Synthesis and Radiosynthesis of a Novel PET Fluorobenzyl Piperazine for Melanoma Tumour Imaging; [18F]MEL054
Stephen R. Taylor A C , Maxine P. Roberts A F , Naomi A. Wyatt A , Tien Q. Pham A , Daniela Stark A D , Thomas Bourdier A E , Peter Roselt B , Andrew Katsifis A E and Ivan Greguric A
+ Author Affiliations
- Author Affiliations
A LifeSciences Division, Australian Nuclear Science and Technology Organisation, Locked Bag 2001, Kirrawee DC, NSW 2232, Australia.
B Centre for Molecular Imaging, The Peter MacCallum Cancer Centre, 12 St Andrew’s Place, East Melbourne, Vic. 3002, Australia.
C Current address: Department of Nuclear Medicine, Level 3, Ned Hanlon Building, Royal Brisbane and Women’s Hospital, Metro North Health Service District, Herston, Qld 4029, Australia.
D Current address: Cyclopet Pty Ltd Macquarie University Hospital, 3 Technology Place, Macquarie University, Lower Northern Sydney, NSW 2341, Australia.
E Current address: Department of PET & Nuclear Medicine, Building 63, Level A7, Royal Prince Alfred Hospital, Missenden Road, Camperdown, NSW 2050, Australia.
F Corresponding author. Email: maxine.roberts@ansto.gov.au
Australian Journal of Chemistry 66(4) 491-499 https://doi.org/10.1071/CH12489
Submitted: 29 October 2012 Accepted: 12 December 2012 Published: 18 February 2013
Abstract
2-{2-[4-(4-[18F]-Fluorobenzyl)piperazin-1-yl]-2-oxoethyl}isoindolin-1-one ([18F]MEL054), is a new potent indolinone-based melanin binder designed to target melanotic tumours. [18F]MEL054 was prepared by an automated two-step radiosynthesis, comprising of the preparation of 4-[18F]fluorobenzaldehyde from 4-formyl-N,N,N-trimethylanilinium triflate, followed by reductive alkylation with 2-(2-oxo-2-piperazin-1-ylethyl)isoindolin-1-one. 4-[18F]Fluorobenzaldehyde was prepared on a GE TRACERlab FXFN module in 68 ± 8 % radiochemical yield (RCY, non-decay corrected), purified by a Sep-Pak Plus C18 cartridge and eluted into the reactor of an in-house modified Nuclear Interface [18F]FDG synthesis module for the subsequent reductive alkylation reaction. HPLC purification produced [18F]MEL054 in a collected RCY of 34 ± 9 % (non-decay corrected), the total preparation time (including Sep-Pak Plus C18 and HPLC purification) did not exceed 105 min. The radiochemical purity of [18F]MEL054 was greater than 99 % with a specific radioactivity of 71–119 GBq μmol–1 and [18F]MEL054 remained stable in saline solution (>98 %) after 3 h.
References
[1] P. Baade, M. Coory, Aust. N. Z. J. Public Health 2005, 29, 383.| Crossref | GoogleScholarGoogle Scholar |
[2] Cancer in Australia: An Overview 2008 (Australian Institute of Health and Welfare Australasian Association of Cancer Registries: Canberra).
[3] T. Z. Belhocine, A. M. Scott, E. Even-Sapir, J.-L. Urbain, R. Essner, J. Nucl. Med. 2006, 47, 957.
[4] G. Mariani, L. Bruselli, T. Kuwert, E. E. Kim, A. Flotats, O. Israel, M. Dondi, N. Watanabe, Eur. J. Nucl. Med. Mol. Imaging 2010, 37, 1959.
| Crossref | GoogleScholarGoogle Scholar |
[5] B. Krug, R. Crott, M. Lonneux, J.-F. Baurain, A.-S. Pirson, T. Vander Borght, Radiology 2008, 249, 836.
| Crossref | GoogleScholarGoogle Scholar |
[6] P. A. Schubiger, R. Alberto, A. Smith, Bioconjug. Chem. 1996, 7, 165.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XhsVGhsLY%3D&md5=5d00476f7bc40aadd124ff32b5a672bcCAS |
[7] M. R. Zalutsky, D. Bigner, Acta Oncol. 1996, 35, 373.
