Table of Contents Author Guidelines Submit a Manuscript
BioMed Research International
Volume 2014, Article ID 454503, 20 pages
http://dx.doi.org/10.1155/2014/454503
Review Article

18F-Labeled Silicon-Based Fluoride Acceptors: Potential Opportunities for Novel Positron Emitting Radiopharmaceuticals

1Division of Experimental Medicine, Department of Medicine, McGill University, 1110 Pine Avenue West, Montreal, QC, Canada H3A 1A3
2Biomedical Chemistry, Department of Clinical Radiology and Nuclear Medicine, Medical Faculty Mannheim of Heidelberg University, 68167 Mannheim, Germany
3McConnell Brain Imaging Centre, Montreal Neurological Institute, McGill University, 3801 University Street, Montreal, QC, Canada H3A 2B4
4Department of Inorganic Chemistry II, Faculty of Chemistry, TU Dortmund, Otto-Hahn-Straße 6, 44221 Dortmund, Germany
5Molecular Imaging and Radiochemistry, Department of Clinical Radiology and Nuclear Medicine, Medical Faculty Mannheim of Heidelberg University, 68167 Mannheim, Germany
6Department of Oncology, University of Alberta, 11560 University Avenue, Edmonton, AB, Canada T6G 1Z2

Received 19 February 2014; Revised 7 April 2014; Accepted 8 April 2014; Published 24 July 2014

Academic Editor: Olaf Prante

Copyright © 2014 Vadim Bernard-Gauthier et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. C. Yoshida, A. B. Tsuji, H. Sudo et al., “Development of positron emission tomography probe of 64Cu-labeled anti-C-kit 12A8 Fab to measure protooncogene C-kit expression,” Nuclear Medicine and Biology, vol. 38, no. 3, pp. 331–337, 2011. View at Publisher · View at Google Scholar · View at Scopus
  2. C. Wängler, B. Wängler, S. Lehner et al., “A universally applicable 68Ga-labeling technique for proteins,” Journal of Nuclear Medicine, vol. 52, no. 4, pp. 586–591, 2011. View at Publisher · View at Google Scholar · View at Scopus
  3. P. Szymański, T. Fraczek, M. Markowicz, and E. Mikiciuk-Olasik, “Development of copper based drugs, radiopharmaceuticals and medical materials,” BioMetals, vol. 25, no. 6, pp. 1089–1112, 2012. View at Publisher · View at Google Scholar · View at Scopus
  4. B. M. Zeglis, J. L. Houghton, M. J. Evans, N. Viola-Villegas, and J. S. Lewis, “Underscoring the influence of inorganic chemistry on nuclear imaging with radiometals,” Inorganic Chemistry, vol. 53, no. 4, pp. 1880–1899, 2014. View at Google Scholar
  5. R. Schirrmacher, G. Bradtmöller, E. Schirrmacher et al., “18F-labeling of peptides by means of an organosilicon-based fluoride acceptor,” Angewandte Chemie International Edition, vol. 45, no. 36, pp. 6047–6050, 2006. View at Publisher · View at Google Scholar · View at Scopus
  6. B. Wängler, G. Quandt, L. Iovkova et al., “Kit-like 18F-labeling of proteins: Synthesis of 4-(Di-tert-butyl[18F]fluorosuyl)benzenethiol (Si[18F]FA-SH) labeled rat serum albumin for blood pool imaging with PET,” Bioconjugate Chemistry, vol. 20, no. 2, pp. 317–321, 2009. View at Publisher · View at Google Scholar · View at Scopus
  7. W. J. McBride, C. A. D'Souza, H. Karacay, R. M. Sharkey, and D. M. Goldenberg, “New lyophilized kit for rapid radiofluorination of peptides,” Bioconjugate Chemistry, vol. 23, no. 3, pp. 538–547, 2012. View at Publisher · View at Google Scholar · View at Scopus
  8. E. Schirrmacher, B. Wängler, M. Cypryk et al., “ynthesis of p-(Di-tert-butyl[(18)f]fluorosilyl)benzaldehyde ([F-18]SiFA-A) with high specific activity by isotopic exchange: a convenient Labeling synthon for the F-18-labeling of n-amino-oxy derivatized peptides,” Bioconjugate Chemistry, vol. 18, no. 6, pp. 2085–2089, 2007. View at Publisher · View at Google Scholar · View at Scopus
