Literature DB >> 31312400

The Dark Side of Fluorine.

Yue Pan1.   

Abstract

Despite the perceived stability of the C-F bond, chemical instability and drug-metabolizing enzymes can lead to its cleavage. The resulting release of fluoride and formation of certain metabolites may cause safety issues and warrant the medicinal chemists' attention.

Entities:  

Year:  2019        PMID： 31312400      PMCID： PMC6627733          DOI： 10.1021/acsmedchemlett.9b00235

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  13 in total

1.  Radiodefluorination of 3-fluoro-5-(2-(2-[18F](fluoromethyl)-thiazol-4-yl)ethynyl)benzonitrile ([18F]SP203), a radioligand for imaging brain metabotropic glutamate subtype-5 receptors with positron emission tomography, occurs by glutathionylation in rat brain.

Authors:  H Umesha Shetty; Sami S Zoghbi; Fabrice G Siméon; Jeih-San Liow; Amira K Brown; Pavitra Kannan; Robert B Innis; Victor W Pike
Journal:  J Pharmacol Exp Ther       Date:  2008-09-19       Impact factor: 4.030

2.  Biologically stable [(18)F]-labeled benzylfluoride derivatives.

Authors:  Y Magata; L Lang; D O Kiesewetter; E M Jagoda; M A Channing; W C Eckelman
Journal:  Nucl Med Biol       Date:  2000-02       Impact factor: 2.408

3.  Fluoride excess and periostitis in transplant patients receiving long-term voriconazole therapy.

Authors:  Robert A Wermers; Kay Cooper; Raymund R Razonable; Paul J Deziel; Gary M Whitford; Walter K Kremers; Thomas P Moyer
Journal:  Clin Infect Dis       Date:  2011-01-16       Impact factor: 9.079

4.  Metabolism, pharmacokinetics, and protein covalent binding of radiolabeled MaxiPost (BMS-204352) in humans.

Authors:  Donglu Zhang; Rajesh Krishna; Lifei Wang; Jianing Zeng; James Mitroka; Renke Dai; Narayanan Narasimhan; Richard A Reeves; Nuggehally R Srinivas; Lewis J Klunk
Journal:  Drug Metab Dispos       Date:  2004-10-22       Impact factor: 3.922

5.  The mode of toxic action of the pesticide gliftor: the metabolism of 1,3-difluoroacetone to (-)-erythro-fluorocitrate.

Authors:  K I Menon; M G Feldwick; P S Noakes; R J Mead
Journal:  J Biochem Mol Toxicol       Date:  2001       Impact factor: 3.642

6.  Metabolic activation of fluoropyrrolidine dipeptidyl peptidase-IV inhibitors by rat liver microsomes.

Authors:  Shiyao Xu; Bing Zhu; Yohannes Teffera; Deborah E Pan; Charles G Caldwell; George Doss; Ralph A Stearns; David C Evans; Maria G Beconi
Journal:  Drug Metab Dispos       Date:  2004-10-14       Impact factor: 3.922

7.  Probing Mechanisms of CYP3A Time-Dependent Inhibition Using a Truncated Model System.

Authors:  Xiaojing Wang; Minghua Sun; Connie New; Spencer Nam; Wesley P Blackaby; Alastair J Hodges; David Nash; Mizio Matteucci; Joseph P Lyssikatos; Peter W Fan; Suzanne Tay; Jae H Chang
Journal:  ACS Med Chem Lett       Date:  2015-07-12       Impact factor: 4.345

8.  Comparative biotransformation of pyrazinone-containing corticotropin-releasing factor receptor-1 antagonists: minimizing the reactive metabolite formation.

Authors:  Xiaoliang Zhuo; Richard A Hartz; Joanne J Bronson; Harvey Wong; Vijay T Ahuja; Vivekananda M Vrudhula; John E Leet; Stella Huang; John E Macor; Yue-Zhong Shu
Journal:  Drug Metab Dispos       Date:  2010-01       Impact factor: 3.922

9.  Kinesin spindle protein (KSP) inhibitors. 9. Discovery of (2S)-4-(2,5-difluorophenyl)-n-[(3R,4S)-3-fluoro-1-methylpiperidin-4-yl]-2-(hydroxymethyl)-N-methyl-2-phenyl-2,5-dihydro-1H-pyrrole-1-carboxamide (MK-0731) for the treatment of taxane-refractory cancer.

