@article {2368, title = {Design, Synthesis, and Imaging of Small Amphiphilic Rhenium and (99m)Technetium Tricarbonyl Complexes}, journal = {Bioconjugate Chemistry}, volume = {20}, number = {5}, year = {2009}, note = {ISI Document Delivery No.: 448WKTimes Cited: 1Cited Reference Count: 24Boros, Eszter Hafeli, Urs O. Patrick, Brian O. Adam, Michael J. Orvig, Chris}, month = {May}, pages = {1002-1009}, type = {Article}, abstract = {The design, synthesis, radiolabeling, evaluation of stability, and in vivo investigation are presented of three variably charged, novel, short C-8 chain derivatized chelators for the [M(CO)(3)](+) core (M = Tc-99m or Re). Labeling with [Tc-99m(CO)3](+) showed complex formation in under 1 h reaction time and high stability toward 24 h histidine and cysteine challenges, as well as distinctive log P values for each complex. Distinct localization of small amphiphilic molecules in in vivo systems depends on the charge of the polar moiety and was studied via biodistribution (4 h) and imaging (15 min, 1, 2, and 4 h) in female C57B1/6 mice.}, keywords = {BIFUNCTIONAL LIGAND, BIOMOLECULES, SMALL-MOLECULE RADIOPHARMACEUTICALS, SYSTEMS, technetium}, isbn = {1043-1802}, url = {://000266292500021}, author = {Boros, E. and Hafeli, U. O. and Patrick, B. O. and Adam,Michael J. and Orvig, Chris} } @article {2368, title = {Design, Synthesis, and Imaging of Small Amphiphilic Rhenium and (99m)Technetium Tricarbonyl Complexes}, journal = {Bioconjugate Chemistry}, volume = {20}, number = {5}, year = {2009}, note = {ISI Document Delivery No.: 448WKTimes Cited: 1Cited Reference Count: 24Boros, Eszter Hafeli, Urs O. Patrick, Brian O. Adam, Michael J. Orvig, Chris}, month = {May}, pages = {1002-1009}, type = {Article}, abstract = {The design, synthesis, radiolabeling, evaluation of stability, and in vivo investigation are presented of three variably charged, novel, short C-8 chain derivatized chelators for the [M(CO)(3)](+) core (M = Tc-99m or Re). Labeling with [Tc-99m(CO)3](+) showed complex formation in under 1 h reaction time and high stability toward 24 h histidine and cysteine challenges, as well as distinctive log P values for each complex. Distinct localization of small amphiphilic molecules in in vivo systems depends on the charge of the polar moiety and was studied via biodistribution (4 h) and imaging (15 min, 1, 2, and 4 h) in female C57B1/6 mice.}, keywords = {BIFUNCTIONAL LIGAND, BIOMOLECULES, SMALL-MOLECULE RADIOPHARMACEUTICALS, SYSTEMS, technetium}, isbn = {1043-1802}, url = {://000266292500021}, author = {Boros, E. and Hafeli, U. O. and Patrick, B. O. and Adam,Michael J. and Orvig, Chris} } @article {2370, title = {Glucosamine conjugates bearing N,N,O-donors: potential imaging agents utilizing the [M(CO)(3)](+) core (M = Re, Tc)}, journal = {Dalton Transactions}, number = {42}, year = {2009}, note = {ISI Document Delivery No.: 508YBTimes Cited: 2Cited Reference Count: 32Bowen, Meryn L. Lim, Nathaniel C. Ewart, Charles B. Misri, Ripen Ferreira, Cara L. Haefeli, Urs Adam, Michael J. Orvig, Chris}, pages = {9216-9227}, type = {Article}, abstract = {The design rationale, synthesis and radiolabeling evaluation of four glucosamine conjugated ligands for the [Tc-99m(CO)(3)](+) core is described. The capability to bind the tricarbonyl core is initially demonstrated using the cold surrogate [Re(CO)(3)](+). The four compounds are competent chelates in binding [Tc-99m(CO)(3)](+) as labeling studies show, with yields ranging from 79 to 96\% and the resulting complexes showing stability in the presence of competing chelates for 24 h at 37 degrees C. The rhenium complexes were tested for hexokinase-catalysed phosphorylation, and the technetium complexes were tested for GLUT-1 mediated cell uptake - they showed a small amount of uptake but it was not glucose dependent, suggesting that it was not via the GLUT-1 transporters.