Erratum: Preparation, characterization, and screening of a high affinity organometallic probe for α-adrenergic receptors (Journal of Medicinal Chemistry (2011) 54 3360-3367) 10.1021/jm2001162);Preparation, characterization, and screening of a high affinity organometallic probe for α-adrenergic receptors

Journal of Medicinal Chemistry

Volumn 54, Issue 9, 2011, Pages 3360-3367

  Louie, Anika S ^a   Vasdev, Neil ^b   Valliant, John F ^a  

^a MCMASTER UNIVERSITY   (Canada)

^b UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

1 [[4 (2 METHOXYPHENYL)PIPERAZIN 1 YL]METHYL] 1,2 DICARBA CLOSO DODECABORANE; 1 [[4 (2 METHOXYPHENYL)PIPERAZIN 1 YL]PROPYL] 1,2 DICARBA CLOSO DODECABORANE; 4 [4 (2 METHOXYPHENYL)PIPERAZIN 1 YL]BUTAN 1 AMINE; ALPHA 1A ADRENERGIC RECEPTOR; ALPHA 1D ADRENERGIC RECEPTOR; ALPHA 2C ADRENERGIC RECEPTOR; ALPHA ADRENERGIC RECEPTOR; CARBORANE DERIVATIVE; DOPAMINE TRANSPORTER; METAL COMPLEX; NORADRENALIN TRANSPORTER; ORGANOMETALLIC COMPOUND; RHENIUM COMPLEX; SEROTONIN RECEPTOR; SEROTONIN TRANSPORTER; SIGMA RECEPTOR LIGAND; SODIUM RAC 1 [[4 (2 METHOXYPHENYL)PIPERAZIN 1 YL]PROPYL] 3,3,3 TRICARBONYL 3 RHENIUM 3,1,2 DICARBA CLOSO DODECABORATE; SODIUM RAC 8 [N [7 [4 (2 METHOXYPHENYL)PIPERAZIN 1 YL]BUTYL]] 2,2,2 TRICARBONYL 2 RHENIUM 2,1,8 DICARBA CLOSO DODECABORATE 1 CARBOXAMIDE; SODIUM RAC 8 [[4 (2 METHOXYPHENYL)PIPERAZIN 1 YL]METHYL] 2,2,2 TRICARBONYL 2 RHENIUM 2,1,8 DICARBA CLOSO DODECABORATE; SODIUM RAC N [7 [4 (2 METHOXYPHENYL)PIPERAZIN 1 YL]BUTYL] 7,8 DICARBA NIDO UNDECABORATE 1 CARBOXAMIDE; TECHNETIUM 99M; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CRYSTAL STRUCTURE; DRUG SCREENING; DRUG SYNTHESIS; MOLECULAR IMAGING; MOLECULAR PROBE;

EID: 79955804772     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm201473j     Document Type: Erratum

References (47)

