Interaction of methimazole with I2: X-ray crystal structure of the charge transfer complex methimazole-I2. implications for the mechanism of action of methimazole-based antithyroid drugs.
The antithyroid drug methimazole (MMI) reacts with molecular iodine to form, in a multistep process, 1-methylimidazole as final product. In this process, the charge transfer complex MMI-I 2 and the ionic disulfide [(C 4H 6N 2S-) 2] (2+) ( 1, dication MMI disulfide) have been isolated and their X-ray crystal structures solved. Dication MMI disulfide perchlorate acts effectively both in reducing I 2 to I (-) ions and in showing antioxidant properties in inactivating the enzyme lactoperoxidase compound I.
Dipartimento di Chimica Inorganica ed Analitica, Università degli Studi di Cagliari, Cittadella Universitaria, I-09042 Monserrato (CA), Italy. isaia@unica.it
Francesco
F
Isaia
M Carla
MC
Aragoni
Massimiliano
M
Arca
Francesco
F
Demartin
Francesco A
FA
Devillanova
Giovanni
G
Floris
Alessandra
A
Garau
Michael B
MB
Hursthouse
Vito
V
Lippolis
Rosaria
R
Medda
Fabio
F
Oppo
Marilena
M
Pira
Gaetano
G
Verani
D013956:Antithyroid Agents / Q000737:chemistry* / Q000494:pharmacology*; D002384:Catalysis; D018360:Crystallography, X-Ray; D004220:Disulfides / Q000737:chemistry; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000494:pharmacology; D007455:Iodine / Q000737:chemistry*; D007477:Ions / Q000737:chemistry; D007784:Lactoperoxidase / Q000037:antagonists & inhibitors / Q000378:metabolism; D008713:Methimazole / Q000737:chemistry* / Q000494:pharmacology*; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013053:Spectrophotometry; D013329:Structure-Activity Relationship
D013956:Antithyroid Agents; D004220:Disulfides; D004791:Enzyme Inhibitors; D007477:Ions; D008713:Methimazole; D007455:Iodine; D007784:Lactoperoxidase