Synthesis of carbon-11-labeled tariquidar derivatives as new PET agents for imaging of breast cancer resistance protein (ABCG2)

Applied Radiation and Isotopes

Volumn 68, Issue 6, 2010, Pages 1098-1103

  Wang, Min ^a   Zheng, David X ^a   Luo, Michael B ^a   Gao, Mingzhang ^a   Miller, Kathy D ^a   Hutchins, Gary D ^a   Zheng, Qi Huang ^a  

^a INDIANA UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Breast cancer resistance protein; Imaging; Positron emission tomography; Radiotracers; Tariquidar derivatives

Indexed keywords

ACID PRECURSORS; BASIC CONDITIONS; BREAST CANCER RESISTANCE PROTEIN; BREAST CANCER RESISTANCE PROTEINS; CARBON-11; IMAGING; RADIOCHEMICAL PURITY; RADIOCHEMICAL YIELD; SOLID PHASE EXTRACTION METHOD; SPECIFIC ACTIVITY; SYNTHESIS TIME;

EXTRACTION; POSITRONS; PROTEINS; RADIOACTIVE TRACERS; SYNTHESIS (CHEMICAL);

POSITRON EMISSION TOMOGRAPHY;

BREAST CANCER RESISTANCE PROTEIN; CARBON 11; CARBON METHYL 4 [[4 [2 (6,7 DIMETHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE 2 YL)ETHYL]PHENYL]AMINOCARBONYL] 2 (QUINOLINE 2 CARBONYLAMINO)BENZOATE C 11; CARBON METHYL 4 [[4 [2 (6,7 DIMETHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE 2 YL)ETHYL]PHENYL]AMINOCARBONYL] 2 (QUINOLINE 3 CARBONYLAMINO)BENZOATE C 11; CARBON METHYL 4 [[4 [2 (6,7 DIMETHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE 2 YL)ETHYL]PHENYL]AMINOCARBONYL] 2 (QUINOLINE 6 CARBONYLAMINO)BENZOATE C 11; CARBON METHYL 4 [[4 [2 (6,7 DIMETHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE 2 YL)ETHYL]PHENYL]AMINOCARBONYL] 2 (QUINOXALINE 2 CARBONYLAMINO)BENZOATE C 11; TARIQUIDAR; TRACER; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CROSS COUPLING REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ELUTION; HYDROGENATION; HYDROLYSIS; ISOTOPE LABELING; METHYLATION; MOLECULAR IMAGING; POSITRON EMISSION TOMOGRAPHY; PRIORITY JOURNAL; PURIFICATION; RADIOACTIVITY; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SOLID PHASE EXTRACTION;

ATP-BINDING CASSETTE TRANSPORTERS; BREAST NEOPLASMS; CARBON RADIOISOTOPES; FEMALE; HUMANS; ISOTOPE LABELING; NEOPLASM PROTEINS; POSITRON-EMISSION TOMOGRAPHY; QUINOLINES;

EID: 77649270443     PISSN: 09698043     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.apradiso.2010.02.008     Document Type: Article

References (18)

1. Barry M., and Kell M.R. Enhancing the adjuvant treatment of hormone receptor positive breast cancer. Breast J. 15 (2009) 194-198
2. Czernin J. FDG-PET in breast cancer: a different view of its clinical usefulness. Mol. Imaging Biol. 4 (2002) 35-45
3. Elslager E., Clarke J., Werbel L.M., and Worth D.F. Folate antagonists. 3. 2,4-diamino-6-(heterocyclic)quinazolines, a novel class of antimetabolites with potent antimalarial and antibacterial activity. J. Med. Chem. 15 (1972) 827-836
4. Escalona, S., Blasco, J.A., Reza, M.M., Andradas, E., Gomez, N., 2009. A systematic review of FDG-PET in breast cancer. Med. Oncol. [Epub ahead of print].
5. Fowler J.S., Volkow N.D., Wang G.J., Ding Y.S., and Dewey S.L. PET and drug research and development. J. Nucl. Med. 40 (1999) 1154-1163
6. Hubensack, M., 2005. Approaches to overcome the blood barrier in the chemotherapy of primary and secondary brain tumors: modulation of p-glycoprotein 170 and targeting of the transferring receptor. Doctoral Thesis. University of Regensburg, Germany.
7. 11C]methyl triflate. Int. J. Rad. Appl. Instrum. A 43 (1992) 1383-1385
8. Kühnle M., Egger M., Müller C., Mahringer A., Bernhardt G., Fricker G., König B., and Buschauer A. Potent and selective inhibitors of breast cancer resistance protein (ABCG2) derived from the p-glycoprotein (ABCB1) modulator tariquidar. J. Med. Chem. 52 (2009) 1190-1197
9. 3-positive breast cancer. Bioconjug. Chem. 18 (2007) 438-446
10. 11C]methyl triflate. Nucl. Med. Biol. 26 (1999) 467-471
11. Mock B.H., Glick-Wilson B.E., Zheng Q.-H., and DeGrado T.R. Automated measurement of specific activity of radiolabeled ligands during synthesis. J. Label. Compd. Radiopharm. 48 (2005) S224
12. 11C-radio-synthesis system. J. Label. Compd. Radiopharm. 48 (2005) S225
13. Okano K., Tokuyama H., and Fukuyama T. Total synthesis of (+)-yatakemycin. J. Am. Chem. Soc. 128 (2006) 7136-7137
14. Pons F., Duch J., and Fuster D. Breast cancer therapy: the role of PET-CT in decision making. Q. J. Nucl. Med. Mol. Imaging 53 (2009) 210-228
15. Wang M., Mickens J., Gao M., Miller K.D., Sledge G.W., Hutchins G.D., and Zheng Q.-H. Design and synthesis of carbon-11-labeled dual aromatase-steroid sulfatase inhibitors as new potential PET agents for imaging of aromatase and steroid sulfatase expression in breast cancer. Steroids 74 (2009) 896-905
16. 11C]β-CIT labeled at nitrogen or oxygen positions. Nucl. Med. Biol. 23 (1996) 981-986
17. Zheng Q.-H., and Mock B.H. Purification of carbon-11 PET radiotracers from unlabeled precursors by preparative HPLC and SPE. Biomed. Chromatogr. 19 (2005) 671-676
18. 18F]hemicholinium-3. Bioorg. Med. Chem. Lett. 17 (2007) 2220-2224