Copper-62-ATSM: A new hypoxia imaging agent with high membrane permeability and low redox potential

Journal of Nuclear Medicine

Volumn 38, Issue 7, 1997, Pages 1155-1160

  Fujibayashi, Yasuhisa ^a   Taniuchi, Hideyuki ^b   Yonekura, Yoshiharu ^b   Ohtani, Hiroshi ^b   Konishi, Junji ^b   Yokoyama, Akira ^b  

^a KYOTO UNIVERSITY   (Japan)

^b NONE

Author keywords

Copper 62 ATSM; Hypoxia; Mitochondria

Indexed keywords

COPPER 62;

ANIMAL TISSUE; ARTICLE; CELL MEMBRANE PERMEABILITY; DIAGNOSTIC IMAGING; ELECTRON SPIN RESONANCE; HYPOXIA; LEFT ANTERIOR DESCENDING CORONARY ARTERY; MITOCHONDRIAL MEMBRANE; NONHUMAN; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; RADIOSENSITIZATION; RAT; RESPIRATORY CHAIN; TISSUE DISTRIBUTION;

ANIMALS; BRAIN; CELL HYPOXIA; CELL MEMBRANE PERMEABILITY; COPPER RADIOISOTOPES; ELECTRON SPIN RESONANCE SPECTROSCOPY; MALE; MICE; MITOCHONDRIA; MYOCARDIAL ISCHEMIA; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; RADIOPHARMACEUTICALS; RATS; RATS, WISTAR; ROTENONE; SUBMITOCHONDRIAL PARTICLES; THIOSEMICARBAZONES;

EID: 0030811565     PISSN: 01615505     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (37)

