A Generator-produced gallium-68 radiopharmaceutical for PET imaging of myocardial perfusion

PLoS ONE

Volumn 9, Issue 10, 2014, Pages

  Sharma, Vijay ^a,b   Sivapackiam, Jothilingam ^a   Harpstrite, Scott E ^a   Prior, Julie L ^a   Gu, Hannah ^a   Rath, Nigam P ^c   Piwnica Worms, David ^a,b  

^a WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c UNIVERSITY OF MISSOURI ST LOUIS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GALLIUM 68; METALLOPROBE GA 67; METALLOPROBE GA 68; TRACER; UNCLASSIFIED DRUG; ETHYLENEDIAMINE DERIVATIVE; GALLIUM; ORGANOMETALLIC COMPOUND; RADIOPHARMACEUTICAL AGENT;

ANIMAL CELL; ARTICLE; BIOASSAY; CARDIAC IMAGING; CELL SCREENING; CONTROLLED STUDY; DRUG CLEARANCE; DRUG DISTRIBUTION; GENERATOR; HUMAN; HUMAN CELL; MALE; MYOCARDIAL PERFUSION IMAGING; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; RAT; SYNTHESIS; X RAY CRYSTALLOGRAPHY; ANIMAL; CELL LINE; CHEMISTRY; MCF 7 CELL LINE; MOUSE; PROCEDURES; RADIOACTIVITY; SPRAGUE DAWLEY RAT;

ANIMALS; CELL LINE; ETHYLENEDIAMINES; GALLIUM RADIOISOTOPES; HUMANS; MALE; MCF-7 CELLS; MICE; MYOCARDIAL PERFUSION IMAGING; ORGANOMETALLIC COMPOUNDS; POSITRON-EMISSION TOMOGRAPHY; RADIONUCLIDE GENERATORS; RADIOPHARMACEUTICALS; RATS; RATS, SPRAGUE-DAWLEY;

EID: 84908577290     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0109361     Document Type: Article

References (47)

