@article {2024,
	title = {99m-Technetium carbohydrate conjugates as potential agents in molecular imaging},
	journal = {Chemical Communications},
	number = {41},
	year = {2008},
	note = {ISI Document Delivery No.: 365LHTimes Cited: 19Cited Reference Count: 97Bowen, Meryn L. Orvig, Chris},
	pages = {5077-5091},
	type = {Article},
	abstract = {This feature article covers recent reports of work towards the development of Tc-99m-carbohydrate based agents for use in SPECT imaging, particularly of cancerous tissue. An outline of some of the key biological functions and coordination chemistry of carbohydrates is given, along with an introduction to bioconjugation and molecular imaging. Technetium coordination chemistry and the subset of this involving bioconjugates are discussed before moving into the focus of the article: glycoconjugates of Tc-99m(v) and the more recently developed [Tc-99m(I)(CO)(3)](+). Significant work in the last decade has featured the very attractive [Tc-99m(CO)(3)](+) core, and the ligand sets designed for this core are discussed in detail.},
	keywords = {ANTITUMOR-ACTIVITY, BIFUNCTIONAL CHELATORS, BIOLOGICAL EVALUATION, D-GLUCOSE, IN-VITRO, ISOSTRUCTURAL RE, METAL-COMPLEXES, STRUCTURAL-CHARACTERIZATION, TC-99M COMPLEXES, TRICARBONYL COMPLEXES},
	isbn = {1359-7345},
	url = {<Go to ISI>://000260407400002},
	author = {Bowen, M. L. and Orvig, Chris}
}
@article {1267,
	title = {Carbohydrate-appended 2,2 {\textquoteright}-dipicolylamine metal complexes as potential imaging agents},
	journal = {Inorganic Chemistry},
	volume = {44},
	number = {8},
	year = {2005},
	note = {ISI Document Delivery No.: 916GWTimes Cited: 44Cited Reference Count: 58},
	month = {Apr},
	pages = {2698-2705},
	type = {Article},
	abstract = {Three discrete carbohydrate-appended 2,2{\textquoteright}-dipicolylamine ligands were complexed to the {M(CO)3}(+) (M = Tc-99m/ Re) core: 2-(bis(2-pyridinylmethyl)amino)ethyl-beta-D-glucopyranoside (L-1), 2-(bis(2-pyridinylmethyl)amino)ethyl-beta-Dxylopyranoside (L-2), and 2-(bis(2-pyridinylmethyl)amino)ethyl-alpha-D-mannopyranoside (L-3). An ethylene spacer is used to separate the carbohydrate moiety and the dipicolylamine (DPA) function in all three ligands. The Re complexes [Re(L1-3)(CO)(3)]Br were characterized by H-1 and C-13 1D/2D NMR spectroscopies, which confirmed the pendant nature of the carbohydrate moieties in solution. NMR measurements also established the long-range asymmetric effect of the carbohydrate functions on the chelating portion of the ligand. One analogue, [Re(L-1)(CO)(3)]Cl, was characterized in the solid state by X-ray crystallography. Further characterization was provided by IR spectroscopy, elemental analysis, conductivity, and mass spectrometry. Radiolabeling of L-1-L-3 with [Tc-99m(H2O)(3)(CO)(3)](+) afforded high yield compounds of identical character to the Re analogues. The radiolabeled compounds were found to be stable toward ligand exchange in the presence of a large excess of either cysteine or histidine over a 24-h period.},
	keywords = {AMINO-SUGARS, ANTITUMOR-ACTIVITY, BOMBESIN ANALOG, D-GLUCOSE, HIGH-AFFINITY, IN-VITRO, LIGANDS, PALLADIUM(II) COMPLEXES, RHENIUM CARBONYL-COMPLEXES, STRUCTURAL-CHARACTERIZATION, TRIDENTATE},
	isbn = {0020-1669},
	url = {<Go to ISI>://000228374400020},
	author = {Storr, T. and Sugai, Y. and Barta, C. A. and Mikata, Y. and Adam,Michael J. and Yano, S. and Orvig, Chris}
}
@article {1267,
	title = {Carbohydrate-appended 2,2 {\textquoteright}-dipicolylamine metal complexes as potential imaging agents},
	journal = {Inorganic Chemistry},
	volume = {44},
	number = {8},
	year = {2005},
	note = {ISI Document Delivery No.: 916GWTimes Cited: 44Cited Reference Count: 58},
	month = {Apr},
