-
1
-
-
0041735276
-
Hyperthyroidism
-
(a) Cooper, D. S. Hyperthyroidism. Lancet 2003, 362, 459-468.
-
(2003)
Lancet
, vol.362
, pp. 459-468
-
-
Cooper, D.S.1
-
2
-
-
14544296973
-
Antithyroid drugs
-
and references therein
-
(b) Cooper, D. S. Antithyroid drugs. N. Engl. J. Med. 2005, 352, 905-917, and references therein.
-
(2005)
N. Engl. J. Med
, vol.352
, pp. 905-917
-
-
Cooper, D.S.1
-
3
-
-
0017254963
-
The mechanism of action of the thioureylene antithyroid drugs
-
(a) Taurog, A. The mechanism of action of the thioureylene antithyroid drugs. Endocrinology 1976, 98, 1031-1046.
-
(1976)
Endocrinology
, vol.98
, pp. 1031-1046
-
-
Taurog, A.1
-
4
-
-
0018075631
-
The irreversible inactivation of thyroid peroxidase by methylmercaptoimidazole, thiouracil, and propylthiouracil in vitro and its relationship to in vivo findings
-
(b) Davidson, B.; Soodak, M.; Neary, J. T.; Strout, H. V.; Kieffer, J. D.; Mover, H.; Maloof, F. The irreversible inactivation of thyroid peroxidase by methylmercaptoimidazole, thiouracil, and propylthiouracil in vitro and its relationship to in vivo findings. Endocrinology 1978, 103, 871-882.
-
(1978)
Endocrinology
, vol.103
, pp. 871-882
-
-
Davidson, B.1
Soodak, M.2
Neary, J.T.3
Strout, H.V.4
Kieffer, J.D.5
Mover, H.6
Maloof, F.7
-
5
-
-
0020687748
-
Reversible and irreversible inhibition of thyroid peroxidase-catalyzed iodination by thioureylene drugs
-
(c) Engler, H.; Taurog, A.; Luthy, C.; Dorris, M. L. Reversible and irreversible inhibition of thyroid peroxidase-catalyzed iodination by thioureylene drugs. Endocrinology 1983, 112, 86-95.
-
(1983)
Endocrinology
, vol.112
, pp. 86-95
-
-
Engler, H.1
Taurog, A.2
Luthy, C.3
Dorris, M.L.4
-
6
-
-
0020559777
-
Mechanism of action of thioureylene antithyroid drugs in the rat: Possible inactivation of thyroid peroxidase by propylthiouracil
-
(d) Shiroozu, A.; Taurog, A.; Engler, H.; Dorris, M. L. Mechanism of action of thioureylene antithyroid drugs in the rat: possible inactivation of thyroid peroxidase by propylthiouracil. Endocrinology 1983, 113, 362-370.
-
(1983)
Endocrinology
, vol.113
, pp. 362-370
-
-
Shiroozu, A.1
Taurog, A.2
Engler, H.3
Dorris, M.L.4
-
7
-
-
0038501459
-
-
It has been reported that PTU, but not MMI, also inhibits the selenocysteine-containing enzyme iodothyronine deiodinase (ID, which catalyzes the monodeiodination of the prohormone thyroxine (T4) to its biologically active form T3. For details, see: (a) Köhrle, J. The trace element seienium and the thyroid gland. Biochimie 1999, 81, 527-533
-
It has been reported that PTU, but not MMI, also inhibits the selenocysteine-containing enzyme iodothyronine deiodinase (ID), which catalyzes the monodeiodination of the prohormone thyroxine (T4) to its biologically active form T3. For details, see: (a) Köhrle, J. The trace element seienium and the thyroid gland. Biochimie 1999, 81, 527-533.
-
-
-
-
8
-
-
0035796663
-
Reactions of organoselenenyl iodides with thiouracil drugs: An enzyme mimetic study on the inhibition of iodothyronine deiodinase
-
(b) du Mont, W.-W.; Mugesh, G.; Wismach, C.; Jones, P. G. Reactions of organoselenenyl iodides with thiouracil drugs: an enzyme mimetic study on the inhibition of iodothyronine deiodinase. Angew. Chem., Int. Ed. 2001, 40, 2486-2489.