}, keywords = {BIOMOLECULES, EXPRESSION, GLUT-1, HEXOKINASE, IN-VITRO, METAL-COMPLEXES, TC-99M, technetium, TRANSPORTERS, TRICARBONYL COMPLEXES}, isbn = {1477-9226}, url = {://000270973800020}, author = {Bowen, M. L. and Lim, N. C. and Ewart, C. B. and Misri, R. and Ferreira, C. L. and Hafeli, U. and Adam,Michael J. and Orvig, Chris} } @article {2370, title = {Glucosamine conjugates bearing N,N,O-donors: potential imaging agents utilizing the [M(CO)(3)](+) core (M = Re, Tc)}, journal = {Dalton Transactions}, number = {42}, year = {2009}, note = {ISI Document Delivery No.: 508YBTimes Cited: 2Cited Reference Count: 32Bowen, Meryn L. Lim, Nathaniel C. Ewart, Charles B. Misri, Ripen Ferreira, Cara L. Haefeli, Urs Adam, Michael J. Orvig, Chris}, pages = {9216-9227}, type = {Article}, abstract = {The design rationale, synthesis and radiolabeling evaluation of four glucosamine conjugated ligands for the [Tc-99m(CO)(3)](+) core is described. The capability to bind the tricarbonyl core is initially demonstrated using the cold surrogate [Re(CO)(3)](+). The four compounds are competent chelates in binding [Tc-99m(CO)(3)](+) as labeling studies show, with yields ranging from 79 to 96\% and the resulting complexes showing stability in the presence of competing chelates for 24 h at 37 degrees C. The rhenium complexes were tested for hexokinase-catalysed phosphorylation, and the technetium complexes were tested for GLUT-1 mediated cell uptake - they showed a small amount of uptake but it was not glucose dependent, suggesting that it was not via the GLUT-1 transporters.}, keywords = {BIOMOLECULES, EXPRESSION, GLUT-1, HEXOKINASE, IN-VITRO, METAL-COMPLEXES, TC-99M, technetium, TRANSPORTERS, TRICARBONYL COMPLEXES}, isbn = {1477-9226}, url = {://000270973800020}, author = {Bowen, M. L. and Lim, N. C. and Ewart, C. B. and Misri, R. and Ferreira, C. L. and Hafeli, U. and Adam,Michael J. and Orvig, Chris} } @article {2369, title = {Long-chain rhenium and technetium glucosamine conjugates}, journal = {Dalton Transactions}, number = {42}, year = {2009}, note = {ISI Document Delivery No.: 508YBTimes Cited: 0Cited Reference Count: 44Bowen, Meryn L. Chen, Zhen-Feng Roos, Adrienne M. Misri, Ripen Haefeli, Urs Adam, Michael J. Orvig, Chris}, pages = {9228-9236}, type = {Article}, abstract = {A series of five glucosamine-conjugated organometallic complexes of the tricarbonyl cores of technetium-99m and rhenium were made. Glucosamine was derivatized at the C-2 nitrogen with long chain alkyl spacers linked to either pyridyl-tert-nitrogen-phenol tridentate chelates or cyclopentadienyl ligating groups. The metal complexes of the tridentate ligands were formed by refluxing with [Re(CO)(3)(H2O)(3)]Br, or with a base and [Tc-99m(CO)(3)(H2O)(3)](+). These ligands were found to be competent chelates in binding the [Tc-99m(CO)(3)](+) core as radiolabeling yields ranged from 87 to 93\% and