potency in man and rats and its toxicology [14].
  • The findings described in this report raise the possibility that one of the mechanisms of thermogenesis control may be related to the regulation of Ca(2+)-ATPase isoforms expression by T3 [15].

Anatomical context of thyronine


Associations of thyronine with other chemical compounds


Gene context of thyronine

  • Human OATP-E transported 3,3',5-triiodo-L-thyronine (K(m), 0.9 microM), thyronine, and rT(3) in a Na(+)-independent manner [25].
  • There was no change in alpha mRNA after 3 days of T3 treatment but TSH-beta mRNA had decreased to 60% of control [26].
  • Emulsions incubated with plasma from hypothyroid rats had a decreased ratio of apolipoprotein E/apolipoprotein C compared with control rats or hypothyroid rats treated with T3 [27].
  • CCK-4, CCK-8, and substance P did not increase thyronine secretion measured as release of radioiodine into the circulation of mice pretreated with Na125I and T4 [28].
  • SERCA2 and GLUT4 protein levels were not significantly different between control and the T3 group [20].

Analytical, diagnostic and therapeutic context of thyronine


  1. Primary hormonogenic sites as conserved autoepitopes on thyroglobulin in murine autoimmune thyroiditis. Secondary role of iodination. Kong, Y.C., McCormick, D.J., Wan, Q., Motte, R.W., Fuller, B.E., Giraldo, A.A., David, C.S. J. Immunol. (1995) [Pubmed]
  2. Thyroid hormones in conditions of chronic malnutrition. A study with special reference to cancer cachexia. Persson, H., Bennegård, K., Lundberg, P.A., Svaninger, G., Lundholm, K. Ann. Surg. (1985) [Pubmed]
  3. Melatonin protects against oxidative damage and restores expression of GLUT4 gene in the hyperthyroid rat heart. Ghosh, G., De, K., Maity, S., Bandyopadhyay, D., Bhattacharya, S., Reiter, R.J., Bandyopadhyay, A. J. Pineal Res. (2007) [Pubmed]
  4. Effect of neonatal hyperthyroidism on GH gene expression reprogramming and physiological repercussions in rat adulthood. de Picoli Souza, K., da Silva, F.G., Nunes, M.T. J. Endocrinol. (2006) [Pubmed]
  5. Contribution of de novo protein synthesis to the hypertrophic effect of IGF-1 but not of thyroid hormones in adult ventricular cardiomyocytes. Bell, D., McDermott, B.J. Mol. Cell. Biochem. (2000) [Pubmed]
  6. Remodeling of myocyte dimensions in hypertrophic and atrophic rat hearts. Campbell, S.E., Korecky, B., Rakusan, K. Circ. Res. (1991) [Pubmed]
  7. Mechanism of loss of thermodynamic control in mitochondria due to hyperthyroidism and temperature. Luvisetto, S., Schmehl, I., Intravaia, E., Conti, E., Azzone, G.F. J. Biol. Chem. (1992) [Pubmed]
  8. Evidence for the presence of two active forms of cytosolic 3,5,3'-triiodo-L-thyronine (T3)-binding protein (CTBP) in rat kidney. Specialized functions of two CTBPs in intracellular T3 translocation. Hashizume, K., Miyamoto, T., Ichikawa, K., Yamauchi, K., Sakurai, A., Ohtsuka, H., Kobayashi, M., Nishii, Y., Yamada, T. J. Biol. Chem. (1989) [Pubmed]
  9. Hormonal regulation of myosin heavy chain and alpha-actin gene expression in cultured fetal rat heart myocytes. Gustafson, T.A., Bahl, J.J., Markham, B.E., Roeske, W.R., Morkin, E. J. Biol. Chem. (1987) [Pubmed]
  10. Relationship between inhibitor of extrathyroidal 5'-deiodinase activity and serum free fatty acid in children with nonthyroidal illness and acute ketosis. Hashimoto, H., Igarashi, N., Sato, T., Hashimoto, T. Endocrinol. Jpn. (1992) [Pubmed]
  11. The role of iodine in autoimmune thyroiditis. Rose, N.R., Saboori, A.M., Rasooly, L., Burek, C.L. Crit. Rev. Immunol. (1997) [Pubmed]
  12. 3,3',5'-Triiodothyronine inhibits collagen-induced human platelet aggregation. Masaki, H., Nishikawa, M., Urakami, M., Yoshimura, M., Toyoda, N., Mori, Y., Yoshikawa, N., Inada, M. J. Clin. Endocrinol. Metab. (1992) [Pubmed]
  13. Molecular cloning of the selenocysteine-containing enzyme type I iodothyronine deiodinase. Berry, M.J., Larsen, P.R. Am. J. Clin. Nutr. (1993) [Pubmed]
