Specificity of diastereomers of [99mTc]TRODAT-1 as dopamine transporter imaging agents

Journal of Medicinal Chemistry

Volumn 41, Issue 4, 1998, Pages 428-436

  Meegalla, Sanath K ^a   Plössl, Karl ^a   Kung, Mei Ping ^a   Stevenson, Andrew D ^a   Mu, Mu ^a   Kushner, Steven ^a   Liable Sands, Louise M ^b   Rheingold, Arnold L ^b   Kung, Hank F ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 [[2 [[[3 (4 CHLOROPHENYL) 8 METHYL 8 AZABICYCLO[3.2.1]OCT 2 YL]METHYL](2 MERCAPTOETHYL)AMINO]ETHYL]AMINO]ETHANETHIOLATO OXO TECHNETIUM 99M; DOPAMINE TRANSPORTER; RADIOPHARMACEUTICAL AGENT; RHENIUM; UNCLASSIFIED DRUG; CARRIER PROTEIN; DIAGNOSTIC AGENT; DOPAMINE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; MEMBRANE PROTEIN; NERVE PROTEIN; TECHNETIUM COMPLEX; TECHNETIUM TC 99M TRODAT 1; TECHNETIUM TC 99M TRODAT-1; TROPANE DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BABOON; BINDING AFFINITY; CEREBELLUM; COMPLEX FORMATION; CONTROLLED STUDY; CORPUS STRIATUM; DIASTEREOISOMER; DRUG DISTRIBUTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IMAGING SYSTEM; INTRAVENOUS DRUG ADMINISTRATION; LIPOPHILICITY; MALE; NONHUMAN; RAT; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY; X RAY ANALYSIS; ANIMAL; ANTIBODY SPECIFICITY; BRAIN; CHEMICAL STRUCTURE; CONFORMATION; HUMAN; METABOLISM; PAPIO; SCINTISCANNING; SPRAGUE DAWLEY RAT; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANIMALS; BRAIN; CARRIER PROTEINS; CORPUS STRIATUM; CRYSTALLOGRAPHY, X-RAY; DOPAMINE; DOPAMINE PLASMA MEMBRANE TRANSPORT PROTEINS; HUMANS; INDICATORS AND REAGENTS; MALE; MEMBRANE GLYCOPROTEINS; MEMBRANE TRANSPORT PROTEINS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NERVE TISSUE PROTEINS; ORGAN SPECIFICITY; ORGANOTECHNETIUM COMPOUNDS; PAPIO; RADIOPHARMACEUTICALS; RATS; RATS, SPRAGUE-DAWLEY; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TOMOGRAPHY, EMISSION-COMPUTED, SINGLE-PHOTON; TROPANES;

EID: 0032509859     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970742b     Document Type: Article

References (65)

1. Jurisson, S. S.; Berning, D.; Jia, W.; Ma, D.-S. Coordination compounds in nuclear medicine. Chem. Rev. (Washington, D.C.) 1993, 93, 1137-1156.
2. Steigman, J.; Eckelman, W. C. The Chemistry of Technetium in Medicins; National Academy: Washington, DC, 1992.
3. Tiaato, F.; Refosco, F.; Bandoli, G. Structural survey of technetium complexes. Coord. Chem. Rev. 1994, 135/136, 326-397.
4. 2 core. Inorg. Chem. 1981, 20, 1629-1832.
5. 99TcO(NET-TMDADT)]. Acta Crystallogr., Sect. C: tryst Struct. Commun. 1991, 47, 254-257.
6. Lever, S. Z.; Burns, H. D.; Kervitsky, T. M.; Goldfarb, H. W.; Woo, D. V.; Wong, D. F.; Epps, L. A.; kramer, A. V.; Wagner, H. N., Jr, Design, preparation and biodistribution of a technetium-99m triaminedithiol complex to access regional cerebral blood flow. J. Nucl. Med. 1985, 26, 1287-1294.
7. VO(M = Tc, Re) amine-thiol complex containing a pendent phenylpiperldine group. Inorg. Chem. 1993, 32, 3114-3124.
8. Lever, S. Z.; Baidoo, K. E.; Mahmood, A. Structure proof of syn/ anti isomerism in N-alkylated diaminedithiol (DADT) complexes of technetium, Inorg. Chim. Acta 1990, 170, 183-184.
