TY - JOUR
T1 - A new bifunctional amino acid chelator targeting the glucose transporter
AU - Banerjee, Sangeeta R.
AU - Babich, John W.
AU - Zubieta, Jon
N1 - Funding Information:
This work was supported in part by a grant from the National Institute of Health, National Institute of Allergy and Infectious Diseases, STTR 1R41 A1044080-01.
PY - 2006/3/20
Y1 - 2006/3/20
N2 - The coupling reactions of d-glucosamine, 1,3,4,6-tetra-O-acetylglucosamine, and 4-aminophenyl-galactopyranosine with N,N-bis(quinolinoyl)aminovaleric acid (L1) provided a series of conjugates containing a potentially tridentate donor group terminus linked to a sugar moiety, L2′, L2 and L3, respectively. Reactions of the ligands with [NEt4]2[Re(CO) 3Br3] in refluxing methanol provided the rhenium complexes [Re(CO3)(L1)]Br (ReL1), [Re(CO)3(L2)]Br (ReL2), [Re(CO)3(L2′)]Br (ReL2′) and [Re(CO)3(L3)]Br (ReL3). The ligands and complexes were characterized by elemental analyses, 1H and 13C NMR, mass spectroscopy and, in the case of L1 and ReL1, by X-ray crystallography. The rhenium complexes exhibit fluorescence emissions with long lifetimes, large Stokes shifts, and moderate quantum yields.
AB - The coupling reactions of d-glucosamine, 1,3,4,6-tetra-O-acetylglucosamine, and 4-aminophenyl-galactopyranosine with N,N-bis(quinolinoyl)aminovaleric acid (L1) provided a series of conjugates containing a potentially tridentate donor group terminus linked to a sugar moiety, L2′, L2 and L3, respectively. Reactions of the ligands with [NEt4]2[Re(CO) 3Br3] in refluxing methanol provided the rhenium complexes [Re(CO3)(L1)]Br (ReL1), [Re(CO)3(L2)]Br (ReL2), [Re(CO)3(L2′)]Br (ReL2′) and [Re(CO)3(L3)]Br (ReL3). The ligands and complexes were characterized by elemental analyses, 1H and 13C NMR, mass spectroscopy and, in the case of L1 and ReL1, by X-ray crystallography. The rhenium complexes exhibit fluorescence emissions with long lifetimes, large Stokes shifts, and moderate quantum yields.
KW - Bifunctional chelates
KW - Fluorescent probes
KW - Glucosamine derivatives
KW - Rhenium(I)-tricarbonyl core
KW - Single amino acid chelates
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U2 - 10.1016/j.ica.2005.11.022
DO - 10.1016/j.ica.2005.11.022
M3 - Article
AN - SCOPUS:33644757618
VL - 359
SP - 1603
EP - 1612
JO - Inorganica Chimica Acta
JF - Inorganica Chimica Acta
SN - 0020-1693
IS - 5
ER -