Tamilselvi, A. ; Mugesh, Govindasamy (2010) Interaction of heterocyclic thiols/thiones eliminated from cephalosporins with iodine and its biological implications Bioorganic & Medicinal Chemistry Letters, 20 (12). pp. 3692-3697. ISSN 0960-894X
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Official URL: http://www.sciencedirect.com/science/article/pii/S...
Related URL: http://dx.doi.org/10.1016/j.bmcl.2010.04.087
Abstract
Hydrolysis of β-lactam antibiotics by β-lactamases (e.g., metallo-β-lactamase, mβl) is one of the major bacterial defense systems. These enzymes can catalyze the hydrolysis of a variety of antibiotics including the latest generation of cephalosporins, cephamycins and imipenem. It is shown in this paper that the thiol/thione moieties eliminated from certain cephalosporins by mβl-mediated hydrolysis readily react with molecular iodine to produce ionic compounds having S-I bonds. While the reaction of MTT with iodine produced the corresponding disulfide, MDT and DMETT produced the charge-transfer complexes MDT-I2 and DMETT-I2, respectively. Addition of two equivalents of I2 to MDT produced a novel cationic complex having an almost linear S-I+-S moiety and I-5 counter anion. However, this reaction appears to be highly solvent dependent. When the reaction of MDT with I2 was carried out in water, the reaction produced a monocation having I-5, indicating the reactivity of MDT toward I2 is very similar to that of the most commonly used antithyroid drug methimazole (MMI). In contrast to MMI, MDT and DMETT, the triazine-based compound MTDT acts as a weak donor toward iodine.
Item Type: | Article |
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Source: | Copyright of this article belongs to Elsevier Science. |
Keywords: | Antithyroid Drugs; Charge-transfer Complexes; Iodine; Sulfur Compounds; Thiols |
ID Code: | 79301 |
Deposited On: | 25 Jan 2012 06:35 |
Last Modified: | 25 Jan 2012 06:35 |
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