Authors:  Christopher D Cox; Paul J Coleman; Michael J Breslin; David B Whitman; Robert M Garbaccio; Mark E Fraley; Carolyn A Buser; Eileen S Walsh; Kelly Hamilton; Michael D Schaber; Robert B Lobell; Weikang Tao; Joseph P Davide; Ronald E Diehl; Marc T Abrams; Vicki J South; Hans E Huber; Maricel Torrent; Thomayant Prueksaritanont; Chunze Li; Donald E Slaughter; Elizabeth Mahan; Carmen Fernandez-Metzler; Youwei Yan; Lawrence C Kuo; Nancy E Kohl; George D Hartman
Journal:  J Med Chem       Date:  2008-06-25       Impact factor: 7.446

10.  Oxidative ipso substitution of 2,4-difluoro-benzylphthalazines: identification of a rare stable quinone methide and subsequent GSH conjugate.

Authors:  Mithat Gunduz; Upendra A Argikar; Amin Kamel; Kevin Colizza; Jennifer L Bushee; Amanda Cirello; Franco Lombardo; Shawn Harriman
Journal:  Drug Metab Dispos       Date:  2012-07-30       Impact factor: 3.922
View more
  17 in total

1.  Ex Vivo Analysis of Tryptophan Metabolism Using 19F NMR.

Authors:  Robert J Tombari; Carla M Saunders; Chun-Yi Wu; Lee E Dunlap; Dean J Tantillo; David E Olson
Journal:  ACS Chem Biol       Date:  2019-08-26       Impact factor: 5.100

2.  Mechanism-based design of agents that selectively target drug-resistant glioma.

Authors:  Kingson Lin; Susan E Gueble; Ranjini K Sundaram; Eric D Huseman; Ranjit S Bindra; Seth B Herzon
Journal:  Science       Date:  2022-07-28       Impact factor: 63.714

Review 3.  Carbon-fluorine bond cleavage mediated by metalloenzymes.

Authors:  Yifan Wang; Aimin Liu
Journal:  Chem Soc Rev       Date:  2020-06-08       Impact factor: 54.564

4.  Synthesis and Liver Microsomal Metabolic Stability Studies of a Fluorine-Substituted δ-Tocotrienol Derivative.

Authors:  Xingui Liu; Saikat Poddar; Lin Song; Howard Hendrickson; Xuan Zhang; Yaxia Yuan; Daohong Zhou; Guangrong Zheng
Journal:  ChemMedChem       Date:  2020-02-11       Impact factor: 3.466

5.  Discovery of Orally Active and Nonsteroidal Farnesoid X Receptor (FXR) Antagonist with Propensity for Accumulation and Responsiveness in Ileum.

Authors:  Naoki Teno; Yusuke Iguchi; Keisuke Oda; Yukiko Yamashita; Arisa Masuda; Ko Fujimori; Mizuho Une; Keigo Gohda
Journal:  ACS Med Chem Lett       Date:  2021-02-24       Impact factor: 4.345

Review 6.  Fluorinated Molecules and Nanotechnology: Future 'Avengers' against the Alzheimer's Disease?

Authors:  Meghna Dabur; Joana A Loureiro; Maria Carmo Pereira
Journal:  Int J Mol Sci       Date:  2020-04-23       Impact factor: 5.923

Review 7.  Perfluorocarbons in Chemical Biology.

Authors:  Margeaux A Miller; Ellen M Sletten
Journal:  Chembiochem       Date:  2020-08-05       Impact factor: 3.164

8.  Discovery of Arylsulfonamide Nav1.7 Inhibitors: IVIVC, MPO Methods, and Optimization of Selectivity Profile.

Authors:  Anthony J Roecker; Mark E Layton; Joseph E Pero; Michael J Kelly; Thomas J Greshock; Richard L Kraus; Yuxing Li; Rebecca Klein; Michelle Clements; Christopher Daley; Aneta Jovanovska; Jeanine E Ballard; Deping Wang; Fuqiang Zhao; Andrew P J Brunskill; Xuanjia Peng; Xiu Wang; Haiyan Sun; Andrea K Houghton; Christopher S Burgey
Journal:  ACS Med Chem Lett       Date:  2021-06-01       Impact factor: 4.632

9.  Organophotoredox Hydrodefluorination of Trifluoromethylarenes with Translational Applicability to Drug Discovery.

Authors:  Jeroen B I Sap; Natan J W Straathof; Thomas Knauber; Claudio F Meyer; Maurice Médebielle; Laura Buglioni; Christophe Genicot; Andrés A Trabanco; Timothy Noël; Christopher W Am Ende; Véronique Gouverneur
Journal:  J Am Chem Soc       Date:  2020-05-11       Impact factor: 15.419

10.  Metabolism of a Bioorthogonal PET Tracer Candidate [19F/18F]SiFA-Tetrazine in Mouse Liver Microsomes: Biotransformation Pathways and Defluorination Investigated by UHPLC-HRMS.

Authors:  Sofia Otaru; Hanna Niemikoski; Mirkka Sarparanta; Anu J Airaksinen
Journal:  Mol Pharm       Date:  2020-07-01       Impact factor: 4.939
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.