@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 {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 = {://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 = {://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 {5232, title = {Chemistry of Re with N,N {\textquoteright}-bis(2-pyridylmethyl)ethylenediamine (H(2)pmen): Hydrolysis, dehydrogenation, and ternary complexes}, journal = {Inorganic Chemistry}, volume = {40}, number = {9}, year = {2001}, note = {ISI Document Delivery No.: 423DBTimes Cited: 13Cited Reference Count: 49}, month = {Apr}, pages = {2005-2010}, type = {Article}, abstract = {A number of Re complexes with N,N {\textquoteright} -bis(2-pyridylmethyl)ethylenediamine (H(2)pmen) have been made from [NH4]-[ReO4]. . [ReOCl(2)H(2)pmen)]Cl, [ReOCl(Hpmen)][ReO4], and [ReO2(H(2)pmen)] [ReO4] are related by hydrolysis/HCl substitution [ReOCl(Hpmen)] [ReO4] was structurally characterized and found to contain a water-stable amido-Re bend. Dehydrogenation of the N-donor ligand from each amine to imine with concomitant two-electron reduction of the Re center occurs readily in these systems. With suitable 3-hydroxy-4-pyrones, ternary complexes such as [(ReCl)-Cl-III(ma)(C14H14N4)][ReO4]. CH3OH, 5, were made from [NH4][ReO4], H(2)pmen . 4HCl and pyrones in one-pot syntheses. 5, a seven-coordinate Re-III complex, was structurally characterized.}, keywords = {aluminum, CHELATE COMPLEXES, COORDINATION-COMPOUNDS, gallium, LIGANDS, RADIOPHARMACEUTICALS, RAY CRYSTAL-STRUCTURE, Rhenium complexes, technetium, TRIS(2-PYRIDYLMETHYL)AMINE}, isbn = {0020-1669}, url = {://000168159200007}, author = {Xu, L. and Pierreroy, J. and Patrick, B. O. and Orvig, Chris} } @article {4983, title = {Seven-coordinate [(ReON4X2)-O-V](+) complexes (X = O and Cl)}, journal = {Inorganic Chemistry}, volume = {39}, number = {26}, year = {2000}, note = {ISI Document Delivery No.: 385TFTimes Cited: 10Cited Reference Count: 29}, month = {Dec}, pages = {5958-5963}, type = {Article}, abstract = {The oxorhenium(V) complexes with ligands containing N-4 (H(2)pmen) and N4O2 (H(2)bbpen, H(2)Clbbpen, and H(2)bped) donor atom sets have been synthesized. X-ray crystallographic analyses of the [ReO(H(2)pmen)Cl-2](+), [ReO(bbpen)](+), and [ReO(bped)](+) complexes showed that all three cations share a rate seven-coordinate structure with a distorted pentagonal bipyramidal geometry, which represents a novel and potentially general structural motif in Re-V=O complexes. H-1 NMR spectroscopy shows that the structures of the complexes are retained in the solution.}, keywords = {CHELATION, CHEMISTRY, LIGANDS, N3O2, pyridyl, RADIOPHARMACEUTICALS, rhenium, technetium, TRIS(2-PYRIDYLMETHYL)AMINE}, isbn = {0020-1669}, url = {://000166019200010}, author = {Xu, L. and Setyawati, I. A. and Pierreroy, J. and Pink, M. and Young, V. G. and Patrick, B. O. and Rettig, S. J. and Orvig, Chris} } @article {3751, title = {Rhenium complexes of P,P,P{\textquoteright},P{\textquoteright}-tetrakis(o-hydroxyphenyl)diphosphinoethane}, journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie}, volume = {74}, number = {5}, year = {1996}, note = {ISI Document Delivery No.: UP791Times Cited: 6Cited Reference Count: 25}, month = {May}, pages = {722-729}, type = {Article}, abstract = {Preparation of the hydrochloride salt of a new potentially hexadentate ligand precursor P,P,P{\textquoteright},P{\textquoteright}-tetrakis(o-hydroxyphenyl)diphosphinoethane dihydrochloride (abbreviated H4P2O4 . 2HCl) is described. From H4P2O4 . 