(20 R)-4,5-α-Epoxy-6-(2-[18F])fluoroethoxy)-3-hydroxy-α,17-dimethyl-α-(2-phenyleth-1-yl)-6,14-ethenomorphinan-7-methanol

Review
In: Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004.
[updated ].

Excerpt

Opioids such as morphine are analgesics that are commonly used in clinical practice. Three opioid receptors (mu, µ; delta, δ; and kappa, κ) that mediate opioid effects have been identified by molecular cloning: δ (enkephalin-preferring), κ (dynorphin-preferring), and µ (morphine- and ß-endorphin–preferring) (1). Each type of opioid receptor consists of subtypes of receptors, as suggested by pharmacological studies (2, 3). These receptors exhibit apparent specificity to both the central and the peripheral nervous systems, and their presence is ubiquitous in these systems. The opioid receptors (G-protein–coupled, resulting in decreased adenylyl cyclase activity) play an important role in the regulation of analgesia, shock, appetite, thermoregulation, and cardiovascular, mental, and endocrine function (2-5). Although µ opioid receptors are the major receptors to mediate the analgesic effects of opioids, δ and κ receptors are also important in antinociception. Opioids have been found to protect cells from ischemic injury in the heart and brain via the δ receptors. On the other hand, κ antagonists prevent neurodegeneration.

The µ opioid receptors are localized predominately in the hypothalamus and thalamus, and the δ opioid receptors are localized predominately in the striatum, limbic system, and cerebral cortex (6, 7). The κ opioid receptors (κ1 and κ2) are the most abundant brain opioid receptors and are widely distributed in deeper layers of the neocortex (particularly temporal, parietal, and frontal cortices), striatum, amygdala, and thalamus, with lower levels in the hippocampus, occipital cortex, and cerebellum (8-10). The κ opioid receptors have been implicated in several clinical brain disorders, including drug abuse (11), epilepsy (12), Tourette’s syndrome (13), and Alzheimer’s disease (14).

Diprenorphine is a highly potent and nonselective opioid receptor antagonist with subnanomolar affinity (7). Diprenorphine has been labeled as [6-O-methyl-11C]diprenorphine ([11C]DPN) (15, 16). [11C]DPN is being developed as a positron emission tomography (PET) agent for the noninvasive study of opioid receptors in the brain. However, pharmacological studies in humans (17) and rats (18) have demonstrated minimal competition between the high-efficacy agonists and the non-subtype–selective antagonist radioligand [11C]DPN, which limits the use of [11C]DPN PET to monitor in vivo occupancy (20R). -4,5-α-Epoxy-17-methyl-3-hydroxy-6-methoxy-α,17-dimethyl-α-(2-phenylethyl)-6,14-ethenomorphinan-7-methanol (PEO) has been found to be a highly potent opioid receptor agonist (19). [6-O-methyl-11C]PEO ([11C]PEO) was evaluated for use with PET imaging of opioid receptors in rats, and the agent showed specific accumulation in the striatum, thalamus, and frontal cortex. For 18F-labeling, Riss et al. (20) prepared (20R)-4,5-α-epoxy-6-(2-[18F]fluoroethoxy)-3-hydroxy-α,17-dimethyl-α-(2-phenyleth-1-yl)-6,14-ethenomorphinan-7-methanol ([18F]FE-PEO) for use with PET imaging of opioid receptors in the brain.

Publication types

  • Review