| Crossref | GoogleScholarGoogle Scholar | 1:STN:280:DyaK283nvFKrtg%3D%3D&md5=b9659346a98852e4c346e6cfd771bf4eCAS |
[8] C. S. John, W. D. Bowen, T. Saga, S. Kinuya, B. J. Vilner, J. Baumgold, C. H. Paik, R. C. Reba, R. D. Neumann, V. M. Varma, J. G. McAfee, J. Nucl. Med. 1993, 34, 2169.
| 1:CAS:528:DyaK2cXivFeis74%3D&md5=495d3327c77cbbffacb415bc67c31228CAS |
[9] J. A. Coderre, S. Packer, R. G. Fairchild, D. Greenberg, B. Laster, P. Micca, I. Fand, J. Nucl. Med. 1986, 27, 1157.
| 1:STN:280:DyaL283ltlekug%3D%3D&md5=cf6bb5e5974d864b34eaee1f1c5d1374CAS |
[10] J.-M. Chezal, J. Papon, P. Labarre, C. Lartigue, M.-J. Galmier, C. Decombat, O. Chavignon, J. Maublant, J.-C. Teulade, J.-C. Madelmont, N. Moins, J. Med. Chem. 2008, 51, 3133.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXmtVGhtrs%3D&md5=0419bc153baecb890645be9e25cbfd88CAS |
[11] B. J. Allen, S. Rizvi, Y. Li, Z. Tian, M. Ranson, Crit. Rev. Oncol. Hematol. 2001, 39, 139.
| Crossref | GoogleScholarGoogle Scholar | 1:STN:280:DC%2BD38%2Fit1aitQ%3D%3D&md5=1b1ce8818ffde4e2af84a619bda95c10CAS |
[12] J. Chen, M. F. Giblin, N. Wang, S. S. Jurisson, T. P. Quinn, Nucl. Med. Biol. 1999, 26, 687.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXlvVWksbk%3D&md5=47e28efa6f3a55f2cc183663a3c34a73CAS |
[13] Y. Miao, N. K. Owen, D. Whitener, F. Gallazzi, T. J. Hoffman, T. P. Quinn, Int. J. Cancer 2002, 101, 480.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38Xnt1ehs7o%3D&md5=f21bcb55ddec72f05a4c854cc0e20d83CAS |
[14] Y. Miao, P. Quinn Thomas, Crit. Rev. Oncol. Hematol. 2008, 67, 213.
| Crossref | GoogleScholarGoogle Scholar |
[15] C. M. Boyd, L. M. Lieberman, W. H. Beierwaltes, V. M. Varma, J. Nucl. Med. 1970, 11, 479.
| 1:STN:280:DyaE3c3ms12htw%3D%3D&md5=ccc12c42582a49d919c40412a775841dCAS |
[16] E. M. Link, R. N. Carpenter, Cancer Res. 1992, 52, 4385.
| 1:CAS:528:DyaK38Xls1Krsr8%3D&md5=946871dd76c3f786a4669e3175d1fd11CAS |
[17] G. Sobal, M. Rodrigues, H. Sinzinger, Anticancer Res 2008, 28, 3691.
| 1:CAS:528:DC%2BD1MXhtlemtLY%3D&md5=bd44a78aa0df91067d44cfe5fd84a9a4CAS |
[18] J. M. Michelot, M. F. Moreau, P. G. Labarre, J. C. Madelmont, A. J. Veyre, J. M. Papon, D. F. Parry, J. F. Bonafous, J. Y. Boire, G. G. Desplanches, S. J. Bertrand, G. Meyniel, J. Nucl. Med. 1991, 32, 1573.
