PMID- 28363750
OWN - NLM
STAT- MEDLINE
DCOM- 20170718
LR  - 20171124
IS  - 1464-3405 (Electronic)
IS  - 0960-894X (Linking)
VI  - 27
IP  - 9
DP  - 2017 May 1
TI  - Synthesis of PET probe O(6)-[(3-[(11)C]methyl)benzyl]guanine by Pd(0)-mediated 
      rapid C-[(11)C]methylation toward imaging DNA repair protein 
      O(6)-methylguanine-DNA methyltransferase in glioblastoma.
PG  - 1892-1896
LID - S0960-894X(17)30288-3 [pii]
LID - 10.1016/j.bmcl.2017.03.045 [doi]
AB  - O(6)-Benzylguanine (O(6)-BG) is a substrate of O(6)-methylguanine-DNA 
      methyltransferase (MGMT), which is involved in drug resistance of chemotherapy in 
      the majority of glioblastoma multiform. For clinical diagnosis, it is hoped that 
      the MGMT expression level could be determined by a noninvasive method to 
      understand the detailed biological properties of MGMT-specific tumors. We 
      synthesized (11)C-labeled O(6)-[(3-methyl)benzyl]guanine ([(11)C]mMeBG) as a 
      positron emission tomography probe. Thus, a mixed amine-protected stannyl 
      precursor, 
      N(9)-(tert-butoxycarbonyl)-O(6)-[3-(tributylstannyl)benzyl]-N(2)-(trifluoroacetyl)guanine, 
      was subjected to rapid C-[(11)C]methylation under 
      [(11)C]CH(3)I/[Pd(2)(dba)(3)]/P(o-CH(3)C(6)H(4))(3)/CuCl/K(2)CO(3) in NMP, 
      followed by quick deprotection with LiOH/H(2)O, giving [(11)C]mMeBG with total 
      radioactivity of 1.34GBq and >/=99% radiochemical and chemical purities.
CI  - Copyright (c) 2017 Elsevier Ltd. All rights reserved.
FAU - Koyama, Hiroko
AU  - Koyama H
AD  - Division of Regeneration and Advanced Medical Science, Gifu University Graduate 
      School of Medicine, 1-1 Yanagido, Gifu 501-1194, Japan. Electronic address: 
      hirokok@gifu-u.ac.jp.
FAU - Ikenuma, Hiroshi
AU  - Ikenuma H
AD  - Department of Clinical and Experimental Neuroimaging, Center for Development of 
      Advanced Medicine for Dementia, National Center for Geriatrics and Gerontology, 
      7-430 Morioka-cho, Obu-shi, Aichi 474-8511, Japan.
FAU - Toda, Hiroshi
AU  - Toda H
AD  - Department of Neurosurgery, Nagoya University School of Medicine, 65 
      Tsurumai-cho, Showa-ku, Nagoya 466-8550, Japan.
FAU - Kondo, Goro
AU  - Kondo G
AD  - Department of Neurosurgery, Nagoya University School of Medicine, 65 
      Tsurumai-cho, Showa-ku, Nagoya 466-8550, Japan.
FAU - Hirano, Masaki
AU  - Hirano M
AD  - Department of Neurosurgery, Nagoya University School of Medicine, 65 
      Tsurumai-cho, Showa-ku, Nagoya 466-8550, Japan.
FAU - Kato, Masaya
AU  - Kato M
AD  - Division of Regeneration and Advanced Medical Science, Gifu University Graduate 
      School of Medicine, 1-1 Yanagido, Gifu 501-1194, Japan.
FAU - Abe, Junichiro
AU  - Abe J
AD  - Department of Clinical and Experimental Neuroimaging, Center for Development of 
      Advanced Medicine for Dementia, National Center for Geriatrics and Gerontology, 
      7-430 Morioka-cho, Obu-shi, Aichi 474-8511, Japan.
FAU - Yamada, Takashi
AU  - Yamada T
AD  - Department of Food and Nutritional Science, College of Bioscience and 
      Biotechnology, Chubu University, Matsumoto-cho, Kasugai, Aichi 487-8501, Japan.
FAU - Wakabayashi, Toshihiko
AU  - Wakabayashi T
AD  - Department of Neurosurgery, Nagoya University School of Medicine, 65 
      Tsurumai-cho, Showa-ku, Nagoya 466-8550, Japan.
FAU - Ito, Kengo
AU  - Ito K
AD  - Department of Clinical and Experimental Neuroimaging, Center for Development of 
      Advanced Medicine for Dementia, National Center for Geriatrics and Gerontology, 
      7-430 Morioka-cho, Obu-shi, Aichi 474-8511, Japan.
FAU - Natsume, Atsushi
AU  - Natsume A
AD  - Department of Neurosurgery, Nagoya University School of Medicine, 65 
      Tsurumai-cho, Showa-ku, Nagoya 466-8550, Japan. Electronic address: 
      anatsume@med.nagoya-u.ac.jp.
FAU - Suzuki, Masaaki
AU  - Suzuki M
AD  - Department of Clinical and Experimental Neuroimaging, Center for Development of 
      Advanced Medicine for Dementia, National Center for Geriatrics and Gerontology, 
      7-430 Morioka-cho, Obu-shi, Aichi 474-8511, Japan. Electronic address: 
      suzukims@ncgg.go.jp.
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20170318
PL  - England
TA  - Bioorg Med Chem Lett
JT  - Bioorganic & medicinal chemistry letters
JID - 9107377
RN  - 0 (Carbon Radioisotopes)
RN  - 01KC87F8FE (O(6)-benzylguanine)
RN  - 5TWQ1V240M (Palladium)
RN  - 5Z93L87A1R (Guanine)
RN  - EC 2.1.1.63 (O(6)-Methylguanine-DNA Methyltransferase)
SB  - IM
MH  - Brain/*diagnostic imaging
MH  - Brain Neoplasms/*diagnostic imaging
MH  - Carbon Radioisotopes/*chemistry/metabolism
MH  - Glioblastoma/*diagnostic imaging
MH  - Guanine/*analogs & derivatives/chemistry/metabolism
MH  - Humans
MH  - Methylation
MH  - O(6)-Methylguanine-DNA Methyltransferase/*analysis/metabolism
MH  - Palladium/chemistry
MH  - Positron-Emission Tomography/*methods
OTO - NOTNLM
OT  - (11)C labeling
OT  - Brain cancer imaging
OT  - O(6)-Benzylguanine
OT  - Positron emission tomography probe
OT  - Rapid C-[(11)C]methylation
EDAT- 2017/04/02 06:00
MHDA- 2017/07/19 06:00
CRDT- 2017/04/02 06:00
PHST- 2016/12/26 00:00 [received]
PHST- 2017/02/28 00:00 [revised]
PHST- 2017/03/17 00:00 [accepted]
PHST- 2017/04/02 06:00 [pubmed]
PHST- 2017/07/19 06:00 [medline]
PHST- 2017/04/02 06:00 [entrez]
AID - S0960-894X(17)30288-3 [pii]
AID - 10.1016/j.bmcl.2017.03.045 [doi]
PST - ppublish
SO  - Bioorg Med Chem Lett. 2017 May 1;27(9):1892-1896. doi: 
      10.1016/j.bmcl.2017.03.045. Epub 2017 Mar 18.