the resulting complexes are stable to cysteine and histidine challenges for 24 h. The cyclopentadienyl analogues were formed using a double ligand transfer reaction for the rhenium complexes and a single ligand transfer for the technetium-99m complexes. All five rhenium complexes were tested as substrates of hexokinase; two of these complexes were tested as hexokinase inhibitors and they were found to be competent inhibitors, suggesting that they may be able to interact with hexokinase. MTT cytotoxicity studies were performed and the complexes tested were found to be non-toxic to the concentrations tested (100 mu M or 1 mM). GLUT-1 mediated cell uptake studies were performed on all five technetium-99m complexes, and their cell entry was found to parallel their lipophilicities, suggesting that cellular uptake is by passive diffusion and is not mediated by GLUT-1.}, keywords = {99M-TECHNETIUM, BIOMOLECULES, BREAST-CANCER, DERIVATIVES, HEXOKINASE, IN-VITRO, METAL-COMPLEXES, RE, TC-99M, TRANSPORT}, isbn = {1477-9226}, url = {://000270973800021}, author = {Bowen, M. L. and Chen, Z. F. and Roos, A. M. and Misri, R. and Hafeli, U. and Adam,Michael J. and Orvig, Chris} } @article {2369, title = {Long-chain rhenium and technetium glucosamine conjugates}, journal = {Dalton Transactions}, number = {42}, year = {2009}, note = {ISI Document Delivery No.: 508YBTimes Cited: 0Cited Reference Count: 44Bowen, Meryn L. Chen, Zhen-Feng Roos, Adrienne M. Misri, Ripen Haefeli, Urs Adam, Michael J. Orvig, Chris}, pages = {9228-9236}, type = {Article}, abstract = {A series of five glucosamine-conjugated organometallic complexes of the tricarbonyl cores of technetium-99m and rhenium were made. Glucosamine was derivatized at the C-2 nitrogen with long chain alkyl spacers linked to either pyridyl-tert-nitrogen-phenol tridentate chelates or cyclopentadienyl ligating groups. The metal complexes of the tridentate ligands were formed by refluxing with [Re(CO)(3)(H2O)(3)]Br, or with a base and [Tc-99m(CO)(3)(H2O)(3)](+). These ligands were found to be competent chelates in binding the [Tc-99m(CO)(3)](+) core as radiolabeling yields ranged from 87 to 93\% and the resulting complexes are stable to cysteine and histidine challenges for 24 h. The cyclopentadienyl analogues were formed using a double ligand transfer reaction for the rhenium complexes and a single ligand transfer for the technetium-99m complexes. All five rhenium complexes were tested as substrates of hexokinase; two of these complexes were tested as hexokinase inhibitors and they were found to be competent inhibitors, suggesting that they may be able to interact with hexokinase. MTT cytotoxicity studies were performed and the complexes tested were found to be non-toxic to the concentrations tested (100 mu M or 1 mM). GLUT-1 mediated cell uptake studies were performed on all five technetium-99m complexes, and their cell entry was found to parallel their lipophilicities, suggesting that cellular uptake is by passive diffusion and is not mediated by GLUT-1.