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

28 Citationer (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.

Originalsprog	Engelsk
Tidsskrift	Bioorganic & Medicinal Chemistry Letters
Vol/bind	18
Udgave nummer	4
Sider (fra-til)	1515-9
Antal sider	5
ISSN	0960-894X
DOI	https://doi.org/10.1016/j.bmcl.2007.12.054
Status	Udgivet - 15 feb. 2008
Udgivet eksternt	Ja

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10.1016/j.bmcl.2007.12.054

Citationsformater

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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/diagnostic imaging, Fluorine Radioisotopes/chemistry, Fluorobenzenes/chemical synthesis, Isotope Labeling, Ketanserin/analogs \& derivatives, Kinetics, Piperidines/chemical synthesis, Radioligand Assay, Radionuclide Imaging, Radiopharmaceuticals/chemical synthesis, Rats, Receptor, Serotonin, 5-HT2A/metabolism, Serotonin 5-HT2 Receptor Antagonists, Serotonin Antagonists/chemical synthesis",

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",

month = feb,

day = "15",

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

language = "English",

volume = "18",

pages = "1515--9",

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 - 2008/2/15

Y1 - 2008/2/15

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/diagnostic imaging

KW - Fluorine Radioisotopes/chemistry

KW - Fluorobenzenes/chemical synthesis

KW - Isotope Labeling

KW - Ketanserin/analogs & derivatives

KW - Kinetics

KW - Piperidines/chemical synthesis

KW - Radioligand Assay

KW - Radionuclide Imaging

KW - Radiopharmaceuticals/chemical synthesis

KW - Rats

KW - Receptor, Serotonin, 5-HT2A/metabolism

KW - Serotonin 5-HT2 Receptor Antagonists

KW - Serotonin Antagonists/chemical synthesis

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

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