Abstract:
:The chemical structures of the pentavalent antimonial drugs, meglumine antimonate (MA) and sodium stibogluconate (SSG), were re-evaluated using electrospray ionization mass spectrometry (ESI-MS) and osmolarity measurements. Both MA and SSG were found to contain 1:1, 1:2, 2:2 and 2:3 Sb(V)-ligand complexes. ESI-MS analysis of MA showed negatively-charged 1:1 (m/z 364) and 2:2 (m/z 765) Sb(V)-meglumine complexes, supporting the predominance of zwitterionic species in solution. Our data are consistent with a structure for the 1:2 Sb(V)-meglumine, which differs from that previously postulated, with two positively-charged amino groups and one negatively-charged antimonate group. Instead of the commonly hypothesized structure for SSG, in which two Sb atoms are linked by an oxygen, an alternative structure is proposed, based on the ability of Sb(V)-gluconate complexes to polymerize. MA (or SSG) in concentrated aqueous solutions, such as of MA (or SSG) in its commercial form, is expected to consist mainly of a mixture of 2:2, 2:3 and 2:1 Sb(V)-ligand complexes, as suggested by the 2:1 Sb-to-particle ratio found by osmometry. 1:1 Sb(V)-ligand complexes in MA and SSG are expected to play an important pharmacological role, as suggested by the slow increase of osmolarity of MA solution upon dilution at 37 degrees C (half-time of 20min).
journal_name
J Inorg Biochemjournal_title
Journal of inorganic biochemistryauthors
Frézard F,Martins PS,Barbosa MC,Pimenta AM,Ferreira WA,de Melo JE,Mangrum JB,Demicheli Cdoi
10.1016/j.jinorgbio.2007.10.010subject
Has Abstractpub_date
2008-04-01 00:00:00pages
656-65issue
4eissn
0162-0134issn
1873-3344pii
S0162-0134(07)00286-3journal_volume
102pub_type
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