1. Schibli, R.; Schubiger, P. A. Current Use and Future Potential of Organometallic Radiopharmaceuticals Eur. J. Nucl. Med. 2002, 29, 1529-1542 (Pubitemid 35232058)
2. Alberto, R. New Organometallic Technetium Complexes for Radiopharmaceutical Imaging Top. Curr. Chem. 2005, 252, 1-44 (Pubitemid 44420845)
3. Hartinger, C. G.; Dyson, P. J. Bioorganometallic Chemistry - From Teaching Paradigms to Medicinal Applications Chem. Soc. Rev. 2009, 38, 391-401
4. Allardyce, C. S.; Dorcier, A.; Scolaro, C.; Dyson, P. J. Development of Organometallic (Organo-Transition Metal) Pharmaceuticals Appl. Organomet. Chem. 2005, 19, 1-10 (Pubitemid 40173971)
5. Metzler-Nolte, N.; Severin, K. Concepts and Models in Bioinorganic Chemistry. In Bioorganometallic Chemistry; Kraatz, H.-B.; Metzler-Nolte, N., Eds; Wiley-VCH: Weinheim, Germany, 2006; p 113.
6. Herschman, H. R. Molecular Imaging: Looking at Problems, Seeing Solutions Science 2003, 302, 605-608 (Pubitemid 37310909)
7. Schlotter, K.; Boeckler, F.; Hübner, H.; Gmeiner, P. Fancy Bioisosters: Metallocene-Derived G-Protein Coupled Receptor Ligands with Subnanomolar Binding Affinity and Novel Selectivity Profiles J. Med. Chem. 2005, 48, 3696-3699 (Pubitemid 40776844)
8. Bernard, J.; Ortner, K.; Spingler, B.; Pietzsch, H.-J.; Alberto, R. Aqueous Synthesis of Derivatized Cyclopentadienyl Complexes of Technetium and Rhenium Directed toward Radiopharmaceutical Application Inorg. Chem. 2003, 42, 1014-1022
9. 99mTc, Re) Complexes J. Am. Chem. Soc. 2008, 130, 1554-1555 (Pubitemid 351214062)
10. Wang, G. T.; Mui, C.; Musgrave, C. B.; Bent, S. F. Cycloaddition of Cyclopentadiene and Dicyclopentadiene on Si(100)-2 - 1: Comparison of Monomer and Dimer Adsorption J. Phys. Chem. B 1999, 103, 6803-6808 (Pubitemid 129613804)
11. Minutolo, F.; Katzenellenbogen, J. A. Boronic Acids in the Three-Component Synthesis of Carbon-Substituted Cyclopentadienyl Tricarbonyl Rhenium Complexes J. Am. Chem. Soc. 1998, 120, 13264-13265 (Pubitemid 29024093)
12. Johannsen, B.; Pietzsch, H.-J. Development of Technetium-99m-Based CNS Receptor Ligands: Have There Been Any Advances? Eur. J. Nucl. Med. 2002, 29, 263-275
13. 1a Adrenergic Antagonists Bioorg. Med. Chem. Lett. 2002, 12, 2443-2446 (Pubitemid 34879886)
14. Li, Y.; Kusari, U.; Carroll, P. J.; Bradley, M. G.; Sneddon, L. G. Polyborane Reactions in Ionic Liquids Pure Appl. Chem. 2006, 78, 1349-1355
15. Kusari, U.; Li, Y.; Bradley, M. G.; Sneddon, L. G. Polyborane Reactions in Ionic Liquids: New Efficient Routes to Functionalized Decaborane and o -Carborane Clusters J. Am. Chem. Soc. 2004, 126, 8662-8663 (Pubitemid 38955725)
16. Sogbein, O. O.; Green, A. E. C.; Schaffer, P.; Chankalal, R.; Lee, E.; Healy, B. D.; Morel, P.; Valliant, J. F. Synthesis of ortho-and meta -Re(I)-metallocarboranes in Water Inorg. Chem. 2005, 44, 9574-9584
17. 99mTc(I)-Metallocarborane Complexes Inorg. Chem. 2006, 45, 5727-5729
18. Armstrong, A. F.; Valliant, J. F. Microwave-Assisted Synthesis of Tricarbonyl Rhenacarboranes: Steric and Electronic Effects on the 1,2 ? 1,7 Carborane Cage Isomerization Inorg. Chem. 2007, 46, 2148-2158
19. 1A Receptor Antagonist Br. J. Pharmacol. 1994, 112, 91P
20. 1A Receptor Antagonist Brain Res. 1995, 673, 217-225
21. van Waarde, A.; Vaalburg, W.; Doze, P.; Bosker, F. J.; Elsinga, P. H. PET Imaging of Beta-Adrenoceptors in Human Brain: A Realistic Goal or a Mirage? Curr. Pharm. Des. 2004, 10, 1519-1536 (Pubitemid 38559764)
22. 2A-Adrenergic Receptors Bioorg. Med. Chem. Lett. 2010, 20, 3654-3657
23. 2-Adrenoceptor Antagonist Bioorg. Med. Chem. 2006, 14, 4526-4534 (Pubitemid 43728666)
24. 11C-Yohimbine J. Nucl. Med. 2006, 47, 2008-2015 (Pubitemid 47544989)