| 1:CAS:528:DyaK38XivV2n&md5=7b78973679c6f0449af9d680da7240b3CAS |
[19] N. Desbois, M. Gardette, J. Papon, P. Labarre, A. Maisonial, P. Auzeloux, C. Lartigue, B. Bouchon, E. Debiton, Y. Blache, O. Chavignon, J.-C. Teulade, J. Maublant, J.-C. Madelmont, N. Moins, J.-M. Chezal, Bioorg. Med. Chem. 2008, 16, 7671.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtVSisr3I&md5=57b953572e51be9c779352b8ccc061fbCAS |
[20] T. Q. Pham, I. Greguric, X. Liu, P. Berghofer, P. Ballantyne, J. Chapman, F. Mattner, B. Dikic, T. Jackson, C. Loc’h, A. Katsifis, J. Med. Chem. 2007, 50, 3561.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXmvFKqsL0%3D&md5=2dc34e3fc0e6a6539755294ae821fa4bCAS |
[21] S. Garg, K. Kothari, S. R. Thopate, A. K. Doke, P. K. Garg, Bioconjug. Chem. 2009, 20, 583.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhvFGmsbw%3D&md5=45038a12ae41090741bcc323aecdfb3eCAS |
[22] G. Ren, Z. Miao, H. Liu, L. Jiang, N. Limpa-Amara, A. Mahmood, S. S. Gambhir, Z. Cheng, J. Nucl. Med. 2009, 50, 1692.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtlehsbnO&md5=e3dc93489c8844a665ca946b627e9599CAS |
[23] N. Moins, M. D’Incan, J. Bonafous, F. Bacin, P. Labarre, M.-F. Moreau, D. Mestas, E. Noirault, F. Chossat, E. Berthommier, J. Papon, M. Bayle, P. Souteyrand, J.-C. Madelmont, A. Veyre, Eur. J. Nucl. Med. Mol. Imaging 2002, 29, 1478.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XotV2itr0%3D&md5=bfd39786da01d02c35ce2b772025e228CAS |
[24] J. M. Michelot, M. F. Moreau, A. J. Veyre, J. F. Bonafous, F. J. Bacin, J. C. Madelmont, F. Bussiere, P. A. Souteyrand, L. P. Mauclaire, F. M. Chossat, J. M. Papon, P. G. Labarre, Ph. Kauffmann, R. J. Plagne, J. Nucl. Med. 1993, 34, 1260.
| 1:STN:280:DyaK3szhs1Wlsg%3D%3D&md5=ccff09b75f6d468cf1463bdf3dcfb6ccCAS |
[25] P. Labarre, J. Papon, A. H. Rose, J.-L. Guerquin-Kern, L. Morandeau, T.-d. Wu, M.-F. Moreau, M. Bayle, J.-M. Chezal, A. Croisy, J.-C. Madelmont, H. Turner, N. Moins, Nucl. Med. Biol. 2008, 35, 783.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXht1egtb7P&md5=3f1da6ffbc10beb2bef96f07556a3747CAS |
[26] W. Brandau, T. Niehoff, P. Pulawski, M. Jonas, K. Dutschka, J. Sciuk, H. H. Coenen, O. Schober, J. Nucl. Med. 1996, 37, 1865.
| 1:CAS:528:DyaK28XntF2ksLY%3D&md5=d583a05ecae36dd89a29f257438e26eaCAS |
[27] I. Sillaire-Houtmann, J. Bonafous, A. Veyre, D. Mestas, M. d’Incan, N. Moins, J.-L. Kemeny, F. Chossat, F. Bacin, J. Fr. Ophtalmol. 2004, 27, 34.