9. Wolff, J. A. Synthesis and study of technetium(V) complexes of tetradentate nitrogen-,sulfur-donor Uganda, Thesis, Massachusetts Institute of Technology, 1992.
10. Eckelman, W. C. Designing a molecular probe for muscarinic acetylcholine-receptor (mAChR) imaging. J. Nucl. Med. 1995, 36, S5-S7.
11. Lever, S. Z.; Baidoo, K. E.; Mahmood, A.; Matsumura, K.; Scheffel, U. A.; Wagner, H. N., Jr. Novel technetium Uganda with affinity for the muscarinic chnlinergic receptor. Nucl. Med. Biol. 1994, 21, 157-164.
12. 99m/99Tc]-DADT-benzovesamicol: a potential marker for cholinergic neurons. Nucl. Med. Biol. 1994, 21, 197-203.
13. 2A serotonin receptor binding: structureaffinity considerations, Nucl. Med. Biol. 1996, 23, 429-438.
14. 99mTc]bisaminoethanethiol spiperone derivatives: possible Uganda for receptor imaging with SPECT. Nucl. Med. Biol. 1995, 22, 573-583.
15. Baidoo, K. E.; Zhan, Y.; Lin, K.-S.; Finley, P.; Lever, S. Z.; Scheffel, U. Design and synthesis of new neutral technetium diaminedithiolate complexes that bind with high affinity to serotonin (5-HT) receptors. J. Nucl. Med. 1997, 38, 100P.
16. 1 receptor imaging agent. Proceedings of the XIIth International Symposium on Radiopkarmacol Chemistry, Uppsala, Sweden, 1997; Abstract VI-14, pp 437-438.
17. 2 receptor binding benzamldes [abstract]. J. Nucl. Med. 1997, 35, 99P.
18. Eisenhut, M.; Brandau, W.; Missfeldt, M. Synthesis and in vivo testing of a bromobutyl substituted 1,2-dithia-5,9-diazacycloundecane: a vesatile precursor for new 99m-Tc-bis(aminoethanethiol) complexes. Nucl. Med. Biol. 1989, 16, 805-811.
19. Chi, D. Y.; O'Neil, J. P.; Anderson, C. J.; Welch, M. J.; Katzenellenbogen, J. A, Homodimeric and heterodimeric bis(aminothiol) oxometal complexes with rhenium(V) and technetium(V). Control of heterodimeric complex formation and an approach to metal complexes that mimic steroid hormones. J. Med. Chem. 1994, 37, 928-937.
20. Chi, D. Y.; Katzenellenbogen, J. A. Selective formation of heterodimeric bis-bidentate aminothiol-oxometal complexes of rhenium(V). J. Am. Chem. Soc. 1993, 115, 7045-7046.
21. DiZio, J. P.; Fiaschi, R.; Davison, A.; Jones, A. O.; Katzenellenbogen, J. A. Progestin-rhenium complexes: metal-labeled steroids with high receptor binding affinity, potential receptordirected agents for diagnostic imaging or therapy. Bioconjugate Chem. 1991, 2, 353-366.
22. DiZio, J. P.; Anderson, C. J.; Davison, A.; Ehrhardt, O. J.; Carlson, K. E.; Welch, M. J.; Katzenellenbogen, J. A. Technetium- and rhenium-labeled progestins: synthesis, receptor binding and in vivo distribution of an 11-β-substituted progestin labeled with technetium-99 and rhenium-186, J. Nucl. Med. 1992, 33, 558-569.
23. O'Neil, J. P.; Wilson, S. R.; Katzenellenbogen, J. A. Preparation and structural characterization of monoamine-monoamide bis(thiol) oxo complexes of technetium(V) and rhenium(V). Inorg. Chem. 1994, 33, 319-323.
24. 2-metal conjugate. Bioconjugate Chem. 1994, 5, 182-193.
25. Hom, R. K.; Chi, D. Y.; Katzenellenbogen, J. A. Heterodimeric bis(amino thiol) complexes of oxorhenium(V) that mimic the structure of steroid hormones. Synthesis and stereochemical issues. J. Org. Chem. 1990, 61, 2624-2631.