1. Adams GE, Flockhart IR, Smithen CE, et al. Electron-affinic sensitization VII. A correlation between structures, one-electron reduction potentials and efficiencies of nitroimidazoles as hypoxic cell radiosensitizers. Radiat Res 1976;67:9-20.
2. Chapman JD, Baer K, Lee J. Characteristics of the metabolism-induced binding of misonidazole to hypoxic mammalian cells. Cancer Res 1983;43:1523-1528.
3. 3H]misonidazole in cerebral ischemia. Stroke 1987;18:168-176.
4. 18F-labeled fluoronitroimidazoles: potential in vivo markers of hypoxic tissue. Int J Radiat App Instrum [A] 1986;37:599-605.
5. 123I-iodoazomycin arabinoside: preliminary report of a clinical study. Br J Cancer 1992;65:90-95.
6. Mannan RH, Mercer JR, Wiebe LI, et al. Radioiodinated 1-(2-fluoro-4-iodo-2,4-dideoxy-beta-L-xylopyranosyl)-2-nitroimidazole: a novel probe for the noninvasive assessment of tumor hypoxia. Radiat Res 1992;132:368-374.
7. Linder KE, Chan YW, Cyr JE, et al. Technetium-O(PnAO-(2-nitroimidazole)) [BMS181321], a new technetium-containing nitroimidazole complex for imaging hypoxia: synthesis characterization and xanthine oxidase-catalyzed reduction. J Med Chem 1994;37:9-17.
8. Linder KE, Chan YW, Cyr JE, et al. Synthesis, characterization and in vitro evaluation of nitroimidazole-BATO complexes: new technetium compounds designed for imaging hypoxic tissue. Bioconjug Chem 1993;4:326-333.
9. Brown JM, Workman P. Partition coefficient as a guide to the development of radiosensitizers which are less toxic than misonidazole. Radiat Res 1980;82:171-190.
10. Ng CK, Sinusas AJ, Zaret BL, Soufer R. Kinetic analysis of technetium-99m-labeled nitroimidazole (BMS-181321) as a tracer of myocardial hypoxia. Circulation 1995;92:1261-1268.
11. Nunn A, Linder K, Strauss HW. Nitroimidazoles and imaging hypoxia. Eur J Nucl Med 1995;22:265-280.
12. Rumsey WL, Patel B, Linder KE. Effect of graded hypoxia on retention of technetium-99m-nitroheterocycle in perfused rat heart. J Nucl Med 1995;36:632-636.
13. Hall EJ. Radiosensitizers and bioreductive drugs. In: Radiology for the radiologist, 4th ed. Philadelphia, PA: JB Lippincott; 1994:165-181.
14. Aboagye EO, Lewis AD, Johnson A, et al. The novel fluorinated 2-nitroimidazole hypoxia probe SR-4554: reductive metabolism and semiquantitative localization in human ovarian cancer multicellular spheroids as measured by electron energy loss spectroscopic analysis. Br J Cancer 1995;72:312-318.
15. Hearse DJ, Manning AS, Downey JM, Yellon DM. Xanthine oxidase: a critical mediator of myocardial injury during ischemia and reperfusion. Acta Physiol Scand 1986;548(suppl):65-78.
16. McGilvery RW, Goldstein GW. Turnover of nucleotides. In: Biochemistry, a functional approach, 3rd ed. Philadelphia, PA: WB Saunders; 1983:675-696.
17. Fujibayashi Y, Matsumoto K, Yonekura Y, et al. A new zinc-62/copper-62 generator as a copper-62 source for PET radiopharmaceuticals. J Nucl Med 1989;30:1838-1842.
18. 62Cu-PTSM. Nucl Med Biol 1992;19:39-44.
19. 62Cu-labeled HSA-DTS. J Nucl Med 1997:in press.
20. 4-methylthiosemicarbazone) (Cu-PTSM) by brain and tumor: a novel radiopharmaceutical for positron emission tomography imaging. Ann Nuklearmedizin 1995;9:1-5.
21. Minkel DT, Saryan LA, Petering DH. Structure-function correlations in the reaction of bis(thiosemicarbazonato) copper(II) complexes with Ehrlich ascites tumor cells. Cancer Res 1978;38:124-129.
22. 4-methylthiosemicarbazone) (Cu-PTSM), a metal complex with selective NADH-dependent reduction by Complex I in brain mitochondria; a potential radiopharmaceutical for mitochondria-functional imaging with positron emission tomography. Biol Pharm Bull 1995;18:1126-1129.
23. John EK, Green MA. Structure-activity relationships for metal-labeled blood flow tracers: comparison of keto aldehyde bis(thiosemicarbazonato) copper(II) derivatives. J Med Chem 1990;33:1764-1770.
24. Archer CM, Edwards B, Kelly JD, et al. Technetium-labeled agents for imaging tissue hypoxia in vivo. In: Nicolini M, Bandoli G, Mazzi U, eds. Technetium and rhenium in chemistry and nuclear medicine 4. Padova, Italy: SGE Ditoriali; 1995:535-549.
25. Gingas BA, Suprunchuk T, Bayley CH. The preparation of some thiosemicarbazones and their copper complexes. Part III. Can J Chem 1962;40:1053-1059.
26. Higuti T, Arakaki N, Niimi S, et al. Anisotropic inhibition of energy transduction in oxidative phosphorylation in rat liver mitochondria by tetraphenylarsonium. J Biol Chem 1980;255:7631-7636.
27. 1 preparation using a modified chloroform method. Anal Biochem 1984;140:581-588.
28. Ohmomo Y, Hirata M, Murakami K, et al. Synthesis of fluorine and iodine analogs of clorgyline and selective inhibition of monoamine oxidase A. Chem Pharm Bull 1991;39:1038-1040.
29. Pennington RJ. Biochemistry of dystrophic muscle. Mitochondrial succinate-tetrazolium reductase and adenosine triphosphatase. Biochem J 1961;80:649-654.
30. Ochoa S. Malic dehydrogenase from pig heart. Methods Enzymol 1955;1:735-739.
31. Sakai K, Shiraki Y. A device for recording left ventricular contraction and electrocardiogram in nonworking isolated perfused rat heart. Jpn J Pharmacol 1978;28:223-229.
32. Ohtani H, Callahan RJ, Khaw BA, et al. Comparison of technetium-99m-glucarate and thallium-201 for the identification of acute myocardial infarction in rats. J Nucl Med 1992;33:1988-1993.
33. McGilvery RW, Goldstein GW. Oxidations and phosphorylations. In: Biochemistry, a functional approach, 3rd ed. Philadelphia, PA: WB Saunders; 1983:390-420.
34. Shelton ME, Dence CS, Hwang DR, et al. Myocardial kinetics of fluorine-18 misonidazole: a marker of hypoxic myocardium. J Nucl Med 1989;30:351-358.
35. Hesslewood IP, Cramp WA, McBrien DCH, et al. Copper as a hypoxic cell sensitizer of mammalian cells. Br J Cancer 1978;37(suppl):95-97.
36. Barlow CH, Harken AH, Chance B. Evaluation of cardiac ischemia by NADH fluorescence photography. Ann Surg 1977;186:737-740.
37. 14C-iodoantipyrine. Nucl Med Biol 1994;21:613-617.