Journal of Radiopharmaceuticals and Molecular Probes (대한방사성의약품학회지)

Korean Society of Radiopharmaceuticals and Molecular Probes (대한방사성의약품학회)
권호 표지
DOI QR코드

DOI QR Code

Radiolabeling of 11C-sertraline by fast and easy loop method with [11C]CH3OTf

  • Lee, Hak Jeong (Department of Nuclear Medicine, Seoul National University College of Medicine and Institute of Radiation Medicine, Medical Research Center) ;
  • Jeong, Jae Min (Department of Nuclear Medicine, Seoul National University College of Medicine and Institute of Radiation Medicine, Medical Research Center) ;
  • Lee, Sang-Yoon (Neuroscience Research Institute, Gachon University) ;
  • Ido, Tatsuo (Neuroscience Research Institute, Gachon University)
  • Received : 2017.05.11
  • Accepted : 2017.06.20
  • Published : 2017.06.30
Download PDF
⟨ Previous Next ⟩

Abstract

Cis-(1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tertrahydro-N-methyl-1-naphthalenamine (sertraline) hydrochloride from among selective serotonin reuptake inhibitors (SSRIs) is a treatment of major depression. For the differential diagnosis by metabolizing serotonin in a patient with neurological disorders, the radiolabeled $^{11}C$-sertraline was developed for non-invasive positron emission tomography in living brain and use the evaluation of new drug for SSRIs. We release the results of a fast and easy radiolabeling method applied a one-step loop method with $[^{11}C]CH_3OTf$ for routine clinical applications of $^{11}C$-sertraline. 1 mg of a precursor for $^{11}C$-sertraline in 0.1 mL DMF and $5{\mu}L$ of 1N NaOH, were injected into the loop of semi-prep high-performance liquid chromatography (HPLC). $[^{11}C]CH_3OTf$ was passed through the loop at room temperature (RT). The $^{11}C$-sertraline was separated by the semi-preparative HPLC. $^{11}C$-sertraline was eluted at 28.0 min was collected and evaluated by analytical HPLC and mass spectrometer. The total radiolabeling efficiency of $^{11}C$-sertraline was $30.7{\pm}8.7%$. The specific activity was $64.8{\pm}51.4GBq/{\mu}mol$. The radiochemical and chemical purities were higher than 99%. The mass spectrum of the product showed m/z peaks at 307.1 (M+1), indicating the mass of sertraline. By the one-step loop method with $[^{11}C]CH_3OTf$, $^{11}C$-sertraline could be quickly and easily prepared for clinical application.

Keywords

References

  1. Murphy D, Lesch K, Aulakh C, Pigott T. Serotoninselective arylpiperazines with neuroendocrine, behavioral, temperature, and cardiovascular effects in humans. Pharmacol Rev 1991;43:527-52.
  2. Bowen DM, Francis PT, Chessell IP, Webster MT. Neurotransmission - The link integrating Alzheimer research? Trends in Neurosciences 1994;17:149-50. https://doi.org/10.1016/0166-2236(94)90091-4
  3. McLoughlin DM, Lucey JV, Dinan TG. Central serotonergic hyperresponsivity in late-onset Alzheimer's disease. American Journal of Psychiatry 1994;151:1701-3. https://doi.org/10.1176/ajp.151.11.1701
  4. Lucki I. The spectrum of behaviors influenced by serotonin. Biological Psychiatry 1998;44:151-62. https://doi.org/10.1016/S0006-3223(98)00139-5
  5. Vaswani M, Linda FK, Ramesh S. Role of selective serotonin reuptake inhibitors in psychiatric disorders: a comprehensive review. Progress in Neuro-Psychopharmacology and Biological Psychiatry 2003;27:85-102. https://doi.org/10.1016/S0278-5846(02)00338-X
  6. Welch WM, Kraska AR, Sarges R, Koe BK. Nontricyclic antidepressant agents derived from cis- and trans-1- amino-4-aryltetralins. Journal of Medicinal Chemistry 1984;27:1508-15. https://doi.org/10.1021/jm00377a021
  7. Vukics K, Fodor T, Fischer J, Fellegvari I, Levai S. Improved Industrial Synthesis of Antidepressant Sertraline. Organic Process Research & Development 2001;6:82-5.
  8. Lepola U, Arato M, Zhu Y, Austin C. Sertraline versus imipramine treatment of comorbid panic disorder and major depressive disorder. J Clin Psychiatry 2003;64:654-62. https://doi.org/10.4088/JCP.v64n0606
  9. Lasne MC, Pike VW, Turton DR. The radiosynthesis of [N-methyl-$^{11}C$]-sertraline. Applied Radiation and Isotopes 1989;40:147-51. https://doi.org/10.1016/0883-2889(89)90190-1
  10. Wilson AA, Garcia A, Jin L, Houle S. Radiotracer synthesis from [$(^{11})C$]-iodomethane: a remarkably simple captive solvent method. Nucl. Med. Biol. 2000;27:529-32. https://doi.org/10.1016/S0969-8051(00)00132-3
  11. Iwata R, Pascali C, Yuasa M, Yanai K, Takahashi T, Ido T. On-line [$^{11}C$]methylation using [$^{11}C$]methyl iodide for the automated preparation of $^{11}C$-radiopharmaceuticals. Applied Radiation and Isotopes 1992;43:1083-8. https://doi.org/10.1016/0883-2889(92)90048-J
  12. Wilson AA, Garcia A, Jin L, Houle S. Radiotracer synthesis from [$^{11}C$]-iodomethane: a remarkably simple captive solvent method. Nuclear Medicine and Biology 2000;27:529-32. https://doi.org/10.1016/S0969-8051(00)00132-3
  13. Iwata R, Pascali C, Bogni A, Miyake Y, Yanai K, Ido T. A simple loop method for the automated preparation of [$^{11}C$] raclopride from [$^{11}C$]methyl triflate. Applied Radiation and Isotopes 2001;55:17-22. https://doi.org/10.1016/S0969-8043(00)00368-7
  14. Jewett DM. A simple synthesis of [$^{11}C$]methyl triflate. Applied Radiation and Isotopes 1992;43:1383-5. https://doi.org/10.1016/0883-2889(92)90012-4
  15. Han Z, Koenig SG, Zhao H, Su X, Singh SP, Bakale RP. Development of a Large-Scale Stereoselective Process for (1R,4S)-4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydronaphthalen- 1-amine Hydrochloride. Organic Process Research & Development 2007;11:726-30. https://doi.org/10.1021/op7000589
  16. Jewett DM. A simple synthesis of [$^{11}C$]methyl triflate. Applied Radiation and Isotopes 1992;43:1383-5. https://doi.org/10.1016/0883-2889(92)90012-4
  17. Pavese N, Gerhard A, Tai YF, Ho AK, Turkheimer F, Barker RA, Brooks DJ, Piccini P. Microglial activation correlates with severity in Huntington disease: a clinical and PET study. Neurology 2006;66:1638-43. https://doi.org/10.1212/01.wnl.0000222734.56412.17
  18. Lee HJ, Jeong JM, Lee Y, Kim HW, Lee E, Lee DS, Chung J, Lee MC. Radiosynthesis of [$^{11}C$]6-OH-BTA-1 in Different Media and Confirmation of Reaction Byproducts. Nucl Med Mol Imaging 2007;41:241-6.