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Chemical Compound Review

SureCN677645     2-amino-3-[4-(4-hydroxy-3- iodo-phenoxy)-3...

Synonyms: CHEMBL1743303, CHEBI:35430, CTK8I7880, AC1L23HP, 3,3'-T2, ...
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Disease relevance of 3,3'-T2

  • In hyperthyroidism, the excretions of free and glucuronidated iodothyronines were increased, whereas the increase of the excretions of sulfated iodothyronines were less pronounced, only reaching statistical significance for 3,3'-T2 (P less than 0.02) [1].
  • Serum concentrations of 3,3'-T2 were measured in 4 groups of patients with nonthyroidal illnesses (NTI), i.e. brain injuries (n = 15), sepsis (n = 24), liver disease (n = 22), and brain tumors (n = 23) [2].
  • Serum T4, T3, and 3,3'-T2 levels were reduced in patients with liver cirrhosis, whereas serum rT3 and 3',5'-T2 levels were increased, Serum 3'-T1 levels were unaltered [3].
  • In conclusion, our results show that, contrary to expectation, a low T3 syndrome in NTI is not always associated with low serum concentrations of 3,3'-T2 [2].
  • The inner ring monodeiodination [T4 to rT3, T3 to 3,3'-diiodothyronine(3,3'-T2)] as well as the outer ring monodeiodination (T4 to T3, rT3 to 3,3'-T2) was demonstrated with thyroid tissues obtained from patients with Graves' disease by measuring the products by RIAs [4].

High impact information on 3,3'-T2


Chemical compound and disease context of 3,3'-T2


Biological context of 3,3'-T2

  • A statistical disorder model for the ligand was applied with a 50% occupancy to account for the discrepancy between the crystallographic 2-fold symmetry of the binding sites and the lack of such symmetry for 3,3'-T2 [12].
  • Transfection of COS1 and JEG3 cells with hMCT8 cDNA resulted in 2- to 3-fold increases in uptake of T(3) and T(4) but little or no increase in rT(3) or 3,3'-diiodothyronine (3,3'-T(2)) uptake [13].
  • The latter submodel was patterned initially after 3,3'-diiodothyronine kinetics [14].
  • The rabbit antiserum to rT3S was highly specific; T4, T3, rT3, and 3,3'-T2 showed less than 0.002% cross-reaction with the antiserum [15].
  • In pre- and prometamorphic tadpoles, any T3 produced from T4 is rapidly converted to 3,3'-diiodothyronine by the 5 D system and thus accumulation is prevented [16].

Anatomical context of 3,3'-T2

  • In conclusion, significant production of 3,3'-T2 from rT3 by rat hepatocytes is only observed if further sulfation is inhibited [5].
  • The inhibition profiles of the 3,3'-T2 sulfotransferase activities of liver and kidney cytosol obtained by addition of 10 micromol/L of the various analogs were better correlated with the inhibition profile of SULT1A1 than with that of SULT1A3 [17].
  • After 20-h incubation, the percentage of added radioactivity present as conjugates in the media and oocytes amounted to 0.9 +/- 0.2 and 1.0 +/- 0.1 for T4, less than 0.1 and less than 0.1 for T3, 32.5 +/- 0.4 and 29.3 +/- 0.2 for rT3, and 3.8 +/- 0.3 and 2.3 +/- 0.2 for 3,3'-T2, respectively (mean +/- SEM; n = 3) [18].
  • For the nonhormonal iodothyronines, about 6% of injected monoiodothyronine, 3% of injected 3',5'-T2, 2% of injected 3,3'-T2, and less than 1% of injected rT3 were excreted in feces as such, indicating that these substances are nearly completely deiodinated in vivo [19].
  • As confirmed by incubations with isolated rat liver microsomes, direct inner ring deiodination of T3 is largely mediated by a low Km, PTU-insensitive, type III-like iodothyronine deiodinase, and production of 3,3'-T2 is only observed if its rapid sulfation is prevented [20].

Associations of 3,3'-T2 with other chemical compounds


Gene context of 3,3'-T2


Analytical, diagnostic and therapeutic context of 3,3'-T2

  • In five experiments, the percent composition of 125I-labeled iodothyronines in the perfusion buffer and placenta effluent was 95.3 +/- 1.0 (mean +/- SE) and 70.2 +/- 2.1 for T3 (P less than 0.01), 2.5 +/- 0.7 and 20.1 +/- 1.8 for 3,3'-T2 (P less than 0.01), and 0 and 8.2 +/- 0.9 for 3'-T1 [29].
  • The sulfates and sulfamates of T4, T3, rT3, and 3,3'-diiodothyronine could be separated by reverse phase HPLC [30].
  • This low value was attributable to two factors: 1) the use of a diet low enough in iodine content to produce extreme iodine deficiency, and 2) the use of a paper chromatography system that successfully separates T4 from the minor iodothyronines, 3,3'-diiodothyronine (T2) and 3',5',3-triiodothyronine (reverse T3; T3') [31].
  • The development of a highly sensitive and specific radioimmunoassay for 3,3'-di-iodothyronine (3,3'-T2) is described [32].
  • The results indicate that the high serum rT3 observed during treatment with PTU is not due to an increase in rT3 production, but to a decrease in the metabolic clearance rate of rT3. rT3 infusion was followed by an increase in serum 3,3'-T2 which was similar whether PTU or MMI was given [10].