	pages = {2698-2705},
	type = {Article},
	abstract = {Three discrete carbohydrate-appended 2,2{\textquoteright}-dipicolylamine ligands were complexed to the {M(CO)3}(+) (M = Tc-99m/ Re) core: 2-(bis(2-pyridinylmethyl)amino)ethyl-beta-D-glucopyranoside (L-1), 2-(bis(2-pyridinylmethyl)amino)ethyl-beta-Dxylopyranoside (L-2), and 2-(bis(2-pyridinylmethyl)amino)ethyl-alpha-D-mannopyranoside (L-3). An ethylene spacer is used to separate the carbohydrate moiety and the dipicolylamine (DPA) function in all three ligands. The Re complexes [Re(L1-3)(CO)(3)]Br were characterized by H-1 and C-13 1D/2D NMR spectroscopies, which confirmed the pendant nature of the carbohydrate moieties in solution. NMR measurements also established the long-range asymmetric effect of the carbohydrate functions on the chelating portion of the ligand. One analogue, [Re(L-1)(CO)(3)]Cl, was characterized in the solid state by X-ray crystallography. Further characterization was provided by IR spectroscopy, elemental analysis, conductivity, and mass spectrometry. Radiolabeling of L-1-L-3 with [Tc-99m(H2O)(3)(CO)(3)](+) afforded high yield compounds of identical character to the Re analogues. The radiolabeled compounds were found to be stable toward ligand exchange in the presence of a large excess of either cysteine or histidine over a 24-h period.},
	keywords = {AMINO-SUGARS, ANTITUMOR-ACTIVITY, BOMBESIN ANALOG, D-GLUCOSE, HIGH-AFFINITY, IN-VITRO, LIGANDS, PALLADIUM(II) COMPLEXES, RHENIUM CARBONYL-COMPLEXES, STRUCTURAL-CHARACTERIZATION, TRIDENTATE},
	isbn = {0020-1669},
	url = {<Go to ISI>://000228374400020},
	author = {Storr, T. and Sugai, Y. and Barta, C. A. and Mikata, Y. and Adam,Michael J. and Yano, S. and Orvig, Chris}
}
@article {1266,
	title = {Novel carbohydrate-appended metal complexes for potential use in molecular imaging},
	journal = {Chemistry-a European Journal},
	volume = {11},
	number = {1},
	year = {2005},
	note = {ISI Document Delivery No.: 887BZTimes Cited: 27Cited Reference Count: 60},
	month = {Dec},
	pages = {195-203},
	type = {Article},
	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.},
	keywords = {AMINO-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},
	isbn = {0947-6539},
	url = {<Go to ISI>://000226278700018},
	author = {Storr, T. and Obata, M. and Fisher, C. L. and Bayly, S. R. and Green, D. E. and Brudzinska, I. and Mikata, Y. and Patrick, B. O. and Adam,Michael J. and Yano, S. and Orvig, Chris}
}
@article {1266,
	title = {Novel carbohydrate-appended metal complexes for potential use in molecular imaging},
	journal = {Chemistry-a European Journal},
	volume = {11},
	number = {1},
	year = {2005},
	note = {ISI Document Delivery No.: 887BZTimes Cited: 27Cited Reference Count: 60},
	month = {Dec},
	pages = {195-203},
	type = {Article},
	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.},
	keywords = {AMINO-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},
	isbn = {0947-6539},
	url = {<Go to ISI>://000226278700018},
	author = {Storr, T. and Obata, M. and Fisher, C. L. and Bayly, S. R. and Green, D. E. and Brudzinska, I. and Mikata, Y. and Patrick, B. O. and Adam,Michael J. and Yano, S. and Orvig, Chris}
}
@article {5208,
	title = {Sugar nucleotide-modifying enzymes},
	journal = {Current Organic Chemistry},
	volume = {5},
	number = {2},
	year = {2001},
	note = {ISI Document Delivery No.: 411FKTimes Cited: 12Cited Reference Count: 170},
	month = {Feb},
	pages = {169-192},
	type = {Review},
