Glutathione-mediated metabolism of technetium-99m SNS/S mixed ligand complexes: A proposed mechanism of brain retention

Journal of Medicinal Chemistry

Volumn 42, Issue 6, 1999, Pages 1066-1075

  Nock, Berthold A ^a   Maina, Theodosia ^a   Yannoukakos, Drakoulis ^a   Pirmettis, Ioannis C ^a   Papadopoulos, Minas S ^a   Chiotellis, Efstratios ^a  

^a INSTITUTE OF NANOSCIENCE AND NANOTECHNOLOGY   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; BIS(2 MERCAPTOETHYL) AMINE TC 99M; CYSTEINE; GLUCOHEPTONIC ACID; GLUTATHIONE; HEXAMETHYLPROPYLENE AMINE OXIME TECHNETIUM TC 99M; N DIETHYLAMINOETHYL TC 99M; PHENYLTHIOLATE; RADIOPHARMACEUTICAL AGENT; TIN CHLORIDE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BLOOD; BODY FLUID; BRAIN HOMOGENATE; COMPLEX FORMATION; DRUG BILE LEVEL; DRUG BLOOD LEVEL; DRUG BRAIN LEVEL; DRUG DISTRIBUTION; DRUG METABOLISM; ELECTRON; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INTRAVENOUS DRUG ADMINISTRATION; MOUSE; NONHUMAN;

ANIMALS; BRAIN; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYSTEAMINE; CYSTEINE; GLUTATHIONE; LIGANDS; MICE; ORGANOMETALLIC COMPOUNDS; ORGANOTECHNETIUM COMPOUNDS; RHENIUM; STEREOISOMERISM; TECHNETIUM TC 99M EXAMETAZIME; TISSUE DISTRIBUTION;

EID: 0033602530     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980174f     Document Type: Article

References (85)

1. (a) McIntosh, T. K. Neurochemical sequela of traumatic brain injury: therapeutic implications. Cerebrovasc. Brain Metab. Rev. 1980, 6, 109-162.
2. (b) Hill, T. C.; Holman, B. L. SPECT brain imaging: finding a niche in neurological diagnosis. Diag. Imag. 1985, 7, 64-68.
3. (c) Holman, B. L.; Hill, T. C. Functional imaging of the brain with SPECT. Appl. Radiol. 1984, 13, 21-27.
4. (d) Pickard, J. D.; Read, D. H.; Lovick, A. H. J. Use of cerebral blood flow measurements in the prediction of delayed cerebral ischemia following subarachnoid hemorrhage. Cerebral blood flow and metabolism measurement; Springer-Verlag: Berlin, Heidelberg, 1985; pp 149-152.
5. (e) Bonte, F. J. SPECT study of brain blood flow in seizure disorders and psychiatric diseases. Curr. Concepts in Diag. Nucl. Med. 1987, 9-15.
6. (f) Ell, P. J.; Jarritt, P. H.; Costa, D. C.; Cullum, I. D.; Lui, D. Functional imaging of the brain. Semin. Nucl. Med. 1987, 17, 214-229.
7. (a) Holmes, R. A.; Chaplin, S. B.; Royston, K. G.; et al. Cerebral uptake and retention of Tc-99m hexamethylpropylene amine oxime (Tc-99m HM-PAO). Nucl. Med. Commun. 1985, 6, 443-447.
8. (b) Sharp, P. F.; Smith, F. W.; Gemmell, H. G.; et al. Technetium-99m HM-PAO stereoisomers as potential agents for imaging regional cerebral blood flow. J. Nucl. Med. 1986, 27, 171-177.
9. (c) Nowotnik, D. P.; Canning, L. R.; Cumming, S. A.; et al. Tc-99m-HM-PAO: a new radiopharmaceutical for imaging regional cerebral blood flow. J. Nucl. Med. Allied Sci. 1985, 29, 208.
10. (d) Neirinckx, R. D.; Canning, L. R.; Piper, I. M.; Nowotnik, D. P.; et al. Technetium-99m d, 1-HM-PAO: A new radiopharmaceutical for SPECT imaging of regional cerebral blood perfusion. J. Nucl. Med. 1987, 28, 191-202.
11. (a) Hung, J. C.; Corlija, M.; Volkert, W. A.; Holmes, R. A. Kinetic analysis of technetium-99m d,1-HM-PAO decomposition in aqueous media. J. Nucl. Med. 1988, 29, 1568-1576.
