Synthesis of carbon-11-labeled casimiroin analogues as new potential PET agents for imaging of quinone reductase 2 and aromatase expression in breast cancer

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

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Carbon-11-labeled casimiroin analogues were first designed and synthesized as new potential PET agents for imaging of quinone reductase (QR) 2 and aromatase expression in breast cancer. [11C]casimiroin (6-[ 11C]methoxy-9-methyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one, [ 11C]11) and its carbon-11-labeled analogues 5,6,8-trimethoxy-1-[ 11C]methyl-4-methylquinolin-2(1H)-one ([11C]17), 8-methoxy-1-[11C]methyl-4-methylquinolin-2(1H)-one ([ 11C]21a), 6,8-dimethoxy-1-[11C]methyl-4-methylquinolin- 2(1H)-one ([11C]21b), and 5,8-dimethoxy-1-[11C]methyl-4- methylquinolin-2(1H)-one ([11C]21c), were prepared from their corresponding precursors with [11C]methyl triflate ([ 11C]CH3OTf) under basic conditions (NaH) through either O- or N-[11C]methylation and isolated by semi-preparative HPLC method in 40-50% radiochemical yields decay corrected to end of bombardment (EOB), based on [11C]CO2, and 111-185 GBq/μmol specific activity at the end of synthesis (EOS).

Original languageEnglish
Pages (from-to)967-973
Number of pages7
JournalSteroids
Volume75
Issue number12
DOIs
StatePublished - Dec 2010

Fingerprint

NAD(P)H Dehydrogenase (Quinone)
Aromatase
Carbon
Breast Neoplasms
Imaging techniques
Methylation
High Pressure Liquid Chromatography
4-methylquinoline
6-methoxy-9-methyl-(1,3)dioxolo(4,5-h)quinolin-8(9H)-one

Keywords

  • Aromatase
  • Cancer imaging
  • Casimiroin analogues
  • Positron emission tomography (PET)
  • Quinone reductase (QR) 2
  • Radiotracers

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Endocrinology
  • Molecular Biology
  • Organic Chemistry
  • Pharmacology

Cite this

Synthesis of carbon-11-labeled casimiroin analogues as new potential PET agents for imaging of quinone reductase 2 and aromatase expression in breast cancer. / Wang, Min; Gao, Mingzhang; Miller, Kathy; Sledge, George W.; Hutchins, Gary; Zheng, Qi-Huang.

In: Steroids, Vol. 75, No. 12, 12.2010, p. 967-973.

Research output: Contribution to journalArticle

@article{3b48c290dc3447c8a10d966c5d85b2e1,
title = "Synthesis of carbon-11-labeled casimiroin analogues as new potential PET agents for imaging of quinone reductase 2 and aromatase expression in breast cancer",
abstract = "Carbon-11-labeled casimiroin analogues were first designed and synthesized as new potential PET agents for imaging of quinone reductase (QR) 2 and aromatase expression in breast cancer. [11C]casimiroin (6-[ 11C]methoxy-9-methyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one, [ 11C]11) and its carbon-11-labeled analogues 5,6,8-trimethoxy-1-[ 11C]methyl-4-methylquinolin-2(1H)-one ([11C]17), 8-methoxy-1-[11C]methyl-4-methylquinolin-2(1H)-one ([ 11C]21a), 6,8-dimethoxy-1-[11C]methyl-4-methylquinolin- 2(1H)-one ([11C]21b), and 5,8-dimethoxy-1-[11C]methyl-4- methylquinolin-2(1H)-one ([11C]21c), were prepared from their corresponding precursors with [11C]methyl triflate ([ 11C]CH3OTf) under basic conditions (NaH) through either O- or N-[11C]methylation and isolated by semi-preparative HPLC method in 40-50{\%} radiochemical yields decay corrected to end of bombardment (EOB), based on [11C]CO2, and 111-185 GBq/μmol specific activity at the end of synthesis (EOS).",
keywords = "Aromatase, Cancer imaging, Casimiroin analogues, Positron emission tomography (PET), Quinone reductase (QR) 2, Radiotracers",
author = "Min Wang and Mingzhang Gao and Kathy Miller and Sledge, {George W.} and Gary Hutchins and Qi-Huang Zheng",
year = "2010",
month = "12",
doi = "10.1016/j.steroids.2010.06.004",
language = "English",
volume = "75",
pages = "967--973",
journal = "Steroids",
issn = "0039-128X",
publisher = "Elsevier Inc.",
number = "12",