  9. A. Höhne, L. Mu, M. Honer et al., “Synthesis, 18F-labeling, and in vitro and in vivo studies of bombesin peptides modified with silicon-based building blocks,” Bioconjugate Chemistry, vol. 19, no. 9, pp. 1871–1879, 2008. View at Publisher · View at Google Scholar · View at Scopus
  10. C. Wängler, A. Kostikov, J. Zhu, J. Chin, B. Wängler, and R. Schirrmacher, “Silicon-[18F]Fluorine radiochemistry: basics, application and challenges,” Applied Sciences, vol. 2, pp. 227–302, 2012. View at Google Scholar
  11. R. Ting, M. J. Adam, T. J. Ruth, and D. M. Perrin, “Arylfluoroborates and alkylfluorosilicates as potential PET imaging agents: high-yielding aqueous biomolecular18F-labeling,” Journal of the American Chemical Society, vol. 127, no. 38, pp. 13094–13095, 2005. View at Publisher · View at Google Scholar · View at Scopus
  12. R. Ting, C. Harwig, U. Auf Dem Keller et al., “Toward [18F]-labeled aryltrifluoroborate radiotracers: in vivo positron emission tomography imaging of stable aryltrifluoroborate clearance in mice,” Journal of the American Chemical Society, vol. 130, no. 36, pp. 12045–12055, 2008. View at Publisher · View at Google Scholar · View at Scopus
  13. U. A. D. Keller, C. L. Bellac, Y. Li et al., “Novel matrix metalloproteinase inhibitor [18F]marimastat- aryltrifluoroborate as a probe for in vivo positron emission tomography imaging in cancer,” Cancer Research, vol. 70, no. 19, pp. 7562–7569, 2010. View at Publisher · View at Google Scholar · View at Scopus
  14. L. Mu, P. A. Schubiger, and S. M. Ametamey, “[18F]fluorosilicon- and [18F]fluoroboron-based biomolecules for PET imaging,” Current Radiopharmaceuticals, vol. 3, no. 3, pp. 224–242, 2010. View at Publisher · View at Google Scholar · View at Scopus
  15. W. J. McBride, R. M. Sharkey, H. Karacay et al., “A novel method of 18F radiolabeling for PET,” Journal of Nuclear Medicine, vol. 50, no. 6, pp. 991–998, 2009. View at Publisher · View at Google Scholar · View at Scopus
  16. W. J. McBride, C. A. D'souza, R. M. Sharkey et al., “Improved 18F labeling of peptides with a fluoride-aluminum-chelate complex,” Bioconjugate Chemistry, vol. 21, no. 7, pp. 1331–1340, 2010. View at Publisher · View at Google Scholar · View at Scopus
  17. P. Laverman, W. J. McBride, R. M. Sharkey et al., “A novel facile method of labeling octreotide with 18F-fluorine,” Journal of Nuclear Medicine, vol. 51, no. 3, pp. 454–461, 2010. View at Publisher · View at Google Scholar · View at Scopus
  18. W. J. McBride, R. M. Sharkey, and D. M. Goldenberg, “Radiofluorination using aluminum-fluoride (Al18F),” EJNMMI Research, vol. 3, no. 1, pp. 1–11, 2013. View at Publisher · View at Google Scholar · View at Scopus
  19. G. E. Smith, H. L. Sladen, S. C. G. Biagini, and P. J. Blower, “Inorganic approaches for radiolabelling biomolecules with fluorine-18 for imaging with Positron Emission Tomography,” Dalton Transactions, vol. 40, no. 23, pp. 6196–6205, 2011. View at Publisher · View at Google Scholar · View at Scopus
  20. U. Choudhry, K. E. Martin, S. Biagini, and P. J. Blower, “Alkoxysilane groups for instant labeling of biomolecules with 18F,” Nuclear Medicine Communications, vol. 27, no. 3, p. 27, 2006. View at Google Scholar