}, keywords = {99M-TECHNETIUM, BIOMOLECULES, BREAST-CANCER, DERIVATIVES, HEXOKINASE, IN-VITRO, METAL-COMPLEXES, RE, TC-99M, TRANSPORT}, isbn = {1477-9226}, url = {://000270973800021}, author = {Bowen, M. L. and Chen, Z. F. and Roos, A. M. and Misri, R. and Hafeli, U. and Adam,Michael J. and Orvig, Chris} } @article {1390, title = {Carbohydrate-appended 3-hydroxy-4-pyridinone complexes of the [M(CO)(3)](+) core (M) Re, Tc-99m, Re-186)}, journal = {Bioconjugate Chemistry}, volume = {17}, number = {5}, year = {2006}, note = {ISI Document Delivery No.: 085LXTimes Cited: 21Cited Reference Count: 69Ferreira, Cara L. Bayly, Simon R. Green, David E. Storr, Tim Barta, Cheri A. Steele, Jennifer Adam, Michael J. Orvig, Chris}, month = {Sep}, pages = {1321-1329}, type = {Article}, abstract = {This work describes the use of 3-hydroxy-4-pyridinone ligands for binding the [M(CO)(3)](+) core ( M) Re, Tc) in the context of preparing novel Tc( I) and Re( I) glucose conjugates. Five pyridinone ligands bearing pendent carbohydrate moieties, HL1-5, were coordinated to the [M(CO)(3)](+0) core on the macroscopic scale ( M) Re) and on the tracer scale (M) = Tc-99m, Re-186). On the macroscopic scale the complexes, ReL1-5(CO)(3)(H{\O}-2), were thoroughly characterized by mass spectrometry, IR spectroscopy, UV-visible spectroscopy, elemental analysis, and 1D/2D NMR spectroscopy. Characterization confirmed the bidentate coordination of the pyridinone and the pendent nature of the carbohydrate and suggests the presence of a water molecule in the sixth coordination site. In preliminary biological evaluation, both the ligands and complexes were assessed as potential substrates or inhibitors of hexokinase, but showed no activity. Labeling via the [Tc-99m(CO)(3)(H2O)(3)](+) precursor gave the tracer species (TcL1-5)-Tc-99m(CO)(3)(H2O) in high radiochemical yields. Similar high radiochemical yields when labeling with Re-186 were facilitated by in situ preparation of the [Re-186( CO)(3)(H2O)(3)](+) species in the presence of HL1-5 to give (ReL1-5)-Re-186(CO)(3)(H2O). Stability challenges, incubating (TcL1-5)-Tc-99m(CO)(3)(H2O) in the presence of excess cysteine and histidine, confirmed complex stability up to 24 h.}, keywords = {5-HT1A RECEPTOR, BIFUNCTIONAL LIGAND, BIOMOLECULES, GLUCOSE, IMAGING AGENTS, IN-VITRO, METAL-COMPLEXES, STRUCTURAL-CHARACTERIZATION, TRICARBONYL COMPLEXES, TRIDENTATE LIGANDS}, isbn = {1043-1802}, url = {://000240606700027}, author = {Ferreira, C. L. and Bayly, S. R. and Green, D. E. and Storr, T. and Barta, C. A. and Steele, J. and Adam,Michael J. and Orvig, Chris} } @article {1390, title = {Carbohydrate-appended 3-hydroxy-4-pyridinone complexes of the [M(CO)(3)](+) core (M) Re, Tc-99m, Re-186)}, journal = {Bioconjugate Chemistry}, volume = {17}, number = {5}, year = {2006}, note = {ISI Document Delivery No.: 085LXTimes Cited: 21Cited Reference Count: 69Ferreira, Cara L. Bayly, Simon R. Green, David E. Storr, Tim Barta, Cheri A. Steele, Jennifer Adam, Michael J. Orvig, Chris}, month = {Sep}, pages = {1321-1329}, type = {Article}, abstract = {This work describes the use of 3-hydroxy-4-pyridinone ligands for binding the [M(CO)(3)](+) core ( M) Re, Tc) in the context of preparing novel Tc( I) and Re( I) glucose conjugates. Five pyridinone ligands bearing pendent carbohydrate moieties, HL1-5, were coordinated to the [M(CO)(3)](+0) core on the macroscopic scale ( M) Re) and on the tracer scale (M) = Tc-99m, Re-186). On the macroscopic scale the complexes, ReL1-5(CO)(3)(H{\O}-2), were thoroughly characterized by mass spectrometry, IR spectroscopy, UV-visible spectroscopy, elemental analysis, and 1D/2D NMR spectroscopy. Characterization confirmed the bidentate coordination of the pyridinone and the pendent