1. Bonow R (2009) Clinical practice. Should coronary calcium screening be used in cardiovascular prevention strategies? N Engl J Med 361: 990-997.
2. Beller G (2010) Recent advances and future trends in multimodality cardiac imaging. Heart Lung Circ 19: 193-209.
3. Slart RH, Bax JJ, van Veldhuisen DJ, van der Wall EE, Dierckx RA, et al. (2006) Imaging techniques in nuclear cardiology for the assessment of myocardial viability. Int J Cardiovasc Imaging 22: 63-80.
4. SNM (2010) Available: http://www.snm.org/index.cfm?PageID=9760.
5. Atcher R (2011) US still vulnerable to isotope shortage. RSNA News 21: 9-10.
6. EANM (2011) Available: http://eanm11.eanm.org/abstracts/abstract-detail.php?abstractId=OP145&referer=session-detail.php&navId=65.
7. Gould P (2009) Medical isotope shortage reaches crisis level. Nature 460: 312-313.
8. Benard F, Buckley KR, Ruth TJ, Zeisler SK, Klug J, et al. (2014) Implementation of Multi-Curie Production of 99mTc by Conventional Medical Cyclotrons. J Nucl Med 55: 1017-1022.
9. Rowland D, Cherry S (2008) Small-animal preclinical nuclear medicine instrumentation and methodology. Semin Nucl Med 38: 209-222.
10. Radeke H, Hanson K, Yalamanchili P, Hayes M, Zhang ZQ, et al. (2007) Synthesis and biological evaluation of the mitochondrial complex 1 inhibitor 2- [4-(4-fluorobutyl)benzylsulfanyl]-3-methylchromene-4-one as a potential cardiac positron emission tomography tracer. J Med Chem 50: 4304-4315.
11. Purohit A, Radeke H, Azure M, Hanson K, Benetti R, et al. (2008) Synthesis and biological evaluation of pyridazinone analogues as potential cardiac positron emission tomography tracers. J Med Chem 51: 2954-2970.
12. Pagou M, Zerizer I, Al-Nahhas A (2009) Can gallium-68 compounds partly replace (18)F-FDG in PET molecular imaging? Hell J Nucl Med 12: 102-105.
13. Fani M, Andre JP, Maecke HR (2008) 68Ga-PET: a powerful generator-based alternative to cyclotron-based PET radiopharmaceuticals. Contrast Media Mol Imaging 3: 67-77.
14. Tsang B, Mathias C, Green M (1993) A gallium-68 radiopharmaceutical that is retained in myocardium: 68Ga-[(4,6-MeO)2sal)2BAPEN] + . J Nucl Med 34: 1127-1131.
15. Tsang B, Mathias C, Fanwick P, Green M (1994) Structure-distribution relationship for metal-labelled myocardial imaging agents: Comparison of a series of cationic gallium(III) complexes with hexadentate bis(salicylaldimine) ligands. J Med Chem 37: 4400-4406.
16. Sharma V, Wey SP, Bass L, Crankshaw CL, Green MA, et al. (1996) Monocationic N4O2 Schiff-Base phenolate complexes of gallium(III): novel PET imaging agents of the human multidrug resistance (MDR1) P-glycoprotein. J Nucl Med 37: 51P.
17. Wong E, Caravan P, Liu S, Rettig S, Orvig C (1996) Selectivity of potentially hexadentate amine phenols for Ga +3 and In +3 in aqueous solution. Inorg Chem 35: 715-724.
18. Cutler CS, Giron MC, Reichert DE, Snyder AZ, Herrero P, et al. (1999) Evaluation of gallium-68 tris(2-mercaptobenzyl)amine: a complex with brain and myocardial uptake. Nucl Med Biol 26: 305-316.
19. Sharma V, Piwnica-Worms D (1999) Metal complexes for therapy and diagnosis of drug resistance. Chem Rev 99: 2545-2560.
20. Sharma V, Beatty A, Wey S-P, Dahlheimer J, Pica C, et al. (2000) Novel gallium(III) complexes transported by MDR1 P-glycoprotein: potential PET imaging agents for probing P-glycoprotein-mediated transport activity in vivo. Chem Biol 7: 335-343.
21. Fellner M, Dillenburg W, Buchholz HG, Bausbacher N, Schreckenberger M, et al. (2011) Assessing p-glycoprotein (Pgp) activity in vivo utilizing 68Ga-Schiff base complexes. Mol Imaging Biol 13: 985-994.
22. Sivapackiam J, Harpstrite SE, Prior JL, Gu H, Rath NP, et al. (2010) Synthesis, molecular structure, and validation of metalloprobes for assessment of MDR1 Pglycoprotein- mediated functional transport. Dalton Trans 39: 5842-5850.
23. Plossl K, Chandra R, Qu W, Lieberman BP, Kung MP, et al. (2008) A novel gallium bisaminothiolate complex as a myocardial perfusion imaging agent. Nucl Med Biol 35: 83-90.
24. Sharma V, Prior J, Belinsky M, Kruh G, Piwnica-Worms D (2005) Characterization of a gallium-67/gallium-68 radiopharmaceutical for SPECT and PET imaging of MDR1 P-glycoprotein transport activity in vivo: Validation in multidrug resistant tumors and at the blood-brain barrier. J Nucl Med 46: 354-364.
25. Blesssing R (1995) ACTA Cryst A51: 33-38.
26. Luker G, Rao V, Crankshaw C, Dahlheimer J, Piwnica-Worms D (1997) Characterization of phosphine complexes of technetium (III) as transport substrates of the multidrug resistance (MDR1) P-glycoprotein and functional markers of P-glycoprotein at the blood-brain barrier. Biochemistry 36: 14218-14227.