  21. L. Mu, A. Höhne, P. A. Schubiger et al., “Silicon-based building blocks for one-step 18F-radiolabeling of peptides for PET imaging,” Angewandte Chemie International Edition, vol. 47, no. 26, pp. 4922–4925, 2008. View at Publisher · View at Google Scholar · View at Scopus
  22. T. A. Gens, J. A. Wethington Jr., and A. R. Brosi, “The exchange of F-18 between metallic fluorides and silicon tetrafluoride,” Journal of Physical Chemistry, vol. 62, no. 12, p. 1593, 1959. View at Google Scholar · View at Scopus
  23. R. T. Poole and J. M. Winfield, “Radiotracers in fluorine chemistry. Part IV. Fluorine-18 exchange between labelled alkylfluorosilanes and fluorides, or fluoride methoxides, of tungsten(VI), molybdenum(VI), tellurium(VI), and iodine(V),” Journal of the Chemical Society: Dalton Transactions, vol. 12, no. 16, pp. 1557–1560, 1976. View at Publisher · View at Google Scholar · View at Scopus
  24. J. M. Winfield, “Preparation and use of 18-fluorine labelled inorganic compounds,” Journal of Fluorine Chemistry, vol. 16, no. 1, pp. 1–17, 1980. View at Publisher · View at Google Scholar · View at Scopus
  25. B. W. Fry, G. M. Whitford, and D. H. Pashley, “A method for increasing the amount of 18F at the laboratory by recovery during transport from the reactor,” The International Journal Of Applied Radiation and Isotopes, vol. 29, no. 2, pp. 123–125, 1978. View at Publisher · View at Google Scholar · View at Scopus
  26. M. S. Rosenthal, A. L. Bosch, R. J. Nickles, and S. J. Gatley, “Synthesis and some characteristics of no-carrier added [18F]fluorotrimethylsilane,” The International Journal of Applied Radiation and Isotopes, vol. 36, no. 4, pp. 318–319, 1985. View at Publisher · View at Google Scholar · View at Scopus
  27. S. J. Gatley, “Rapid production and trapping of [F-18] fluorotrimethylsilane, and its use in nucleophilic F-18 labeling without an aqueous evaporation step,” Applied Radiation and Isotopes, vol. 40, no. 6, pp. 541–544, 1989. View at Publisher · View at Google Scholar · View at Scopus
  28. G. K. Mulholland, “Recovery and purification of no-carrier-added [18F]fluoride with bistrimethylsilylsulfate (BTMSS),” International Journal of Radiation Applications and Instrumentation, vol. 42, no. 11, pp. 1003–1008, 1991. View at Publisher · View at Google Scholar · View at Scopus
  29. E. Schirrmacher, B. Wängler, M. Cypryk et al., “Synthesis of p-(Di-tert-butyl[18F]fluorosilyl)benzaldehyde ([18F]SiFA-A) with high specific activity by isotopic exchange: a convenient labeling synthon for the 18F-labeling of N-amino-oxy derivatized peptides,” Bioconjugate Chemistry, vol. 18, no. 6, pp. 2085–2089, 2007. View at Publisher · View at Google Scholar · View at Scopus
  30. R. Damrauer, L. W. Burggraf, L. P. Davis, and M. S. Gordon, “Gas-phase and computational studies of pentacoordinate silicon,” Journal of the American Chemical Society, vol. 110, no. 20, pp. 6601–6606, 1988. View at Publisher · View at Google Scholar · View at Scopus
  31. I. H. Krouse and P. G. Wenthold, “Formation and decomposition of hydroxysiliconates in the gas phase,” Organometallics, vol. 23, no. 11, pp. 2573–2582, 2004. View at Publisher · View at Google Scholar · View at Scopus
  32. A. P. Kostikov, L. Iovkova, J. Chin et al., “N-(4-(di-tert-butyl[18F]fluorosilyl)benzyl)-2-hydroxy-N,N- dimethylethylammonium bromide ([18F]SiFAN+Br-): a novel lead compound for the development of hydrophilic SiFA-based prosthetic groups for 18F-labeling,” Journal of Fluorine Chemistry, vol. 132, no. 1, pp. 27–34, 2011. View at Publisher · View at Google Scholar · View at Scopus