12. (b) Newton, M. R.; Austin, M. C.; Chan, J. G.; McKay, W. J.; Rowe, C. C.; Berkovic, S. F. Ictal SPECT using technetium-99m-HMPAO: methods for rapid preparation and optimal deployment of tracer during spontaneous seizures. J. Nucl. Med. 1993, 34, 666-670.
13. (a) Walovitch, R. C.; Makuch, J.; Garrity, S.; et al. Neuropharmacological characterization of Tc99m ECD in human and nonhuman primates. Neurology 1988, 38, 363.
14. (b) Walovitch, R. C.; Hill, T. C.; Garrity, S. T.; Cheesman, E. H.; et al. Characterization of technetium-99m-L,L-ECD for brain perfusion imaging, Part 1: Pharmacology of technetium-99m ECD in nonhuman primates. J. Nucl. Med. 1989, 30, 1892-1901.
15. (c) Leveille, J.; Demonceau, G.; DeRoo, M.; et al. Characterization of technetium-99m-L,L-ECD for brain perfusion imaging, Part 2: Biodistribution and brain imaging in humans. J. Nucl. Med. 1989, 30, 1902-1910.
16. (d) Papazyan, J. P.; Delavelle, J.; Burkhard, P.; Rossier, P.; et al. Discrepancies between HMPAO and ECD SPECT imaging in brain tumors. J. Nucl. Med. 1997, 38, 592-596.
17. (a) Neirinckx, R. D.; Burke, J. F.; Harrison, R. C.; Forster, A. M.; Andersen, A. R.; Lassen, N. A. The retention mechanism of technetium-99m-HM-PAO: Intracellular reaction with glutathione. J. Cereb. Blood Flow Metab. 1988, 8, S4-S12.
18. (b) Suess, E.; Malessa, S.; Ungersboeck, K.; Kitz, P.; Podreka, I.; Heimberger, K.; Hornykiewicz, O.; Deecke, L. Technetium-99m-d,1-hexamethylpropyleneamine oxime (HMPAO) uptake and glutathione content in brain tumors. J. Nucl. Med. 1991, 32, 1675-1681.
19. (c) Jacquier-Sarlin, M. R.; Polla, B. S.; Slosman, D. O. Oxido-reductive state: The major determinant for cellular retention of technetium-99m-HMPAO. J. Nucl. Med. 1996, 37, 1413-1416.
20. (d) Sasaki, T.; Toyama, H.; Oda, K.; Ogihara-Umeda, I.; Nishigori, H.; Senda, M. Assessment of antioxidative ability in brain: Technetium-99m-meso-HMPAO as an imaging agent for glutathione localization. J. Nucl. Med. 1996, 37, 1698-1701.
21. (e) Sasaki, T.; Senda, M. Technetium-99m-meso-HMPAO as a potential agent to image cerebral glutathione content. J. Nucl. Med. 1997, 38, 1125-1129.
22. (f) Ballinger, J. R.; Reid, R. H.; Gulenchyn, K. Y. Technetium-99m HM-PAO stereoisomers: Differences in interaction with glutathione.
23. Jacquier-Sarlin, M. R.; Polla, B. S.; Slosman, D. O. Cellular Basis of ECD brain retention. J. Nucl. Med. 1996, 37, 1694-1697.
24. 99mTc-bicisate (ECD, Neurolite) measured by SPECT on the same day. J. Cereb. Blood Flow Metab. 1994, 14, S44-S48.
25. (b) Moretti, J. L.; Caglar, M.; Weinmann, P. Cerebral perfusion imaging tracers for SPECT: Which one to choose? J. Nucl. Med. 1995, 36, 359-363.
26. (a) Pietzsch, H. J.; Spies, H.; Hoffmann, S.; Stach, J. Lipophilic technetium complexes-V. Synthesis and characterization of (3-thiapentane-1,5-dithiolato) (thiophenolato) oxotechnetium(V). Inorg. Chim. Acta 1989, 161, 15-16.
27. (b) Pietzsch, H. J.; Spies, H.; Hoffmann, H.; Scheller, D. Lipophilic technetium complexes-VII. Neutral oxotechnetium(V) complexes of tridentate Schiff-bases containing monothiols as co-ligands. Appl. Radiat. Isot. 1990, 41, 185-188.
28. (c) Spies, H.; Pietzsch, H. J.; Syhre, R.; Hoffmann, S. Lipophilic technetium complexes-VIII. Preparation and animal studies of oxotechnetium(V) complexes with tridentate/monodentate ligand coordination. Isotopenpraxis 1990, 26, 159-162.