	abstract = {Sugar nucleotides serve as the activated forms of carbohydrates that are used in a wide range of biosynthetic pathways. Instead of building up the sugar nucleotide from the free sugar itself, nature often chooses to modify the "donor" portion of a pre-existing sugar nucleotide in a biosynthetically efficient manner. In doing so a rich variety of catalytic strategies are employed and this review focuses on recent mechanistic and structural studies of the sugar nucleotide-modifying enzymes. The review is organized around the types of reactions catalyzed and contains the following sections: Epimerases/Mutases/Decarboxylases, Eliminations and Substitutions, Oxidation and Reduction, and Substitutions on the Periphery of Sugar Nucleotides.},
	keywords = {4, 6-DEHYDRATASE, 6-DIDEOXYHEXOSES, ACETYLGLUCOSAMINE 2-EPIMERASE/N-ACETYLMANNOSAMINE, ACETYLNEURAMINIC ACID, biosynthesis, CYTIDINE DIPHOSPHATE 3, D-GLUCOSE, ESCHERICHIA-COLI K-12, FIRST 2, GDP-FUCOSE SYNTHETASE, KINASE, N-ACETYLGLUCOSAMINE, SITE-DIRECTED MUTAGENESIS, STEPS, UDP-GALACTOSE 4-EPIMERASE},
	isbn = {1385-2728},
	url = {<Go to ISI>://000167487300004},
	author = {Tanner, M. E.}
}
@article {5150,
	title = {Sugar-pendant diamines},
	journal = {Journal of Organic Chemistry},
	volume = {66},
	number = {11},
	year = {2001},
	note = {ISI Document Delivery No.: 435ZDTimes Cited: 19Cited Reference Count: 62},
	month = {Jun},
	pages = {3783-3789},
	type = {Article},
	abstract = {A set of 1,3-propanediamine derivatives connected to carbohydrates (5) has been prepared in four steps from peracetylated sugar and 1,3-dibromo-2-propanol in 60-73\% yields. D-Glucose, D-mannose, D-galactose, D-xylose, D-ribose, and maltose are utilized as sugar molecules in this work. The diamine moiety was connected to the C1 carbon of the glycopyranose ring via an O-glycoside bond. All of the anomeric configurations and sugar puckering conformations, except in the D-maltose derivative, were determined by X-ray crystallography of the diazido or dibromo precursors. While glycosidation of peracetylated galactopyranose with 1,3-dibromo-2-propanol in the presence of boron trifluoride afforded both anomers, the neighboring group participation of the 2-acetoxy group yielded a single anomer for the other substrates. This method has been used to synthesize a library of sugar-pendant diamines including an OH-protected derivative (6), and an N,N {\textquoteright} -diisopropyl-substituted derivative (7). A similar series of reactions using 2,3-dibromo-1-propanol gave ethylenediamine-type derivatives (11), and bis(bromomethyl)bis(hydroxymethyl)methane (12) gave bisglucose-pendant derivatives (16).},
	keywords = {BINDING-PROPERTIES, C-2 EPIMERIZATION, CARBON SKELETON, D-GLUCOSE, ETHYLENEDIAMINE, LIGANDS, N-GLYCOSIDES, NICKEL(II) COMPLEXES, PHOTOCYTOTOXICITY, WATER},
	isbn = {0022-3263},
	url = {<Go to ISI>://000168911300018},
	author = {Mikata, Y. and Shinohara, Y. and Yoneda, K. and Nakamura, Y. and Esaki, K. and Tanahashi, M. and Brudzinska, I. and Hirohara, S. and Yokoyama, M. and Mogami, K. and Tanase, T. and Kitayama, T. and Takashiba, K. and Nabeshima, K. and Takagi, R. and Takatani, M. and Okamoto, T. and Kinoshita, I. and Doe, M. and Hamazawa, A. and Morita, M. and Nishida, F. and Sakakibara, T. and Orvig, Chris and Yano, S.}
}
@article {3444,
	title = {SYNTHESES, RADIOLABELING, AND KINETIC EVALUATION OF 2-DEOXY-2-FLUORO-2-IODO-D-HEXOSES FOR MEDICAL IMAGING},
	journal = {Carbohydrate Research},
	volume = {266},
	number = {2},
	year = {1995},
	note = {ISI Document Delivery No.: QE571Times Cited: 13Cited Reference Count: 10},
	month = {Jan},
	pages = {273-277},
	type = {Note},
	keywords = {2-DEOXY-2-FLUORO-2-IODO-D-GLUCOSE, 2-DEOXY-2-FLUORO-2-IODO-D-MANNOSE, D-GLUCOSE, HEXOKINASE SUBSTRATES, MEDICAL IMAGING, RADIOLABELED 2-DEOXY-2-FLUORO-2-IODO-D-HEXOSES},
	isbn = {0008-6215},
	url = {<Go to ISI>://A1995QE57100010},
	author = {McCarter, J. D. and Adam,Michael J. and Withers, S. G.}
}
