دورية أكاديمية

A protocol for controlled reactivity shift in the 2,2-difluorovinyl motif used for selective S- 18 F and C- 18 F bond formation.

التفاصيل البيبلوغرافية
العنوان: A protocol for controlled reactivity shift in the 2,2-difluorovinyl motif used for selective S- 18 F and C- 18 F bond formation.
المؤلفون: Maqbool M; Department of Clinical Neurocience, OUS-Ullevål, Oslo, Norway.; Department of Chemistry, University of Oslo, Oslo, Norway., Jakobsson JE; Department of Clinical Neurocience, OUS-Ullevål, Oslo, Norway., Alluri SR; Department of Clinical Neurocience, OUS-Ullevål, Oslo, Norway., Kramer V; Positronpharma SA, Rancangua, Santiago de Chile, Santiago, Chile., Riss PJ; Department of Clinical Neurocience, OUS-Ullevål, Oslo, Norway. priss@uni-mainz.de.; Department of Chemistry, University of Oslo, Oslo, Norway. priss@uni-mainz.de.; Department of Chemistry, Johannes Gutenberg-University, Fritz-Strassmann-Weg 2, 55128, Mainz, Germany. priss@uni-mainz.de.
المصدر: Communications chemistry [Commun Chem] 2024 Apr 29; Vol. 7 (1), pp. 97. Date of Electronic Publication: 2024 Apr 29.
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: Springer Nature Country of Publication: England NLM ID: 101725670 Publication Model: Electronic Cited Medium: Internet ISSN: 2399-3669 (Electronic) Linking ISSN: 23993669 NLM ISO Abbreviation: Commun Chem Subsets: PubMed not MEDLINE
أسماء مطبوعة: Original Publication: [London] : Springer Nature, [2018]-
مستخلص: Positron emission tomography (PET) is a powerful imaging technique for biomedical research, drug development and medical diagnosis. The power of PET lies in biochemically selective radiotracers, labelled with positron emitters like fluorine-18 image chemical processes in vivo. A rapid and remarkably efficient, unprecedented protocol to select between S-F and C-F bond formation based on activation of 1,1-difluoroethylene groups followed by selective oxidation or reduction is described. While transition metal mediated conditions can be employed, the reaction proceeds in high yield using unobjectionable chemical reagents amenable to routine radiotracer production. The latter bodes well for facile clinical translation of the method. The new technique affords radiotracers and the labelling reagent 2,2-difluoro-2-(fluoro- 18 F)ethyl 4-methylbenzenesulfonate ([ 18 F]1b) in excellent yield. Following oxygenation of the reaction mixture with medical oxygen or air, sulfonyl fluorides are obtained as the primary product. The new protocol was employed in a proof of principle to develop a radiometric assay for quantitation of sulfonylation yield with sulfonyl fluoride reagents. With operational ease and mild conditions, the method bodes a high potential for radiolabelling of biomolecules, known enzyme inhibitors and other temperature-sensitive compounds.
(© 2024. The Author(s).)
References: Inorg Chem. 2019 Aug 5;58(15):10194-10200. (PMID: 31283193)
Eur J Nucl Med. 1998 Feb;25(2):173-6. (PMID: 9473266)
Bioorg Med Chem. 2011 Apr 1;19(7):2287-97. (PMID: 21398131)
Drugs. 2010 Feb 12;70(3):287-312. (PMID: 20166767)
ACS Omega. 2018 Jul 31;3(7):7567-7579. (PMID: 30087917)
Chem Sci. 2014 Dec 1;5(12):4545-4553. (PMID: 25379166)
Org Lett. 2021 Apr 2;23(7):2766-2771. (PMID: 33725454)
Org Lett. 2020 Jul 17;22(14):5511-5516. (PMID: 32589035)
Commun Chem. 2018;1(1):. (PMID: 34291178)
Eur J Nucl Med. 1995 Dec;22(12):1420-32. (PMID: 8586089)
Org Biomol Chem. 2012 Sep 14;10(34):6980-6. (PMID: 22833145)
Neurotherapeutics. 2007 Jan;4(1):117-22. (PMID: 17199025)
ACS Chem Neurosci. 2020 Feb 5;11(3):427-435. (PMID: 31898886)
Chem Commun (Camb). 2011 Nov 21;47(43):11873-5. (PMID: 21987078)
J Med Chem. 2007 Nov 15;50(23):5752-64. (PMID: 17956082)
Neurosci Biobehav Rev. 2012 Apr;36(4):1188-216. (PMID: 22342372)
ACS Chem Neurosci. 2022 Jan 5;13(1):1-15. (PMID: 34908391)
Chem Sci. 2020 Jan 7;11(7):1832-1838. (PMID: 34123276)
Angew Chem Int Ed Engl. 2012 Mar 12;51(11):2698-702. (PMID: 22308017)
Commun Chem. 2023 Apr 29;6(1):83. (PMID: 37120482)
Curr Pharm Des. 2002;8(16):1497-511. (PMID: 12052208)
J Org Chem. 2023 May 5;88(9):6263-6273. (PMID: 37032486)
Org Lett. 2013 Jun 21;15(12):2954-7. (PMID: 23734872)
ACS Chem Neurosci. 2021 Feb 3;12(3):517-530. (PMID: 33491441)
Angew Chem Int Ed Engl. 2012 Jan 27;51(5):1106-9. (PMID: 22213395)
Chem Soc Rev. 2011 Jan;40(1):149-62. (PMID: 20818455)
J Med Chem. 2013 Sep 12;56(17):6858-70. (PMID: 23899323)
معلومات مُعتمدة: ES 231553 Norges Forskningsråd (Research Council of Norway); 2019112 Ministry of Health and Care Services | Helse Sør-Øst RHF (Southern and Eastern Norway Regional Health Authority)
تواريخ الأحداث: Date Created: 20240429 Latest Revision: 20240502
رمز التحديث: 20240502
مُعرف محوري في PubMed: PMC11058245
DOI: 10.1038/s42004-024-01132-3
PMID: 38684771
قاعدة البيانات: MEDLINE
الوصف
تدمد:2399-3669
DOI:10.1038/s42004-024-01132-3