29. 3-donor ligands as new backbone for reduced technetium. Eur. J. Nucl. Med. 1990, 16, 109.
30. (b) Mastrostamatis, S.; Papadopoulos, M. S.; Pirmettis, I. C.; Paschali, E.; et al. Tridentate ligands containing the SNS donor atom set as a novel backbone for the development of technetium brain imaging agents. J. Med. Chem. 1994, 37, 3212-3218.
31. (c) Spyriounis, D. M.; Pelecanou, M.; Stassinopoulou, C. I.; Raptopoulou, C. P.; Terzis, A.; Chiotellis, E. Synthesis and characteriztion of oxotechnetium(V) complexes with aza-substituted 2,6-dimethyl-4-azaheptane-2,6-dithiol ligands and benzyl mercaptan as coligand. Inorg. Chem. 1995, 34, 1077-1082.
32. (d) Pirmettis, I. C.; Papadopoulos, M. S.; Mastrostamatis, C. P.; Raptopoulou, C. P.; Terzis, A.; Chiotellis, E. Synthesis and characterization of oxotechnetium(V) mixed-ligand complexes containing a tridentate N-substituted bis(2-mercaptoethyl)amine and a monodentate thiol. Inorg. Chem. 1996, 35, 1685-1691.
33. (e) Papadopoulos, M. S.; Pirmettis, I. C.; Pelecanou, M.; Raptopoulou, C. P.; Terzis, A.; Stassinopoulou, C. I.; Chiotellis, E. Syn-Anti isomerism in a mixed-ligand oxorhenium complex ReO[SN(R)S][S]. Inorg. Chem. 1996, 35, 7377-7383.
34. 99mTc aminobisthiolato/monothiolato "3 + 1" mixed ligand complexes: Structure-activity relationships and preliminary in vivo validation as brain blood flow imaging agents. J. Med. Chem. 1997, 40, 2539-2546.
35. (g) Papadopoulos, M.; Pirmettis, I.; Raptopoulou, C.; Chiotellis, E.; Friebe, M.; Berger, R.; Spies, H.; Johannsen, B. Synthesis, structure, lipophilicity and protonation behaviour of mixed ligand rhenium chelates functionalized by amine groups. Appl. Radiat. Isot. 1998, 49, 961-966.
36. (h) Jaipetch, T.; Pirmettis, I.; Papadopoulos, M.; Nock, B.; Maina, T.; Raptopoulou, C. P.; Terzis, A.; Chiotellis, E. Synthesis and characterization of two novel TcO and ReO mixed ligand complexes (3+1 combination, SNS/S) for hypoxia imaging. IAEA TEC-DOC-1029 1998, 231-242.
37. 99mTc SNS/S mixed ligand complex in mice brain. Czech. J. Phys. 1998, 48, 75-80.
38. 99mTc SNS/S complex containing a pendant ester functionality. IAEA TEC-DOC-1029 1998, 79-89.
39. 99mTc complexes containing monothiols of differing nucleophilicity. Eur. J. Nucl. Med. 1997, 24, 990.
40. 99mTc) mixed ligand complexes. Isolation and characterization of the adduct. Inorg. Chim. Acta 1998, 281, 148-152.
41. (a) Meister, A.; Anderson, M. E. Glutathione. Annu. Rev. Biochem. 1983, 52, 711-760.
42. (b) Reichert, D. Toxication of foreign substances by conjugation reactions. Angew. Chem. 1981, 20, 135-216.
43. (c) Griffith, O. W.; Meister, A. Glutathione: Interorgan translocation, turnover, and metabolism. Proc. Natl. Acad. Sci. U.S.A. 1979, 76, 5606-5610.
44. (d) Plummer, J. L.; Smith, B. R.; Sies, H.; Bend, J. R. Chemical depletion of glutathione in vivo. Methods Enzymol. 1981, 77, 50-59.
45. Papadopoulos, M.; Pirmettis, I.; Tsoukalas, C.; Nock, B.; Maina, T.; Raptopoulou, C. P.; Terzis, A.; Friebe, M.; Spies, H.; Johannsen, B.; Chiotellis, E. Study on the formation of mixed ligand oxorhenium and oxotechnetium complexes (SNS/S) combination. IAEA TEC-DOC-1029 1998, 141-155.
46. (a) Rabenstein, D. L. Nuclear magnetic resonance studies of the acid-base chemistry of amino acids and peptides. I. Microscopic ionization constants of glutathione and methylmercury-complexed glutathione. J. Am. Chem. Soc. 1973, 95, 2797-2803.
