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Thyroid hormone uptake by hepatocytes: structure-activity relationships of phenylanthranilic acids with inhibitory activity

Cite this: J. Med. Chem. 1993, 36, 9, 1272–1277
Publication Date (Print):April 1, 1993
https://doi.org/10.1021/jm00061a019
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    12. Rong Hu, Yunping Zhoujin, Meng Liu, Mingtao Zhang, Sean Parkin, Panpan Zhou, Jianzhi Wang, Faquan Yu, Sihui Long. Solution growth and thermal treatment of crystals lead to two new forms of 2-((2,6-dimethylphenyl)amino)benzoic acid. RSC Advances 2018, 8 (28) , 15459-15470. https://doi.org/10.1039/C7RA13353G
    13. AlberTinka J. Murk, Eddy Rijntjes, Bas J. Blaauboer, Rebecca Clewell, Kevin M. Crofton, Milou M.L. Dingemans, J. David Furlow, Robert Kavlock, Josef Köhrle, Robert Opitz, Theo Traas, Theo J. Visser, Menghang Xia, Arno C. Gutleb. Mechanism-based testing strategy using in vitro approaches for identification of thyroid hormone disrupting chemicals. Toxicology in Vitro 2013, 27 (4) , 1320-1346. https://doi.org/10.1016/j.tiv.2013.02.012
    14. Yurong Lai. Organic anion-transporting polypeptides (OATPs/SLCOs). 2013, 353-454. https://doi.org/10.1533/9781908818287.353
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    20. Daniel E. Westholm, David D. Stenehjem, Jon N. Rumbley, Lester R. Drewes, Grant W. Anderson. Competitive Inhibition of Organic Anion Transporting Polypeptide 1c1-Mediated Thyroxine Transport by the Fenamate Class of Nonsteroidal Antiinflammatory Drugs. Endocrinology 2009, 150 (2) , 1025-1032. https://doi.org/10.1210/en.2008-0188
    21. Vaso N. Dokorou, Dimitra Kovala-Demertzi, Maria Louloudi, Anca Silvestru, Mavroudis A. Demertzis. Synthesis, characterization and catalytic properties of diorganotin derivatives. Crystal and molecular structure of the first complex of 2-(2-methyl-3-nitroanilino)benzoic acid of 1,2:3,4-di-μ2-2-(2-methyl-3-nitroanilino)benzoato-O,O-1,3-bis-2-(2-methyl-3-nitroanilino)benzoato-O-1,2,4:2,3,4-di-μ3-oxo-tetrakis[di-methyltin(IV)]. Journal of Organometallic Chemistry 2008, 693 (24) , 3587-3592. https://doi.org/10.1016/j.jorganchem.2008.07.011
    22. Hanakere R. Girisha, Gejjalagere R. Srinivasa, D. Channe Gowda. A simple and environmentally friendly method for the synthesis of N -phenylanthranilic acid derivatives. Journal of Chemical Research 2006, 2006 (5) , 342-344. https://doi.org/10.3184/030823406777411098
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    24. Dimitra Kovala‐Demertzi, Vaso Dokorou, Rafal Kruszynski, Joanna Wiecek, Tadeusz J. Bartczak, Mavroudis A. Demertzis. Condensation Reaction of Dimethyltin(IV) Oxide with 2‐(2,3‐Dichloroanilino)benzoic Acid Synthesis and Study of a Novel Dimeric Tetraorganodistannoxane. Zeitschrift für anorganische und allgemeine Chemie 2005, 631 (12) , 2481-2484. https://doi.org/10.1002/zaac.200500242
    25. Vaso Dokorou, Dimitra Kovala‐Demertzi, Jerry P. Jasinski, Angeliki Galani, Mavroudis A. Demertzis. Synthesis, Spectroscopic Studies, and Crystal Structures of Phenylorganotin Derivatives with [Bis(2,6‐dimethylphenyl)amino]benzoic Acid: Novel Antituberculosis Agents. Helvetica Chimica Acta 2004, 87 (8) , 1940-1950. https://doi.org/10.1002/hlca.200490175
    26. Vaso Dokorou, Mavroudis A Demertzis, Jerry P Jasinski, Dimitra Kovala-Demertzi. Synthesis and spectroscopic studies of diorganotin derivatives with 2-[(2,6-dimethylphenyl)amino]benzoic acid. Crystal and molecular structure of the first complexes of 2-[(2,6-dimethylphenyl)amino]benzoic acid. Crystal and molecular structures of 1,2:3,4-di-μ2-2-[(2,6-dimethylphenyl)amino]-benzoato-O,O-1,3-bis-2-[(2,6-dimethylphenyl)amino]benzoato-O-1,2,4:2,3,4-di-μ3-oxo-tetrakis[di-butyltin(IV)] and bis-2-[(2,6-dimethylphenyl)amino]benzoato-di-n-butyltin(IV). Journal of Organometallic Chemistry 2004, 689 (2) , 317-325. https://doi.org/10.1016/j.jorganchem.2003.10.018
    27. Sylvie Daminet, Duncan C. Ferguson. Influence of Drugs on Thyroid Function in Dogs. Journal of Veterinary Internal Medicine 2003, 17 (4) , 463-472. https://doi.org/10.1111/j.1939-1676.2003.tb02467.x
    28. Georg Hennemann, Roelof Docter, Edith C. H. Friesema, Marion de Jong, Eric P. Krenning, Theo J. Visser. Plasma Membrane Transport of Thyroid Hormones and Its Role in Thyroid Hormone Metabolism and Bioavailability. Endocrine Reviews 2001, 22 (4) , 451-476. https://doi.org/10.1210/edrv.22.4.0435
    29. Hennemann, Everts, De Jong, Lim, Krenning, Docter. The significance of plasma membrane transport in the bioavailability of thyroid hormone. Clinical Endocrinology 1998, 48 (1) , 1-8. https://doi.org/10.1046/j.1365-2265.1998.00377.x
    30. J. W. Barlow, T. C. Crowe, D. J. Topliss. Thyroid Hormone Antagonism. 1997, 319-342. https://doi.org/10.1007/978-3-642-60709-7_13
    31. J. R. Stockigt, C.-F. Lim, J. W. Barlow, D. J. Topliss. Thyroid Hormone Transport. 1997, 119-150. https://doi.org/10.1007/978-3-642-60709-7_5
    32. Ralff C.J. Ribeiro, Ralph R. Cavalieri, Noureddine Lomri, Cherradi M. Rahmaoui, John D. Baxter, Bruce F. Scharschmidt. Thyroid Hormone Export Regulates Cellular Hormone Content and Response. Journal of Biological Chemistry 1996, 271 (29) , 17147-17151. https://doi.org/10.1074/jbc.271.29.17147
    33. Ronald P.J. Oude Elferink, Dirk K.F. Meijer, Folkert Kuipers, Peter L.M. Jansen, Albert K. Groen, Geny M.M. Groothuis. Hepatobiliary secretion of organic compounds; molecular mechanisms of membrane transport. Biochimica et Biophysica Acta (BBA) - Reviews on Biomembranes 1995, 1241 (2) , 215-268. https://doi.org/10.1016/0304-4157(95)00006-D
    34. Laura Kragie. Membrane iodothyronine transporters part I: Review of physiology. Endocrine Research 1994, 20 (4) , 319-341. https://doi.org/10.1080/07435809409030410

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