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Volumn 61, Issue , 2012, Pages 156-164

The site-specific basicity of thyroid hormones and their precursors as regulators of their biological functions

Author keywords

Microspeciation; NMR; Protonation constants; Thyroid hormone biosynthesis; Thyroxine

Indexed keywords

3,3',5' TRIIODOTHYRONINE; IODOTYROSINE; LIOTHYRONINE; PROTON; THYROGLOBULIN; THYROXINE;

EID: 84856085563     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2011.11.020     Document Type: Article
Times cited : (12)

References (37)
  • 1
    • 76649101465 scopus 로고    scopus 로고
    • Chemistry of thyroxine: an historical perspective and recent progress on its synthesis
    • 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.
    • (2010) Tetrahedron , vol.66 , pp. 1955-1962
    • Chemburkar, S.R.1    Deming, K.C.2    Reddy, R.E.3
  • 2
    • 49649096773 scopus 로고    scopus 로고
    • Pendred syndrome and iodide transport in the thyroid
    • Kopp P., Pesce L., Solis S.J.C. Pendred syndrome and iodide transport in the thyroid. Trends Endocrinol. Metab. 2008, 19:260-268.
    • (2008) Trends Endocrinol. Metab. , vol.19 , pp. 260-268
    • Kopp, P.1    Pesce, L.2    Solis, S.J.C.3
  • 3
    • 79960325538 scopus 로고    scopus 로고
    • Influence of thyroidectomy on thyroxine metabolism and turnover rate in rats
    • Nagao H., Imazu T., Hayashi H., Takahashi K., Minato K. Influence of thyroidectomy on thyroxine metabolism and turnover rate in rats. J. Endocrinol. 2011, 210:117-123.
    • (2011) J. Endocrinol. , vol.210 , pp. 117-123
    • Nagao, H.1    Imazu, T.2    Hayashi, H.3    Takahashi, K.4    Minato, K.5
  • 4
    • 18744419707 scopus 로고    scopus 로고
    • Effects of thyroxine as compared with thyroxine plus triiodothyronine in patients with hypothyroidism
    • Bunevičius R., KaŽanavičius G., Žalinkevičius R., Prange A.J. Effects of thyroxine as compared with thyroxine plus triiodothyronine in patients with hypothyroidism. N. Engl. J. Med. 1999, 340:424-429.
    • (1999) N. Engl. J. Med. , vol.340 , pp. 424-429
    • Bunevičius, R.1    Kažanavičius, G.2    Žalinkevičius, R.3    Prange, A.J.4
  • 7
    • 84856114912 scopus 로고    scopus 로고
    • Marvin program 5.3.8.
    • Marvin program 5.3.8. , 2010. http://www.chemaxon.com/.
    • (2010)
  • 8
    • 0034892914 scopus 로고    scopus 로고
    • Plasma membrane transport of thyroid hormones and its role in thyroid hormone metabolism and bioavailability
    • 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.
    • (2001) Endocr. Rev. , vol.22 , pp. 451-476
    • Hennemann, G.1    Docter, R.2    Friesema, E.C.3    de Jong, M.4    Krenning, E.P.5    Visser, T.J.6
  • 10
    • 0018995029 scopus 로고
    • Thyroid hormone interactions: molecular conformation, protein binding, and hormone action
    • Cody V. Thyroid hormone interactions: molecular conformation, protein binding, and hormone action. Endocr. Rev. 1980, 1:140-166.
    • (1980) Endocr. Rev. , vol.1 , pp. 140-166
    • Cody, V.1
  • 12
    • 17944384102 scopus 로고
    • Physical chemistry of thyroid hormones. II. Effect of dimethyl sulfoxide concentration on protonation constants measured in water-dimethylsulfoxide media containing 0.5M sodium perchlorate. Extrapolation to aqueous medium
    • Collance E., Paris M. Physical chemistry of thyroid hormones. II. Effect of dimethyl sulfoxide concentration on protonation constants measured in water-dimethylsulfoxide media containing 0.5M sodium perchlorate. Extrapolation to aqueous medium. Bull. Soc. Chim. Fr. 1983, 7-8I:I-149-I-154.
    • (1983) Bull. Soc. Chim. Fr.
    • Collance, E.1    Paris, M.2
  • 13
    • 0142074175 scopus 로고
    • Academic Press, New York.
    • Analytical Profiles of Drug Substances 1976, vol. 5. Academic Press, New York, pp. 225-282.
    • (1976) Analytical Profiles of Drug Substances , vol.5 , pp. 225-282
  • 14
    • 60749105377 scopus 로고    scopus 로고
    • Using measured pK(a), LogP and solubility to investigate supersaturation and predict BCS class
    • Comer J.E.A., Box K.J. Using measured pK(a), LogP and solubility to investigate supersaturation and predict BCS class. Curr. Drug Metab. 2008, 9:869-878.
