2-Fluoroadenine

2-fluoroadenine chemical structure.svg 200px 2-Fluoro-7H-purin-6-amine 2-FA 700-49-2 72457 580404 624-159-6 12790 2C8H3H4EBG 12264 C1=NC2=NC(=NC(=C2N1)N)F InChI=1S/C5H4FN5/c6-5-10-3(7)2-4(11-5)9-1-8-2/h1H,(H3,7,8,9,10,11) WKMPTBDYDNUJLF-UHFFFAOYSA-N 5 4 1 5 < 0.5 mMKayushin Alexey L. Tokunova Julia A. Fateev Ilja V. Arnautova Alexandra O. Berzina Maria Ya. Paramonov Alexander S. Lutonina Olga I. Dorofeeva Elena V. Antonov Konstantin V. Esipov Roman S. Mikhailopulo Igor A. Miroshnikov Anatoly I. Konstantinova Irina D. Radical Dehalogenation and Purine Nucleoside Phosphorylase E. coli: How Does an Admixture of 2′,3′-Anhydroinosine Hinder 2-fluoro-cordycepin Synthesis Biomolecules MDPI AG 11 4 2021-04-07 2218-273X 10.3390/biom11040539 539 33917025 8067715 free >=10 mM in DMSO 2-Fluoroadenine https://pubchem.ncbi.nlm.nih.gov/compound/12790#section=Safety-and-Hazards pubchem.ncbi.nlm.nih.gov 4 May 2022 07 Warning 315 319 335 261 264 264+265 271 280 302+352 304+340 305+351+338 319 321 332+317 337+317 362+364 403+233 405 501 2-Fluoroadenine (2-FA) is a toxic adenine antimetabolite which can be used in laboratory biological research for counterselection of wildtype bacterialRiley Lauren A. Guss Adam M. Approaches to genetic tool development for rapid domestication of non-model microorganisms Biotechnology for Biofuels Springer Science and Business Media LLC 14 1 2021-01-25 1754-6834 10.1186/s13068-020-01872-z 30 33494801 7830746 free or eukaryotic (i.e. animals,Schaff D A Jarrett R A Dlouhy S R Ponniah S Stockelman M Stambrook P J Tischfield J A Mouse transgenes in human cells detect specific base substitutions. Proceedings of the National Academy of Sciences of the United States of America 1990 87 21 8675–8679 2236079 10.1073/pnas.87.21.8675 55020 1990PNAS...87.8675S free yeast,Sahota Amrik Ranjekar Prabhakar K. Alfonzo Juan Lewin Alfred S. Taylor Milton W. Mutants of Saccharomyces cerevisiae deficient in adenine phosphoribosyltransferase Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis Elsevier BV 180 1 1987 0027-5107 10.1016/0027-5107(87)90069-8 81–87 3306356 plants,Schaff Dennis A. The adenine phosphoribosyltransferase (APRT) selectable marker system Plant Science Elsevier BV 101 1 1994 0168-9452 10.1016/0168-9452(94)90159-7 3–9 diatoms,Serif Manuel Dubois Gwendoline Finoux Anne-Laure Teste Marie-Ange Jallet Denis Daboussi Fayza One-step generation of multiple gene knock-outs in the diatom Phaeodactylum tricornutum by DNA-free genome editing Nature Communications Springer Science and Business Media LLC 9 1 2018-09-25 2041-1723 10.1038/s41467-018-06378-9 free 3924 30254261 6156588 2018NatCo...9.3924S brown algaeBadis Yacine Scornet Delphine Harada Minori Caillard Céline Godfroy Olivier Raphalen Morgane Gachon Claire M. M. Coelho Susana M. Motomura Taizo Nagasato Chikako Cock J. Mark Targeted CRISPR-Cas9-based gene knockouts in the model brown alga Ectocarpus New Phytologist Wiley 231 5 2021-07-10 0028-646X 10.1111/nph.17525 2077–2091 34076889 235295486 https://hal-cnrs.archives-ouvertes.fr/hal-03356727/file/Ectocarpus_CRISPR_paper_25may21.pdf ) APT (adenine phosphoribosyltransferase) genes. Therefore, knockouts or mutants for APT, which are resistant to 2-FA, can be selected. 2-Fluoroadenine is a critical intermediate for pharmaceutical drugs and can be synthesized within the lab from 2,6-diaminopurine, which is an inexpensive and readily available compound.Salehi Marzijarani Nastaran Snead David R. McMullen Jonathan P. Lévesque François Weisel Mark Varsolona Richard J. Lam Yu-hong Liu Zhijian Naber John R. 2019-08-16 One-Step Synthesis of 2-Fluoroadenine Using Hydrogen Fluoride Pyridine in a Continuous Flow Operation https://pubs.acs.org/doi/10.1021/acs.oprd.9b00178 Organic Process Research & Development 23 8 1522–1528 10.1021/acs.oprd.9b00178 1083-6160 subscription  In the cell, 2-Fluoroadenine is synthesized and exhibits a large range of antibacterial activity. 2-Fluoroadenine acts as an inhibitor of blood-platelet adhesion, and when combined with actinobolin, produces a greater combined effect of preventing or treating infections.Montgomery John Hewson Kathleen May 1969 Nucleosides of 2-Fluoroadenine https://pubs.acs.org/doi/abs/10.1021/jm00303a605 Journal of Medicinal Chemistry 12 3 498–504 10.1021/jm00303a605 0022-2623 subscription In cancer treatments, 2-Fluoroadenine, has been used to treat head and neck cell carcinoma by the progressive removal of RNA and protein synthesis within tumor cells.Behbahani Turang E. Rosenthal Eben L. Parker William B. Sorscher Eric J. June 2019 Intratumoral generation of 2-fluoroadenine to treat solid malignancies of the head and neck Head & Neck 41 6 1979–1983 10.1002/hed.25627 1097-0347 6531318 30633420 See also 5-Fluoroorotic acid (5-FOA) References Category:Fluoroarenes Category:Purines