  1. Urinary excretion of free and conjugated 3',5'-diiodothyronine and 3,3'-diiodothyronine. Faber, J., Busch-Sørensen, M., Rogowski, P., Kirkegaard, C., Siersbaek-Nielsen, K., Friis, T. J. Clin. Endocrinol. Metab. (1981) [Pubmed]
  2. 3,3'-Diiodothyronine concentrations in the sera of patients with nonthyroidal illnesses and brain tumors and of healthy subjects during acute stress. Pinna, G., Hiedra, L., Meinhold, H., Eravci, M., Prengel, H., Brödel, O., Gräf, K.J., Stoltenburg-Didinger, G., Bauer, M., Baumgartner, A. J. Clin. Endocrinol. Metab. (1998) [Pubmed]
  3. Kinetic studies of thyroxine, 3,5,3'-triiodothyronine, 3,3,5'-triiodothyronine, 3',5'-diiodothyronine, 3,3'-diiodothyronine, and 3'-monoiodothyronine in patients with liver cirrhosis. Faber, J., Thomsen, H.F., Lumholtz, I.B., Kirkegaard, C., Siersbaek-Nielsen, K., Friis, T. J. Clin. Endocrinol. Metab. (1981) [Pubmed]
  4. Sequential deiodination of thyroxine in human thyroid gland. Ishii, H., Inada, M., Tanaka, K., Mashio, Y., Naito, K., Nishikawa, M., Matsuzuka, F., Kuma, K., Imura, H. J. Clin. Endocrinol. Metab. (1982) [Pubmed]
  5. Metabolism of reverse triiodothyronine by isolated rat hepatocytes. Rooda, S.J., van Loon, M.A., Visser, T.J. J. Clin. Invest. (1987) [Pubmed]
  6. Hepatic extraction and renal production of 3,3'-diiodothyronine and 3',5'-diiodothyronine in man. Faber, J., Faber, O.K., Lund, B., Kirkegaard, C., Wahren, J. J. Clin. Invest. (1980) [Pubmed]
  7. Thyroid hormonelike actions of 3,3',5'-L-triiodothyronine nad 3,3'-diiodothyronine. Papavasiliou, S.S., Martial, J.A., Latham, K.R., Baxter, J.D. J. Clin. Invest. (1977) [Pubmed]
  8. Structural aspects of inotropic bipyridine binding. Crystal structure determination to 1.9 A of the human serum transthyretin-milrinone complex. Wojtczak, A., Luft, J.R., Cody, V. J. Biol. Chem. (1993) [Pubmed]
  9. Serum levels of T4, T3, reverse T3, 3,3'-diiodothyronine and 3',5'-diiodothyronine in obesity, before and after jejuno-ileal bypass. Faber, J., Sørensen, T.I., Lumholtz, I.B., Klein, H.C., Kirkegaard, C., Blickert-Toft, M. Clin. Endocrinol. (Oxf) (1981) [Pubmed]
  10. Dynamics of serum rT3 and 3,3'-T2 during rT3 infusion in patients treated for thyrotoxicosis with propylthiouracil or methimazole. Laurberg, P., Weeke, J. Clin. Endocrinol. (Oxf) (1980) [Pubmed]
  11. Phenolic ring deiodination in cultured rat hepatoma cells, and subcellular localization of deiodinases in cultured rat hepatoma, monkey hepatocarcinoma cells and normal rat liver homogenates. Sorimachi, K., Niwa, A., Yasumura, Y. Biochim. Biophys. Acta (1980) [Pubmed]
  12. Mechanism of molecular recognition. Structural aspects of 3,3'-diiodo-L-thyronine binding to human serum transthyretin. Wojtczak, A., Luft, J., Cody, V. J. Biol. Chem. (1992) [Pubmed]
  13. Thyroid hormone transport by the human monocarboxylate transporter 8 and its rate-limiting role in intracellular metabolism. Friesema, E.C., Kuiper, G.G., Jansen, J., Visser, T.J., Kester, M.H. Mol. Endocrinol. (2006) [Pubmed]
  14. A kinetic model of human thyroid hormones and their conversion products. McGuire, R.A., Hays, M.T. J. Clin. Endocrinol. Metab. (1981) [Pubmed]
  15. The development of a radioimmunoassay for reverse triiodothyronine sulfate in human serum and amniotic fluid. Wu, S.Y., Huang, W.S., Polk, D., Chen, W.L., Reviczky, A., Williams, J., Chopra, I.J., Fisher, D.A. J. Clin. Endocrinol. Metab. (1993) [Pubmed]
  16. Hepatic iodothyronine 5-deiodinase activity in Rana catesbeiana tadpoles at different stages of the life cycle. Galton, V.A., Hiebert, A. Endocrinology (1987) [Pubmed]