-
(2001)
Angew. Chem., Int. Ed
, vol.40
, pp. 2486-2489
-
-
du Mont, W.-W.1
Mugesh, G.2
Wismach, C.3
Jones, P.G.4
-
9
-
-
0036191639
-
Biochemistry, cellular and molecular biology, and physiological roles of the iodothyronine selenodeiodinases
-
(c) Bianco, A. C.; Salvatore, D.; Gereben, B.; Berry, M. J.; Larsen, P. R. Biochemistry, cellular and molecular biology, and physiological roles of the iodothyronine selenodeiodinases. Endocr. Rev. 2002, 23, 38-89.
-
(2002)
Endocr. Rev
, vol.23
, pp. 38-89
-
-
Bianco, A.C.1
Salvatore, D.2
Gereben, B.3
Berry, M.J.4
Larsen, P.R.5
-
10
-
-
0036125773
-
Iodothyronine deiodinases
-
(d) Köhrle, J. Iodothyronine deiodinases. Methods Enzymol. 2002, 347, 125-167.
-
(2002)
Methods Enzymol
, vol.347
, pp. 125-167
-
-
Köhrle, J.1
-
11
-
-
0018597527
-
Rapid conversion of carbimazole to methimazole in serum; evidence for an enzymatic mechanism
-
(a) Nakashima, T.; Tourog, A. Rapid conversion of carbimazole to methimazole in serum; evidence for an enzymatic mechanism. Clin. Endocrinol. 1979, 10, 637-648.
-
(1979)
Clin. Endocrinol
, vol.10
, pp. 637-648
-
-
Nakashima, T.1
Tourog, A.2
-
12
-
-
0020612478
-
Comparative bioavailability of carbimazole and methimazole
-
(b) Jansson, R.; Dahlberg, P. A.; Lindström, B. Comparative bioavailability of carbimazole and methimazole. Int. J. Clin. Pharmacol. Ther. Toxicol. 1983, 21, 505-510.
-
(1983)
Int. J. Clin. Pharmacol. Ther. Toxicol
, vol.21
, pp. 505-510
-
-
Jansson, R.1
Dahlberg, P.A.2
Lindström, B.3
-
13
-
-
0027051113
-
Selenoracil derivatives are potent inhibitors of the selenoenzyme type I iodothyronine deiodinase
-
(a) Visser, T. J.; Kaptein, E.; Aboul-Enein, H. Y. Selenoracil derivatives are potent inhibitors of the selenoenzyme type I iodothyronine deiodinase. Biochem. Biophys. Res. Commun. 1992, 189, 1362-1367.
-
(1992)
Biochem. Biophys. Res. Commun
, vol.189
, pp. 1362-1367
-
-
Visser, T.J.1
Kaptein, E.2
Aboul-Enein, H.Y.3
-
14
-
-
0027380292
-
Synthesis and the antiperoxidase activity of seleno analogues of the antithyroid drug propylthiouracil
-
(b) Aboul-Enein, H. Y.; Awad, A. A.; Al-Andis, N. M. Synthesis and the antiperoxidase activity of seleno analogues of the antithyroid drug propylthiouracil. J. Enzyme. Inhib. 1993, 7, 147-150.
-
(1993)
J. Enzyme. Inhib
, vol.7
, pp. 147-150
-
-
Aboul-Enein, H.Y.1
Awad, A.A.2
Al-Andis, N.M.3
-
15
-
-
0027965163
-
A directed metalation route to the selenium analog of methimazole
-
(c) Guziec, L. J.; Guziec, F. S. Jr. A directed metalation route to the selenium analog of methimazole. J. Org. Chem. 1994, 59, 4691-4692.