26. Sugano, Y.; Katzenellenbogen, J. A. Synthesis of tetradentate bisamino-bisthiol complexes of oxorhenium(V) as structural mimics of steroids. Bioorg. Med. Chem. Lett. 1996, 6, 361-366.
27. Hom, R. K.; Katzenellenbogen, J. A. Technetium-99m-labeled receptor-specific small-molecule radiopharmaceuticals: recent developments and encouraging results [review]. Nucl. Med. Biol. 1997, 24, 485-498.
28. Jurisson, S. S.; Pirro, J.; Di Rocco, R. J.; Rosenspire, K. C.; Jagoda, E.; Nanjappan, P.; Eckelman, W. C.; Nowotnik, D. P.; Nunn, A. D. Boronic acid adducts of technetium dioxime (BATO) complexes derived from quinuclidine benzilate (QNB) boronic acid stereoisomers: syntheses and studies of their binding to the muscarinic acetylcholine receptor. Nucl. Med. Biol. 1995, 22, 269-281.
29. Carroll, F. I.; Scheffel, U.; Dannals, R. F.; Boja, J. W.; Kuhar, M. J. Development of imaging agents for the dopamine transporter. Med. Res. Rev. 1995, 15, 419-444.
30. Carroll, F. L; Mascarella, S. W.; Kuzemko, M. A.; Gao, Y.; Abraham, P.; Lewin, A. H.; Boja, J. W.; Kuhar, M. J. Synthesis, ligand binding, and QSAR (CoMFA and classical) study of 3β(3′-substituted phenyl)-, 3β-(4′-substituted phenyl)-, and 3β-(3′,4′disubstituted pheny)tropane-2β-carboxylic acid methyl esters. J. Med. Chem. 1994, 37, 2865-2873.
31. Carroll, F. I.; Kotian, P.; Dehghani, A.; Gray, J. L.; Kuzemko, M. A.; Parham, K. A.; Abraham, P.; Lewin, A. H.; Boja, J. W.; Kuhar, M. J. Cocaine and 3β-(4′-substituted phenyl)tropane-2βcarboxylic acid ester and amide analogues. New high-affinity and selective compounds for the dopamine transporter. J. Med. Chem. 1995, 35, 379-388.
32. Yu, D.-W.; Gatley, S. J.; Wolf, A. P.; MacGregor, R. R.; Dewey, S. L.; Fowler, J. S.; Schlyer, D. J. Synthesis of carbon-11-labeled iodinated cocaine derivatives and their distribution in baboon brain measured using positron emission tomography. J. Med. Chem. 1992, 35, 2178-2183.
33. Fowler, J. S.; Volkow, N, D.; MacGregor, R. R.; Logan, J.; Dewey, S. L.; Gatley, S. J.; Wolf, A. P. Comparative PET studies of the kinetics and distribution of cocaine and cocaethylene in baboon brain. Synapse 1992, 12, 220-227.
34. 11C]WIN 35,428 reveals marked declines in mild Parkinson's disease [see comments], Ann. Neurol. 1993, 34, 423-431.
35. 11C]WIN35,428. Synapse 1993, 15, 130-142.
36. Ding, Y. S.; Fowler, J. S.; Volkow, N. D.; Logan, J.; Gatley, S. J.; Sugano, Y. Carbon-11-d-threo-methylphenidate binding to dopamine transporter in baboon brain. J. Nucl. Med. 1995, 36, 2298-2305.
37. Innis, R. B.; Seibyl, J. P.; Scanley, B. E.; Laruelle, M.; AbiDargham, A.; Wallace, E.; Baldwin, R. M.; Zea-Ponce, Y.; Zoghbi, S.; Wang, S.; Gao, Y.; Neumeyer, J. L.; Charney, D. S.; Hoffer, P. B.; Marek, K. L. Single photon emission computed tomographic imaging demonstrates loss of striatal dopamine transporters in Parkinson's disease. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 11965-11969.
38. Innis, R. B. Single photon emission tomography imaging of dopamine terminal innervation: a potential clinical tool in Parkinson's disease [editorial, review]. Eur. J. Nucl. Med. 1994, 21, 1-5.
