Abstract：
:Hydrolysis of beta-lactam antibiotics by beta-lactamases (e.g., metallo-beta-lactamase, mbetal) 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 mbetal-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 I(2) was carried out in water, the reaction produced a monocation having I(5)(-), indicating the reactivity of MDT toward I(2) 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.
journal_name
Bioorg Med Chem Lettjournal_title
Bioorganic & medicinal chemistry lettersauthors
Tamilselvi A,Mugesh Gdoi
10.1016/j.bmcl.2010.04.087subject
Has Abstractpub_date
2010-06-15 00:00:00pages
3692-7issue
12eissn
0960-894Xissn
1464-3405pii
S0960-894X(10)00557-3journal_volume
20pub_type
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