Synthesis and evaluation of (S)-2-(2-[18F]fluoroethoxy)-4-([3-methyl-1-(2-piperidin-1-yl-phenyl)-butyl-carbamoyl]-methyl)-benzoic acid ([18F]repaglinide): a promising radioligand for quantification of pancreatic beta-cell mass with positron emission tomography (PET)

Nuclear Medicine and Biology
Björn WänglerR Schirrmacher

Abstract

18F-labeled non-sulfonylurea hypoglycemic agent (S)-2-(2-[(18)F]fluoroethoxy)-4-((3-methyl-1-(2-piperidin-1-yl-phenyl)-butylcarbamoyl)-methyl)-benzoic acid ([(18)F]repaglinide), a derivative of the sulfonylurea-receptor (SUR) ligand repaglinide, was synthesized as a potential tracer for the non-invasive investigation of the sulfonylurea 1 receptor status of pancreatic beta-cells by positron emission tomography (PET) in the context of type 1 and type 2 diabetes. [(18)F]Repaglinide could be obtained in an overall radiochemical yield (RCY) of 20% after 135 min with a radiochemical purity higher than 98% applying the secondary labeling precursor 2-[(18)F]fluoroethyltosylate. Specific activity was in the range of 50-60 GBq/micromol. Labeling was conducted by exchanging the ethoxy-moiety into a 2-[(18)F]fluoroethoxy group. To characterize the properties of fluorinated repaglinide, the affinity of the analogous non-radioactive (19)F-compound for binding to the human SUR1 isoform was assessed. [(19)F]Repaglinide induced a complete monophasic inhibition curve with a Hill coefficient close to 1 (1.03) yielding a dissociation constant (K(D)) of 134 nM. Biological activity was proven via insulin secretion experiments on isolated rat islets...Continue Reading

References

May 1, 1988·Proceedings of the National Academy of Sciences of the United States of America·G Gimenez-GallegoM L Garcia
Dec 19, 1998·Journal of Medicinal Chemistry·W GrellP Müller
Apr 13, 1999·Cell·S I Taylor

❮ Previous
Next ❯

Citations

May 24, 2013·Journal of Molecular Medicine : Official Organ of the Gesellschaft Deutscher Naturforscher Und Ärzte·Lu YangLiangyi Chen
Sep 21, 2011·European Journal of Nuclear Medicine and Molecular Imaging·Olof Eriksson, Abass Alavi
Sep 9, 2010·Molecular Imaging and Biology : MIB : the Official Publication of the Academy of Molecular Imaging·Tarun SinghalGary W Cline
Feb 16, 2013·Molecular Imaging and Biology : MIB : the Official Publication of the Academy of Molecular Imaging·Björn A BlombergAbass Alavi
Oct 18, 2008·Diabetes, Obesity & Metabolism·S Schneider
Dec 17, 2011·Journal of Transplantation·Daniel EspesPer-Ola Carlsson
May 30, 2008·Frontiers in Bioscience : a Journal and Virtual Library·Mai LinXiankai Sun
May 17, 2008·Experimental Diabetes Research·John K AmarteyFutwan Al-Mohanna
Mar 6, 2009·European Journal of Radiology·Anna Moore
Oct 19, 2004·Radiologic Clinics of North America·Chyng-Yann Shiue, Michael J Welch
Nov 26, 2014·Organic & Biomolecular Chemistry·Yusuke YagiHideo Saji
May 25, 2006·Cell Transplantation·Barjor GimiBrian B Roman
May 9, 2018·Nuclear Medicine Communications·Zhi LuYanjun Zhang
Aug 15, 2012·Endocrine Reviews·Valentina Di GialleonardoAlberto Signore
May 27, 2009·Nature Reviews. Endocrinology·Willy J MalaisseAbdullah Sener
Feb 22, 2012·Radiation Research·Adriana Haimovitz-FriedmanMarcel Verheij
Oct 7, 2020·International Journal of Molecular Sciences·Stephane DemineDecio L Eizirik
Jun 17, 2008·Journal of Nuclear Medicine : Official Publication, Society of Nuclear Medicine·Mei-Ping KungHank F Kung
Jul 18, 2008·Journal of Nuclear Medicine : Official Publication, Society of Nuclear Medicine·Mathias SchreckenbergerPeter Bartenstein
Jul 13, 2021·Frontiers in Endocrinology·Takaaki MurakamiNobuya Inagaki
Sep 22, 2010·Advanced Drug Delivery Reviews·Zhanhong Wu, Fouad Kandeel
Aug 6, 2019·Advanced Drug Delivery Reviews·Weijun WeiWeibo Cai

❮ Previous
Next ❯

Related Concepts

Related Feeds

Antimicrobial Resistance (ASM)

Antimicrobial resistance poses a significant threat to the continued successful use of antimicrobial agents for the treatment of bacterial infections.

Antimicrobial Resistance

Antimicrobial resistance poses a significant threat to the continued successful use of antimicrobial agents for the treatment of bacterial infections.