-
(1994)
J. Org. Chem
, vol.59
, pp. 4691-4692
-
-
Guziec, L.J.1
Guziec Jr., F.S.2
-
16
-
-
0027944003
-
The selenium analog of methimazole. Measurement of its inhibitory effect on type I 5′-deiodinase and of its antithyroid activity
-
(d) Taurog, A.; Dorris, M. L.; Guziec, L. J.; Guziec, F. S., Jr. The selenium analog of methimazole. Measurement of its inhibitory effect on type I 5′-deiodinase and of its antithyroid activity. Biochem. Pharmacol. 1994, 48, 1447-1453.
-
(1994)
Biochem. Pharmacol
, vol.48
, pp. 1447-1453
-
-
Taurog, A.1
Dorris, M.L.2
Guziec, L.J.3
Guziec Jr., F.S.4
-
17
-
-
0028946498
-
The selenium analog of 6-propylthiouracil. Measurement of its inhibitory effect on type I iodothyronine deiodinase and of its antithyroid activity
-
(e) Taurog, A.; Dorris, M. L.; Hu, W.-X.; Guziec, F. S. Jr. The selenium analog of 6-propylthiouracil. Measurement of its inhibitory effect on type I iodothyronine deiodinase and of its antithyroid activity. Biochem. Pharmacol. 1995, 49, 701-709.
-
(1995)
Biochem. Pharmacol
, vol.49
, pp. 701-709
-
-
Taurog, A.1
Dorris, M.L.2
Hu, W.-X.3
Guziec Jr., F.S.4
-
18
-
-
33749180636
-
Synthesis and structural characterization of 1-mesityl-1,3-dihydro- imidazole-2-selone and bis(1-mesitylimidazol-2-yl)diselenide: Experimental evidence that the selone is more stable than the selenol tautomer
-
(f) Landry, V. K.; Minoura, M.; Pang, K.; Buccella, D.; Kelly, B. V.; Parkin, G. Synthesis and structural characterization of 1-mesityl-1,3-dihydro- imidazole-2-selone and bis(1-mesitylimidazol-2-yl)diselenide: experimental evidence that the selone is more stable than the selenol tautomer. J. Am. Chem. Soc. 2006, 128, 12490-12497.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 12490-12497
-
-
Landry, V.K.1
Minoura, M.2
Pang, K.3
Buccella, D.4
Kelly, B.V.5
Parkin, G.6
-
19
-
-
33748556877
-
Synthesis and structures of Se analogues of the antithyroid drug 6-n-propyl-2-thiouracil and its alkyl derivatives: Formation of dimeric Se-Se compounds and deselenation reactions of charge-transfer adducts of diiodine
-
(g) Antoniadis, C. D.; Hadjikakou, S. K.; Hadjiliadis, N.; Papakyriakou, A.; Baril, M.; Butler, I. S. Synthesis and structures of Se analogues of the antithyroid drug 6-n-propyl-2-thiouracil and its alkyl derivatives: formation of dimeric Se-Se compounds and deselenation reactions of charge-transfer adducts of diiodine. Chem. - Eur. J. 2006, 12, 6888-6897.
-
(2006)
Chem. - Eur. J
, vol.12
, pp. 6888-6897
-
-
Antoniadis, C.D.1
Hadjikakou, S.K.2
Hadjiliadis, N.3
Papakyriakou, A.4
Baril, M.5
Butler, I.S.6
-
20
-
-
1542287649
-
Biomimetic studies on antithyroid drugs and thyroid hormone synthesis
-
(a) Roy, G.; Nethaji, M.; Mugesh, G. Biomimetic studies on antithyroid drugs and thyroid hormone synthesis. J. Am. Chem. Soc. 2004, 126, 2712-2713.
