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Re(CO)3 Complexes Synthesized via an Improved Preparation of Aqueous fac-[Re(CO)3(H2O)3]+ as an Aid in Assessing 99mTc Imaging Agents. Structural Characterization and Solution Behavior of Complexes with Thioether-Bearing Amino Acids as Tridentate Ligands

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Department of Radiology, Emory University, Atlanta, Georgia 30322, and Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803
Cite this: Inorg. Chem. 2005, 44, 15, 5437–5446
Publication Date (Web):June 18, 2005
https://doi.org/10.1021/ic0501869
Copyright © 2005 American Chemical Society

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    Parallel studies of the preparation of Re and 99mTc agents aid in interpreting the nature of tracer 99mTc radiopharmaceuticals. Aqueous solutions of the fac-[99mTc(CO)3(H2O)3]+ cation are gaining wide use and are readily prepared, but such solutions of the fac-[Re(CO)3(H2O)3]+ cation (1) are not so easily accessible. Herein we describe a new, reliable, and straightforward preparation of aqueous solutions of 1, characterized by HPLC and ESI-MS. Treatment of solutions of 1 with thioether-bearing amino acids, AAH = S-methyl-l-cysteine (MECYSH), S-propyl-l-cysteine (PRCYSH), and methionine (METH), gave high yields of fac-Re(CO)3AA complexes. X-ray crystallographic and NMR analyses indicated that MECYS-, PRCYS-, and MET- were bound in fac-Re(CO)3AA complexes as tridentate monoanionic ligands through amino, thioether, and α-carboxyl groups. In CD3OD, 1H NMR spectra have broad signals but have two sets of signals at −10 °C, consistent with two isomers with different configurations at the pyramidal sulfur; these interconvert slowly on the NMR time scale at low temperatures. Indeed, the crystal structure of the fac-Re(CO)3(PRCYS) reveals a mixture of the two possible diastereoisomers. S-(Carboxymethyl)-l-cysteine (CCMH2) and 1 gave two products, 5A (kinetically favored) and 5B (thermodynamically favored). X-ray crystallographic analyses of a crystal of 5B and of a 1:1 cocrystal of 5A and 5B showed that 5A and 5B are diastereoisomers with the CCMH- α-carboxyl group dangling. In addition to the amino and thioether groups, the S-(carboxymethyl) carboxyl group is coordinated, a feature that slows interconversion of diastereoisomers relative to the other fac-Re(CO)3AA complexes because interconversion can now occur only after the rupture of Re−ligand bonds. These N, O, and S tridentate adducts are quite stable, and the grouping has promise in 99mTc(CO)3 tracer development.

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     Emory University.

     Louisiana State University.

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     Author to whom correspondence should be addressed. E-mail:  [email protected]. Tel.:  225-578-0933. Fax:  225-578-3463.

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    X-ray crystallographic data for structure determinations of compounds 3, 4, and 5B and the cocrystal of 5A and 5B in CIF format, a one-dimensional hydrogen-bonded strand formed by Re(CO)3(d-MET) within crystals of 4 viewed along the b axis and along the c axis, and a table of selected bond angles of 3, 4, and 5A and 5B. This material is available free of charge via the Internet at http://pubs.acs.org.

