Determination of the cation-chelating potential of C-methylthiolated beta-lactams and their sulfones by electrospray ionization mass spectrometry.
The chelation potential of highly lipophilic C-dimethylthiolated monocyclic beta-lactams was examined using electrospray ionization mass spectrometry (ESI-MS). The metal salts NaCl, KCl, CaCl2, ZnCl2, Cu(NO3)2, CdSO4, MnCl2, and Mg(NO3)2 were used for the analysis. The K+ adducts of the compounds studied were more responsive in ESI analysis, compared to their Na+ adducts, regardless of the oxidation state of the sulfur (in the methylthio or the sulfone groups) and the type of the group adjacent to the lactam carbonyl. Opening of the beta-lactam ring, leading to formation of a chargeable N-atom, had little to no effect on the K+ adduct formation. Interactions of the methylthio group with the divalent zinc ion were also observed.
Konaklieva
Monika I
MI
Department of Chemistry, American University, 4400 Massachusetts Ave., NW, Washington, DC 20016, USA. mkonak@american.edu
Suwandi
Lita S
LS
Kostova
Maya B
MB
Gu
Jianghong
J
D002412:Cations / Q000737:chemistry / Q000378:metabolism; D013058:Mass Spectrometry; D008670:Metals / Q000737:chemistry*; D015394:Molecular Structure; D012996:Solutions / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D013450:Sulfones / Q000737:chemistry / Q000378:metabolism*; D014867:Water / Q000737:chemistry; D047090:beta-Lactams / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*
D002412:Cations; D008670:Metals; D012996:Solutions; D013450:Sulfones; D047090:beta-Lactams; D014867:Water