Fluorine-18 labeling of three novel D-peptides by conjugation with N-succinimidyl-4-[18F]fluorobenzoate and preliminary examination by postmortem whole-hemisphere human brain autoradiography

Nucl Med Biol. 2012 Apr;39(3):315-23. doi: 10.1016/j.nucmedbio.2011.09.008. Epub 2011 Dec 1.

Abstract

Introduction: β-Amyloid (Aβ) plaques and neurofibrillary tangles are the main characteristics of Alzheimer's disease (AD). Positron emission tomography (PET), a high-resolution, sensitive, and noninvasive imaging technique, has been widely utilized in visualizing the localization of plaques and tangles and thereby distinguishing between AD and healthy controls. A small 12-mer D-enantiomeric peptide (amino acid sequence=QSHYRHISPAQV), denoted as D1, has high binding affinity to Aβ in vitro in the sub-micromolar range, and consequently, its radiolabeled analogues have a potential as radioligands for visualizing amyloid plaques in vivo by PET.

Aim: The aims of the present work were to develop three different potent D1 derivative peptides labeled with fluorine-18 and to examine them in the AD and control postmortem human brain by autoradiography (ARG).

Methods: Three different D1 derivative peptides were radiolabeled with fluorine-18 ([(18)F]ACI-87, [(18)F]ACI-88, [(18)F]ACI-89) using the prosthetic group N-succinimidyl-4-[(18)F]fluorobenzoate ([(18)F]SFB) and purified by high performance liquid chromatography (HPLC). Preliminary ARG measurements were performed in AD and control brains.

Results: The three fluorine-18-labeled d-peptides were obtained in a total synthesis time of 140 min with radiochemical purity higher than 98%. The specific radioactivities of the three different D1 derivative peptides were between 9 and 113 GBq/μmol. ARG demonstrated a higher radioligand uptake in the cortical gray matter and the hippocampus in the AD brain as compared to age-matched control brain.

Conclusions: Fluorine-18 labeling of the three novel D1 derivative peptides using [(18)F]SFB was successfully accomplished. Higher contrast between AD and control brain slices demonstrates their potential applicability for further use in vivo by PET.

MeSH terms

  • Alzheimer Disease / diagnosis
  • Alzheimer Disease / diagnostic imaging
  • Autoradiography / methods*
  • Benzoates / chemical synthesis
  • Benzoates / chemistry*
  • Binding, Competitive
  • Brain / diagnostic imaging*
  • Brain / metabolism
  • Female
  • Fluorine Radioisotopes / chemistry*
  • Hippocampus / diagnostic imaging
  • Hippocampus / metabolism
  • Humans
  • Isotope Labeling / methods
  • Male
  • Middle Aged
  • Molecular Structure
  • Oligopeptides / chemical synthesis
  • Oligopeptides / chemistry*
  • Radiographic Image Enhancement
  • Radionuclide Imaging
  • Radiopharmaceuticals / chemical synthesis*
  • Radiopharmaceuticals / chemistry
  • Succinimides / chemical synthesis
  • Succinimides / chemistry*

Substances

  • Benzoates
  • D1 peptide
  • Fluorine Radioisotopes
  • Oligopeptides
  • Radiopharmaceuticals
  • Succinimides
  • N-succinimidyl-4-fluorobenzoate