-
(2004)
J. Am. Chem. Soc
, vol.126
, pp. 2712-2713
-
-
Roy, G.1
Nethaji, M.2
Mugesh, G.3
-
21
-
-
84962338794
-
Antithyroid drugs and thyroid hormone synthesis: Effect of methimazole derivatives on peroxidase-catalyzed reactions
-
(b) Roy, G.; Mugesh, G. Antithyroid drugs and thyroid hormone synthesis: effect of methimazole derivatives on peroxidase-catalyzed reactions. J. Am. Chem. Soc. 2005, 127, 15207-15217.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 15207-15217
-
-
Roy, G.1
Mugesh, G.2
-
22
-
-
84961979106
-
Interaction of antithyroid drugs with iodine: The isolation of two unusual ionic compounds derived from Se-methimazole
-
(c) Roy, G.; Nethaji, M.; Mugesh, G. Interaction of antithyroid drugs with iodine: the isolation of two unusual ionic compounds derived from Se-methimazole. Org. Biomol. Chem. 2006, 4, 2883-2887.
-
(2006)
Org. Biomol. Chem
, vol.4
, pp. 2883-2887
-
-
Roy, G.1
Nethaji, M.2
Mugesh, G.3
-
23
-
-
33751535780
-
Bioinorganic chemistry aspects of the inhibition of thyroid hormone biosynthesis by antihyperthyroid drugs
-
(d) Roy, G.; Das, D.; Mugesh, G. Bioinorganic chemistry aspects of the inhibition of thyroid hormone biosynthesis by antihyperthyroid drugs. Inorg. Chim. Acta 2007, 360, 303-316.
-
(2007)
Inorg. Chim. Acta
, vol.360
, pp. 303-316
-
-
Roy, G.1
Das, D.2
Mugesh, G.3
-
24
-
-
45549109618
-
Selenium analogues of antithyroid drugs-recent developments
-
(e) Roy, G.; Mugesh, G. Selenium analogues of antithyroid drugs-recent developments. Chem. Biodiversity 2008, 5, 414-439.
-
(2008)
Chem. Biodiversity
, vol.5
, pp. 414-439
-
-
Roy, G.1
Mugesh, G.2
-
25
-
-
0002138516
-
Stable carbenes
-
and references therein
-
Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Stable carbenes. Chem. Rev. 2000, 100, 39-91, and references therein.
-
(2000)
Chem. Rev
, vol.100
, pp. 39-91
-
-
Bourissou, D.1
Guerret, O.2
Gabbaï, F.P.3
Bertrand, G.4
-
26
-
-
0027608975
-
Completion and refinement of crystal structures with S1R92
-
(a) Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A. Completion and refinement of crystal structures with S1R92. J. Appl. Crystallogr. 1993, 26, 343-350.
-
(1993)
J. Appl. Crystallogr
, vol.26
, pp. 343-350
-
-
Altomare, A.1
Cascarano, G.2
Giacovazzo, C.3
Guagliardi, A.4
-
27
-
-
84943920736
-
Phase annealing in SHELX-90: Direct methods for larger structures
-
(b) Sheldrick, G. M. Phase annealing in SHELX-90: direct methods for larger structures. Acta Crystallogr. Sect. A: Found. Crystallogr. 1990, 46, 467-473.
