Species-specific lipophilicity of thyroid hormones and their precursors in view of their membrane transport properties

Journal of Pharmaceutical and Biomedical Analysis

Volumn 76, Issue , 2013, Pages 112-118

  Tóth, Gergo ^a   Mazák, Károly ^a   Hosztafi, Sándor ^a   Kökösi, József ^a   Noszál, Béla ^a  

^a SEMMELWEIS UNIVERSITY   (Hungary)

Author keywords

Liothyronine; Lipophilicity; Logp; Membrane transport; Microscopic partition coefficient; Thyroid hormone

Indexed keywords

3,3',5' TRIIODOTHYRONINE; AMINO ACID; DIIODOTYROSINE; IODOTYROSINE; LIOTHYRONINE; THYROXINE;

ARTICLE; DIFFUSION; IODINATION; ISOMER; LIPOPHILICITY; MEMBRANE TRANSPORT; PARTITION COEFFICIENT; PH; PHYSICAL CHEMISTRY; PRECURSOR; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; SPECIES DIFFERENCE; TITRIMETRY; ULTRAVIOLET RADIATION;

BIOLOGICAL TRANSPORT; DIIODOTYROSINE; HYDROGEN-ION CONCENTRATION; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MONOIODOTYROSINE; SPECIES SPECIFICITY; THYROXINE; TRIIODOTHYRONINE; TRIIODOTHYRONINE, REVERSE;

EID: 84872202115     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2012.12.010     Document Type: Article

References (32)