nature of the carbohydrate and suggests the presence of a water molecule in the sixth coordination site. In preliminary biological evaluation, both the ligands and complexes were assessed as potential substrates or inhibitors of hexokinase, but showed no activity. Labeling via the [Tc-99m(CO)(3)(H2O)(3)](+) precursor gave the tracer species (TcL1-5)-Tc-99m(CO)(3)(H2O) in high radiochemical yields. Similar high radiochemical yields when labeling with Re-186 were facilitated by in situ preparation of the [Re-186( CO)(3)(H2O)(3)](+) species in the presence of HL1-5 to give (ReL1-5)-Re-186(CO)(3)(H2O). Stability challenges, incubating (TcL1-5)-Tc-99m(CO)(3)(H2O) in the presence of excess cysteine and histidine, confirmed complex stability up to 24 h.}, keywords = {5-HT1A RECEPTOR, BIFUNCTIONAL LIGAND, BIOMOLECULES, GLUCOSE, IMAGING AGENTS, IN-VITRO, METAL-COMPLEXES, STRUCTURAL-CHARACTERIZATION, TRICARBONYL COMPLEXES, TRIDENTATE LIGANDS}, isbn = {1043-1802}, url = {://000240606700027}, author = {Ferreira, C. L. and Bayly, S. R. and Green, D. E. and Storr, T. and Barta, C. A. and Steele, J. and Adam,Michael J. and Orvig, Chris} } @article {1392, title = {Glucosamine conjugates of tricarbonylcyclopentadienyl rhenium(I) and technetium(I) cores}, journal = {Inorganic Chemistry}, volume = {45}, number = {17}, year = {2006}, note = {ISI Document Delivery No.: 073DPTimes Cited: 13Cited Reference Count: 43Ferreira, Cara L. Ewart, Charles B. Bayly, Simon R. Patrick, Brian O. Steele, Jennifer Adam, Michael J. Orvig, Chris}, month = {Aug}, pages = {6979-6987}, type = {Article}, abstract = {To obtain a Tc-99m glucose conjugate for imaging, double-ligand transfer (DLT) and related reactions were examined for the preparation of CpM(CO)(3) (Cp = cyclopentadienyl; M = Re, Tc) complexes with pendant carbohydrates at Cp. Tricarbonyl {N-(1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-beta-D-glucopyranose) cyclopentadienyl carboxamide} rhenium(I) (1a) and tricarbonyl {N-(2-amino-2-deoxy-beta-D-glucopyranose) cyclopentadienyl carboxamide} rhenium(I) (2a) were prepared. The compounds were fully characterized by mass spectrometry, elemental analysis, IR, and NMR spectroscopy. Full assignment of the NMR spectra verified the pendant nature of the glucosamine moieties in the solution state and that 2a exists as both anomers. The solid-state structure of 2a was determined by X-ray crystallography, again confirming the pendant nature of the glucosamine, but differing from the solution state in that the, anomer crystallized preferentially (93\%). Compound 2a was determined to be a high-affinity competitive inhibitor (K-i = 330 +/- 70 mu M) of the glucose metabolism enzyme hexokinase, demonstrating that it retains certain biological activity. The Tc-99m analogues 1b and 2b were prepared in moderate radiochemical yields by means of the single-ligand transfer (SLT) route, which is more pertinent to radiopharmaceutical synthesis.