Synthesis of a new carbon-11-labeled sulfamate derivative as a potential PET tracer for imaging of breast cancer aromatase and steroid sulfatase expression

Min Wang, Mingzhang Gao, Kathy Miller, Qi-Huang Zheng

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4 Citations (Scopus)

Abstract

A carbon-11-labeled sulfamate derivative was designed and synthesized as a new potential positron-emission-tomography dual aromatase-steroid sulfatase inhibitor radiotracer for imaging of aromatase and steroid sulfatase expression in breast cancer. The target tracer 2-chloro-4-(((4-cyanophenyl)(4H-1,2,4- triazol-4-yl)amino)methyl)-6-[11C]methoxyphenyl sulfamate ([ 11C]7) was prepared from its corresponding precursor 2-chloro-4-(((4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino)methyl) -6-hydroxyphenyl sulfamate (18) with [11C]CH3OTf under basic conditions through the O-[11C]methylation and isolated by the reversed-phase high-performance liquid chromatography in 40-45% radiochemical yields based on [11C]CO2 and decay corrected to end of bombardment. The specific activity at end of synthesis was 111-185GBq/mol.

Original languageEnglish
Pages (from-to)1127-1140
Number of pages14
JournalSynthetic Communications
Volume41
Issue number8
DOIs
StatePublished - Jan 2011

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Steryl-Sulfatase
Aromatase
Carbon
Derivatives
Imaging techniques
Positron emission tomography
Methylation
High performance liquid chromatography
sulfamic acid

Keywords

  • Aromatase
  • cancer imaging
  • positron emission tomography
  • radiotracer
  • steroid sulfatase
  • sulfamate derivative

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Synthesis of a new carbon-11-labeled sulfamate derivative as a potential PET tracer for imaging of breast cancer aromatase and steroid sulfatase expression",
abstract = "A carbon-11-labeled sulfamate derivative was designed and synthesized as a new potential positron-emission-tomography dual aromatase-steroid sulfatase inhibitor radiotracer for imaging of aromatase and steroid sulfatase expression in breast cancer. The target tracer 2-chloro-4-(((4-cyanophenyl)(4H-1,2,4- triazol-4-yl)amino)methyl)-6-[11C]methoxyphenyl sulfamate ([ 11C]7) was prepared from its corresponding precursor 2-chloro-4-(((4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino)methyl) -6-hydroxyphenyl sulfamate (18) with [11C]CH3OTf under basic conditions through the O-[11C]methylation and isolated by the reversed-phase high-performance liquid chromatography in 40-45{\%} radiochemical yields based on [11C]CO2 and decay corrected to end of bombardment. The specific activity at end of synthesis was 111-185GBq/mol.",
keywords = "Aromatase, cancer imaging, positron emission tomography, radiotracer, steroid sulfatase, sulfamate derivative",
author = "Min Wang and Mingzhang Gao and Kathy Miller and Qi-Huang Zheng",
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AU - Wang, Min

AU - Gao, Mingzhang

AU - Miller, Kathy

AU - Zheng, Qi-Huang

PY - 2011/1

Y1 - 2011/1

N2 - A carbon-11-labeled sulfamate derivative was designed and synthesized as a new potential positron-emission-tomography dual aromatase-steroid sulfatase inhibitor radiotracer for imaging of aromatase and steroid sulfatase expression in breast cancer. The target tracer 2-chloro-4-(((4-cyanophenyl)(4H-1,2,4- triazol-4-yl)amino)methyl)-6-[11C]methoxyphenyl sulfamate ([ 11C]7) was prepared from its corresponding precursor 2-chloro-4-(((4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino)methyl) -6-hydroxyphenyl sulfamate (18) with [11C]CH3OTf under basic conditions through the O-[11C]methylation and isolated by the reversed-phase high-performance liquid chromatography in 40-45% radiochemical yields based on [11C]CO2 and decay corrected to end of bombardment. The specific activity at end of synthesis was 111-185GBq/mol.

AB - A carbon-11-labeled sulfamate derivative was designed and synthesized as a new potential positron-emission-tomography dual aromatase-steroid sulfatase inhibitor radiotracer for imaging of aromatase and steroid sulfatase expression in breast cancer. The target tracer 2-chloro-4-(((4-cyanophenyl)(4H-1,2,4- triazol-4-yl)amino)methyl)-6-[11C]methoxyphenyl sulfamate ([ 11C]7) was prepared from its corresponding precursor 2-chloro-4-(((4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino)methyl) -6-hydroxyphenyl sulfamate (18) with [11C]CH3OTf under basic conditions through the O-[11C]methylation and isolated by the reversed-phase high-performance liquid chromatography in 40-45% radiochemical yields based on [11C]CO2 and decay corrected to end of bombardment. The specific activity at end of synthesis was 111-185GBq/mol.

KW - Aromatase

KW - cancer imaging

KW - positron emission tomography

KW - radiotracer

KW - steroid sulfatase

KW - sulfamate derivative

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