Premium
Derivatization of Glucose and 2‐Deoxyglucose for Transition Metal Complexation: Substitution Reactions with Organometallic 99m Tc and Re Precursors and Fundamental NMR Investigations
Author(s) -
Petrig Jeannine,
Schibli Roger,
Dumas Cécile,
Alberto Roger,
Schubiger P. A.
Publication year - 2001
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20010504)7:9<1868::aid-chem1868>3.0.co;2-h
Subject(s) - chemistry , iminodiacetic acid , derivatization , nuclear magnetic resonance spectroscopy , moiety , transition metal , yield (engineering) , chelation , organic chemistry , polymer chemistry , nuclear chemistry , catalysis , high performance liquid chromatography , materials science , metallurgy
Synthetic strategies for the bifunctionalization of glucose and 2‐deoxyglucose at position C‐1 for transition metal coordination are reported. In particular organometallic technetium and rhenium complexes for potential use in diagnostic nuclear medicine were synthesized and investigated. Specifically, a common iminodiacetic acid (IDA) moiety was O‐glycosidically connected through an ethylene spacer group to produce the pure α ‐ (in case of 2‐deoxyglucose) and β ‐anomer (in case of glucose). Reaction of the sugar derivatives with the organometallic precursor [M(H 2 O) 3 (CO) 3 ] + (M= 99m Tc, Re) produced single products in high yield, which are water‐soluble and water‐stable. The displacement of the three water molecules of the metal precursor and thus the tridentate coordination of the metal‐tricarbonyl core exclusively via the amine and the two carboxylic acid functionalities of the IDA chelate was verified by means of 1D and 2D 1 H NMR spectroscopy, mass spectrometry, and IR spectroscopy. The radioactive‐labeled products ( 99m Tc) proved their excellent stability in vitro in physiological phosphate buffer (pH=7.4) and human plasma over a period of 24 h at 37 °C.