Synthesis and in vivo evaluation of 18F-fluoroethyl GF120918 and XR9576 as positron emission tomography probes for assessing the function of drug efflux transporters

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 2, 2011, Pages 861-870

  Kawamura, Kazunori ^a   Yamasaki, Tomoteru ^a   Konno, Fujiko ^a   Yui, Joji ^a   Hatori, Akiko ^a   Yanamoto, Kazuhiko ^a   Wakizaka, Hidekatsu ^a   Ogawa, Masanao ^a,b   Yoshida, Yuichiro ^a,b   Nengaki, Nobuki ^a,b   Fukumura, Toshimitsu ^a   Zhang, Ming Rong ^a  

^a NATIONAL INSTITUTE OF RADIOLOGICAL SCIENCES   (Japan)

^b 141 0032   (Japan)

Author keywords

Breast cancer resistance protein (BCRP); Drug efflux transporter; Fluorine 18; GF120918 (elacridar); P Glycoprotein (P gp); Positron emission tomography (PET); XR9576 (tariquidar)

Indexed keywords

BREAST CANCER RESISTANCE PROTEIN; BROMIDE; ELACRIDAR; FLUORODEOXYGLUCOSE F 18; GLYCOPROTEIN P; GLYCOPROTEIN P INHIBITOR; N (4 (2 (1,2,3,4 TETRAHYDRO 6,7 DIMETHOXY 2 ISOQUINOLINYL)ETHYL)PHENYL) 9,10 DIHYDRO 5 FLUOROETHOXY 9 OXO 4 ACRIDINE CARBOXAMIDE FLUORODEOXYGLUCOSE F18; QUINOLINE 3 CARBOXYLIC ACID [2 (4 {2 [7 (2 FLUOROETHOXY) 6 METHOXY 3,4 DIHYDRO 1H ISOQUINOLIN 2 YL]ETHYL}PHENYLCARBAMOYL) 4,5 DIMETHOXYPHENYL]AMIDE; TARIQUIDAR; UNCLASSIFIED DRUG;

ALKYLATION; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BRAIN METABOLISM; CONTROLLED STUDY; DRUG STRUCTURE; GENE OVEREXPRESSION; IN VITRO STUDY; IN VIVO STUDY; MOUSE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; RADIOACTIVITY; SYNTHESIS; WILD TYPE;

ACRIDINES; ANIMALS; ATP-BINDING CASSETTE TRANSPORTERS; CELL LINE, TUMOR; FLUORINE RADIOISOTOPES; HUMANS; MICE; MOLECULAR PROBES; P-GLYCOPROTEIN; POSITRON-EMISSION TOMOGRAPHY; QUINOLINES; RADIOPHARMACEUTICALS; TETRAHYDROISOQUINOLINES; TISSUE DISTRIBUTION;

MUS;

EID: 78651481940     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.12.004     Document Type: Article

References (35)