}, keywords = {BIOMOLECULES, COORDINATION, CYCLOPENTADIENYL-TRICARBONYL COMPLEXES, DERIVATIVES, FUNCTIONALIZATION, IN-VITRO, METAL-COMPLEXES, RE-186(I), RECEPTOR, TC-99M}, isbn = {0020-1669}, url = {://000239723300060}, author = {Ferreira, C. L. and Ewart, C. B. and Bayly, S. R. and Patrick, B. O. and Steele, J. and Adam,Michael J. and Orvig, Chris} } @article {1392, title = {Glucosamine conjugates of tricarbonylcyclopentadienyl rhenium(I) and technetium(I) cores}, journal = {Inorganic Chemistry}, volume = {45}, number = {17}, year = {2006}, note = {ISI Document Delivery No.: 073DPTimes Cited: 13Cited Reference Count: 43Ferreira, Cara L. Ewart, Charles B. Bayly, Simon R. Patrick, Brian O. Steele, Jennifer Adam, Michael J. Orvig, Chris}, month = {Aug}, pages = {6979-6987}, type = {Article}, abstract = {To obtain a Tc-99m glucose conjugate for imaging, double-ligand transfer (DLT) and related reactions were examined for the preparation of CpM(CO)(3) (Cp = cyclopentadienyl; M = Re, Tc) complexes with pendant carbohydrates at Cp. Tricarbonyl {N-(1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-beta-D-glucopyranose) cyclopentadienyl carboxamide} rhenium(I) (1a) and tricarbonyl {N-(2-amino-2-deoxy-beta-D-glucopyranose) cyclopentadienyl carboxamide} rhenium(I) (2a) were prepared. The compounds were fully characterized by mass spectrometry, elemental analysis, IR, and NMR spectroscopy. Full assignment of the NMR spectra verified the pendant nature of the glucosamine moieties in the solution state and that 2a exists as both anomers. The solid-state structure of 2a was determined by X-ray crystallography, again confirming the pendant nature of the glucosamine, but differing from the solution state in that the, anomer crystallized preferentially (93\%). Compound 2a was determined to be a high-affinity competitive inhibitor (K-i = 330 +/- 70 mu M) of the glucose metabolism enzyme hexokinase, demonstrating that it retains certain biological activity. The Tc-99m analogues 1b and 2b were prepared in moderate radiochemical yields by means of the single-ligand transfer (SLT) route, which is more pertinent to radiopharmaceutical synthesis.}, keywords = {BIOMOLECULES, COORDINATION, CYCLOPENTADIENYL-TRICARBONYL COMPLEXES, DERIVATIVES, FUNCTIONALIZATION, IN-VITRO, METAL-COMPLEXES, RE-186(I), RECEPTOR, TC-99M}, isbn = {0020-1669}, url = {://000239723300060}, author = {Ferreira, C. L. and Ewart, C. B. and Bayly, S. R. and Patrick, B. O. and Steele, J. and Adam,Michael J. and Orvig, Chris} } @article {1265, title = {A glucosamine dipicolylamine conjugate of Tc-99m(I) and Re-186(I) for use in imaging and therapy}, journal = {Dalton Transactions}, number = {4}, year = {2005}, note = {ISI Document Delivery No.: 895EYTimes Cited: 32Cited Reference Count: 16}, pages = {654-655}, type = {Article}, abstract = {The synthesis and metal complexation of a glucosamine-appended 2,2{\textquoteright}-dipicolylamine ligand to the tricarbonyls of Tc-99m and Re-186 is described; the ligand was found to bind in a tridentate fashion with the glucosamine function remaining pendant, and the Tc-99m complex was found to exhibit exceptional stability towards in vitro ligand exchange experiments.}, keywords = {ACID, BIOMOLECULES, COMPLEXES, RADIOPHARMACEUTICALS, RE}, isbn = {1477-9226}, url = {://000226844900003}, author = {Storr, T. and Fisher, C. L. and Mikata, Y. and Yano, S. and Adam,Michael J. and Orvig, Chris} } @article {1265, title = {A glucosamine dipicolylamine conjugate of Tc-99m(I) and Re-186(I) for use in imaging and therapy}, journal = {Dalton Transactions}, number = {4}, year = {2005}, note = {ISI Document Delivery No.: 895EYTimes Cited: 32Cited Reference Count: 16}, pages = {654-655}, type = {Article}, abstract = {The synthesis and metal complexation of a glucosamine-appended 2,2{\textquoteright}-dipicolylamine ligand to the tricarbonyls of Tc-99m and Re-186 is described; the ligand was found to bind in a tridentate fashion with the glucosamine function remaining pendant, and the Tc-99m complex was found to exhibit exceptional stability towards in vitro ligand exchange experiments.