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    57. Jeffrey Klenc, Malgorzata Lipowska, Andrew T. Taylor, Luigi G. Marzilli. Synthesis and Characterization of fac ‐Re(CO) 3 ‐aspartic‐ N ‐monoacetic Acid: Structural Analogue of a Potential Renal Tracer, fac ‐ 99m Tc(CO) 3 (ASMA). European Journal of Inorganic Chemistry 2012, 2012 (27) , 4334-4341. https://doi.org/10.1002/ejic.201200599
    58. George Makris, Ourania Karagiorgou, Dionysia Papagiannopoulou, Angeliki Panagiotopoulou, Catherine P. Raptopoulou, Aris Terzis, Vassilis Psycharis, Maria Pelecanou, Ioannis Pirmettis, Minas S. Papadopoulos. Rhenium(I) and Technetium(I) Tricarbonyl Complexes with [NSO]‐Type Chelators: Synthesis, Structural Characterization, and Radiochemistry. European Journal of Inorganic Chemistry 2012, 2012 (19) , 3132-3139. https://doi.org/10.1002/ejic.201200056
    59. Jinxia Xu, Ruiying Wang, Yameng Li, Zhiyang Gao, Rui Yao, Song Wang, Benlai Wu. Chiral Supramolecular Frameworks Based on Chiral Metallocycles: Crystal Structures and Photophysical Properties. European Journal of Inorganic Chemistry 2012, 2012 (20) , 3349-3360. https://doi.org/10.1002/ejic.201200100
    60. A. Chiotellis, C. Tsoukalas, M. Pelecanou, I. Pirmettis, M. Papadopoulos. Synthesis, characterization and biological evaluation of novel neutral fac-M(CO)3(SNO) complexes (M=Re, 99mTc) bearing the o-methoxyphenylpiperazine moiety. Applied Radiation and Isotopes 2012, 70 (6) , 957-964. https://doi.org/10.1016/j.apradiso.2012.03.003
    61. Theshini Perera, Pramuditha Abhayawardhana, Frank R. Fronczek, Patricia A. Marzilli, Luigi G. Marzilli. Iminoether Complexes of the Type, fac ‐[Re(CO) 3 L{HNC(CH 3 )OCH 3 }]BF 4 (L = Bipyridine or a Substituted Bipyridine): Synthesis and Properties. European Journal of Inorganic Chemistry 2012, 2012 (4) , 618-627. https://doi.org/10.1002/ejic.201100768
    62. Dipak Kumar Nayak, Rinku Baishya, Kamal Krishna Halder, Tuhinadri Sen, Bharat R. Sarkar, Shantanu Ganguly, M. K. Das, Mita Chatterjee Debnath. Evaluation of 99mTc(i)-tricarbonyl complexes of fluoroquinolones for targeting bacterial infection. Metallomics 2012, 4 (11) , 1197. https://doi.org/10.1039/c2mt20132a
    63. Cheng Wang, Wei Zhou, Junfeng Yu, Lan Zhang, Ni Wang. A study of the radiosynthesis of fac-[188Re(CO)3(H2O)3]+ and its application in labeling 1,2,3-triazole analogs obtained by click chemistry. Nuclear Medicine Communications 2012, 33 (1) , 84-89. https://doi.org/10.1097/MNM.0b013e32834d3ba7
    64. Carolina Moura, Lurdes Gano, Isabel C. Santos, Isabel Santos, António Paulo. 99m Tc I /Re I Tricarbonyl Complexes with Tridentate Cysteamine Based Ligands: Synthesis, Characterization and in vitro/in vivo Evaluation. European Journal of Inorganic Chemistry 2011, 2011 (35) , 5405-5413. https://doi.org/10.1002/ejic.201100796
    65. Dionysia Papagiannopoulou, Charalambos Tsoukalas, George Makris, Catherine P. Raptopoulou, Vassilis Psycharis, Leondios Leondiadis, Ewa Gniazdowska, Przemyslaw Koźmiński, Leon Fuks, Maria Pelecanou, Ioannis Pirmettis, Minas S. Papadopoulos. Histidine derivatives as tridentate chelators for the fac-[MI(CO)3] (Re, 99mTc, 188Re) core: Synthesis, structural characterization, radiochemistry and stability. Inorganica Chimica Acta 2011, 378 (1) , 333-337. https://doi.org/10.1016/j.ica.2011.08.062
    66. T.I.A. Gerber, R. Betz, I.N. Booysen, K.C. Potgieter, P. Mayer. Coordination of bidentate aniline derivatives to the fac-[Re(CO)3]+ core. Polyhedron 2011, 30 (10) , 1739-1745. https://doi.org/10.1016/j.poly.2011.04.019
    67. Marta Sánchez-Lozano, Ezequiel M. Vázquez-López, José M. Hermida-Ramón, Carlos M. Estévez. Synthesis, spectral studies, crystal structures and TDDFT studies of the rhenium(I) complexes of 2,4-dihydroxy-N′-(4-hydroxybenzilidene) benzohydrazide. Polyhedron 2011, 30 (6) , 953-962. https://doi.org/10.1016/j.poly.2010.12.038
    68. Wei Xu, Wen Liu, Fang-Yang Yao, Yue-Qing Zheng. Synthesis, crystal structure and properties of the novel chiral 3D coordination polymer with S-carboxymethyl-l-cysteine. Inorganica Chimica Acta 2011, 365 (1) , 297-301. https://doi.org/10.1016/j.ica.2010.09.026
    69. Paul D. Benny, Glenn A. Fugate, Tanushree Ganguly, Brendan Twamley, Dejan-Krešimir Bučar, Leonard R. MacGillivray. Unusual reactivity of acetylacetone with imidazole/histamine complexes and (M=Re, 99mTc). Inorganica Chimica Acta 2011, 365 (1) , 356-362. https://doi.org/10.1016/j.ica.2010.09.050
    70. Sarah L. Binkley, Thomas C. Leeper, Roger S. Rowlett, Richard S. Herrick, Christopher J. Ziegler. Re(CO)3(H2O)3+ binding to lysozyme: structure and reactivity. Metallomics 2011, 3 (9) , 909. https://doi.org/10.1039/c1mt00065a
