A new nitroxyl-probe with high retention in the brain and its application for brain imaging

Free Radical Biology and Medicine

Volumn 28, Issue 6, 2000, Pages 959-969

  Sano, Hiroaki ^a   Naruse, Masaichi ^b   Matsumoto, Ken Ichiro ^a,c   Tetsuo, O I ^b   Utsumi, Hideo ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b Daiichi Radioisotope Laboratories Ltd   (Japan)

^c SHOWA PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

ESR CT; Free radicals; In vivo ESR; Nitroxyl radicals; Oxidative injury; Reactive oxygen species

Indexed keywords

2,2,5,5 TETRAMETHYLPYRROLIDINE 1 OXYL 3 CARBOXYLIC ACID ACETOXYMETHYL ESTER; 2,2,5,5 TETRAMETHYLPYRROLIDINE 1 OXYL 3 CARBOXYLIC ACID METHYL ESTER; 3 CARBOXY 2,2,5,5 TETRAMETHYLPYRROLIDINE 1 OXYL; CONTRAST MEDIUM; FREE RADICAL; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; BLOOD BRAIN BARRIER; BRAIN; COMPUTER ASSISTED TOMOGRAPHY; CONTROLLED STUDY; DRUG SYNTHESIS; ELECTRON SPIN RESONANCE; FEMALE; HYDROLYSIS; IMAGING; IN VITRO STUDY; MOUSE; NONHUMAN; PARTITION COEFFICIENT; PRIORITY JOURNAL; SPIN LABELING; TECHNIQUE;

ANIMALS; BLOOD-BRAIN BARRIER; BRAIN; BRAIN DISEASES; CARBOXYLESTERASE; CARBOXYLIC ESTER HYDROLASES; CYCLIC N-OXIDES; DIAGNOSTIC IMAGING; ELECTRON SPIN RESONANCE SPECTROSCOPY; FEMALE; FREE RADICALS; MICE; MICE, INBRED STRAINS; PYRROLIDINES; SPIN LABELS;

ANIMALIA;

EID: 0034653836     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(00)00184-2     Document Type: Article

References (49)