| Crossref | GoogleScholarGoogle Scholar | 1:STN:280:DC%2BD2c%2FnvVensw%3D%3D&md5=daaa3485546930f54ee9dfd262be6a2cCAS |
[28] D. Denoyer, I. Greguric, P. Roselt, O. C. Neels, N. Aide, S. R. Taylor, A. Katsifis, D. S. Dorow, R. J. Hicks, J. Nucl. Med. 2010, 51, 441.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXksVylsr0%3D&md5=212067e6015af78f9ff6b4f3634e6d39CAS |
[29] I. Greguric, S. R. Taylor, D. Denoyer, P. Ballantyne, P. Berghofer, P. Roselt, T. Q. Pham, F. Mattner, T. Bourdier, O. C. Neels, D. S. Dorow, C. Loc’h, R. J. Hicks, A. Katsifis, J. Med. Chem. 2009, 52, 5299.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtVWntbfP&md5=568ca0176a17f7f7d070161965f55af4CAS |
[30] I. Greguric, S. Taylor, T. Pham, N. Wyatt, C. D. Jiang, T. Bourdier, C. Loc’h, P. Roselt, O. C. Neels, A. Katsifis, Aust. J. Chem. 2011, 64, 873.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXovFyisbk%3D&md5=b72aed006a89a3c93a4dca3ffbd03fa5CAS |
[31] T. Q. Pham, P. Berghofer, X. Liu, I. Greguric, B. Dikic, P. Ballantyne, F. Mattner, V. Nguyen, C. Loc’h, A. Katsifis, J. Nucl. Med. 2007, 48, 1348.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtVSktbzL&md5=4bdfc5e4f0a339de120ddb643ea9eab0CAS |
[32] X. Liu, T. Q. Pham, P. Berghofer, J. Chapman, I. Greguric, P. Mitchell, F. Mattner, C. Loc’h, A. Katsifis, Nucl. Med. Biol. 2008, 35, 769.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXht1egtb7O&md5=b7b7d6093aee8e89a76438ebdf9c1b47CAS |
[33] P. Berghofer, I. Greguric, C. Loch, N. Wyatt, T. Q. Pham, P. Ballantyne, V. Nguyen, D. Denoyer, R. Hicks, A. Katsifis, M. Gregoire, S. Taylor, Eur. J. Nucl. Med. Mol. Imaging 2013, in progress
[34] M. P. Roberts, V. Nguyen, M. E. Ashford, P. Berghofer, N. A. Wyatt, S. R. Taylor, L. Burgess, A. M. Krause-Heuer, T. Q. Pham, B. H. Fraser, N. A. Lengkeek, L. Matesic, M. Gregoire, D. Denoyer, R. Hicks, A. Katsifis, I. Greguric, J. Med. Chem. 2013, in progress
[35] A. F. Abdel-Magid, K. G. Carson, B. D. Harris, C. A. Maryanoff, R. D. Shah, J. Org. Chem. 1996, 61, 3849.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XivFShu7o%3D&md5=6e9fe94f7377ad1a3aab1b46eaca09f7CAS |
[36] A. F. Abdel-Magid, S. J. Mehrman, Org. Process Res. Dev. 2006, 10, 971.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XpsVymurk%3D&md5=28d17a745e01077a3c8e9517d2d91480CAS |
[37] T. Poethko, M. Schottelius, G. Thumshirn, U. Hersel, M. Herz, G. Henriksen, H. Kessler, M. Schwaiger, H.-J. Wester, J. Nucl. Med. 2004, 45, 892.
| 1:CAS:528:DC%2BD2cXnsFygtLc%3D&md5=24c5991bb04e5caabff349009055877aCAS |
[38] T. Poethko, M. Schottelius, G. Thumshirn, M. Herz, R. Haubner, G. Henriksen, H. Kessler, M. Schwaiger, H.-J. Wester, Radiochim. Acta 2004, 92, 317.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXmvVKlsbc%3D&md5=e06d988a62d66aea3a827179ea87acd6CAS |
[39] M. Berndt, J. Pietzsch, F. Wuest, Nucl. Med. Biol. 2007, 34, 5.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXisVajuw%3D%3D&md5=1f98d72ef57fa91ebb2e6ae5820d8635CAS |
[40] A. Speranza, G. Ortosecco, E. Castaldi, A. Nardelli, L. Pace, M. Salvatore, Appl. Radiat. Isot. 2009, 67, 1664.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXnt1Cjt78%3D&md5=f2aa8737d2698b02f7a57b18f82f20dcCAS |
[41] T. Hai-Bin, Y. Duan-Zhi, L. Jun-Ling, Z. Lan, Z. Cun-Fu, W. Yong-Xian, Z. Wei, Radiochim. Acta 2003, 91, 241.
| Crossref | GoogleScholarGoogle Scholar |
[42] P. Mäding, F. Füchtner, B. Johannsen, J. Steinbach, C. S. Hilger, M. Friebe, M. Halks-Miller, R. Horuk, R. Mohan, J. Labelled Comp. Radiopharm. 2006, 49, 253.
| Crossref | GoogleScholarGoogle Scholar |
[43] C. Wichmann, N. A. Wyatt, M. P. Roberts, P. Roselt, T. Q. Pham, I. Greguric, Aust. J. Chem. 2013, in progress