    71. Paula Barbazán, Adelheid Hagenbach, Elisabeth Oehlke, Ulrich Abram, Rosa Carballo, Sabina Rodríguez‐Hermida, Ezequiel M. Vázquez‐López. Tricarbonyl Rhenium(I) and Technetium(I) Complexes with Hydrazones Derived from 4,5‐Diazafluoren‐9‐one and 1,10‐Phenanthroline‐5,6‐dione. European Journal of Inorganic Chemistry 2010, 2010 (29) , 4622-4630. https://doi.org/10.1002/ejic.201000522
    72. Sarah L. Binkley, Natalie V. Barone, Adam C. Underwood, Amy Milsted, Brenton R. Franklin, Richard S. Herrick, Christopher J. Ziegler. The synthesis and toxicity of tripodal tricarbonyl rhenium complexes as radiopharmaceutical models. Journal of Inorganic Biochemistry 2010, 104 (6) , 632-638. https://doi.org/10.1016/j.jinorgbio.2010.02.004
    73. Dionysia Papagiannopoulou, George Makris, Charalambos Tsoukalas, Catherine P. Raptopoulou, Aris Terzis, Maria Pelecanou, Ioannis Pirmettis, Minas S. Papadopoulos. Rhenium(I) and technetium(I) fac-M(NSO)(CO)3 (M=Re, 99mTc) tricarbonyl complexes, with a tridentate NSO bifunctional agent: Synthesis, structural characterization, and radiochemistry. Polyhedron 2010, 29 (2) , 876-880. https://doi.org/10.1016/j.poly.2009.10.009
    74. Sarah L. Binkley, Christopher J. Ziegler, Richard S. Herrick, Roger S. Rowlett. Specific derivatization of lysozyme in aqueous solution with Re(CO)3(H2O)3+. Chemical Communications 2010, 46 (8) , 1203. https://doi.org/10.1039/b923688k
    75. Paul Bichler, Alex D. Sun, Brian O. Patrick, Jennifer A. Love. Design, synthesis and coordination chemistry of sidearm substituted bisoxazoline ligands. Inorganica Chimica Acta 2009, 362 (12) , 4546-4552. https://doi.org/10.1016/j.ica.2009.04.039
    76. Malgorzata Lipowska, Luigi G. Marzilli, Andrew T. Taylor. 99m Tc(CO) 3 -Nitrilotriacetic Acid: A New Renal Radiopharmaceutical Showing Pharmacokinetic Properties in Rats Comparable to Those of 131 I-OIH. Journal of Nuclear Medicine 2009, 50 (3) , 454-460. https://doi.org/10.2967/jnumed.108.058768
    77. Vladimir A. Alfonsov, Alexander A. Bredikhin, Zemfira A. Bredikhina, Rimma M. Eliseenkova, Olga N. Kataeva, Igor A. Litvinov, Michael A. Pudovik. First examples of the cocrystallization of diastereomers of chiral phosphorus compounds. Structural Chemistry 2008, 19 (6) , 873-878. https://doi.org/10.1007/s11224-008-9353-4
    78. Maxim N. Sokolov, Pavel A. Abramov, Eugenia V. Peresypkina, Alexander V. Virovets, Vladimir P. Fedin. In situ generation of H2Se and hydrothermal synthesis of new polynuclear rhenium carbonyl polyselenides. Polyhedron 2008, 27 (15) , 3259-3262. https://doi.org/10.1016/j.poly.2008.07.021
    79. Anna Maria Christoforou, Patricia A. Marzilli, Frank R. Fronczek, Luigi G. Marzilli. fac-[Re(CO)3L] Complexes Containing Tridentate Monoanionic Ligands (L−) Having a Terminal Amido and Two Amine Ligating Groups. Journal of Chemical Crystallography 2008, 38 (2) , 115-121. https://doi.org/10.1007/s10870-007-9274-x
    80. Lukas Kromer, Bernhard Spingler, Roger Alberto. Substitution reactions with [ReBr2(CO)2(NCCH3)2]−: a convenient route to complexes with the cis-[Re(CO)2]+ core. Dalton Transactions 2008, 192 (42) , 5800. https://doi.org/10.1039/b805410j
    81. Haiyang He, Malgorzata Lipowska, Anna Maria Christoforou, Luigi G. Marzilli, Andrew T. Taylor. Initial evaluation of new 99mTc(CO)3 renal imaging agents having carboxyl-rich thioether ligands and chemical characterization of Re(CO)3 analogues. Nuclear Medicine and Biology 2007, 34 (6) , 709-716. https://doi.org/10.1016/j.nucmedbio.2007.06.007
    82. Richard S. Herrick, Christopher J. Ziegler, Aníl Çetin, Brenton R. Franklin. Structure of the Triaquatricarbonylrhenium(I) Cation and Its Conjugate Base. European Journal of Inorganic Chemistry 2007, 2007 (12) , 1632-1634. https://doi.org/10.1002/ejic.200700118
    83. Catarina Xavier, Jae-Kyoung Pak, Isabel Santos, Roger Alberto. Evaluation of two chelators for labelling a PNA monomer with the fac-[99mTc(CO)3]+ moiety. Journal of Organometallic Chemistry 2007, 692 (6) , 1332-1339. https://doi.org/10.1016/j.jorganchem.2006.10.007
    84. Cara L. Ferreira, Simon R. Bayly, David E. Green, Tim Storr, Cheri A. Barta, Jennifer Steele, Michael J. Adam, Chris Orvig. Carbohydrate-Appended 3-Hydroxy-4-pyridinone Complexes of the [M(CO) 3 ] + Core (M = Re, 99m Tc, 186 Re). Bioconjugate Chemistry 2006, 17 (5) , 1321-1329. https://doi.org/10.1021/bc060085e
    85. David S. Urch, Michael J. Welch. Radiochemistry and radiopharmaceuticals. Annual Reports Section "A" (Inorganic Chemistry) 2006, 102 , 542. https://doi.org/10.1039/b508283h