Synthesis of a new fluorine-18-labeled bexarotene analogue for PET imaging of retinoid X receptor

Min Wang, Toni Davis, Mingzhang Gao, Qi-Huang Zheng

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

The reference standard 2-fluoro-4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8- tetrahydronaphthalen-2-yl)vinyl)benzoic acid was synthesized from 2,5-dimethyl-2,5-hexanediol and 2-fluoro-4-methylbenzoic acid in 10 steps with 3% overall chemical yield. The precursor 2-nitro-4-(1-(3,5,5,8,8-pentamethyl-5, 6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoic acid was synthesized from 2,5-dimethyl-2,5-hexanediol and dimethyl-2-nitroterephthalate in seven steps with 2% overall chemical yield. The target tracer 2-[18F]fluoro-4-(1- (3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoic acid was synthesized from its nitro-precursor by the nucleophilic substitution with K[18F]F/Kryptofix 2.2.2 and isolated by HPLC combined with solid-phase extraction (SPE) purification in 20-30% radiochemical yield with 37-370 GBq/μmol specific activity at end of bombardment (EOB).

Original languageEnglish
Pages (from-to)1742-1747
Number of pages6
JournalBioorganic and Medicinal Chemistry Letters
Volume24
Issue number7
DOIs
StatePublished - Apr 1 2014

Fingerprint

Retinoid X Receptors
Benzoic Acid
Fluorine
Imaging techniques
Solid Phase Extraction
Purification
Substitution reactions
High Pressure Liquid Chromatography
bexarotene
2,5-hexanediol

Keywords

  • Alzheimer's disease (AD)
  • Apolipoprotein E (APOE)
  • Bexarotene
  • Cancer
  • Positron emission tomography (PET)
  • Retinoid X receptor (RXR)

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Molecular Biology
  • Molecular Medicine
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science
  • Medicine(all)

Cite this

Synthesis of a new fluorine-18-labeled bexarotene analogue for PET imaging of retinoid X receptor. / Wang, Min; Davis, Toni; Gao, Mingzhang; Zheng, Qi-Huang.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 24, No. 7, 01.04.2014, p. 1742-1747.

Research output: Contribution to journalArticle

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