}

TY - JOUR

T1 - Synthesis of carbon-11-labeled casimiroin analogues as new potential PET agents for imaging of quinone reductase 2 and aromatase expression in breast cancer

AU - Wang, Min

AU - Gao, Mingzhang

AU - Miller, Kathy

AU - Sledge, George W.

AU - Hutchins, Gary

AU - Zheng, Qi-Huang

PY - 2010/12

Y1 - 2010/12

N2 - Carbon-11-labeled casimiroin analogues were first designed and synthesized as new potential PET agents for imaging of quinone reductase (QR) 2 and aromatase expression in breast cancer. [11C]casimiroin (6-[ 11C]methoxy-9-methyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one, [ 11C]11) and its carbon-11-labeled analogues 5,6,8-trimethoxy-1-[ 11C]methyl-4-methylquinolin-2(1H)-one ([11C]17), 8-methoxy-1-[11C]methyl-4-methylquinolin-2(1H)-one ([ 11C]21a), 6,8-dimethoxy-1-[11C]methyl-4-methylquinolin- 2(1H)-one ([11C]21b), and 5,8-dimethoxy-1-[11C]methyl-4- methylquinolin-2(1H)-one ([11C]21c), were prepared from their corresponding precursors with [11C]methyl triflate ([ 11C]CH3OTf) under basic conditions (NaH) through either O- or N-[11C]methylation and isolated by semi-preparative HPLC method in 40-50% radiochemical yields decay corrected to end of bombardment (EOB), based on [11C]CO2, and 111-185 GBq/μmol specific activity at the end of synthesis (EOS).

AB - Carbon-11-labeled casimiroin analogues were first designed and synthesized as new potential PET agents for imaging of quinone reductase (QR) 2 and aromatase expression in breast cancer. [11C]casimiroin (6-[ 11C]methoxy-9-methyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one, [ 11C]11) and its carbon-11-labeled analogues 5,6,8-trimethoxy-1-[ 11C]methyl-4-methylquinolin-2(1H)-one ([11C]17), 8-methoxy-1-[11C]methyl-4-methylquinolin-2(1H)-one ([ 11C]21a), 6,8-dimethoxy-1-[11C]methyl-4-methylquinolin- 2(1H)-one ([11C]21b), and 5,8-dimethoxy-1-[11C]methyl-4- methylquinolin-2(1H)-one ([11C]21c), were prepared from their corresponding precursors with [11C]methyl triflate ([ 11C]CH3OTf) under basic conditions (NaH) through either O- or N-[11C]methylation and isolated by semi-preparative HPLC method in 40-50% radiochemical yields decay corrected to end of bombardment (EOB), based on [11C]CO2, and 111-185 GBq/μmol specific activity at the end of synthesis (EOS).

KW - Aromatase

KW - Cancer imaging

KW - Casimiroin analogues

KW - Positron emission tomography (PET)

KW - Quinone reductase (QR) 2

KW - Radiotracers

UR - http://www.scopus.com/inward/record.url?scp=77955926765&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77955926765&partnerID=8YFLogxK

U2 - 10.1016/j.steroids.2010.06.004

DO - 10.1016/j.steroids.2010.06.004

M3 - Article

C2 - 20558190

AN - SCOPUS:77955926765

VL - 75

SP - 967

EP - 973

JO - Steroids

JF - Steroids

SN - 0039-128X

IS - 12

ER -