1. Cody V. Thyroid hormone interactions: molecular conformation, protein binding, and hormone action. Endocr. Rev. 1980, 1:140-166.
2. Chemburkar S.R., Deming K.C., Reddy R.E. Chemistry of thyroxine: an historical perspective and recent progress on its synthesis. Tetrahedron 2010, 66:1955-1962.
3. De Vijlder J.J.M., Den Hartog M.T. Anionic iodotyrosine residues are required for iodothyronine synthesis. Eur. J. Endocrinol. 1998, 138:227-231.
4. Farwell A.P., Braverma: Thyroid L.E. Antithyroid Drugs. Goodman & Gilman's the pharmacological basis of therapeutics 2006, 1383-1409. McGraw-Hill, New York. 11th ed. L.L. Brunton, J.S. Lazo, K.L. Parker (Eds.).
5. Hennemann G., Docter R., Friesema E.C., de Jong M., Krenning E.P., Visser T.J. Plasma membrane transport of thyroid hormones and its role in thyroid hormone metabolism and bioavailability. Endocr. Rev. 2001, 22:451-476.
6. Hulbert A.J. Thyroid hormones and their effects: a new perspective. Biol. Rev. 2000, 75:519-631.
7. Chehin R.N., Rintoul M.R., Morero R.D., Farias R.N. Differential effect of triiodothyronine and thyroxine on liposomes containing cholesterol: physiological speculations. J. Membr. Biol. 1995, 147:217-221.
8. Avdeef A. Physicochemical profiling. Curr. Topics Med. Chem. 2002, 1:277-351.
9. Comer J., Tam K. Lipophilicity profiles: theory and measurement. Pharmacokinetic Optimization in Drug Research-Biological, Physicochemical, and Computational Strategies 2001, 275-304. Verlag Helvetica Chimica Acta, Zurich. B. Testa, H. van de Waterbeemd, G. Folkers, R. Guy (Eds.).
10. Hansch C. On the future of QSAR. Medicinal chemistry for the 21st century 1994, 281-293. Metcalf Blackwell, Oxford. C.G. Wermuth, N. Koga, H. König (Eds.).
11. Pagliara A., Carrupt P.A., Caron G., Gaillard P., Testa B. Lipophilicity profiles of ampholytes. Chem. Rev. 1997, 97:3385-3400.
12. Mazák K., Kökösi J., Noszál B. Lipophilicity of zwitterions and related species: a new insight. Eur. J. Pham. Sci. 2011, 44:68-73.
13. Mazák K., Noszál B. Zwitterions can be predominant in membrane penetration of drugs: an experimental proof. J. Med. Chem. 2012, 55:6942-6947.
14. Tóth G., Hosztafi S., Zs Kovács, Noszál B. The site-specific basicity of thyroid hormones and their precursors as regulators of their biological functions. J. Pharm. Biomed. Anal. 2012, 61:156-164.
15. Mazák K., Tóth G., Kökösi J., Noszál B. Thyroxine lipophilicity is dominated by its zwitterionic microspecies. Eur. J. Pharm. Sci. 2012, 921-925.
16. Hillier A.P. The binding of thyroid hormones to phospholipid membranes. J. Physiol. 1970, 211:585-597.
17. Dickson P.W., Aldred A.R., Menting J.G.T., Marley P.D., Sawyer W.H., Schreiber G. Thyroxine transport in choroid plexus. J. Biol. Chem. 1987, 262:13907-13915.
18. Ishigami K., Katsuta R., Shibata C., Hayakawa Y., Watanabe H., Kitahara T. Synthesis and structure revision of tyroscherin, and bioactivities of its stereoisomers against IGF-1-dependent tumor cells. Tetrahedron 2009, 65:3629-3638.
19. Loeser A., Ruland H., Trikojus: Darstellung V.M. Eigenschaften und biologische Wirkungen von Derivaten (Äthern) des Thyroxins, Dijodthyronins und Dijodtyrosins, Naunyn-Schmiedebergs. Arch. Exp. Path. Pharm. 1938, 189:664-665.
20. Mazák K., Vámos J., Nemes A., Rácz Á., Noszál B. Lipophilicity of vinpocetine and related compounds characterized by reversed-phase thin-layer chromatography. J. Chromatogr. A. 2003, 996:95-203.
21. Noszál B. Acid-Base Properties of Bioligands. Biocoordination Chemistry: Coordination Equilibria in Biologically Active Systems 1990, 18-55. Ellis Horwood, Chichester. K. Burger (Ed.).
22. Mazák K., Noszál B. Lipophilicity of morphine microspecies and their contribution to the lipophilicity profile. Eur. J. Pham. Sci. 2012, 45:205-210.
23. Marvin program (2011), http://www.chemaxon.com/marvin/sketch/index.php.
24. Rozmer Zs., Perjési P., Takács-Novák K. Use of RP-TLC for determination of log P of isomeric chalcones and cyclic chalcone analogues. J. Planar. Chrom. Mod. TLC 2006, 19:124-128.
25. Altomare C., Carrupt P., Tayar N., Testa B., Nagatsu: Electronic T. Conformational effects on the lipophilicity of isomers and analogs of the neurotoxin 1-methyl-4-phenylpyridinium (MPP+). Helv. Chim. Acta 1991, 74:290-296.
26. Károlyházi L., Szabó D., Anwair M.A.S., Borosy A.P., Takács-Novák K., Mátyus P. Lipophilicity of regioisomers: a case study on 3(2H)-pyridazinones. J. Mol. Struc. Theochem. 2002, 578:89-91.
27. Wang Y., Mathis C.A., Huang G.F., Debnath M.L., Holt D.P., Shao L., Klunk W.E. Effects of lipophilicity on the affinity and nonspecific binding of iodinated benzothiazole derivatives. J. Mol. Neurosci. 2003, 20:255-260.
28. Schreiber G., Richardson S.J. The evolution of gene expression, structure and function of transthyretin. Comp. Biochem. Physiol. B: Biochem. Mol. Biol. 1997, 116:137-160.
29. Lai C.S., Krytowski W., Niuw C.H., Cheng S.Y. Transverse motion of spin-labelled 3,3',5-triiodothyronine in phospholipid bilayers. Biochem. Biophys. Res. Commun. 1985, 131:408-412.
30. Kragie L. Membrane iodothyronine transporters. Part 1. Review of physiology. Endocr. Res. 1994, 20:319-341.
31. Kragie L. Membrane iodothyronine transporters. Part 2. Review of protein biochemistry. Endocr. Res. 1996, 22:95-119.
32. Pabla D., Akhlaghi F., Zia H. Intestinal permeability enhancement of levothyroxine sodium by straight chain fatty acids studied in MDCK epithelial cell line. Eur. J. Pharm. Sci. 2010, 40:466-472.