1. Chan, P. H. Role of oxidants in ischemic brain damage. Stroke 27:1124-1129; 1996.
2. Cobbs, C. S.; Levi, D. S.; Aldape, K.; Israel, M. A. Manganese Superoxide dismutase expression in human central nervous system tumors. Cancer Res. 56:3192-3195; 1996.
3. Stadtman, E. R. Protein oxidation and aging. Science 257:1220 1224; 1992.
4. Rose, D. R.; Siddique, T.; Patterson, D.; Figlewicz, D. Z.; Sapp, P.; Hentati, A.; Donaldson, D.; Goto, J.; O'Regan, J. P.; Deng, H.-Q.; Rahmani, Z.; Krizus, A.; McKenna-Yasek, D.; Cayabyab, A.; Gaston, S. M.; Berger, R.; Tanzi, R. E.; Halperin, J. J.; Herzfeld, B.; van den Berg, R.; Hung, W.-Y.; Bird, T.; Deng, G.; Mulder, D. W.; Smyth, C.; Lang, N. G.; Soriano, E.; PerocakVance, M. A.; Haines, J.; Rouleau, G. A.; Gusella, J. S.; Horritz, H. R.; Brown R. H. Jr. Mutations in Cu/Zn Superoxide dismutase gene are associated with familial amyotrophic lateral sclerosis. Nature 362:59-62; 1993.
5. Smith, M. A.; Harris, P. L. R.; Sayre, L. M.; Perry, G. Iron accumulation in Alzheimer disease is a source of redox-generated free radicals. Proc. Natl. Acad. Sei. USA 94:9866-9868; 1997.
6. Evans, P. H. Free radicals in brain metabolism and pathology. Br. Med. Bull. 49:577-587; 1993.
7. Inoue, M.; Utsumi, H.; Kirino, Y. A comparative ESR study of some paramagnetic materials as probes for the noninvasive measurement of dissolved oxygen in biological systems. Chem. Pharm. Bull. 42:2346-2348; 1994.
8. Finkelstein, E.; Rosen, G. M.; Rauckman, E. J. Superoxidedependent reduction of nitroxides by thiols. Biochim. Biophys. Acta. 802:90-98; 1984.
9. Krishna, M. C.; Samuni, A.; Taira, J.; Goldstein, S.; Mitchell, J. B.; Russo, A. Stimulation by nitroxides of catalase-like activity of hemeproteins. J. Biol. Chem. 271:26018-26025; 1996.
10. ̇- or as SOD mimics? J. Biol. Chem. 271:26026-26031; 1996.
11. Nigam, S.; Asmus, K.-D. Electron transfer and addition reactions of free nitroxyl radicals with radiation induced radicals. Phys. Org. Chem. 85:2324-2340; 1976.
12. Utsumi, H.; Shimakura, A; Kashiwagi, M.; Hamada, A. Localization of the active center of nitroxide radical reduction in rat liver microsomes: its relation to cytochrome P-450 and membrane fluidity./ Biochem. 105:239-244; 1989.
13. lannone, A.; Tomasi, A.; Vannini, V.; Swartz, H. M. Metabolism of nitroxide spin labels in subcellular fraction of rat liver. I. Reduction by microsomes. Biochim. Biophys. Acta 1034:285 289; 1990.
14. Quintanilha, A. T.; Packer, L. Surface localization of sites of reduction of nitroxide spin-labeled molecules in mitochondria. Proc. Nad. Acad. Sei. USA 74:570-574; 1977.
15. lannone, A.; Tomasi, A.; Vannini, V.; Swartz, H. M. Metabolism of nitroxide spin labels in subcellular fraction of rat liver. II. Reduction in the cytosol. Biochim. Biophys. Acta 1034:290-293; 1990.
16. Utsumi, H.; Muto, E.; Masuda, S.; Hamada, A. In vivo ESR measurement of free radicals in whole mice. Biochem. Biophys. Res. Commun. 172:1342-1348; 1990.
17. Glockner, J. F.; Chang, H.-C.; Swartz, H. M. In vivo oximetry using a nitroxide-liposome system. Magn. Reson. Med. 20:123-133; 1991.
18. Komarov, A. M.; Joseph, J.; Lai, C.-S. In vivo pharmacokinetics of nitroxides in mice. Biochem. Biophys. Res. Commun. 201: 1035-1042; 1994.
19. Kuppusamy, P.; Chzhan, M.; Vij, K.; Shteynbuk, M.; Lefer, D. J.; Giannella, E.; Zweier, J. L. Three-dimensional spectral-spatial EPR imaging of free radicals in the heart: a technique for imaging tissue metabolism and oxygenation. Proc. Natl. Acad. Sei. USA 91:3388-3392; 1994.
20. Gomi, F.; Utsumi, H.; Hamada, A.; Matsuo, M. Aging retards spin clearance from mouse brain and food restriction prevents its age-dependent retardation. Life Sei. 52:2027-2033; 1993.
21. Takeshita, K.; Hamada, A.; Utsumi, H. Mechanisms related to reduction of radical in mouse lung using an L-band ESR spectrometer. Free Radie. Biol. Med. 26:951-960; 1999.
22. Miura, Y.; Utsumi, H.; Hamada, A. Effects of inspired oxygen concentration on in vivo redox reaction of nitroxide radicals in whole mice. Biochem. Biophys. Res. Commun. 182:1108-1114; 1992.
23. Miura, Y.; Hamada, A.; Utsumi, H. In vivo ESR studies of antioxidant activity on free radical reaction in living mice under oxidative stress. Free Radie. Res. 22:209-214; 1995.
24. Utsumi, H.; Takeshita, K.; Miura, Y.; Masuda, S.; Hamada, A. In vivo EPR measurement of radical reaction in whole mice: influence of inspired oxygen and ischemia-reperfusion injury on nitroxide reaction. Free Radie. Res. Commun. 19:8219-8225; 1993.
25. Kuppusamy, P.; Wang, P.; Zweier, J. L. Electron paramagnetic resonance imaging of rat heart with nitroxide and polynitroxylalbumin. Biochem. 35:7051-7057; 1996.
