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Interaction of heterocyclic thiols/thiones eliminated from cephalosporins with iodine and its biological implications

Tamilselvi, A and Mugesh, Govindasamy (2010) Interaction of heterocyclic thiols/thiones eliminated from cephalosporins with iodine and its biological implications. In: Bioorganic & Medicinal Chemistry Letters, 20 (12). pp. 3692-3697.

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Official URL: http://dx.doi.org/10.1016/j.bmcl.2010.04.087

Abstract

Hydrolysis of beta-lactam antibiotics by beta-lactamases (e. g., metallo-beta-lactamase, m beta l) 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 m beta l-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-I-2 and DMETT-I-2, respectively. Addition of two equivalents of I-2 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. (C)2010 Elsevier Ltd. All rights reserved.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Elsevier science.
Keywords: Antithyroid drugs;Charge-transfer complexes;Iodine;Sulfur compounds;Thiols
Department/Centre: Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited: 25 Jun 2010 04:55
Last Modified: 19 Sep 2010 06:09
URI: http://eprints.iisc.ernet.in/id/eprint/28563

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