Mitochondrial avid radioprobes. Preparation and evaluation of 7′(Z)-[125I]iodorotenone and 7′(Z)-[125I]iodorotenol

Nuclear Medicine and Biology

Volumn 34, Issue 1, 2007, Pages 109-116

  VanBrocklin, Henry F ^a   Hanrahan, Stephen M ^a   Enas, Joel D ^a   Nandanan, Erathodiyil ^a   O'Neil, James P ^a  

^a LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

Author keywords

Complex I; Iodine 125; Mitochondria; Rotenone

Indexed keywords

7' IODOROTENOL I 125; 7' IODOROTENONE I 125; METHOXY ISOBUTYL ISONITRILE TECHNETIUM TC 99M; TETROFOSMIN TC 99M; TRACER; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BLOOD; CONTROLLED STUDY; DRUG DISTRIBUTION; ELECTRON TRANSPORT; HEART; ISOTOPE LABELING; LIVER; LUNG; MALE; MITOCHONDRION; NONHUMAN; PERFUSION; RAT; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY; STATISTICAL SIGNIFICANCE;

ANIMALS; DRUG EVALUATION, PRECLINICAL; IODINE RADIOISOTOPES; MALE; METABOLIC CLEARANCE RATE; MITOCHONDRIA, HEART; ORGAN SPECIFICITY; RADIOPHARMACEUTICALS; RATS; RATS, SPRAGUE-DAWLEY; ROTENONE; TISSUE DISTRIBUTION;

EID: 33845926898     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2006.10.005     Document Type: Article

References (33)