-
(1990)
Acta Crystallogr. Sect. A: Found. Crystallogr
, vol.46
, pp. 467-473
-
-
Sheldrick, G.M.1
-
28
-
-
56749139518
-
-
Sheldrick, G. M. SHELX-97, Program for the Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997; CCDC-693450 (for compound 5), CCDC-693451 (for compound 15), CCDC-693452 (for compound 20), CCDC-693453 (for compound 14), and CCDC-693454 (for compound 6) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
-
(c) Sheldrick, G. M. SHELX-97, Program for the Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997; CCDC-693450 (for compound 5), CCDC-693451 (for compound 15), CCDC-693452 (for compound 20), CCDC-693453 (for compound 14), and CCDC-693454 (for compound 6) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
-
-
-
-
29
-
-
56749171748
-
-
All the calculations were carried out by using the Gaussian suite of quantum chemical programs. Frisch, M. J, Trucks, G. W, Schlegel, H. B, Scusera, G. E, Robb, M. A, Cheeseman, J. R, Zakrzewski, V. G, Montgomery, J. A, Jr, Stratmann, R. E, Burant, J. C, Dapprich, S, Millam, J. M, Daniels, A. D, Kudin, K. N, Strain, M. C, Farkas, O, Tomasi, J, Barone, V, Cossi, M, Cammi, R, Mennucci, B, Pomelli, C, Adamo, C, Clifford, S, Ochterski, J, Petersson, G. A, Ayala, P. Y, Cui, Q, Morokuma, K, Malick, D. K, Rabuck, A. D, Raghavachari, K, Foresman, J. B, Cioslowski, J, Ortiz, J. V, Stefanov, B. B, Liu, G, Liashenko, A, Piskorz, P, Komaromi, I, Gomperts, R, Martin, R. L, Fox, D. J, Keith, T, Al-Laham, M. A, Peng, C. Y, Nanayakkara, A, Gonzalez, C, Challacombe, M, Gill, P. M. W, Johnson, B. G, Chen, W, Wong, M. W, Andres, J. L, Gonzale, C, Head-Gordon, M, Replogle, E. S, Pople, J. A. Gaussian 98, revision A 11.3; Gaussian, Inc, Pitt
-
All the calculations were carried out by using the Gaussian suite of quantum chemical programs. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scusera, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzale, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A 11.3; Gaussian, Inc.; Pittsburgh, PA, 1998.
-
-
-
-
30
-
-
0011083499
-
Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint
-
(a) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chem. Rev. 1988, 88, 899-926.
-
(1988)
Chem. Rev
, vol.88
, pp. 899-926
-
-
Reed, A.E.1
Curtiss, L.A.2
Weinhold, F.3
-
31
-
-
56749090030
-
-
Glendening, E. D, Reed, J. E, Carpenter, J. E, Weinhold, F. Natural Bond Orbital NBO, version 3.1
-
(b) Glendening, E. D.; Reed, J. E.; Carpenter, J. E.; Weinhold, F. Natural Bond Orbital (NBO), version 3.1.
-
-
-
-
32
-
-
0345491105
-
Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density
-
(a) Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 1988, 37, 785-789.
-
(1988)
Phys. Rev. B
, vol.37
, pp. 785-789
-
-
Lee, C.1
Yang, W.2
Parr, R.G.3
-
33
-
-
0000189651
-
Density-functional thermochemistry. III. The role of exact exchange
-
(b) Becke, A. D. Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 1993, 98, 5648-5652.
-
(1993)
J. Chem. Phys
, vol.98
, pp. 5648-5652
-
-
Becke, A.D.1
-
34
-
-
0016248790
-
-
The enzyme inhibition experiments were carried out with Fe-containing lactoperoxidase (LPO) because it is readily available in purified form. Furthermore, LPO has been shown to behave very similarly to TPO with respect to iodination of thyroglobulin, the natural substrate, and other iodide acceptors. Taurog, A.; Dorris, M. L.; Lamas, L. Comparison of lactoperoxidase- and thyroid peroxidase-catalyzed iodination and coupling. Endocrinology 1974, 94, 1286-1294.
-
The enzyme inhibition experiments were carried out with Fe-containing lactoperoxidase (LPO) because it is readily available in purified form. Furthermore, LPO has been shown to behave very similarly to TPO with respect to iodination of thyroglobulin, the natural substrate, and other iodide acceptors. Taurog, A.; Dorris, M. L.; Lamas, L. Comparison of lactoperoxidase- and thyroid peroxidase-catalyzed iodination and coupling. Endocrinology 1974, 94, 1286-1294.
-
-
-
-
35
-
-
56749145338
-
-
The hydrolysis of N-C bond in assay mixture was confirmed by HPLC analysis. The initial rates for the hydrolysis of N-C bond in various thiones/selones are given in Supporting Information, (Page S18).
-
The hydrolysis of N-C bond in assay mixture was confirmed by HPLC analysis. The initial rates for the hydrolysis of N-C bond in various thiones/selones are given in Supporting Information, (Page S18).
-
-
-
|