39. Seibyl, J. P.; Laruelle, M. A.; Van Dyck, C. H.; Wallace, E.; Baldwin, R. M.; Zoghbi, S. S.; Zea-Ponce, Y.; Neumeyer, J. L.; Charney, D. S.; Hoffer, P. B.; Innis, R. B. Reproducibility of iodine-123-β-CIT SPECT brain measurement of dopamine transporters. J. Nucl. Med. 1996, 37, 222-228.
40. Kuikka, J. T.; Akerman, K.; Bergstrom, K. A.; Karhu, J.; Hiltunen, J.; Haukka, J.; Heikkinen, J.; Tiihonen, J.; Wang, S.; Neumeyer, J. L. Iodine- 123-labeled N-(2-fluoroethylJ-2β-carbomethoxy-3/3-(4-iodophenyl)nortropane for dopamine transporter imaging in the living human brain. Eur. J. Nucl. Med. 1995, 22, 682-686.
41. Neumeyer, J. L.; Wang, S.; Gao, Y.; Milius, R. A.; Kula, N. S.; Campbell, A.; Baldessarini, R. J.; Zea-Ponce, Y.; Baldwin, R. M.; Innis, R. B. N-ω-Fluoroalkyl analogues of (1R)-2β-carbomethoxy-3β-(4-iodophenyl)tropane (β-CIT): radiotracers for positron emission tomography and single photon emission computed tomography imaging of dopamine transporters. J. Med. Chem. 1994, 37, 1558-1561.
42. Goodman, M. M.; Kung, M.-P.; Kabalka, G. W.; Kung, H. F.; Switzer, R. Synthesis and characterization of radioiodinated N-(3-iodopropen-1-yl)-2β-carbomethoxy-3β4-chlorophenyl)tropanes: potential dopamine reuptake site imaging agents. J. Med. Chem. 1994, 37, 1535-1542.
43. Malison, R. T.; Vessotskie, J. M.; Kung, M.-P.; McElgin, W.; Romaniello, G.; Kim, H.-J.; Goodman, M. M.; Kung, H. F. Striatal dopamine transporter imaging in nonhuman primates with iodine-123-IPT SPECT. J. Nucl. Med. 1995, 36, 2290- 2297.
44. Mozley, P. D.; Stubbs, J. B.; Kimn, H.-J.; McElgin, W.; Kung, M.P.; Meegalla, S.; Kung, H. F. Dosimetry of an iodine-123-labeled tropane to image dopamine transporters. J. Nucl. Med. 1996, 37, 151-159.
45. 123I]IPT and singlephoton emission tomography. Eur. J. Nucl. Med. 1997, 24, 415- 421.
46. Abi-Dargham, A.; Gandelman, M. S.; DeErausquin, G. A.; ZeaPonce, Y.; Zoghbi, S. S.; Baldwin, R. M.; Laruelle, M.; Charney, D. S.; Hoffer, P. B.; Neumeyer, J. L.; Innis, R. B. SPECT imaging of dopamine transporters in human brain with iodine-123fluoroalkyl analogues of β-CIT. J. Nucl. Med. 1996, 37, 1129- 1133.
47. Neumeyer, J. L.; Tamagnan, G.; Wang, S.; Gao, Y.; Milius, R. A.; Kula, N. S.; Baldessarini, R. J. N-substituted analogues of 2β-carbomethoxy-3β-(4′-iodophenyl)tropane (β-CIT) with selective affinity to dopamine or serotonin transporters in rat forebrain. J. Med. Chem. 1996, 39, 543-548.
48. Fischman, A. J.; Babich, J. W.; Elmaleh, D. R.; Barrow, S. A.; Meltzer, P.; Hanson, R. N.; Madras, B. K. SPECT imaging of dopamine transporter sites in normal and MPTP-treated rhesus monkeys. J. Nucl. Med. 1997, 38, 144-150.
49. Zoghbi, S. S.; Tamagnan, G.; Baldwin, R. M.; Gao, Y.; Neumeyer, J. L.; Baldessarini, R.; Charney, D. S.; Seibyl, J. P.; Innis, R. B. Synthesis of a dopamine transporter binding cyclopentadiene phenyltropane conjugate complexed with Re and Tc-99m. J. Nucl. Med. 1997, 38, 100P.