  33. A. Höhne, L. Yu, L. Mu et al., “Organofluorosilanes as model compounds for 18F-labeled silicon-based PET tracers and their hydrolytic stability: experimental data and theoretical calculations (PET=Positron Emission Tomography),” Chemistry, vol. 15, no. 15, pp. 3736–3743, 2009. View at Publisher · View at Google Scholar · View at Scopus
  34. S. Lu, S. D. Lepore, Y. L. Song et al., “Nucleophile assisting leaving groups: a strategy for aliphatic 18F-fluorination,” Journal of Organic Chemistry, vol. 74, no. 15, pp. 5290–5296, 2009. View at Publisher · View at Google Scholar · View at Scopus
  35. M. H. Al-Huniti, S. Lu, V. W. Pike, and S. D. Lepore, “Enhanced nucleophilic fluorination and radiofluorination of organosilanes appended with potassium-chelating leaving groups,” Journal of Fluorine Chemistry, vol. 158, pp. 48–52, 2014. View at Google Scholar
  36. L. O. Dialer, S. V. Selivanova, C. J. Muller et al., “Studies toward the development of new silicon-containing building blocks for the direct 18F-labeling of peptides,” Journal of Medicinal Chemistry, vol. 56, no. 19, pp. 7552–7563, 2013. View at Google Scholar
  37. M. Fiorenza, A. Mordini, and A. Ricci, “The mechanism of solvolysis of β-ketosilanes,” Journal of Organometallic Chemistry, vol. 280, no. 2, pp. 177–182, 1985. View at Publisher · View at Google Scholar · View at Scopus
  38. D. O. Kiesewetter, O. Jacobson, L. X. Lang, and X. Y. Chen, “Automated radiochemical synthesis of [18F]FBEM: a thiol reactive synthon for radiofluorination of peptides and proteins,” Applied Radiation and Isotopes, vol. 69, no. 2, pp. 410–414, 2011. View at Publisher · View at Google Scholar · View at Scopus
  39. A. Speranza, G. Ortosecco, E. Castaldi, A. Nardelli, L. Pace, and M. Salvatore, “Fully automated synthesis procedure of 4-[18F]fluorobenzaldehyde by commercial synthesizer: amino-oxi peptide labelling prosthetic group,” Applied Radiation and Isotopes, vol. 67, no. 9, pp. 1664–1669, 2009. View at Publisher · View at Google Scholar · View at Scopus
  40. D. Thonon, D. Goblet, E. Goukens et al., “Fully automated preparation and conjugation of N-succinimidyl 4-[(18)F]fluorobenzoate ([(18)F]SFB) with RGD peptide using a GE FASTlab synthesizer,” Molecular Imaging and Biology, vol. 13, no. 6, pp. 1088–1095, 2011. View at Publisher · View at Google Scholar · View at Scopus
  41. L. Iovkova, D. Könning, B. Wängler et al., “SiFA-modified phenylalanine: a key compound for the efficient synthesis of18F-labelled peptides,” European Journal of Inorganic Chemistry, no. 14, pp. 2238–2246, 2011. View at Publisher · View at Google Scholar · View at Scopus
  42. L. F. Tietze and K. Schmuck, “SiFA azide: a new building block for PET imaging using click chemistry,” Synlett, no. 12, pp. 1697–1700, 2011. View at Publisher · View at Google Scholar · View at Scopus
  43. A. P. Kostikov, J. Chin, K. Orchowski et al., “Oxalic acid supported Si-18F-radiofluorination: one-step radiosynthesis of N-succinimidyl 3-(Di-tert-butyl[18F]fluorosilyl) benzoate ([18F]SiFB) for protein labeling,” Bioconjugate Chemistry, vol. 23, no. 1, pp. 106–114, 2012. View at Publisher · View at Google Scholar · View at Scopus
  44. P. Rosa-Neto, B. Wängler, L. Iovkova et al., “[18F]SiFA-isothiocyanate: a new highly effective radioactive labeling agent for lysine-containing proteins,” ChemBioChem, vol. 10, no. 8, pp. 1321–1324, 2009. View at Publisher · View at Google Scholar · View at Scopus