    • (2008) Curr. Drug Metab. , vol.9 , pp. 869-878
    • Comer, J.E.A.1    Box, K.J.2
  • 15
    • 0032751285 scopus 로고    scopus 로고
    • Proton speciation and microspeciation of vinpocetine and related compounds in aqueous and biomimetic media
    • Mazák K., Nemes A., Noszál B. Proton speciation and microspeciation of vinpocetine and related compounds in aqueous and biomimetic media. Pharm. Res. 1999, 16:1757-1763.
    • (1999) Pharm. Res. , vol.16 , pp. 1757-1763
    • Mazák, K.1    Nemes, A.2    Noszál, B.3
  • 16
    • 33846126544 scopus 로고    scopus 로고
    • Potentiometric and spectrophotometric pKa determination of water-insoluble compounds: validation study in a new cosolvent system
    • Völgyi G., Ruiz R., Box K., Comer J., Bosch E., Takács-Novák K. Potentiometric and spectrophotometric pKa determination of water-insoluble compounds: validation study in a new cosolvent system. Anal. Chim. Acta 2007, 583:418-428.
    • (2007) Anal. Chim. Acta , vol.583 , pp. 418-428
    • Völgyi, G.1    Ruiz, R.2    Box, K.3    Comer, J.4    Bosch, E.5    Takács-Novák, K.6
  • 17
    • 67349226351 scopus 로고    scopus 로고
    • Triprotic acid-base microequilibria and pharmacokinetic sequelae of cetirizine
    • Marosi A., Kovács Z., Béni S., Kökösi J., Noszál B. Triprotic acid-base microequilibria and pharmacokinetic sequelae of cetirizine. Eur. J. Pharm. Sci. 2009, 37:321-328.
    • (2009) Eur. J. Pharm. Sci. , vol.37 , pp. 321-328
    • Marosi, A.1    Kovács, Z.2    Béni, S.3    Kökösi, J.4    Noszál, B.5
  • 19
    • 4444260564 scopus 로고    scopus 로고
    • Determination of microscopic acid-base parameters from NMR-pH titrations
    • Szakács Z., Kraszni M., Noszál B. Determination of microscopic acid-base parameters from NMR-pH titrations. Anal. Bioanal. Chem. 2004, 378:1428-1448.
    • (2004) Anal. Bioanal. Chem. , vol.378 , pp. 1428-1448
    • Szakács, Z.1    Kraszni, M.2    Noszál, B.3
  • 20
    • 0000762050 scopus 로고
    • Determination of double ions in solutions of ampholytes
    • Elbert L. Determination of double ions in solutions of ampholytes. Z. Phys. Chem. 1926, 121:385-400.
    • (1926) Z. Phys. Chem. , vol.121 , pp. 385-400
    • Elbert, L.1
  • 22
    • 0000930525 scopus 로고
    • A complete ionization scheme for tyrosine, and the ionization constants of some tyrosine derivatives
    • Martin R.B., Edsall J.T., Wetlaufer D.B., Hollingworth B.R. A complete ionization scheme for tyrosine, and the ionization constants of some tyrosine derivatives. J. Biol. Chem. 1958, 233:1429-1435.
    • (1958) J. Biol. Chem. , vol.233 , pp. 1429-1435
    • Martin, R.B.1    Edsall, J.T.2    Wetlaufer, D.B.3    Hollingworth, B.R.4
  • 23
    • 0001645022 scopus 로고
    • Microscopic dissociation processes of some tyrosine derivatives
    • Kiss T., Tóth B. Microscopic dissociation processes of some tyrosine derivatives. Talanta 1982, 29:539-544.
    • (1982) Talanta , vol.29 , pp. 539-544
    • Kiss, T.1    Tóth, B.2
  • 24
    • 33750460694 scopus 로고
    • The ionization constants of organic compounds: I. The microscopic ionization constants of tyrosine and related compounds
    • Yamazaki F., Fujiki K., Murata Y. The ionization constants of organic compounds: I. The microscopic ionization constants of tyrosine and related compounds. Bull. Chem. Soc. Jpn. 1965, 38:8-12.
    • (1965) Bull. Chem. Soc. Jpn. , vol.38 , pp. 8-12
    • Yamazaki, F.1    Fujiki, K.2    Murata, Y.3
  • 25
    • 0000591245 scopus 로고
    • The apparent ionization constants of the phenolic hydroxyl groups of thyroxine and related compounds
    • Gemmill C.L. The apparent ionization constants of the phenolic hydroxyl groups of thyroxine and related compounds. Arch. Biochem. Biophys. 1955, 54:359-367.
    • (1955) Arch. Biochem. Biophys. , vol.54 , pp. 359-367
    • Gemmill, C.L.1
  • 26
    • 70449288028 scopus 로고
    • An unusual property of thyroxine and other iodophenols
    • Tata J.R. An unusual property of thyroxine and other iodophenols. Biochem. J. 1959, 72:214-222.
    • (1959) Biochem. J. , vol.72 , pp. 214-222
    • Tata, J.R.1
  • 27