50. Madras, B. K.; Jones, A. G.; Mahmood, A.; Zimmerman, R. E.; Garada, B.; Holman, B. L.; Davison, A.; Blundell, P.; Meltzer, P. C. Technepine: a high affinity technetium-99m probe to label the dopamine transporter in brain by SPECT imaging. Synapse 1996, 22, 239-246.
51. Tamagnan, G.; Gao, Y. G.; Baldwin, R. M.; Zoghbi, S. S.; Neumeyer, J. L. Synthesis of beta-CIT-BAT, a potential Tc-99m imaging ligand for dopamine transporter. Tetrahedron Lett. 1996, 37, 4353-4356.
52. 6-(2β-carbomethoxy-3β-phenyltropane) transition metal complexes. J. Med. Chem. 1996, 30, 1560-1563.
53. Meltzer, P. C.; Blundell, P.; Jones, A. G.; Mahmood, A.; Garada, B.; Zimmerman, R. E.; Davison, A.; Holman, B. L.; Madras, B. K. A technetium-99m SPECT imaging agent which targets the dopamine transporter in primate brain. J. Med, Chem. 1997, 40, 1835-1844.
54. Meegalla, S. K.; Plössl, K.; Kung, M.-P.; Stevenson, D. A.; LiableSands, L. M.; Rheingold, A. L.; Kung, H. F. First example of a Tc-99m complex as a dopamine transporter imaging agent. J. Am. Chem. Soc. 1995, 117, 11037-11038.
55. Meegalla, S. K.; Plössl, K.; Kung, M.-P.; Chumpradit, S.; Stevenson, D. A.; Kushner, S. A.; McElgin, W. T.; Mozley, P. D.; Kung, H. F. Synthesis and characterization of Tc-99m labeled tropanes as dopamine transporter imaging agents. J. Med. Chem. 1997, 40, 9-17.
56. 99mTc]TRODAT-1 derivatives as new dopamine transporter imaging agents. Proceedings of the XIIth International Symposium on Radiopharmacol Chemistry, Uppsala, Sweden, 1997; Abstract VI-13, pp 434-436.
57. Kung, H. F.; Kim, H.-J.; Kung, M.-P.; Meegalla, S. K.; Plössl, K.; Lee, H.-K Imaging of dopamine transporters in humans with technetium-99m TRODAT-1. Eur. J. Nucl. Med. 1996, 23, 1527- 1530.
58. Meegalla, S. K.; Plössl, K.; Kung, M.-P.; Chumpradit, S.; Stevenson, D. A.; Frederick, D.; Kung, H. F. Tc-99m labeled tropanes as dopamine transporter imaging agents. Bioconjugate Chem. 1996, 7, 421-429.
59. Orpen, A. G.; Brammer, L.; Allen, F. H.; Kennar, O.; Watson, D. G.; Taylo, R. Tables of bond lengths determined by X-ray and neutron diffraction. Part 2. Organometallic compounds and coordination complexes of the d- and f-block metals. J. Chem. Soc., Dalton Trans. 1989, S1-S83.
60. O'Neill, J. P.; Wilson, S. R.; Katzenellenbogen, J. A. Preparation and structural characterization of monoamine-monoamide bis(thiol oxo complexes of technetinm(V) and rhenium(V), Inorg. Chem. 1994, 33, 319-323.
61. 2 dithiourea (DTU) chelate ligands: synthesis and structural characterization. Inorg. Chem. 1996, 35, 4227-4231.
62. 3]. J. Organomet. Chem. 1995, 493, 119-127.
63. Kung, H. F.; Molnar, M.; Billings, J. J.; Wicks, R.; Blau, M. Synthesis and biodistribution of neutral lipid-soluble Tc-99m complexes that cross the blood-brain barrier. J. Nucl. Med. 1984, 25, 326-332.
64. Kung, H. F.; Yu, C. C.; Billings, J. J.; Molnar, M.; Blau, M. Synthesis of new bis-aminoethanethiol (BAT) derivatives: possible ligands for Tc-99m brain imaging agents. J. Med. Chem. 1985, 28, 1280-1284.
65. Kung, M.-P.; Essman, W, D.; Frederick, D.; Meegalla, S.; Goodman, M.; Mu, M.; Lucki, I.; Kung, H. F. IPT: a novel iodinated ligand for the CNS dopamine transporter. Synapse 1995, 20, 316-324. JM970742B