47. (b) Backs, S. J.; Rabenstein, D. L. Nuclear magnetic resonance studies of the solution chemistry of metal complexes. 16. Complexation of trimethyllead by sulfydryl-containing amino acids and related molecules. Inorg. Chem. 1981, 20, 410-415.
48. (a) March, J. The neighboring group mechanism. Advanced Organic Chemistry; John Wiley & Sons: New York, Toronto, Singapore, 1985; pp 268-272.
49. (b) Deutsch, E.; Root, M. J.; Nosco, D. L. Mechanistic aspects of transition metal complexes containing coordinated sulphur. In Advances in Inorganic and Bioinorganic Mechanisms; Sykes, E. D., Ed.; Academic Press: London, 1982; Vol. 1, p 269.
50. (c) Asher, L. E.; Deutsch, E. Effect of added ligands on the rate of chromium-sulfur bond fission in thiolatopentaaquochromium(III) complexes. Evidence for a sulfur-induced trans effect in chromium(III) chemistry. Inorg. Chem. 1976, 15, 1531-1537.
51. +). Inorg. Chem. 1973, 12, 1774-1778.
52. (e) Asher, L. E.; Deutsch, E. Preparation and aquation kinetics of the pentaaquo(4-thioanilinium-S)chromium-(III) ion. Catalysis of chromium-sulfur bond breaking by oxygen and other oxidants. Inorg. Chem. 1972, 11, 2927-2933.
53. (a) Ishikawa, T.; Li, Z. S.; Lu, Y. P.; Rea, P. A. The GS-X pump in plant, yeast, and animal cells: Structure, function, and gene expression. Biosci. Rep. 1997, 17, 189-207.
54. (b) Shen, H.; Paul, S.; Breuninger, L. M.; Ciaccio, P. J.; Laing, N. M.; Helt, M.; Tew, K. D.; Kruh, G. D. Cellular and in vitro transport of glutathione conjugates by MRP. Biochemistry 1996, 35, 5719-5725.
55. (c) Khanna, P.; Kumari, K.; Ansari, N. H.; Srivastava, S. K. ATP-dependent transport of glutathione-N-ethylmaleimide conjugate across erythrocyte membrane. Biochem. Med. Metab. Biol. 1994, 53, 105-114.
56. (d) Scott, R. B.; Matin, S.; Hamilton, S. C. Glutathione, glutathione S-transferase, and transmembrane transport of glutathione conjugate in human neutrophil leukocytes. J. Lab. Clin. Med. 1990, 116, 674-680.
57. (a) Griffith, O. W.; Meister, A. Translocation of intracellular glutathione to membrane-bound γ-glutamyl transpeptidase as a discrete step in the γ-glutamyl cycle: Glutathionuria after inhibition of transpeptidase. Proc. Natl. Acad. Sci. U.S.A. 1979, 76, 268-272.
58. (b) Griffith, O. W.; Meister, A. Excretion of cysteine and γ-glutamyl-cysteine moieties in human and experimental animal γ-glutamyl transpeptidase deficiency. Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 3384-3387.
59. (c) Griffith, O. W.; Bridges, R. J.; Meister, A. Formation of γ-glutamylcyst(e)ine in vivo is catalyzed by γ-glutamyl transpeptidase. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 2777-2781.
60. (a) Huang, J.; Philbert, M. A. Distribution of glutathione and glutathione-related enzyme systems in mitochondria and cytosol of cultured cerebellar astrocytes and granule cells. Brain Res. 1995, 680, 16-22.
61. (b) Bellomo, G.; Palladini, G.; Vairetti, M. Intranuclear distribution, function and fate of glutathione and glutathione-S-conjugate in living rat hepatocytes studied by fluorescence microscopy. Microsci. Res. Technol. 1997, 36, 243-252.
62. (c) Bellomo, G.; Vairetti, M.; Stivala, L.; Mirabelli, F.; Richelmi, P.; Orrenius, S. Demonstration of nuclear compartmentalization of glutathione in hepatocytes. Proc. Natl. Acad. Sci. U.S.A 1992, 89, 4412-4416.
63. (a) Yamazaki, M.; Suzuki, H.; Sugiyama, Y. Recent advances in carrier-mediated hepatic uptake and biliary excretion of xenobiotics. Pharm. Res. 1996, 14, 497-513.
