SpringerLink
Log in

Radioiodination of 4-benzyl-1-(3-iodobenzylsulfonyl)piperidine, 4-(3-iodobenzyl)-1-(benzylsulfonyl)piperazine and their derivatives via isotopic and non-isotopic exchange reactions

  • Published:
Journal of Radioanalytical and Nuclear Chemistry Aims and scope Submit manuscript

Abstract

A mild and simple technique for preparing of 4-benzyl-1-(3-[125I]iodobenzylsulfonyl)piperidine, 4-(3-[125I]iodobenzyl)-1-(benzylsulfonyl)piperazine and their derivatives, as sigma-1 receptor ligands, with relatively high radiochemical yields via nucleophilic substitution reaction by means of isotopic and non-isotopic exchange reactions is described. Some factors affecting the radiochemical yield were commonly studied in presence of acidic medium at elevated temperature. Unfortunately, the radiochemical yields were weak. Some attempts were carried out in presence of polar aprotic solvents to enhance the radiochemical yield. N,N-Dimethylformamide was proved highly efficient for preparing of radioiodinated 4-benzyl-1-(3-iodobenzylsulfonyl)piperidine (4-B-[125I]-IBSP, 70 ± 5.7 %) and 4-(3-iodobenzyl)-1-(benzylsulfonyl)piperazine (4-[125I]-IBBSPz, 72 ± 6.0 %) at moderate temperature (100–105 °C) within 8 h. The specific activities of 4-B-[125I]-IBSP and 4-[125I]-IBBSPz (6,534.2 and 5,927.4 MBq/mmol) were obtained respectively.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price includes VAT (United Kingdom)

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1

Similar content being viewed by others

References

  1. Koehler L, Gagnon K, McQuarrie S, Wuest F (2010) Molecules 15:2686–2718

    Article  CAS  Google Scholar 

  2. Eersels JLH, Travis MJ, Herscheid JDM (2005) J Label Compd Radiopharm 48:241–257

    Article  CAS  Google Scholar 

  3. Seevers RH, Counsell RE (1982) Chem Rev 82:575–590

    Article  CAS  Google Scholar 

  4. Rønnest MH, Nissen F, Pedersen PJ, Larsen TO, Mier W, Clausen MH (2013) Eur J Org Chem 2013:3970–3973

    Article  Google Scholar 

  5. Eisenhut M, Hull WE, Mohammed A, Mier W, Lay D, Just W, Gorgas K, Lehmann WD, Haberkorn U (2000) J Med Chem 43:3913–3922