  45. L. Iovkova, B. Wängler, E. Schirrmacher et al., “Para-functionalized aryl-di-tert-butylfluorosilanes as potential labeling synthons for18F radiopharmaceuticals,” Chemistry, vol. 15, no. 9, pp. 2140–2147, 2009. View at Publisher · View at Google Scholar · View at Scopus
  46. E. Balentova, C. Collet, S. Lamandé-Langle et al., “Synthesis and hydrolytic stability of novel 3-[18F] fluoroethoxybis(1-methylethyl)silyl]propanamine-based prosthetic groups,” Journal of Fluorine Chemistry, vol. 132, no. 4, pp. 250–257, 2011. View at Publisher · View at Google Scholar · View at Scopus
  47. C. Wängler, B. Waser, A. Alke et al., “One-step 18F-labeling of carbohydrate-conjugated octreotate-derivatives containing a silicon-fluoride-acceptor (SiFA): in vitro and in vivo evaluation as tumor imaging agents for positron emission tomography (PET),” Bioconjugate Chemistry, vol. 21, no. 12, pp. 2289–2296, 2010. View at Publisher · View at Google Scholar · View at Scopus
  48. M. Schottelius, F. Rau, J. C. Reubi, M. Schwaiger, and H. Wester, “Modulation of pharmacokinetics of radioiodinated sugar-conjugated somatostatin analogues by variation of peptide net charge and carbohydration chemistry,” Bioconjugate Chemistry, vol. 16, no. 2, pp. 429–437, 2005. View at Publisher · View at Google Scholar · View at Scopus
  49. M. Schottelius, H. J. Wester, J. C. Reubi, R. Senekowitsch-Schmidtke, and M. Schwaiger, “Improvement of pharmacokinetics of radioiodinated Tyr3-octreotide by conjugation with carbohydrates,” Bioconjugate Chemistry, vol. 13, no. 5, pp. 1021–1030, 2002. View at Publisher · View at Google Scholar · View at Scopus
  50. P. Antunes, M. Ginj, M. A. Walter, J. H. Chen, J. C. Reubi, and H. R. Maecke, “Influence of different spacers on the biological profile of a DOTA-somatostatin analogue,” Bioconjugate Chemistry, vol. 18, no. 1, pp. 84–92, 2007. View at Publisher · View at Google Scholar · View at Scopus
  51. C. Wängler, S. Niedermoser, J. Chin et al., “One-step 18F-labeling of peptides for positron emission tomography imaging using the SiFA methodology,” Nature Protocols, vol. 7, no. 11, pp. 1946–1955, 2012. View at Publisher · View at Google Scholar · View at Scopus
  52. E. Amigues, J. Schulz, M. Szlosek-Pinaud et al., “[18F]Si-RiboRGD: from design and synthesis to the imaging of αvβ3 integrins in melanoma tumors,” ChemPlusChem, vol. 77, no. 5, pp. 345–349, 2012. View at Publisher · View at Google Scholar · View at Scopus
  53. R. Haubner, B. Kuhnast, C. Mang et al., “[18F]galacto-RGD: synthesis, radiolabeling , metabolic stability, and radiation dose estimates,” Bioconjugate Chemistry, vol. 15, no. 1, pp. 61–69, 2004. View at Publisher · View at Google Scholar · View at Scopus
  54. G. Vaidyanathan and M. R. Zalutsky, “Labeling proteins with fluorine-18 using N-succinimidyl 4-[18F]fluorobenzoate,” Nuclear Medicine and Biology, vol. 19, no. 3, pp. 275–281, 1992. View at Publisher · View at Google Scholar · View at Scopus
  55. G. Vaidyanathan and M. R. Zalutsky, “Improved synthesis of N-succinimidyl 4-[18F]fluorobenzoate and its application to the labeling of a monoclonal antibody fragment,” Bioconjugate Chemistry, vol. 5, no. 4, pp. 352–356, 1994. View at Publisher · View at Google Scholar · View at Scopus
  56. F. Wuest, M. Berndt, R. Bergmann, J. van den Hoff, and J. Pietzsch, “Synthesis and application of [18F]FDG-maleimidehexyloxime ([18F]FDG-MHO): a [18F]FDG-based prosthetic group for the chemoselective 18F-labeling of peptides and proteins,” Bioconjugate Chemistry, vol. 19, no. 6, pp. 1202–1210, 2008. View at Publisher · View at Google Scholar · View at Scopus