    • 0041891602 scopus 로고
    • Walden inversion of amino acids. VI. The synthesis of d-surnamine (N-methyl-d-tyrosine)
    • Izumiya N., Nagamatsu A. Walden inversion of amino acids. VI. The synthesis of d-surnamine (N-methyl-d-tyrosine). Bull. Chem. Soc. Jpn. 1952, 25:265-267.
    • (1952) Bull. Chem. Soc. Jpn. , vol.25 , pp. 265-267
    • Izumiya, N.1    Nagamatsu, A.2
  • 28
    • 63049131054 scopus 로고    scopus 로고
    • Synthesis and structure revision of tyroscherin, and bioactivities of its stereoisomers against IGF-1-dependent tumor cells
    • 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.
    • (2009) Tetrahedron , vol.65 , pp. 3629-3638
    • Ishigami, K.1    Katsuta, R.2    Shibata, C.3    Hayakawa, Y.4    Watanabe, H.5    Kitahara, T.6
  • 29
    • 0001354904 scopus 로고
    • On the solvent isotope effect of deuterium in aqueous acid solutions
    • Purlee E.L. On the solvent isotope effect of deuterium in aqueous acid solutions. J. Am. Chem. Soc. 1959, 81:263-272.
    • (1959) J. Am. Chem. Soc. , vol.81 , pp. 263-272
    • Purlee, E.L.1
  • 30
    • 6444222991 scopus 로고
    • Use of glass electrodes to measure acidities in deuterium oxide
    • Glasoe P.K., Long F.A. Use of glass electrodes to measure acidities in deuterium oxide. J. Phys. Chem. 1960, 64:188-190.
    • (1960) J. Phys. Chem. , vol.64 , pp. 188-190
    • Glasoe, P.K.1    Long, F.A.2
  • 31
    • 4444359838 scopus 로고    scopus 로고
    • 1H/31P NMR pH indicator series to eliminate the glass electrode in NMR spectroscopic pKa determinations
    • Szakács Z., Hägele G., Tyka R. 1H/31P NMR pH indicator series to eliminate the glass electrode in NMR spectroscopic pKa determinations. Anal. Chim. Acta 2004, 522:247-258.
    • (2004) Anal. Chim. Acta , vol.522 , pp. 247-258
    • Szakács, Z.1    Hägele, G.2    Tyka, R.3
  • 32
    • 0034350517 scopus 로고    scopus 로고
    • Protonation microequilibrium treatment of polybasic compounds with any possible symmetry
    • Szakács Z., Noszál B. Protonation microequilibrium treatment of polybasic compounds with any possible symmetry. J. Math. Chem. 1999, 26:139-155.
    • (1999) J. Math. Chem. , vol.26 , pp. 139-155
    • Szakács, Z.1    Noszál, B.2
  • 33
    • 0015290017 scopus 로고
    • Spectral determination of microdissociation constants
    • Niebergall P.J., Schnaare R.L., Sugita E.T. Spectral determination of microdissociation constants. J. Pharm. Sci. 1972, 61:232-234.
    • (1972) J. Pharm. Sci. , vol.61 , pp. 232-234
    • Niebergall, P.J.1    Schnaare, R.L.2    Sugita, E.T.3
  • 34
    • 0031889482 scopus 로고    scopus 로고
    • Anionic iodotyrosine residues are required for iodothyronine synthesis
    • De Vijlder J.J.M., Den Hartog M.T. Anionic iodotyrosine residues are required for iodothyronine synthesis. Eur. J. Endocrinol. 1998, 138:227-231.
    • (1998) Eur. J. Endocrinol. , vol.138 , pp. 227-231
    • De Vijlder, J.J.M.1    Den Hartog, M.T.2
  • 35
    • 0019134825 scopus 로고
    • Molecular interactions between thyroid hormone analogs and the rat liver nuclear receptor. Partitioning of equilibrium binding free energy changes into substituent group interactions
    • Bolger M.B., Jorgensen E.C. Molecular interactions between thyroid hormone analogs and the rat liver nuclear receptor. Partitioning of equilibrium binding free energy changes into substituent group interactions. J. Biol. Chem. 1980, 255:10271-10278.
    • (1980) J. Biol. Chem. , vol.255 , pp. 10271-10278
    • Bolger, M.B.1    Jorgensen, E.C.2
  • 37
    • 0020030975 scopus 로고
    • Thyroid hormone binding to human serum prealbumin and rat liver nuclear receptor: kinetics, contribution of the hormone phenolic hydroxyl group, and accommodation of hormone side-chain bulk
    • Somack R., Andrea T.A., Jorgensen E.C. Thyroid hormone binding to human serum prealbumin and rat liver nuclear receptor: kinetics, contribution of the hormone phenolic hydroxyl group, and accommodation of hormone side-chain bulk. Biochemistry 1982, 21:163-170.
    • (1982) Biochemistry , vol.21 , pp. 163-170
    • Somack, R.1    Andrea, T.A.2    Jorgensen, E.C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.