Synthesis and biological evaluation of a fluorine-18 labeled estrogen receptor-α selective ligand: [18F] propyl pyrazole triol

Dange Vijaykumar; Mohammed H. Al-Qahtani; Michael J. Welch; John A. Katzenellenbogen

doi:10.1016/S0969-8051(02)00446-8

Synthesis and biological evaluation of a fluorine-18 labeled estrogen receptor-α selective ligand: [¹⁸F] propyl pyrazole triol

Dange Vijaykumar, Mohammed H. Al-Qahtani, Michael J. Welch, John A. Katzenellenbogen

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

The two estrogen receptor subtypes, ERα and ERβ, play important roles in breast cancer. To develop an ERα imaging agent, we synthesized fluoropropyl pyrazole triol (FPPT, 2), an analog of our ERα-selective ligand PPT. FPPT retains the high ERα binding selectivity of its parent PPT. We prepared [¹⁸F]FPPT (¹⁸F-2) in high specific activity, but estrogen target tissue uptake in female rats was minimal and was not displaceable by unlabeled estradiol, probably because of the lipophilicity and triphenolic nature of FPPT.

Original language	English (US)
Pages (from-to)	397-404
Number of pages	8
Journal	Nuclear Medicine and Biology
Volume	30
Issue number	4
DOIs	https://doi.org/10.1016/S0969-8051(02)00446-8
State	Published - May 2003

Keywords

Estrogen receptor
Estrogen receptor alpha
Fluorine-18
Pyrazole
Subtype selective

ASJC Scopus subject areas

Molecular Medicine
Radiology Nuclear Medicine and imaging
Cancer Research

Online availability

10.1016/S0969-8051(02)00446-8

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Cite this

@article{a4469a9de05947a9b55a3a3aab440cdd,

title = "Synthesis and biological evaluation of a fluorine-18 labeled estrogen receptor-α selective ligand: [18F] propyl pyrazole triol",

abstract = "The two estrogen receptor subtypes, ERα and ERβ, play important roles in breast cancer. To develop an ERα imaging agent, we synthesized fluoropropyl pyrazole triol (FPPT, 2), an analog of our ERα-selective ligand PPT. FPPT retains the high ERα binding selectivity of its parent PPT. We prepared [18F]FPPT (18F-2) in high specific activity, but estrogen target tissue uptake in female rats was minimal and was not displaceable by unlabeled estradiol, probably because of the lipophilicity and triphenolic nature of FPPT.",

keywords = "Estrogen receptor, Estrogen receptor alpha, Fluorine-18, Pyrazole, Subtype selective",

author = "Dange Vijaykumar and Al-Qahtani, {Mohammed H.} and Welch, {Michael J.} and Katzenellenbogen, {John A.}",

note = "Funding Information: We are grateful for support of this research through grants from the National Institute of Health (PHS 5R37 CA25836 [to J.A.K.] and PHS 5P01 HL13851 [to M.J.W.]) and the Department of Energy (DE FG02 84ER60218 [to M.J.W.]). NMR spectra were obtained in the Varian Oxford Instrument Center for Excellence in NMR Laboratory. Funding for this instrumentation was provided in part from the W. M. Keck Foundation, the National Institutes of Health (PHS 1 S10 RR104444-01), and the National Science Foundation (NSF CHE 96-10502). Mass spectra were obtained on instruments supported by grants from the National Institute of General Medical Sciences (GM 27029), the National Institutes of Health (RR 01575), and the National Science Foundation (PCM 8121494). We also thank Kathryn Carlson for the binding affinity measurements, and Nikki Mercel for the biodistribution studies. ",

year = "2003",

month = may,

doi = "10.1016/S0969-8051(02)00446-8",

language = "English (US)",

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AU - Welch, Michael J.

AU - Katzenellenbogen, John A.

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