25. Kopka, K.; Law, M. P.; Breyholz, H.-J.; Faust, A.; Höltke, C.; Riemann, B.; Schober, O.; Schäfers, M.; Wagner, S. Non-Invasive Molecular Imaging of β-Adrenoceptors in Vivo: Perspectives for PET-Radioligands Curr. Med. Chem. 2005, 12, 2057-2074 (Pubitemid 41086748)
26. 1-Adrenoceptors J. Med. Chem. 2010, 53, 7021-7034
27. Amin, A. E.; Abou Zid, K.; Bayoumi, N. A.; Abd EL-hamid, M. Organic Synthesis and Biological Evaluation of Novel 3 + 1 Mixed Ligands of Technetium-99m Gabapentin as Receptor Imaging Agents J. Radioanal. Nucl. Chem. 2010, 283, 55-62
28. Samnick, S.; Scheuer, C.; Münks, S.; El-Gibaly, A. M.; Menger, M. D.; Kirsch, C.-M. Technetium-99m Labeled 1-(4-Fluorobenzyl)-4-(2-mercapto-2- methyl-4-azapentyl)-4-(2-mercapto-2-methylpropylamino)-piperidine and Iodine-123 Metaiodobenzylguanidine for Studying Cardiac Adrenergic Function: A Comparison of the Uptake Characteristics in Vascular Smooth Muscle Cells and Neonatal Cardiac Myocytes, and an Investigation in Rats Nucl. Med. Biol. 2004, 31, 511-522 (Pubitemid 38490751)
29. 1-Adrenergic Receptor Nucl. Med. Biol. 2002, 29, 375-387 (Pubitemid 34597109)
30. Trumpp-Kallmeyer, S.; Hoflack, J.; Bruinvels, A.; Hibert, M. Modeling of G-Protein Coupled Receptors: Application to Dopamine, Adrenaline, Serotonin, Acetylcholine and Mammalian Opsin Receptors J. Med. Chem. 1992, 35, 3448-3462
31. 99mTc-Carborane Complexes Inorg. Chem. 2005, 44, 9585-9591
32. 1 Adrenoreceptor Function in Health and Disease from Transgenic Animal Studies Trends Endocrinol. Metab. 2003, 14, 107-113 (Pubitemid 36733907)
33. Hong, C.-J.; Wang, Y.-C.; Liu, T.-Y.; Liu, H.-C.; Tsai, S.-J. A Study of Alpha-Adrenoceptor Gene Polymorphisms and Alzheimer Disease J. Neural Transm. 2001, 108, 445-450 (Pubitemid 32703893)
34. A Dysregulation and Apoptosis Brain 2003, 126, 2667-2681 (Pubitemid 37463086)
35. Arnold, J. M. O.; Teasell, R. W.; MacLeod, A. P.; Brown, J. E.; Carruthers, S. G. Increased Venous Alpha-Adrenoreceptor Responsiveness in Patients with Reflex Sympathetic Dystrophy Ann. Intern. Med. 1993, 118, 619-621 (Pubitemid 23102697)
36. 1- Adrenergic Receptor Regulation: Basic Science and Clinical Implications Pharmacol. Ther. 2000, 88, 281-309 (Pubitemid 32406055)
37. Valliant, J. F.; Guenther, K. J.; King, A. S.; Morel, P.; Schaffer, P.; Sogbein, O. O.; Stephenson, K. A. The Medicinal Chemistry of Carboranes Coord. Chem. Rev. 2002, 232, 173-230
38. Hawkins, P. M.; Jelliss, P. A.; Nonaka, N.; Shi, X.; Banks, W. A. Permeability of the Blood-Brain-Barrier to a Rhenacarborane J. Pharmacol. Exp. Ther. 2009, 329, 608-614
39. Kasar, R. A.; Knudsen, G. M.; Kahl, S. B. Synthesis of 3-Amino-1-carboxy- o -carborane and an Improved, General Method for the Synthesis of All Three C-Amino-C-carboxycarboranes Inorg. Chem. 1999, 38, 2936-2940
40. 2Br] Inorg. Chem. Commun. 2004, 7, 1023-1026
41. Causey, P. W.; Besanger, T. R.; Schaffer, P.; Valliant, J. F. Expedient Multi-Step Synthesis of Organometallic Complexes of Tc and Re in High Effective Specific Activity. A New Platform for the Production of Molecular Imaging and Therapy Agents Inorg. Chem. 2008, 47, 8213-8221
42. Chu, W.; Tu, Z.; McElveen, E.; Xu, J.; Taylor, M.; Luedtke, R. R.; Mach, R. H. Synthesis and in Vitro Binding of N -Phenyl Piperazine Analogs as Potential Dopamine D3 Receptor Ligands Bioorg. Med. Chem. 2004, 13, 77-87 (Pubitemid 39575694)
43. Sheldrick, G. M. SMART, release 6.45; Bruker AXS Inc.: Madison, WI, 2003.
44. Sheldrick, G. M. SAINT, release 6.45; Bruker AXS Inc.: Madison, WI, 2003.
45. Sheldrick, G. M. SADABS; Bruker AXS Inc.: Madison, WI, 2003.
46. Britten, J. F.; Guan, W. MAX3D; McMaster University: Hamilton, Ontario, Canada, 2009.
47. Sheldrick, G. M. SHELXTL, release 6.14; Bruker AXS Inc.: Madison, WI, 2000.