26. Utsumi, H.; Ichikawa, K.; Takeshita, K. In vivo ESR measurements of free radical reaction in living mice. Toxicol. Lett. 82/ 83:561-565; 1995.
27. Sano, T.; Umeda, F.; Hashimoto, T.; Nawata, H; Utsumi, H. Oxidative stress measurement by in vivo electron spin resonance spectroscopy in rats with streptozotocin-induced diabetes. Diabetologia 41:1355-1360; 1998.
28. Miura, Y; Anzai, K; Urano, S; Ozawa, T. In vivo electron paramagnetic resonance studies on oxidative stress caused by X-irradiation in whole mice. Free Radie. Biol. Med. 23:533-540; 1997.
29. Kuppusamy, P.; Afeworki, M.; Shankar, R. L.; Coffin, D.; Krishna, M. C.; Hahn, S. M.; Michell, J. B.; Zweier, J. L. In vivo electron paramagnetic resonance imaging of tumor heterogeneity and oxygenation in a murine model. Cancer Res. 58:1562-1568; 1998.
30. Phumala, N.; Ide, T.; Utsumi, H. Noninvasive evaluation of in vivo free radical reactions catalyzed by iron using in vivo ESR spectroscopy. Free Radie. Biol. Med. 26:1209-1217; 1999.
31. Irie, T.; Fukushi, K.; Akimoto, Y.; Tamagami, H.; Nozaki, T. Design and evaluation of radioactive acetylcholine analogs for mapping brain acetylcholinesterase (AchE) in vivo. Nucl. Med. Biol. 21:801-808; 1994.
32. 99mTc-bicisate in the human brain after intracarotid injection. J. Cereb. Blood Flow Metab. 14(Suppl.):S19-S27; 1994.
33. Sano, H.; Matsumoto, K; Utsumi, H. Synthesis and imaging of blood-brain-barrier permeable nitroxyl-probes for free radical reactions in brain of living mice. Biochem. Mol. Biol. Int. 42:641-647; 1997.
34. Yokoyama, H.; Itoh, O.; Ogata, T.; Obara, H.; Ohya-Nishiguchi, H.; Kamada, H. Temporal brain imaging by a rapid scan ESR-CT system in rats receiving intraperitoneal injection of a methyl ester nitroxide radical. Magn. Reson. Imaging 15:1079-1084; 1997.
35. Tsien, R. Y. A non-disruptive technique for loading calcium buffers and indicators into cells. Nature 290:527-528; 1981.
36. Takeshita, K.; Utsumi, H.; Hamada, A. ESR measurement of radical clearance in lung of whole mouse. Biochem. Biophys. Res. Commun. 177:874-880; 1991.
37. Takeshita, K.; Utsumi, H.; Hamada, A. Whole mouse measurement of paramagnetism-loss of nitroxide free radical in lung with a L-band ESR spectrometer. Biochem. Mol. Biol. Int. 29:17-24; 1993.
38. Kinouchi, H.; Epstein, C. J.; Mizui, T.; Carlson, E.; Chen, S. F.; Chan, P. H. Attenuation of focal cerebral ischemic injury in transgenic mice overexpressing CuZn Superoxide dismutase. P roc. Natl. Acad. Sei. USA 88:11158-11162; 1991.
39. Liu, X.-H.; Kalo, H.; Nakata, N.; Kogure, K.; Kalo, K. An immunohistochemical study of copper/zinc Superoxide dismutase and manganese Superoxide dismutase in rat hippocampus after transient cerebral ischemia. Brain Res. 625:29-37; 1993.
40. Ogawa, N. Levodopa and dopamine agonists in the treatment of Parkinson’s disease: advantages and disadvantages. Eur. Neural. 34(Suppl.):20-28; 1994.
41. Cadet, J. L.; All, S. F.; Rothman, R. B.; Epstein, C. J. Neurotoxicity, drug of abuse, and the CuZn-Superoxide dismutase transgenic mice. Mol. Neurobiol. 11:155-163; 1995.
42. Przedborski, S.; Jackson-Lewis, V.; Yokoyama, R.; Shibata, T.; Dawson, V.; Dawson, T. M. Role of neuronal nitric oxide in 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-induced dopaminergic neurotoxicity. Proc. Natl. Acad. Sci. USA 93:4565-4571; 1996.
43. Cadet, J. L.; Brannock, C. Free radicals and the pathobiology of brain dopamine systems. Neurochem. Int. 32:117-131; 1998.
44. Utsumi, H.; Takeshita, K. In vivo ESR measurement of free radical reactions in living animals using nitroxyl probes. In: Ohya-Nishiguchi, H.; Packer, L., eds. Bioradicals detected by ESR spectroscopy. Switzerland: Birkhauser Verlag Basel; 1995: 321-334.
45. Afzal, V.; Brasch, R. C.; Nitecki, D.; Wolff, S. Nitroxyl spin label contrast enhancers for magnetic resonance imaging. Studies of acute toxicity and mutagenesis. Invest. Radial. 19:549-552; 1984.
46. Eriksson, U. G.; Schuhmann, G.; Brasch, R. C.; Tozer, T. N. Pharmacokinetics in the rat and the dog of a nonionic nitroxide contrast agent for magnetic resonance imaging. J. Pharm. Sei. 77:97-103; 1988.
47. Pitt, D.; Barnes, J. C. Calcium homeostasis, signalling and protein phosphorylation during calcium-induced conidiation in Penicillium notatum. J. Gen. Microbiol. 139:3053-3063; 1993.
48. Fuchs, J.; Groth, N.; Herrling, T.; Zimmer, G. Electron paramagnetic resonance studies on nitroxide radical 2,2,5,5-tetramethyl4-piperidin-l-oxyl (TEMPO) redox reactions in human skin. Free Radie. Biol. Med. 22:967-976; 1997.
49. Kocherginsky, N.; Swartz, H. M. Chemical reactivity of nitroxides. In: Kocherginsky, N.; Swartz, H. M., eds. Nitroxide spin labels: Reactions in biology and chemistry. New York: CRC press; 1995:27-66.