[11C]BCTC: Radiosynthesis and in vivo binding to transient receptor potential vanilloid subfamily member 1 (TRPV1) receptor in the mouse trigeminal nerve. Issue 19 (1st October 2017)

• Record Type: Journal Article
• Authors: Kumata, Katsushi; Yui, Joji; Zhang, Yiding; Kurihara, Yusuke; Ogawa, Masanao; Mori, Wakana; Fujinaga, Masayuki; Zhang, Ming-Rong
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 27:Issue 19(2017)
• Page Start: 4521
• Page End: 4524
• Publication Date: 2017-10-01
• Subjects: Capsaicin -- Transient receptor potential vanilloid subfamily member 1 -- TRPV1 -- Positron emission tomography -- [11C]phosgene -- [11C]BCTC -- Trigeminal nerve; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2017.08.061
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Abstract: The purpose of this study was to synthesize a new positron emission tomography radiotracer, N -(4-tertiarybutylphenyl)-4-(3-chloropyridin-2-yl)tetrahydropyrazine-1(2 H )-[ 11 C]carboxamide ([ 11 C]BCTC, [ 11 C]1 ), and assess its in vivo binding to the transient receptor potential vanilloid subfamily member 1 (TRPV1) receptor in mice. [ 11 C]BCTC was synthesized by reacting the hydrochloride of 4-tertiarybutylaniline (2 ·HCl) with [ 11 C]phosgene ([ 11 C]COCl2 ) to give isocyanate [ 11 C]4, followed by reaction with 4-(3-chloropyridin-2-yl)tetrahydropyrazine (3 ). [ 11 C]BCTC was obtained at a 16–20% radiochemical yield, based on the cyclotron-produced [ 11 C]CO2 (decay-corrected to the end of bombardment), with >98% radiochemical purity and 65–110 GBq/μmol specific activity at the end of synthesis. An ex vivo biodistribution study in mice confirmed the specific binding of [ 11 C]BCTC to TRPV1 in the trigeminal nerve, which is a tissue with high TRPV1 expression.