  14. 3'-isopropyl-3,5-diiodo-L-thyronine: a potent synthetic thyromimetic thyronine analog. Studies of its kinetics and biological potency in man and rats and its toxicology. Kaiser, C.A., Salomon-Montavon, N.A., Merkelbach, U., Burger, A.G. J. Clin. Endocrinol. Metab. (1983) [Pubmed]
  15. Thermogenesis and energy expenditure: control of heat production by the Ca(2+)-ATPase of fast and slow muscle. Reis, M., Farage, M., de Meis, L. Mol. Membr. Biol. (2002) [Pubmed]
  16. Preferential binding of tri-substituted thyronine analogs by bullfrog tadpole tail fin cytosol. Kistler, A., Yoshizato, K., Frieden, E. Endocrinology (1977) [Pubmed]
  17. Thyronines and probucol inhibition of human capillary endothelial cell-induced low density lipoprotein oxidation. Hanna, A.N., Titterington, L.C., Lantry, L.E., Stephens, R.E., Newman, H.A. Biochem. Pharmacol. (1995) [Pubmed]
  18. Exercise-induced stimulation of murine macrophage phagocytosis may be mediated by thyroxine. Forner, M.A., Barriga, C., Ortega, E. J. Appl. Physiol. (1996) [Pubmed]
  19. Involvement of K+ channels and calcium-dependent pathways in the action of T3 on amino acid accumulation and membrane potential in Sertoli cells of immature rat testis. Volpato, K.C., Menegaz, D., Leite, L.D., Barreto, K.P., de Vilhena Garcia, E., Silva, F.R. Life Sci. (2004) [Pubmed]
  20. Hyperthyroidism causes mechanical insufficiency of myocardium with possibly increased SR Ca2+-ATPase activity. Takeuchi, K., Minakawa, M., Otaki, M., Odagiri, S., Itoh, K., Murakami, A., Yaku, H., Kitamura, N. Jpn. J. Physiol. (2003) [Pubmed]
  21. Graves' disease associated with familial deficiency of thyroxine-binding globulin. Horwitz, D.L., Refetoff, S. J. Clin. Endocrinol. Metab. (1977) [Pubmed]
  22. A radioimmunoassay for measurement of thyronine and its acetic acid analog in urine. Chopra, I.J., Boado, R.J., Geffner, D.L., Solomon, D.H. J. Clin. Endocrinol. Metab. (1988) [Pubmed]
  23. Low protein-high carbohydrate diet induces alterations in the serum thyronine-binding proteins in the rat. Young, R.A., Braverman, L.E., Rajatanavin, R. Endocrinology (1982) [Pubmed]
  24. A study of the 3,5,3'-triiodothyronine sulfation activity in the adult and the fetal rat. Hurd, R.E., Santini, F., Lee, B., Naim, P., Chopra, I.J. Endocrinology (1993) [Pubmed]
  25. Identification of thyroid hormone transporters in humans: different molecules are involved in a tissue-specific manner. Fujiwara, K., Adachi, H., Nishio, T., Unno, M., Tokui, T., Okabe, M., Onogawa, T., Suzuki, T., Asano, N., Tanemoto, M., Seki, M., Shiiba, K., Suzuki, M., Kondo, Y., Nunoki, K., Shimosegawa, T., Iinuma, K., Ito, S., Matsuno, S., Abe, T. Endocrinology (2001) [Pubmed]
  26. Hormonal regulation of thyrotropin alpha and beta subunit mRNAs. Gurr, J.A., Vrontakis, M.E., Athanasian, E.A., Wagner, C.R., Kourides, I.A. Horm. Metab. Res. (1986) [Pubmed]
  27. Effects of hypothyroidism on the metabolism of lipid emulsion models of triacylglycerol-rich lipoproteins in rats. Redgrave, T.G., Elsegood, C.L., Mamo, J.C., Callow, M.J. Biochem. J. (1991) [Pubmed]
  28. Neuropeptides in the thyroid gland: distribution of substance P and gastrin/cholecystokinin and their effects on the secretion of iodothyronine and calcitonin. Ahrén, B., Grunditz, T., Ekman, R., Håkanson, R., Sundler, F., Uddman, R. Endocrinology (1983) [Pubmed]
  29. Effect of methoxychlor administration to male rats on hepatic, microsomal iodothyronine 5'-deiodinase, form I. Morrell, S.L., Fuchs, J.A., Holtzman, J.L. J. Pharmacol. Exp. Ther. (2000) [Pubmed]
  30. Pretreatment with 3,5,3'triiodo-L-thyronine (T3). Effects on myocyte contractile function after hypothermic cardioplegic arrest and rewarming. Walker, J.D., Crawford, F.A., Spinale, F.G. J. Thorac. Cardiovasc. Surg. (1995) [Pubmed]
  31. Responses to mild cold stress are predicted by different individual characteristics in young and older subjects. Degroot, D.W., Havenith, G., Kenney, W.L. J. Appl. Physiol. (2006) [Pubmed]
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