  17. Characterization of human iodothyronine sulfotransferases. Kester, M.H., Kaptein, E., Roest, T.J., van Dijk, C.H., Tibboel, D., Meinl, W., Glatt, H., Coughtrie, M.W., Visser, T.J. J. Clin. Endocrinol. Metab. (1999) [Pubmed]
  18. Rapid sulfation of 3,3',5'-triiodothyronine in native Xenopus laevis oocytes. Friesema, E.C., Docter, R., Krenning, E.P., Everts, M.E., Hennemann, G., Visser, T.J. Endocrinology (1998) [Pubmed]
  19. Fecal and urinary excretion of six iodothyronines in the rat. DiStefano, J.J., Sapin, V. Endocrinology (1987) [Pubmed]
  20. Metabolism of triiodothyronine in rat hepatocytes. Rooda, S.J., Otten, M.H., van Loon, M.A., Kaptein, E., Visser, T.J. Endocrinology (1989) [Pubmed]
  21. Measurements of serum 3',5'-diiodothyronine and 3,3'-diiodothyronine concentrations in normal subjects and in patients with thyroid and nonthyroid disease: studies of 3',5'-diiodothyronine metabolism. Faber, J., Kirkegaard, C., Lumholtz, I.B., Siersbaek-Nielsen, K., Friis, T. J. Clin. Endocrinol. Metab. (1979) [Pubmed]
  22. A 3,3'-diiodothyronine sulfate cross-reactive compound in serum from pregnant women. Wu, S.Y., Polk, D.H., Chen, W.L., Fisher, D.A., Huang, W.S., Yee, B. J. Clin. Endocrinol. Metab. (1994) [Pubmed]
  23. Human placenta is an active site of thyroxine and 3,3'5-triiodothyronine tyrosyl ring deiodination. Roti, E., Fang, S.L., Green, K., Emerson, C.H., Braverman, L.E. J. Clin. Endocrinol. Metab. (1981) [Pubmed]
  24. The extrathyroidal effect of D,L-propranolol on 3,3',5'-triiodothyronine, 3',5'-diiodothyronine, 3,3'-diiodothyronine, and 3'-monoiodothyronine kinetics. Lumholtz, I.B., Faber, J., Kirkegaard, C., Siersbaek-Nielsen, K., Friis, T. J. Clin. Endocrinol. Metab. (1982) [Pubmed]
  25. Sulfation of thyroid hormone by estrogen sulfotransferase. Kester, M.H., van Dijk, C.H., Tibboel, D., Hood, A.M., Rose, N.J., Meinl, W., Pabel, U., Glatt, H., Falany, C.N., Coughtrie, M.W., Visser, T.J. J. Clin. Endocrinol. Metab. (1999) [Pubmed]
  26. Cloning and characterization of type III iodothyronine deiodinase from the fish Oreochromis niloticus. Sanders, J.P., Van der Geyten, S., Kaptein, E., Darras, V.M., Kühn, E.R., Leonard, J.L., Visser, T.J. Endocrinology (1999) [Pubmed]
  27. Increased thyroxine sulfate levels in critically ill patients as a result of a decreased hepatic type I deiodinase activity. Peeters, R.P., Kester, M.H., Wouters, P.J., Kaptein, E., van Toor, H., Visser, T.J., Van den Berghe, G. J. Clin. Endocrinol. Metab. (2005) [Pubmed]
  28. Identification of thyroid hormone transporters. Friesema, E.C., Docter, R., Moerings, E.P., Stieger, B., Hagenbuch, B., Meier, P.J., Krenning, E.P., Hennemann, G., Visser, T.J. Biochem. Biophys. Res. Commun. (1999) [Pubmed]
  29. Inner-ring deiodination of 3,5,3'-triiodothyronine in the in situ perfused guinea pig placenta. Castro, M.I., Braverman, L.E., Alex, S., Wu, C.F., Emerson, C.H. J. Clin. Invest. (1985) [Pubmed]
  30. Synthesis and some properties of sulfate esters and sulfamates of iodothyronines. Mol, J.A., Visser, T.J. Endocrinology (1985) [Pubmed]
  31. Formation of 3,3'-diiodothyronine and 3',5',3-triiodothyronine (reverse T3) in thyroid glands of rats and in enzymatically iodinated thyroglobulin. Taurog, A., Riesco, G., Larsen, P.R. Endocrinology (1976) [Pubmed]
  32. Radioimmunoassay of 3,3'-di-iodothyronine in unextracted serum: the effect of endogenous tri-iodothyronine. Visser, T.J., Krieger-Quist, L.M., Docter, R., Hennemann, G. J. Endocrinol. (1978) [Pubmed]
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