64. (b) Hinchman, C. A.; Ballatori, N. Glutathione conjugation and conversion to mercapturic acids can occur as an intrahepatic process. J. Toxicol. Environ. Health 1994, 41, 387-409.
65. (c) Sekura, R.; Meister, A. Glutathione turnover in the kidney; considerations relating to the γ-glutamyl cycle and the transport of amino acids. Proc. Natl. Acad. Sci. U.S.A. 1974, 71, 2969-2972.
66. Kannan, R.; Kuhlenkamp, J. F.; Jeandidier, E.; et al. Evidence for carrier-mediated transport of glutathione across the blood-brain barrier in the rat. J. Clin. Invest. 1990, 85, 2009-2013.
67. (a) Marstein, S.; Jellum, E.; Nesbakken, R.; Perry, T. L. Biochemical investigations of biopsied brain tissue and autopsied organs from a patient with pyroglutamic acidemia (5-oxoprolinemia). Clin. Chim. Acta 1981, 111, 219-228.
68. (b) Perry, T.; Yong, V. W. Idiopathic Parkinson's disease, progressive supranuclear palsy and glutathione metabolism in the substantia nigra of patients. Neurosci. Lett. 1986, 67, 269-274.
69. (c) Slivka, A.; Spina, M. B.; Cohen, G. Reduced and oxidized glutathione in human and monkey brain. Neurosci. Lett. 1987, 74, 112-118.
70. (a) Babich, J. W. Technetium-99m-HMPAO retention and the role of glutathione: the debate continues (Editorial). J. Nucl. Med. 1991, 32, 1681-1683.
71. (b) Bates, S. E.; Regis, J. I.; Robey, R. W.; Zhan, Z.; Scala, S.; Meadows, B. J. Chemoresistance in the clinic: overview 1994. Bull. Cancer 1994, 81, 55S-61S.
72. (c) O'Brien, M. L.; Tew, K. D. Glutathione and related enzymes in multidrug resistance. Eur. J. Cancer 1996, 32A, 967-978.
73. (d) Muller, M.; de Vries, E. G.; Jansen, P. L. Role of multidrug resistance protein (MRP) in glutathione S-conjugate transport in mammalian cells. J. Hepatol. 1996, 24, 100-108.
74. (e) Zhang, K.; Wong, K. P. Active transport of glutathione S-conjugate in human colon adenocarcinoma cells. Cancer Lett. 1996, 108, 143-151.
75. (f) Newkirk, K.; Heffern, J.; Slosman-Moll, E.; Sessions, R. B.; Rasmussen, A. A.; Andrews, P. A.; Cullen, K. J. Glutathione content but not glutamyl cysteine synthetase mRNA expression predicts cisplatin resistance in head and neck cancer cell lines. Cancer Chemother. Pharmacol. 1997, 40, 75-80.
76. (g) Kabasakal, L.; Oezker, K.; Hayward, M.; Akansel, G.; Griffith, O.; et al. Technetium-99m sestamibi uptake in human breast carcinoma cell lines displaying glutathione-associated drug-resistance. Eur. J. Nucl. Med. 1996, 23, 568-570.
77. 2A serotonin receptor binding: Structure-affinity considerations. Nucl. Med. Biol. 1996, 23, 429-438.
78. (b) Johannsen, B.; Berger, R.; Brust, P.; Pietzsch, H. J.; Schenker, C.; Seifert, S.; Syhre, R.; Spies, H. Structural modifications of receptor-binding technetium-99m complexes in order to improve brain uptake. Eur. J. Nucl. Med. 1997, 24, 316-319.
79. (c) Meegalla, S.; Ploessl, 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.
80. 99mTc complex as a dopamine transporter imaging agent. J. Am. Chem. Soc. 1995, 117, 11037-11038.
81. 2+ core. Inorg. Chim. Acta 1984, 90, 41-51.
82. (b) Mann, F. Hofman's ethylene bases. Synthesis of β,β′-diaminodiethylamine and β,β′-diaminodiethylmethylamine. J. Chem. Soc. 1934, 461-466.
83. (c) Harley-Mason, J. Some aliphatic thiols and their derivatives. Part I. Aliphatic mercaptans. J. Chem. Soc. 1947, 320-322.
84. (d) Wineman, R. J.; Gollis, M. H.; James, J. C.; Pomponi, A. M. Thioethylation of amines with ethylene sulfide. J. Org. Chem. 1962, 27, 4222-4226.
85. 125I]-iodoaryl β-methyl fatty acids. Int. J. Nucl. Med. Biol. 1985, 12 223-226.