In Vivo Differences between Two Optical Isomers of Radioiodinated o-iodo-trans-decalinvesamicol for Use as a Radioligand for the Vesicular Acetylcholine Transporter

PLoS One. 2016 Jan 11;11(1):e0146719. doi: 10.1371/journal.pone.0146719. eCollection 2016.

Abstract

Purpose: To develop a superior VAChT imaging probe for SPECT, radiolabeled (-)-OIDV and (+)-OIDV were isolated and investigated for differences in their binding affinity and selectivity to VAChT, as well as their in vivo activities.

Procedures: Radioiodinated o-iodo-trans-decalinvesamicol ([125I]OIDV) has a high binding affinity for vesicular acetylcholine transporter (VAChT) both in vitro and in vivo. Racemic [125I]OIDV was separated into its two optical isomers (-)-[125I]OIDV and (+)-[125I]OIDV by HPLC. To investigate VAChT binding affinity (Ki) of two OIDV isomers, in vitro binding assays were performed. In vivo biodistribution study of each [125I]OIDV isomer in blood, brain regions and major organs of rats was performed at 2,30 and 60 min post-injection. In vivo blocking study were performed to reveal the binding selectivity of two [125I]OIDV isomers to VAChT in vivo. Ex vivo autoradiography were performed to reveal the regional brain distribution of two [125I]OIDV isomers and (-)-[123I]OIDV for SPECT at 60 min postinjection.

Results: VAChT binding affinity (Ki) of (-)-[125I]OIDV and (+)-[125I]OIDV was 22.1 nM and 79.0 nM, respectively. At 2 min post-injection, accumulation of (-)-[125I]OIDV was the same as that of (+)-[125I]OIDV. However, (+)-[125I]OIDV clearance from the brain was faster than (-)-[125I]OIDV. At 30 min post-injection, accumulation of (-)-[125I]OIDV (0.62 ± 0.10%ID/g) was higher than (+)-[125I]OIDV (0.46 ± 0.07%ID/g) in the cortex. Inhibition of OIDV binding showed that (-)-[125I]OIDV was selectively accumulated in regions known to express VAChT in the rat brain, and ex vivo autoradiography further confirmed these results showing similar accumulation of (-)-[125I]OIDV in these regions. Furthermore, (-)-[123I]OIDV for SPECT showed the same regional brain distribution as (-)-[125I]OIDV.

Conclusion: These results suggest that radioiodinated (-)-OIDV may be a potentially useful tool for studying presynaptic cholinergic neurons in the brain.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Autoradiography
  • Binding, Competitive
  • Crystallography, X-Ray
  • Halogenation*
  • Isomerism
  • Ligands
  • Male
  • Optical Phenomena*
  • Piperidines / chemistry*
  • Piperidines / metabolism*
  • Radiopharmaceuticals / chemistry
  • Radiopharmaceuticals / metabolism*
  • Rats, Sprague-Dawley
  • Receptors, sigma / metabolism
  • Tissue Distribution
  • Vesicular Acetylcholine Transport Proteins / metabolism*

Substances

  • Ligands
  • Piperidines
  • Radiopharmaceuticals
  • Receptors, sigma
  • Vesicular Acetylcholine Transport Proteins
  • o-iodo-trans-decalinvesamicol

Grants and funding

This work was supported by a Grant-in-Aid for Scientific Research (B) (No. 26293273) from the Ministry of Education, Culture, Sports, Science and Technology of Japan.