}, keywords = {ACID, BIOMOLECULES, COMPLEXES, RADIOPHARMACEUTICALS, RE}, isbn = {1477-9226}, url = {://000226844900003}, author = {Storr, T. and Fisher, C. L. and Mikata, Y. and Yano, S. and Adam,Michael J. and Orvig, Chris} } @article {805, title = {Carbohydrate conjugates for molecular imaging and radiotherapy: Tc-99m(I) and Re-186(I) tricarbonyl complexes of N-(2 {\textquoteright}-hydroxybenzyl)-2-amino-2-deoxy-D-glucose}, journal = {Bioconjugate Chemistry}, volume = {15}, number = {4}, year = {2004}, note = {ISI Document Delivery No.: 840SWTimes Cited: 39Cited Reference Count: 17}, month = {Jul-Aug}, pages = {923-926}, type = {Article}, abstract = {An approach to a new class of potential radiopharmaceuticals is demonstrated by the labeling of a glucosamine derivative with the tricarbonyls of Tc-99m and Re-186. The proligand HL2 (N-(2{\textquoteright}-hydroxybenzyl)-2-amino-2-deoxy-d-glucose) was produced by hydrogenation of the corresponding Schiff base and reacted with [NEt4](2)[Re(CO)(3)Br-3] to form the neutral complex [(L-2)Re(CO)(3)] in 40\% yield. H-1 and C-13 NMR spectra indicate that the {Re(CO)(3)} core is bound in a tridentate fashion via the amino N, phenolato O, and C-3 hydroxyl O atoms of the ligand. At the tracer-level, labeling of HL2 with [Tc-99m(CO)(3)(H2O)(3)](+) and [Re-186(CO)(3)(H2O)(3)](+) was achieved in aqueous conditions in 95 +/- 2\% and 94 +/- 3\% average radiochemical yields, respectively.}, keywords = {BIOMOLECULES, GLUCOSE, LIGAND SYSTEMS, RADIOPHARMACEUTICALS, SUGARS}, isbn = {1043-1802}, url = {://000222880900032}, author = {Bayly, S. R. and Fisher, C. L. and Storr, T. and Adam,Michael J. and Orvig, Chris} } @article {805, title = {Carbohydrate conjugates for molecular imaging and radiotherapy: Tc-99m(I) and Re-186(I) tricarbonyl complexes of N-(2 {\textquoteright}-hydroxybenzyl)-2-amino-2-deoxy-D-glucose}, journal = {Bioconjugate Chemistry}, volume = {15}, number = {4}, year = {2004}, note = {ISI Document Delivery No.: 840SWTimes Cited: 39Cited Reference Count: 17}, month = {Jul-Aug}, pages = {923-926}, type = {Article}, abstract = {An approach to a new class of potential radiopharmaceuticals is demonstrated by the labeling of a glucosamine derivative with the tricarbonyls of Tc-99m and Re-186. The proligand HL2 (N-(2{\textquoteright}-hydroxybenzyl)-2-amino-2-deoxy-d-glucose) was produced by hydrogenation of the corresponding Schiff base and reacted with [NEt4](2)[Re(CO)(3)Br-3] to form the neutral complex [(L-2)Re(CO)(3)] in 40\% yield. H-1 and C-13 NMR spectra indicate that the {Re(CO)(3)} core is bound in a tridentate fashion via the amino N, phenolato O, and C-3 hydroxyl O atoms of the ligand. At the tracer-level, labeling of HL2 with [Tc-99m(CO)(3)(H2O)(3)](+) and [Re-186(CO)(3)(H2O)(3)](+) was achieved in aqueous conditions in 95 +/- 2\% and 94 +/- 3\% average radiochemical yields, respectively.}, keywords = {BIOMOLECULES, GLUCOSE, LIGAND SYSTEMS, RADIOPHARMACEUTICALS, SUGARS}, isbn = {1043-1802}, url = {://000222880900032}, author = {Bayly, S. R. and Fisher, C. L. and Storr, T. and Adam,Michael J. and Orvig, Chris} }