Research & Teaching Faculty

Default Header Image

Novel carbohydrate-appended metal complexes for potential use in molecular imaging

TitleNovel carbohydrate-appended metal complexes for potential use in molecular imaging
Publication TypeJournal Article
Year of Publication2005
AuthorsStorr, T, Obata, M, Fisher, CL, Bayly, SR, Green, DE, Brudzinska, I, Mikata, Y, Patrick, BO, Adam, MJ, Yano, S, Orvig, C
JournalChemistry-a European Journal
Volume11
Pagination195-203
Date PublishedDec
Type of ArticleArticle
ISBN Number0947-6539
KeywordsAMINO-SUGARS, ANTITUMOR-ACTIVITY, carbohydrates, CRYSTAL-STRUCTURES, D-GLUCOSE, HIGH-AFFINITY, IN-VITRO, molecular imaging, PALLADIUM(II) COMPLEXES, RADIOPHARMACEUTICALS, rhenium, STRUCTURAL-CHARACTERIZATION, SUGAR-PENDANT, TC-99M, technetium
Abstract

Seven discrete sugar-pendant diamines were complexed to the {M(CO)(3)}(+) (Tc-99m/Re) core: 1,3-diamino-2-propyl beta-D-glucopyranoside (L-1), 1,3-diamino-2-propyl beta-D-xylopyranoside (L-2), 1,3-diamino-2-propyl alpha-D-mannopyranoside (L-3), 1,3-diamino-2-propyl alpha-D-galactopyranoside (L-4), 1,3diamino-2-propyl beta-D-galactopyranoside (L-5), 1,3-diamino-2-propyl beta-(alpha-D-glucopyranosyl-(1,4)-D-glucopyrano- side) (L-6), and bis(aminomethyl)bis[(beta-D-glucopyranosyloxy)methyl]methane (L-7). The Re complexes [Re((LL7)-L-1)(Br)(CO)(3)] were characterized by H-1 and C-13 1D/2D NMR spectroscopy which confirmed the pendant nature of the carbohydrate moieties in solution. Additional characterization was provided by IR spectroscopy, elemental analysis, and mass spectrometry. Two analogues, [Re(L-2)(CO)(3)Br] and [Re(L-3)(CO)(3)Br], were characterized in the solid state by X-ray crystallography and represent the first reported structures of Re organometallic carbohydrate compounds. Conductivity measurements in H2O established that the complexes exist as [Re(L-1-L-7)- (H2O)(CO)(3)]Br in aqueous conditions. Radiolabelling of V-L 7 with [Tc-99m(H2O)(3)(CO)(3)](+) afforded in high yield compounds of identical character to the Re analogues. The radiolabelled compounds were determined to exhibit high in vitro stability towards ligand exchange in the presence of an excess of either cysteine or histidine over a 24 h period.

URL<Go to ISI>://000226278700018