A glucosamine–dipicolylamine conjugate of^99mTc(i) and¹⁸⁶Re(i) for use in imaging and therapy

Abstract

The synthesis and metal complexation of a glucosamine-appended 2,2'-dipicolylamine ligand to the tricarbonyls of 99mTc and 186Re is described; the ligand was found to bind in a tridentate fashion with the glucosamine function remaining pendant, and the 99mTc complex was found to exhibit exceptional stability towards in vitro ligand exchange experiments.

Synthesis and Structure of Novel Sugar‐Substituted Bipyridine Complexes of Rhenium and 99m‐Technetium

“…In a histidine challenge experiment, the glucose-substituted 99m Tc complex 17, which is representative of all the complexes, is stable in vitro for 4.5 h. This stability is rather low compared to other sugar-containing complexes derived from 2,2'-dipicolylamine for instance. [17] In light of the intrinsic fluorescence and the possibility of binding different carbohydrates externally, future in vivo experiments are expected to show a sugar-dependent biodistribution.…”

“…[15] Metal complexes functionalised with carbohydrates but containing other cores for metal complexation are increasingly being studied in medicinal inorganic chemistry; examples include Re and Tc complexes for use as radiotracers. [16] 2,2'-Dipicolylamine, [17] 3-hydroxypyridone [18] and 2-hydroxybenzyl [19] derivatives of different monosaccharides, for example, have been used as chelators for Tc and Re carbonyl cores, and similar complexes have been reported from 1,3-diamines of sugars. [20] Saccharide-functionalised bis(quinolinolyl)amino acids have also been complexed to a rhenium tricarbonyl core, [21] and glucose and 2-deoxyglucose have been functionalised at C-1 with iminodiacetic acid and the resulting ligands complexed with Re and Tc.…”

InIII and GaIII Complexes of Sugar‐Substituted Tripodal Trisalicylidene Imines: The First 68Ga‐Labelled Sugar Derivative

“…[29] However, a number of carbohydrate-appending radiolabelled compounds have been synthesised, comprised of bi-and tridentate ligands. 2,2Ј-Bipyridyl, [30] 2,2Ј-dipicolylamine, [31,32] 3-hydroxypyridone, [33] 2-hydroxybenzyl- [34] and 2-(iminodiacetato)ethyl-functionalised [35] derivatives of different monosaccharides could be used as chelators for radionuclides. Similar complexes have been reported from 1,3-diamines of sugars.…”

Carbohydrate– N -heterocyclic carbene metal complexes: Synthesis, catalysis and biological studies

“…For the purposes of discovering novel classes of metal drugs, many carbohydrate ligands have been designed, synthesized and attached to different metal centres. There are many reviews [8][9][10][11] on this topic, including a detailed book chapter covering the research up to 2013 [62]. Despite a number of studies of NHC-metal complexes and carbohydrate-metal complexes in the bio-related research fields mentioned above, the medicinal properties of metal complexes containing both NHC ligands and carbohydrates are rarely discussed.…”

“…Thus, carbohydrates have been widely studied across many fields [8][9][10][11]. Methods for the synthesis of a variety of carbohydrate-functionalised alkyl halides, amines, azides and alkynes are well established and many of these compounds are readily available.…”