2HCl, neutral [Re2O2Cl2(PPh(3))(2)(mu-P2O4)] and dianionic [Re2O2Br4(mu-P2O4)](2-) dinuclear rhenium(V) complexes were synthesized. The complexes have been characterized by elemental analysis, infrared spectroscopy, mass spectrometry, and (HP)-H-1-P-31{H-1} NMR spectra. P-31{H-1} NMR revealed that only one isomer, presumably the anti, was present for [Re2O2Cl2(PPh(3))(2)(mu-P2O4)], and that two isomers, both anti and syn isomers, were observed for [Re2O2Br4(mu-P2O4)](2-). The coligands (PPh, for the former, Br- for the latter) of both complexes underwent ligand exchange with pyridine.}, keywords = {CHEMISTRY, COORDINATION, CRYSTAL, DIMER, ISOMERS, NITRIDO COMPLEXES, P, P{\textquoteright}, P{\textquoteright}-tetrakis(o-hydroxyphenyl)diphosphinoethane, rhenium, technetium}, isbn = {0008-4042}, url = {://A1996UP79100012}, author = {Luo, H. Y. and Orvig, Chris} } @article {3435, title = {Rhenium and technetium complexes from pentadentate (N3O2) and tetradentate (N2O2) Schiff base ligands}, journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie}, volume = {73}, number = {12}, year = {1995}, note = {ISI Document Delivery No.: TV232Times Cited: 16Cited Reference Count: 32}, month = {Dec}, pages = {2272-2281}, type = {Article}, abstract = {{The rhenium(V) and technetium(V) complexes: [ReO(apa)], [{ReO(epa)}O-2], and [TcOCl(epa)] have been prepared from a potentially pentadentate N3O2 ligand, N,N{\textquoteright}-3-azapentane-1,5-diylbis(3-(1-iminoethyl)-6-methyl-2H-pyran-2,4(3H) -dione) (H(3)apa), or a potentially tetradentate N2O2 ligand, N,N{\textquoteright}-ethylene-diylbis(3-(1-iminoethyl)-6-methyl-2H-pyran-2,4 (3H)-dione) (H(2)epa). The N2O2 complexes were synthesized in low yields. There was also evidence indicating that H(2)ppa, N,H{\textquoteright}-propylene-diylbis(3-(1-iminoethyl)-6-methyl-2H-pyran- 2,4(3H)-dione), hydrolyzed in the course of coordination, forms a rhenium complex of the bidentate monoprotic (O,O) dehydroacetate (dha(-)), [Re(dha)Cl-2(OPPh(3))(PPh(3))]. EtOH. The structure of this complex was determined by X-ray crystallography. Crystals of [Re(dha)Cl-2(OPPh(3))(PPh(3))]. EtOH (C44H37Cl2O5P2Re . C2H6O) are monoclinic}, keywords = {AMINE PHENOL LIGANDS, ATOM TRANSFER-REACTIONS, CRYSTAL-STRUCTURES, dehydroacetic acetate based Schiff base ligands, N2O2 Schiff base, N3O2 Schiff base, OXO-COMPLEXES, oxygen transfer, rhenium, technetium, X-ray structures}, isbn = {0008-4042}, url = {://A1995TV23200022}, author = {Luo, H. Y. and Liu, S. and Rettig, S. J. and Orvig, Chris} } @article {3021, title = {CHARACTERIZATION OF TRIS(N-SUBSTITUTED-2-METHYL-3-HYDROXY-4-PYRIDINONATO)TECHNETIUM(IV) CATIONS}, journal = {Inorganic Chemistry}, volume = {33}, number = {24}, year = {1994}, note = {ISI Document Delivery No.: PU080Times Cited: 14Cited Reference Count: 20}, month = {Nov}, pages = {5607-5609}, type = {Note}, keywords = {3-HYDROXY-4-PYRIDINONES, AGENTS, aluminum, CHEMISTRY, COMPLEXES, gallium, INVIVO, RADIOPHARMACEUTICALS, TC-99M, technetium}, isbn = {0020-1669}, url = {://A1994PU08000042}, author = {Edwards, D. S. and Liu, S. and Poirier, M. J. and Zhang, Z. H. and Webb, G. A. and Orvig, Chris} } @article {7264, title = {DESIGN AND SYNTHESIS OF MULTIDENTATE 2-(2{\textquoteright}-HYDROXYPHENYL)-2-THIAZOLINES FOR BIOMEDICAL APPLICATION}, journal = {Tetrahedron}, volume = {48}, number = {25}, year = {1992}, note = {ISI Document Delivery No.: JA148Times Cited: 13Cited Reference Count: 16}, month = {Jun}, pages = {5219-5226}, type = {Article}, abstract = {A variety of multidentate ligands based on the 2-(2{\textquoteright}-hydroxyphenyl)-2-thiazoline functionality have been synthesized by the formation of amide linkages at the carboxyl moiety in 2-(2{\textquoteright}-hydroxyphenyl)-2-thiazoline-4-carboxylic acid 1 with a number of polyamines, using DCC and/or CDI activation methodologies.}, keywords = {CHEMISTRY, COMPLEXES, COORDINATION, SIDEROPHORES, technetium}, isbn = {0040-4020}, url = {://A1992JA14800001}, author = {Hoveyda, H. R. and Karunaratne, V. and Orvig, Chris} }