Radiofluorinated histamine H3 receptor antagonist as a potential probe for in vivo PET imaging: Radiosynthesis and pharmacological evaluation

Selivanova, Svetlana V.; Honer, Michael; Combe, Francine; Isensee, Kathleen; Stark, Holger; Krämer, Stefanie-Dorothea; Schubiger, P. August; Ametamey, Simon M.

doi:10.1016/j.bmc.2012.03.024

Cited by 12 publications

(4 citation statements)

References 39 publications

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“…For the radiosynthesis of [ 18 F]ST‐889, the mesyl group of the corresponding precursor was substituted by [ 18 F]fluoride within 30 min (Scheme ). In a total synthesis time of ~100 min, the radioligand could be obtained with an RCY of 8–20%, an RCP >99%, and a specific activity ≥65 GBq/µmol . PET imaging in rats demonstrated only a remarkably high and persistent glandular accumulation of the radioligand.…”

Section: Radioligands For the Histamine H3 Receptormentioning

confidence: 99%

¹¹C‐labeled and ¹⁸F‐labeled PET ligands for subtype‐specific imaging of histamine receptors in the brain

Funke

Vugts

Janssen

et al. 2013

Labelled Comp Radiopharmac

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The signaling molecule histamine plays a key role in the mediation of immune reactions, in gastric secretion, and in the sensory system. In addition, it has an important function as a neurotransmitter in the central nervous system, acting in pituitary hormone secretion, wakefulness, motor and cognitive functions, as well as in itch and nociception. This has raised interest in the role of the histaminergic system for the treatment and diagnosis of various pathologies such as allergy, sleeping and eating disorders, neurodegeneration, neuroinflammation, mood disorders, and pruritus. In the past 20 years, several ligands targeting the four different histamine receptor subtypes have been explored as potential radiotracers for positron emission tomography (PET). This contribution provides an overview of the developments of subtype-selective carbon-11-labeled and fluorine-18-labeled compounds for imaging in the brain. Using specific radioligands, the H1 R expression in human brain could be examined in diseases such as schizophrenia, depression, and anorexia nervosa. In addition, the sedative effects of antihistamines could be investigated in terms of H1 R occupancy. The H3 R is of special interest because of its regulatory role in the release of various other neurotransmitters, and initial H3 R PET imaging studies in humans have been reported. The H4 R is the youngest member of the histamine receptor family and is involved in neuroinflammation and various sensory pathways. To date, two H4 R-specific (11) C-labeled ligands have been synthesized, and the imaging of the H4 R in vivo is in the early stage.

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Section: Radioligands For the Histamine H3 Receptormentioning

confidence: 99%

¹¹C‐labeled and ¹⁸F‐labeled PET ligands for subtype‐specific imaging of histamine receptors in the brain

Funke

Vugts

Janssen

et al. 2013

Labelled Comp Radiopharmac

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“…It is often just a matter of taste and convenience, which group will be displaced by the radioactive fluorine, with tosylate being the most popular. Recent examples include the labelling of pyridaben 86 derivatives, a histamine H-3 receptor antagonist, 87 FE-PE21 (for imaging dopamine transporters) 88 and fluoroethyl cyclofenil analogs. 89 Other good leaving groups in a nucleophilic aromatic substitution are nitro-as in the preparation of 4-[F18]fluoro-3-nitro-N-2-propyn-1-yl-benzamide, 90 from the 3,4-dinitro-compound, and in the labelling of brain histamine sub-type-3 receptors; 91 trimethylammonium is also easily replaced by fluoride-18, a key step in preparation of [F18] hippurate 92 and of labelled fluorobenzyl halide 93 derivatives.…”

Section: Fluorine (F 18 )mentioning

confidence: 99%

Radiochemistry

Urch

2013

Annu. Rep. Prog. Chem., Sect. A: Inorg. Chem.

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In this year's review of recent progress in radiochemistry, new radiochemical methods for isotope production, advances in labelling procedures, radioactive isotopes in the environment and miscellaneous topics of radiochemical interest, will be covered but not radiation chemistry, neutron activation analysis and the chemistry of elements that happen to be radioactive. HighlightsThe incorporation of radioisotopes into, sometimes onto, nanoparticles, is becoming increasingly important in nuclear medicine, for therapy and also in diagnosis (ref. 108, 109, 148, 149, 153 and 261-264). Another important piece of work was the use of density functional theory to predict the properties and behaviour of a labelled molecule (ref. 130). General introductionIt is with great sadness that the death of Michael J. Welch in May of 2012 must be recorded. He it was who brought radiochemistry to the medical world, who demonstrated, to a sceptical audience, the potential that radioactive molecules had, when combined with tomography, for diagnosis and tumour location. For forty years he ceaselessly developed nuclear medicine, extending its range to more and more positron emitting isotopes and developing new chemical ways of incorporating them into increasingly complex bio-molecules, 'radiopharmaceuticals'.No new books on radiochemistry in 2012, but a review 1 of the discovery of artificial radioactivity and the report 2 of a conference on the synthesis and applications of labelled compounds have been published. Other conferences have been more focused on specific aspects of the preparation and uses of radioactive compounds, for medical diagnosis and therapy, 3 for autoradiography 4 and to study drug metabolism. 5 A history of the use of radio-iodine has published 6 and the design of bifunctional chelating molecules, 7,8 which can both encapsulate a radioactive atom and join benignly (one hopes so) to a protein or other bio-molecule, reviewed.

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“…Histamine is a biogenic amine that influences a wide range of pathophysiological processes through the activation of different G-protein-coupled receptors (GPCRs). Four subtypes of histamine GPCRs are known [8,9,10,11,12,13]. Histamine H 3 receptor is a G protein-coupled receptor whose activation inhibits the synthesis and release of histamine; in addition to other neurotransmitters from nerve endings and is involved in the modulation of different central nervous system functions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2-[{4-(t-amino-1-yl) but-2-yn-1-yl }oxy]-1,3- benzothiazole derivatives as H3-antagonists

Rahmani¹,

kaissi²,

Arafat³

et al. 2014

iosrphr

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Radiofluorinated histamine H3 receptor antagonist as a potential probe for in vivo PET imaging: Radiosynthesis and pharmacological evaluation

Cited by 12 publications

References 39 publications

¹¹C‐labeled and ¹⁸F‐labeled PET ligands for subtype‐specific imaging of histamine receptors in the brain

¹¹C‐labeled and ¹⁸F‐labeled PET ligands for subtype‐specific imaging of histamine receptors in the brain

Radiochemistry

Synthesis of 2-[{4-(t-amino-1-yl) but-2-yn-1-yl }oxy]-1,3- benzothiazole derivatives as H3-antagonists

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Radiofluorinated histamine H3 receptor antagonist as a potential probe for in vivo PET imaging: Radiosynthesis and pharmacological evaluation

Cited by 12 publications

References 39 publications

11C‐labeled and 18F‐labeled PET ligands for subtype‐specific imaging of histamine receptors in the brain

11C‐labeled and 18F‐labeled PET ligands for subtype‐specific imaging of histamine receptors in the brain

Radiochemistry

Synthesis of 2-[{4-(t-amino-1-yl) but-2-yn-1-yl }oxy]-1,3- benzothiazole derivatives as H3-antagonists

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¹¹C‐labeled and ¹⁸F‐labeled PET ligands for subtype‐specific imaging of histamine receptors in the brain

¹¹C‐labeled and ¹⁸F‐labeled PET ligands for subtype‐specific imaging of histamine receptors in the brain