1. A. Ayrton, and P. Morgan Xenobiotica 31 2001 469
2. P. Borst, and R.O. Elferink Annu. Rev. Biochem. 71 2002 537
3. A.H. Schinkel, and J.W. Jonker Adv. Drug Deliv. Rev. 55 2003 3
4. W. Löscher, and H. Potschka Prog. Neurobiol. 76 2005 22
5. M.M. Gottesman, T. Fojo, and S.E. Bates Nat. Rev. Cancer 2 2002 48
6. F. Hyafil, C. Vergely, P. Du Vignaud, and T. Grand-Perret Cancer Res. 53 1993 4595
7. M. Roe, A. Folkes, P. Ashworth, J. Brumwell, L. Chima, S. Hunjan, I. Pretswell, W. Dangerfield, H. Ryder, and P. Charlton Bioorg. Med. Chem. Lett. 9 1999 595
8. M. de Bruin, K. Miyake, T. Litman, R. Robey, and S.E. Bates Cancer Lett. 146 1999 117
9. J.D. Allen, R.F. Brinkhuis, J. Wijnholds, and A.H. Schinkel Cancer Res. 59 1999 4237
10. C. Martin, G. Berridge, P. Mistry, C. Higgins, P. Charlton, and R. Callaghan Br. J. Pharmacol. 128 1999 403
11. A. Pick, H. Müller, and M. Wiese Bioorg. Med. Chem. 16 2008 8224
12. B. Dörner, C. Kuntner, J.P. Bankstahl, M. Bankstahl, J. Stanek, T. Wanek, G. Stundner, S. Mairinger, W. Löscher, M. Müller, O. Langer, and T. Erker J. Med. Chem. 52 2009 6073
13. K. Kawamura, T. Yamasaki, F. Konno, J. Yui, A. Hatori, K. Yanamoto, H. Wakizaka, M. Takei, Y. Kimura, T. Fukumura, and M.-R. Zhang Mol. Imaging Biol. 2010 10.1007/s11307-010-0313-1
14. K. Kawamura, F. Konno, J. Yui, T. Yamasaki, A. Hatori, K. Yanamoto, H. Wakizaka, M. Takei, N. Nengaki, T. Fukumura, and M.-R. Zhang Ann. Nucl. Med. 24 2010 403
15. F. Bauer, C. Kuntner, J.P. Bankstahl, T. Wanek, M. Bankstahl, J. Stanek, S. Mairinger, B. Dörner, W. Löscher, M. Müller, T. Erker, and O. Langer Bioorg. Med. Chem. 18 2010 5489
16. T. Fukumura, H. Suzuki, K. Mukai, M.-R. Zhang, Y. Yoshida, K. Nemoto, and K. Suzuki J. Labelled Compd. Radiopharm. 50 2007 S202
17. M.-R. Zhang, A. Tsuchiyama, T. Haradahira, Y. Yoshida, K. Furutsuka, and K. Suzuki Appl. Radiat. Isot. 57 2002 335
18. W.G. Harker, and B.I. Sikic Cancer Res. 45 1985 4091
19. J.S. Koo, W.C. Choi, Y.H. Rhee, H.J. Lee, E.O. Lee, K.S. Ahn, H.S. Bae, K.S. Ahn, J.M. Kang, S.U. Choi, M.O. Kim, J. Lu, and S.H. Kim Life Sci. 83 2008 700
20. G. Wu, J. Liu, L. Bi, M. Zhao, C. Wang, B.-F. Michle, J. Ju, and F. Peng Tetrahedron 63 2007 5510
21. N.A. de Vries, J. Zhao, E. Kroon, T. Buckle, J.H. Beijnen, and O. van Tellingen Clin. Cancer Res. 13 2007 6440
22. P. Kannan, K.R. Brimacombe, S.S. Zoghbi, J.S. Liow, C. Morse, A.K. Taku, V.W. Pike, C. Halldin, R.B. Innis, M.M. Gottesman, and M.D. Hall Drug Metab. Dispos. 38 2010 917
23. G. Luurtsema, R.C. Schuit, R.P. Klok, J. Verbeek, J.E. Leysen, A.A. Lammertsma, and A.D. Windhorst Nucl. Med. Biol. 36 2009 643
24. S. Cisternino, C. Mercier, F. Bourasset, F. Roux, and J.M. Scherrmann Cancer Res. 64 2004 3296
25. L. Zhou, K. Schmidt, F.R. Nelson, V. Zelesky, M.D. Troutman, and B. Feng Drug Metab. Dispos. 37 2009 946
26. V.W.P.E.T. Pike Trends Pharmacol. Sci. 30 2009 431
27. N. Dodic, B. Dumaitre, A. Daugan, and P. Pianetti J. Med. Chem. 38 1995 2418
28. Gilday, J. P.; Moody, D. PCT. Int. Appl. WO/2004/024703 A1, 2004.
29. T. Yamasaki, K. Kumata, K. Yanamoto, A. Hatori, M. Takei, Y. Nakamura, S. Koike, K. Ando, K. Suzuki, and M.-R. Zhang Nucl. Med. Biol. 36 2009 801
30. A. Angelini, M. Iezzi, C. Di Febbo, C. Di Ilio, F. Cuccurullo, and E. Porreca Oncol. Rep. 20 2008 731
31. A.H. Schinkel, U. Mayer, E. Wagenaar, C.A. Mol, L. van Deemter, J.J. Smit, M.A. van der Valk, A.C. Voordouw, H. Spits, O. van Tellingen, J.M. Zijlmans, W.E. Fibbe, and P. Borst Proc. Natl. Acad. Sci. U.S.A. 94 1997 4028
32. J.W. Jonker, M. Buitelaar, E. Wagenaar, M.A. Van Der Valk, G.L. Scheffer, R.J. Scheper, T. Plosch, F. Kuipers, R.P. Elferink, H. Rosing, J.H. Beijnen, and A.H. Schinkel Proc. Natl. Acad. Sci. U.S.A. 99 2002 15649
33. J.W. Jonker, J. Freeman, E. Bolscher, S. Musters, A. Alvi, and I. Titley Stem Cells 23 2005 1059
34. K. Kawamura, T. Yamasaki, J. Yui, A. Hatori, F. Konno, K. Kumata, T. Irie, T. Fukumura, K. Suzuki, I. Kanno, and M.-R. Zhang Nucl. Med. Biol. 36 2009 239
35. M. Takei, T. Kida, and K. Suzuki Appl. Radiat. Isot. 55 2001 229