  57. Z. Miao, G. Ren, H. Liu, S. Qi, S. Wu, and Z. Cheng, “PET of EGFR expression with an 18F-labeled affibody molecule,” Journal of Nuclear Medicine, vol. 53, no. 7, pp. 1110–1118, 2012. View at Publisher · View at Google Scholar · View at Scopus
  58. A. P. Kostikov, J. Chin, K. Orchowski et al., “Synthesis of [18F]SiFB: a prosthetic group for direct protein radiolabeling for application in positron emission tomography,” Nature Protocols, vol. 7, no. 11, pp. 1956–1963, 2012. View at Publisher · View at Google Scholar · View at Scopus
  59. B. Wängler, A. P. Kostikov, S. Niedermoser et al., “Protein labeling with the labeling precursor [18F]SiFA-SH for positron emission tomography,” Nature Protocols, vol. 7, no. 11, pp. 1964–1969, 2012. View at Publisher · View at Google Scholar · View at Scopus
  60. M. Glaser, P. Iveson, S. Hoppmann et al., “Three methods for 18F labeling of the HER2-binding affibody molecules ZHER2:2891 including preclinical assessment,” Journal of Nuclear Medicine, vol. 54, no. 11, pp. 1981–1988, 2013. View at Google Scholar
  61. S. H. Wessmann, G. Henriksen, and H.-J. Wester, “Cryptate mediated nucleophilic 18F-fluorination without azeotropic drying,” NuklearMedizin, vol. 51, no. 1, pp. 1–8, 2012. View at Publisher · View at Google Scholar · View at Scopus
  62. P. Bohn, A. Deyine, R. Azzouz et al., “Design of silicon-based misonidazole analogues and 18F-radiolabelling,” Nuclear Medicine and Biology, vol. 36, no. 8, pp. 895–905, 2009. View at Publisher · View at Google Scholar · View at Scopus
  63. Y. Joyard, R. Azzouz, L. Bischoff et al., “Synthesis of new 18F-radiolabeled silicon-based nitroimidazole compounds,” Bioorganic and Medicinal Chemistry, vol. 21, no. 13, pp. 3680–3688, 2013. View at Publisher · View at Google Scholar · View at Scopus
  64. J. Schulz, D. Vimont, T. Bordenave et al., “Silicon-based chemistry: an original and efficient one-step approach to [18F]-Nucleosides and [18F]-Oligonucleotides for PET imaging,” Chemistry, vol. 17, no. 11, pp. 3096–3100, 2011. View at Publisher · View at Google Scholar · View at Scopus
  65. L. Iovkova-Berends, C. Wängler, T. Zöller et al., “t-Bu2SiF-derivatized D2-receptor ligands: the first SiFA-containing small molecule radiotracers for target-specific PET-imaging,” Molecules, vol. 16, no. 9, pp. 7458–7479, 2011. View at Publisher · View at Google Scholar · View at Scopus
  66. P. P. Hazari, J. Schulz, D. Vimont et al., “A new SiF-dipropargyl glycerol scaffold as a versatile prosthetic group to design dimeric radioligands: synthesis of the [18F]BMPPSiF tracer to image serotonin receptors,” ChemMedChem, vol. 8, pp. 1–14, 2013. View at Google Scholar
  67. M. J. Shashack, K. A. Cunningham, P. K. Seitz et al., “Synthesis and evaluation of dimeric derivatives of 5-HT 2A receptor (5-HT 2AR) antagonist M-100907,” ACS Chemical Neuroscience, vol. 2, no. 11, pp. 640–644, 2011. View at Publisher · View at Google Scholar · View at Scopus
  68. S. Niedermoser, C. Wängler, J. Chin et al., “Chemical and biological evaluation of new hydrophilic [18F] SiFA-derivatized somatostatin analogues,” Journal of Nuclear Medicine, vol. 54, supplement 2, p. 60, 2013. View at Google Scholar
  69. S. K. Lindner, C. Michler, S. Leidner et al., “Synthesis, in vitro and in vivo evaluation of SiFA -tagged bombesin and RGD peptides as tumor imaging probes for positron emission tomography (PET),” Bioconjugate Chemistry, 2014. View at Google Scholar