1. Albers D.S., and Beal M.F. Mitochondrial dysfunction and oxidative stress in aging and neurodegenerative disease. J Neural Transm Suppl 59 (2000) 133-154
2. Wallace D.C. A mitochondrial paradigm of metabolic and degenerative diseases, aging, and cancer: a dawn for evolutionary medicine. Annu Rev Genet 39 (2005) 359-407
3. Beal M.F. Mitochondrial dysfunction and oxidative damage in Alzheimer's and Parkinson's diseases and coenzyme Q10 as a potential treatment. J Bioenerg Biomembr 36 (2004) 381-386
4. Sherer T.B., Betarbet R., and Greenamyre J.T. Environment, mitochondria, and Parkinson's disease. Neuroscientist 8 (2002) 192-197
5. Haley T.J. A review of the literature of rotenone, 1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-1-benzopyrano[3,5-b]furo[2,3-h][1]benzopyran-6(6h)-one. J Environ Pathol Toxicol 1 (1978) 315-337
6. Fukami H., and Nakajima M. In: Jacobson M., and Crosby D.G. (Eds). Naturally occurring insecticides (1971), Marcel Dekker Inc, New York 71-75
7. Rach J.J., and Gingerich W.H. Distribution and accumulation of rotenone in tissues of warmwater fishes. Trans Am Fish Soc 115 (1986) 214-219
8. Crombie L., and Whiting D.A. Review article number 135. Biosynthesis in the rotenoid group of natural products: applications of isotope methodology. Phytochemistry 49 (1998) 1479-1507
9. Greenamyre J.T., Higgins D.S., and Eller R.V. Quantitative autoradiography of dihydrorotenone binding to complex I of the electron transport chain. J Neurochem 59 (1992) 746-749
10. 3H labeled dihydrorotenone. J Labelled Comp Radiopharm 39 (1997) 215-221
11. Talpade D.J., Greene J.G., Higgins Jr. D.S., and Greenamyre J.T. In vivo labeling of mitochondrial complex I (NADH:ubiquinone oxidoreductase) in rat brain using [(3)H]dihydrorotenone. J Neurochem 75 (2000) 2611-2621
12. 3H]Dihydrorotenone binding to NADH: ubiquinone reductase (complex I) of the electron transport chain: an autoradiographic study. J Neurosci 16 (1996) 3807-3816
13. 3H]dihydrorotenone binding to complex I in intact human platelets. Anal Biochem 230 (1995) 16-19
14. 11C]methoxy)-6′,7′-dihydrorotenol, a second generation rotenoid for marking mitochondrial complex I activity. Nucl Med Biol 22 (1995) 491-496
15. 11C]methoxy)rotenone, a marker of mitochondrial complex I activity. Nucl Med Biol 22 (1995) 65-69
16. 11C]DHROL) for in vivo measurement of mitochondrial complex I. J Labelled Comp Radiopharm 47 (1999) 641-652
17. Kilbourn M.R., Charalambous A., Frey K.A., Sherman P., Higgins Jr. D.S., and Greenamyre J.T. Intrastriatal neurotoxin injections reduce in vitro and in vivo binding of radiolabeled rotenoids to mitochondrial complex I. J Cereb Blood Flow Metab 17 (1997) 265-272
18. Martarello L., Greenamyre J.T., and Goodman M.M. Synthesis and evaluation of a new fluorine-18 labeled rotenoid as a potential pet probe of mitochondrial complex I activity. J Label Compound Radiopharm 42 (1999) 1039-1051
19. VanBrocklin H., Enas J., Hanrahan S., and O'Neil J. Fluorine-18 labeled dihydrorotenone analogs: preparation and evaluation of PET mitochondrial probes. J Lab Comp Radiopharm 37 (1995) 217-219
20. Kenski D.M., VanBrocklin H.F., and O'Neil J.P. Fluorine-18 labeled rotenone analogs: preparation and evaluation of PET mitochondrial probes. J Labelled Compd Radiopharm 42 Suppl 1 (1999) S333-S335
21. 99mTc]sestamibi. J Nucl Med 42 (2001) 272-281
22. 18F-fluorodihydrorotenone as a deposited myocardial flow tracer: comparison to 201Tl. J Nucl Med 45 (2004) 1950-1959
23. Crane P., Laliberte R., Heminway S., Thoolen M., and Orlandi C. Effect of mitochondrial viability and metabolism on technetium-99m-sestamibi myocardial retention. Eur J Nucl Med 20 (1993) 20-25
24. Carvalho P., Chiu M., Kronauge J., Kawamura M., Jones A., Holman B., et al. Subcellular distribution and analysis of technetium-99m-MIBI in isolated perfused rat hearts. J Nucl Med 33 (1992) 1516-1522
25. Schaper J., Meiser E., and Stammler G. Ultrastructural morphometric analysis of myocardium from dogs, rats, hamsters, mice, and from human hearts. Circ Res 56 (1985) 377-391
26. Buchi G., Crombie L., Godin P., Kaltenbronn J., Siddalingaiah K., and Whiting D. The absolute configuration of rotenone. J Chem Soc (1961) 2843-2860
27. Begley M., Crombie L., Hadi H.A., and Josephs J. Synthesis of novel labile rotenoids with unnatural trans-B/C Ring Systems. J Chem Soc Perkin Trans (1989) 204-205
28. Crombie L., and Godin P. The structure and stereochemistry of the rotenolones, rotenolols, isorotenolones, and isorotenolols. J Chem Soc (1961) 2861-2875
29. Boschi A., Uccelli L., Bolzati C., Duatti A., Sabba N., Moretti E., et al. Synthesis and biologic evaluation of monocationic asymmetric 99mTc-nitride heterocomplexes showing high heart uptake and improved imaging properties. J Nucl Med 44 (2003) 806-814
30. Younes A., Songadele J.A., Maublant J., Platts E., Pickett R., and Veyre A. Mechanism of uptake of technetium-tetrofosmin: II. Uptake into isolated adult rat heart mitochondria. J Nucl Cardiol 2 (1995) 327-333
31. Platts E.A., North T.L., Pickett R.D., and Kelly J.D. Mechanism of uptake of technetium-tetrofosmin: I. Uptake into isolated adult rat ventricular myocytes and subcellular localization. J Nucl Cardiol 2 (1995) 317-326
32. Chiu M., Kronauge J., and Piwnica-Worms D. Effect of mitochondrial and plasma membrane potentials on accumulation of hexakis (2-methoxyisobutylisonitrile) technetium(I) in cultured mouse fibroblasts. J Nucl Med 31 (1990) 1646-1653
33. 99mTc-tetrofosmin in rats. J Nucl Med 45 (2004) 2095-2101