    Article  CAS  Google Scholar 

  6. Vaidyanathan G, White B, Affleck DJ, McDougald D, Zalutsky MR (2011) Nucl Med Biol 38:77–92

    Article  CAS  Google Scholar 

  7. Akgu E, Portoghese PS, Sajjad M, Nabi HA (2007) J Label Compd Radiopharm 50:165–170

    Article  Google Scholar 

  8. Kabalka GW, Yao ML, Akula MR, Yong L (2012) Pure Appl Chem 84:2309–2315

    Article  CAS  Google Scholar 

  9. Akula MR, Yao ML, Kabalka GW (2011) J Label Compd Radiopharm 54:132–134

    Article  CAS  Google Scholar 

  10. Stahlschmidt A, Machulla H-J, Reischl G, Knaus EE, Wiebe LI (2008) Appl Radiat Isot 66:1221–1228

    Article  CAS  Google Scholar 

  11. Tsopelas C (1999) Nucl Med Biol 26:591–595

    Article  CAS  Google Scholar 

  12. Schneider RF, Engelhardt EL, Stobbe CC, Fenning MC, Chapman JD (1997) J Label Compd Radiopharm 39:541–557

    Article  CAS  Google Scholar 

  13. Wafelman AR, Konings MCP, Hoefnagel CA, Maes RAA, Beijnen JH (1994) Appl Radiat Isot 45:997–1007

    Article  CAS  Google Scholar 

  14. Liefhold J, Eisenhut M (1986) J Label Compd Radiopharm 23:1239

    Google Scholar 

  15. Eisenhut M (1982) Int J Appl Radiat Isot 33:499–504

    Article  CAS  Google Scholar 

  16. Adam MJ, Wilbur DS (2005) Chem Soc Rev 34:153–163

    Article  CAS  Google Scholar 

  17. Farah K, El-Mohty AA, El-Ghany EA (1999) J Radioanal Nucl Chem 240:243–249

    Article  CAS  Google Scholar 

  18. Owens J, Murray T, McCulloch J, Wyper D (1992) J Label Compd Radiopharm 31:45–60

    Article  CAS  Google Scholar 

  19. Martin WR, Eades CG, Thompson JA, Huppler RE, Gilbert PE (1976) J Pharmac Exp Ther 197:517–532

    CAS  Google Scholar 

  20. Abou-Gharbia M, Ablordeppey SY, Glennon RA (1993) Annu Rep Med Chem 28:1–10

    Article  CAS  Google Scholar 

  21. Guitart X, Codony X, Monroy X (2004) Psychopharmacology 174:301–319

    Article  CAS  Google Scholar 

  22. Hou C, Tu Z, Mach R, Kung HF, Kung M-P (2006) Nucl Med Biol 33:203–209

    Article  CAS  Google Scholar 

  23. Akhter N, Shiba K, Ogawa K, Tsuji S, Kinuya S, Nakajima K, Mori H (2008) Nucl Med Biol 35:29–34

    Article  CAS  Google Scholar 

  24. Kawamura K, Kubota K, Kobayashi T, Elsinga PH, Ono M, Maeda M, Ishiwata K (2005) Ann Nucl Med 19:701–709

    Article  CAS  Google Scholar 

  25. Chu W, Xu J, Zhou D, Zhang F, Jones LA, Wheeler KT, Mach RH (2009) Bioorg Med Chem 17:1222–1231

    Article  CAS  Google Scholar 

  26. Waterhouse RN, Mardon K, O’Brien JC (1997) Nucl Med Biol 24:45–51

    Article  CAS  Google Scholar 

  27. Waterhouse RN, Chapman J, Izard B, Donald A, Belbin K, O’Brien JC, Collier TL (1997) Nucl Med Biol 24:587–593

    Article  CAS  Google Scholar 

  28. Collier TL, O’Brien JC, Waterhouse RN (1996) J Label Compd Radiopharm 38:785–794

    Article  CAS  Google Scholar 

  29. Waterhouse RN, Collier TL (1997) Nucl Med Biol 24:127–134

    Article  CAS  Google Scholar 

  30. Sadeghzadeh M, Sheibani S, Ghandi M, Johari Daha F, Amanlou M, Arjmand M, Hasani Bozcheloie A (2013) Eur J Med Chem 64:488–497

    Article  CAS  Google Scholar 

  31. Moroz MA, Serganova I, Zanzonico P, Ageyeva L, Beresten T, Dyomina E, Burnazi E, Finn RD, Doubrovin M, Blasberg RG (2007) J Nucl Med 48:827–836

    Article  CAS  Google Scholar 

  32. Reischl G, Dorow DS, Cullinane C, Katsifis A, Roselt P, Binns D, Hicks RJ (2007) J Pharm Pharmaceut Sci 10:203–211

    CAS  Google Scholar 

  33. Zanzonico P, O’Donoghue J, Chapman JD, Schneider R, Cai S, Larson SD, Wen BX, Chen YC, Finn R, Ruan ST, Gerweck L, Humm J, Ling C (2004) Eur J Nucl Med 31:117–128

    Article  Google Scholar 

  34. The dielectric constant values of the solvents were obtained from ChemFinder Web Server, the CRC, or Vogel’s Practical Organic Chemistry (5th ed.); T = 20 °C unless specified otherwise

  35. Carey FA, Sundberg RJ (2007) Advanced organic chemistry Part A: structure and mechanisms. Springer, New York

    Google Scholar 

  36. Kahn M, Wahl AC (1953) J Chem Phys 21:1185–1189

    Article  CAS  Google Scholar 

  37. Cvoric J (1969) J Chromatogr 44:349–361

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Financial support by Radiation Application research School of Nuclear Science & Technology Research Institute is gratefully acknowledged.

Author information

Authors and Affiliations

  1. Radiation Application Research School, Nuclear Science and Technology Research Institute, NSTRI, P.O. Box 11365-3486, Tehran, Iran

    Masoud Sadeghzadeh, Fariba Johari Daha, Shahab Sheibani & Mostafa Erfani

Authors
  1. Masoud Sadeghzadeh
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Fariba Johari Daha
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Shahab Sheibani
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Mostafa Erfani
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Masoud Sadeghzadeh.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sadeghzadeh, M., Johari Daha, F., Sheibani, S. et al. Radioiodination of 4-benzyl-1-(3-iodobenzylsulfonyl)piperidine, 4-(3-iodobenzyl)-1-(benzylsulfonyl)piperazine and their derivatives via isotopic and non-isotopic exchange reactions. J Radioanal Nucl Chem 302, 1119–1125 (2014). https://doi.org/10.1007/s10967-014-3347-z

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10967-014-3347-z

Keywords

Search

Navigation