Synthesis of carbon-11 labeled biaryl 1,2,3,4-tetrahydroisoquinoline derivatives and conformationally flexible analogues as new potential PET glioma tumor imaging agents

Min Wang, Mingzhang Gao, Kathy Miller, George W. Sledge, Qi-Huang Zheng

Research output: Contribution to journalArticle

Abstract

Carbon-11 labeled biaryl 1,2,3,4-tetrahydroisoquinoline derivatives and conformationally flexible analogues, 2-(2-(biphenyl-4-yl)ethyl)-6-[11C]methoxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline ([11C]3); 1-(biphenyl-4-yl)methyl-6,7-dimethoxy-2-[11C]methyl-1,2,3,4-tetrahydroisoquinoline (N-[11C]7) and 1-(biphenyl-4-yl)methyl-6-[11C]methoxy-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (O-[11C]7); and 2-(biphenyl-4-yl)-N-(3,4-dimethoxy-phenethyl)-N-[11C]methyl-ethanamine (N-[11C]10) and 2-(biphenyl-4-yl)-N-(3-methoxy-4-[11C]methoxy-phenethyl)-N-methyl-ethanamine (O-[11C]10), have been synthesized as new potential positron emission tomography (PET) glioma tumor imaging agents, either by O-[11C]methylation or by N-[11C]methylation of the appropriate precursors using [11C]CH3OTf and isolated either by a simplified solid-phase extraction (SPE) purification procedure or by HPLC method in 30-55% radiochemical yields decay corrected to EOB, 15-25 min overall synthesis time, and 4.0-6.0 Ci/μmol specific activity at EOB.

Original languageEnglish
Pages (from-to)1152-1159
Number of pages8
JournalApplied Radiation and Isotopes
Volume65
Issue number10
DOIs
StatePublished - Oct 2007

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methylation
positrons
tumors
tomography
analogs
carbon
synthesis
purification
solid phases
decay

Keywords

  • Biaryl 1,2,3,4-tetrahydroisoquinoline derivatives
  • Carbon-11
  • Conformationally flexible analogues
  • Gliomas
  • Imaging
  • Positron emission tomography (PET)

ASJC Scopus subject areas

  • Radiation

Cite this

@article{b40151680e5845118c897f9ae8132500,
title = "Synthesis of carbon-11 labeled biaryl 1,2,3,4-tetrahydroisoquinoline derivatives and conformationally flexible analogues as new potential PET glioma tumor imaging agents",
abstract = "Carbon-11 labeled biaryl 1,2,3,4-tetrahydroisoquinoline derivatives and conformationally flexible analogues, 2-(2-(biphenyl-4-yl)ethyl)-6-[11C]methoxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline ([11C]3); 1-(biphenyl-4-yl)methyl-6,7-dimethoxy-2-[11C]methyl-1,2,3,4-tetrahydroisoquinoline (N-[11C]7) and 1-(biphenyl-4-yl)methyl-6-[11C]methoxy-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (O-[11C]7); and 2-(biphenyl-4-yl)-N-(3,4-dimethoxy-phenethyl)-N-[11C]methyl-ethanamine (N-[11C]10) and 2-(biphenyl-4-yl)-N-(3-methoxy-4-[11C]methoxy-phenethyl)-N-methyl-ethanamine (O-[11C]10), have been synthesized as new potential positron emission tomography (PET) glioma tumor imaging agents, either by O-[11C]methylation or by N-[11C]methylation of the appropriate precursors using [11C]CH3OTf and isolated either by a simplified solid-phase extraction (SPE) purification procedure or by HPLC method in 30-55{\%} radiochemical yields decay corrected to EOB, 15-25 min overall synthesis time, and 4.0-6.0 Ci/μmol specific activity at EOB.",
keywords = "Biaryl 1,2,3,4-tetrahydroisoquinoline derivatives, Carbon-11, Conformationally flexible analogues, Gliomas, Imaging, Positron emission tomography (PET)",
author = "Min Wang and Mingzhang Gao and Kathy Miller and Sledge, {George W.} and Qi-Huang Zheng",
year = "2007",
month = "10",
doi = "10.1016/j.apradiso.2007.05.006",
language = "English",
volume = "65",
pages = "1152--1159",
journal = "Applied Radiation and Isotopes",
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T1 - Synthesis of carbon-11 labeled biaryl 1,2,3,4-tetrahydroisoquinoline derivatives and conformationally flexible analogues as new potential PET glioma tumor imaging agents

AU - Wang, Min

AU - Gao, Mingzhang

AU - Miller, Kathy

AU - Sledge, George W.

AU - Zheng, Qi-Huang

PY - 2007/10

Y1 - 2007/10

N2 - Carbon-11 labeled biaryl 1,2,3,4-tetrahydroisoquinoline derivatives and conformationally flexible analogues, 2-(2-(biphenyl-4-yl)ethyl)-6-[11C]methoxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline ([11C]3); 1-(biphenyl-4-yl)methyl-6,7-dimethoxy-2-[11C]methyl-1,2,3,4-tetrahydroisoquinoline (N-[11C]7) and 1-(biphenyl-4-yl)methyl-6-[11C]methoxy-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (O-[11C]7); and 2-(biphenyl-4-yl)-N-(3,4-dimethoxy-phenethyl)-N-[11C]methyl-ethanamine (N-[11C]10) and 2-(biphenyl-4-yl)-N-(3-methoxy-4-[11C]methoxy-phenethyl)-N-methyl-ethanamine (O-[11C]10), have been synthesized as new potential positron emission tomography (PET) glioma tumor imaging agents, either by O-[11C]methylation or by N-[11C]methylation of the appropriate precursors using [11C]CH3OTf and isolated either by a simplified solid-phase extraction (SPE) purification procedure or by HPLC method in 30-55% radiochemical yields decay corrected to EOB, 15-25 min overall synthesis time, and 4.0-6.0 Ci/μmol specific activity at EOB.

AB - Carbon-11 labeled biaryl 1,2,3,4-tetrahydroisoquinoline derivatives and conformationally flexible analogues, 2-(2-(biphenyl-4-yl)ethyl)-6-[11C]methoxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline ([11C]3); 1-(biphenyl-4-yl)methyl-6,7-dimethoxy-2-[11C]methyl-1,2,3,4-tetrahydroisoquinoline (N-[11C]7) and 1-(biphenyl-4-yl)methyl-6-[11C]methoxy-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (O-[11C]7); and 2-(biphenyl-4-yl)-N-(3,4-dimethoxy-phenethyl)-N-[11C]methyl-ethanamine (N-[11C]10) and 2-(biphenyl-4-yl)-N-(3-methoxy-4-[11C]methoxy-phenethyl)-N-methyl-ethanamine (O-[11C]10), have been synthesized as new potential positron emission tomography (PET) glioma tumor imaging agents, either by O-[11C]methylation or by N-[11C]methylation of the appropriate precursors using [11C]CH3OTf and isolated either by a simplified solid-phase extraction (SPE) purification procedure or by HPLC method in 30-55% radiochemical yields decay corrected to EOB, 15-25 min overall synthesis time, and 4.0-6.0 Ci/μmol specific activity at EOB.

KW - Biaryl 1,2,3,4-tetrahydroisoquinoline derivatives

KW - Carbon-11

KW - Conformationally flexible analogues

KW - Gliomas

KW - Imaging

KW - Positron emission tomography (PET)

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DO - 10.1016/j.apradiso.2007.05.006

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VL - 65

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EP - 1159

JO - Applied Radiation and Isotopes

JF - Applied Radiation and Isotopes

SN - 0969-8043

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