27. Luker GD, Flagg TP, Sha Q, Luker KE, Pica CM, et al. (2001) MDR1 Pglycoprotein reduces influx of substrates without affecting membrane potential. J Biol Chem 276: 49053-49060.
28. Luker GD, Fracasso PM, Dobkin J, Piwnica-Worms D (1997) Modulation of the multidrug resistance P-glycoprotein: detection with Tc-99m-Sestamibi in vivo. J Nucl Med 38: 369-372.
29. Piwnica-Worms D, Kronauge J, Chiu M (1990) Uptake and retention of hexakis (2-methoxy isobutyl isonitrile) technetium(I) in cultured chick myocardial cells: mitochondrial and plasma membrane potential dependence. Circulation 82: 1826-1838.
30. Sharma V, Crankshaw C, Piwnica-Worms D (1996) Effects of multidrug resistance (MDR1) P-glycoprotein expression levels and coordination metal on the cytotoxic potency of multidentate (N4O2) ethylenediamine-bis[propyl(Rbenzylimino)] metal(III) cations. J Med Chem 39: 3483-3490.
31. Hsiao YM, Mathias CJ, Wey SP, Fanwick PE, Green MA (2009) Synthesis and biodistribution of lipophilic and monocationic gallium radiopharmaceuticals derived from N,N'-bis(3-aminopropyl)-N,N'-dimethylethylenediamine: potential agents for PET myocardial imaging with 68Ga. Nucl Med Biol 36: 39-45.
32. Harpstrite SE, Prior JL, Rath NP, Sharma V (2007) Metalloprobes: synthesis, characterization, and potency of a novel gallium(III) complex in human epidermal carcinoma cells. J Inorg Biochem 101: 1347-1353.
33. Piwnica-Worms D, Chiu M, Budding M, Kronauge J, Kramer R, et al. (1993) Functional imaging of multidrug-resistant P-glycoprotein with an organotechnetium complex. Cancer Res 53: 977-984.
34. Hendrikse N, Franssen E, van der Graaf W, Meijer C, Piers D, et al. (1998) 99mTc-sestamibi is a substrate for P-glycoprotein and the multidrug resistanceassociated protein. Br J Cancer 77: 353-358.
35. Piwnica-Worms D, Kronauge J, Holman B, Lister-James J, Davison A, et al. (1988) Hexakis(carbomethoxyisopropylisonitrile) technetium(I), a new myocardial perfusion imaging agent: binding characteristics in cultured chick heart cells. J Nucl Med 29: 55-61.
36. Herman LW, Sharma V, Kronauge JF, Barbarics E, Herman LA, et al. (1995) Novel hexakis(areneisonitrile)technetium(I) complexes as radioligands targeted to the multidrug resistance P-glycoprotein. J Med Chem 38: 2955-2963.
37. Sharma V (2004) Radiopharmaceuticals for assessment of multidrug resistance P-glycoprotein-mediated drug transport activity. Bioconjugate Chem 15: 1464-1474.
38. Chen W, Luker K, Dahlheimer J, Pica C, Luker G, et al. (2000) Effects of MDR1 and MDR3 P-glycoproteins, MRP1 and BCRP/MXR/ABCP on transport of Tc-99m-Tetrofosmin. Biochem Pharmacol 60: 413-426.
39. Schinkel AH, Mol CAAM, Wagenaar E, van Deemter L, Smit JJM, et al. (1995) Multidrug resistance and the role of P-glycoprotein knockout mice. Eur J Cancer 31A: 1295-1298.
40. Schinkel A, Smit J, van Tellingen O, Beijnen JH, Wagenaar E, et al. (1994) Disruption of the mouse mdr1a P-glycoprotein gene leads to a deficiency in the blood-brain barrier and to increased sensitivity to drugs. Cell 77: 491-502.
41. Damiani D, Michieli M, Ermacora A, Candoni A, Raspadori D, et al. (1998) Pglycoprotein (PGP), and not lung resistance-related protein (LRP), is a negative prognostic factor in secondary leukemias. Haematologica 83: 290-297.
42. Tarkia M, Saraste A, Saanijoki T, Oikonen V, Vähäsilta T, et al. (2012) Evaluation of 68Ga-labeled tracers for PET imaging of myocardial perfusion in pigs. Nucl Med Biol 39: 715-723.
43. Sivapackiam J, Gammon ST, Harpstrite SE, Sharma V (2010) Targeted chemotherapy in drug-resistant tumors, noninvasive imaging of p-glycoproteinmediated functional transport in cancer, and emerging role of pgp in neurodegenerative diseases. Methods Mol Biol 596: 141-181.
44. Jin Z, Qiu L, Li Y, Song H, Fang J (2010) Insight into steric and electronic effects of ancillary ligands: synthesis and structure-reactivity relationships of welldefined, air- and mositure stable (NHC)Pd(sal)Cl complexes (sal = Salicylaldimine). Organometallics 29: 6578-6586.
45. Del Vecchio S, Ciarmiello A, Pace L, Potena M, Carriero M, et al. (1997) Fractional retention of technetium-99m-sestamibi as an index of P-glycoprotein expression in untreated breast cancer patients. J Nucl Med 38: 1348-1351.
46. Cirrito JR, Deane R, Fagan AM, Spinner ML, Parsadanian M, et al. (2005) Pglycoprotein deficiency at the blood-brain barrier increases amyloid-beta deposition in an Alzheimer's disease mouse model. J Clin Invest 115: 3285-3290.
47. Madar I, Ravert H, Nelkin B, Abro M, Pomper M, et al. (2007) Characterization of membrane potential-dependent uptake of the novel PET tracer 18F-fluorobenzyl triphenylphosphonium cation. Eur J Nucl Med Mol Imaging 34: 2057-2065.