Total synthesis and evaluation of [18F]MHMZ

Matthias M Herth; Fabian Debus; Markus Piel; Mikael Palner; Gitte M Knudsen; Hartmut Lüddens; Frank Rösch

doi:10.1016/j.bmcl.2007.12.054

Total synthesis and evaluation of [18F]MHMZ

Matthias M Herth, Fabian Debus, Markus Piel, Mikael Palner, Gitte M Knudsen, Hartmut Lüddens, Frank Rösch

22 Citations (Scopus)

Abstract

Radiochemical labeling of MDL 105725 using the secondary labeling precursor 2-[(18)F]fluoroethyltosylate ([(18)F]FETos) was carried out in yields of approximately 90% synthesizing [(18)F]MHMZ in a specific activity of approximately 50MBq/nmol with a starting activity of approximately 3GBq. Overall radiochemical yield including [(18)F]FETos synthon synthesis, [(18)F]fluoroalkylation and preparing the injectable [(18)F]MHMZ solution was 42% within a synthesis time of approximately 100 min. The novel compound showed excellent specific binding to the 5-HT(2A) receptor (K(i)=9.0 nM) in vitro and promising in vivo characteristics.

Original language	English
Journal	Bioorganic & Medicinal Chemistry Letters
Volume	18
Issue number	4
Pages (from-to)	1515-1519
Number of pages	5
ISSN	0960-894X
DOIs	https://doi.org/10.1016/j.bmcl.2007.12.054
Publication status	Published - 2008

Keywords

Animals
Binding, Competitive
Brain
Fluorine Radioisotopes
Fluorobenzenes
Isotope Labeling
Ketanserin
Kinetics
Piperidines
Radioligand Assay
Radiopharmaceuticals
Rats
Receptor, Serotonin, 5-HT2A
Serotonin 5-HT2 Receptor Antagonists
Serotonin Antagonists

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10.1016/j.bmcl.2007.12.054

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title = "Total synthesis and evaluation of [18F]MHMZ",

abstract = "Radiochemical labeling of MDL 105725 using the secondary labeling precursor 2-[(18)F]fluoroethyltosylate ([(18)F]FETos) was carried out in yields of approximately 90% synthesizing [(18)F]MHMZ in a specific activity of approximately 50MBq/nmol with a starting activity of approximately 3GBq. Overall radiochemical yield including [(18)F]FETos synthon synthesis, [(18)F]fluoroalkylation and preparing the injectable [(18)F]MHMZ solution was 42% within a synthesis time of approximately 100 min. The novel compound showed excellent specific binding to the 5-HT(2A) receptor (K(i)=9.0 nM) in vitro and promising in vivo characteristics.",

keywords = "Animals, Binding, Competitive, Brain, Fluorine Radioisotopes, Fluorobenzenes, Isotope Labeling, Ketanserin, Kinetics, Piperidines, Radioligand Assay, Radiopharmaceuticals, Rats, Receptor, Serotonin, 5-HT2A, Serotonin 5-HT2 Receptor Antagonists, Serotonin Antagonists",

author = "Herth, {Matthias M} and Fabian Debus and Markus Piel and Mikael Palner and Knudsen, {Gitte M} and Hartmut L{\"u}ddens and Frank R{\"o}sch",

year = "2008",

doi = "10.1016/j.bmcl.2007.12.054",

language = "English",

volume = "18",

pages = "1515--1519",

journal = "Bioorganic & Medicinal Chemistry Letters",

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TY - JOUR

T1 - Total synthesis and evaluation of [18F]MHMZ

AU - Herth, Matthias M

AU - Debus, Fabian

AU - Piel, Markus

AU - Palner, Mikael

AU - Knudsen, Gitte M

AU - Lüddens, Hartmut

AU - Rösch, Frank

PY - 2008

Y1 - 2008

N2 - Radiochemical labeling of MDL 105725 using the secondary labeling precursor 2-[(18)F]fluoroethyltosylate ([(18)F]FETos) was carried out in yields of approximately 90% synthesizing [(18)F]MHMZ in a specific activity of approximately 50MBq/nmol with a starting activity of approximately 3GBq. Overall radiochemical yield including [(18)F]FETos synthon synthesis, [(18)F]fluoroalkylation and preparing the injectable [(18)F]MHMZ solution was 42% within a synthesis time of approximately 100 min. The novel compound showed excellent specific binding to the 5-HT(2A) receptor (K(i)=9.0 nM) in vitro and promising in vivo characteristics.

AB - Radiochemical labeling of MDL 105725 using the secondary labeling precursor 2-[(18)F]fluoroethyltosylate ([(18)F]FETos) was carried out in yields of approximately 90% synthesizing [(18)F]MHMZ in a specific activity of approximately 50MBq/nmol with a starting activity of approximately 3GBq. Overall radiochemical yield including [(18)F]FETos synthon synthesis, [(18)F]fluoroalkylation and preparing the injectable [(18)F]MHMZ solution was 42% within a synthesis time of approximately 100 min. The novel compound showed excellent specific binding to the 5-HT(2A) receptor (K(i)=9.0 nM) in vitro and promising in vivo characteristics.

KW - Animals

KW - Binding, Competitive

KW - Brain

KW - Fluorine Radioisotopes

KW - Fluorobenzenes

KW - Isotope Labeling

KW - Ketanserin

KW - Kinetics

KW - Piperidines

KW - Radioligand Assay

KW - Radiopharmaceuticals

KW - Rats

KW - Receptor, Serotonin, 5-HT2A

KW - Serotonin 5-HT2 Receptor Antagonists

KW - Serotonin Antagonists

U2 - 10.1016/j.bmcl.2007.12.054

DO - 10.1016/j.bmcl.2007.12.054

M3 - Journal article

C2 - 18187324

SN - 0960-894X

VL - 18

SP - 1515

EP - 1519

JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

IS - 4

ER -

Total synthesis and evaluation of [18F]MHMZ

Abstract

Keywords

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