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2-Fluoroadenine

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2-Fluoroadenine
Names
IUPAC name 2-Fluoro-7H-purin-6-amine
Other names 2-FA
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.152.774 Edit this at Wikidata
EC Number
  • 624-159-6
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H4FN5/c6-5-10-3(7)2-4(11-5)9-1-8-2/h1H,(H3,7,8,9,10,11)Key: WKMPTBDYDNUJLF-UHFFFAOYSA-N
SMILES
  • C1=NC2=NC(=NC(=C2N1)N)F
Properties
Chemical formula C5H4FN5
Molar mass 153.120 g·mol
Solubility in water < 0.5 mM
Solubility >=10 mM in DMSO
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

2-Fluoroadenine (2-FA) is a toxic adenine antimetabolite which can be used in laboratory biological research for counterselection of wildtype bacterial or eukaryotic (i.e. animals, yeast, plants, diatoms, brown algae) 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.  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. 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.

See also

References

  1. Kayushin, 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. (2021-04-07). "Radical Dehalogenation and Purine Nucleoside Phosphorylase E. coli: How Does an Admixture of 2′,3′-Anhydroinosine Hinder 2-fluoro-cordycepin Synthesis". Biomolecules. 11 (4). MDPI AG: 539. doi:10.3390/biom11040539. ISSN 2218-273X. PMC 8067715. PMID 33917025.
  2. "2-Fluoroadenine". pubchem.ncbi.nlm.nih.gov. Retrieved 4 May 2022.
  3. Riley, Lauren A.; Guss, Adam M. (2021-01-25). "Approaches to genetic tool development for rapid domestication of non-model microorganisms". Biotechnology for Biofuels. 14 (1). Springer Science and Business Media LLC: 30. doi:10.1186/s13068-020-01872-z. ISSN 1754-6834. PMC 7830746. PMID 33494801.
  4. Schaff, D A; Jarrett, R A; Dlouhy, S R; Ponniah, S; Stockelman, M; Stambrook, P J; Tischfield, J A (1990). "Mouse transgenes in human cells detect specific base substitutions". Proceedings of the National Academy of Sciences of the United States of America. 87 (21): 8675–8679. Bibcode:1990PNAS...87.8675S. doi:10.1073/pnas.87.21.8675. PMC 55020. PMID 2236079.
  5. Sahota, Amrik; Ranjekar, Prabhakar K.; Alfonzo, Juan; Lewin, Alfred S.; Taylor, Milton W. (1987). "Mutants of Saccharomyces cerevisiae deficient in adenine phosphoribosyltransferase". Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis. 180 (1). Elsevier BV: 81–87. doi:10.1016/0027-5107(87)90069-8. ISSN 0027-5107. PMID 3306356.
  6. Schaff, Dennis A. (1994). "The adenine phosphoribosyltransferase (APRT) selectable marker system". Plant Science. 101 (1). Elsevier BV: 3–9. doi:10.1016/0168-9452(94)90159-7. ISSN 0168-9452.
  7. Serif, Manuel; Dubois, Gwendoline; Finoux, Anne-Laure; Teste, Marie-Ange; Jallet, Denis; Daboussi, Fayza (2018-09-25). "One-step generation of multiple gene knock-outs in the diatom Phaeodactylum tricornutum by DNA-free genome editing". Nature Communications. 9 (1). Springer Science and Business Media LLC: 3924. Bibcode:2018NatCo...9.3924S. doi:10.1038/s41467-018-06378-9. ISSN 2041-1723. PMC 6156588. PMID 30254261.
  8. Badis, 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 (2021-07-10). "Targeted CRISPR-Cas9-based gene knockouts in the model brown alga Ectocarpus" (PDF). New Phytologist. 231 (5). Wiley: 2077–2091. doi:10.1111/nph.17525. ISSN 0028-646X. PMID 34076889. S2CID 235295486.
  9. 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". Organic Process Research & Development. 23 (8): 1522–1528. doi:10.1021/acs.oprd.9b00178. ISSN 1083-6160.
  10. Montgomery, John; Hewson, Kathleen (May 1969). "Nucleosides of 2-Fluoroadenine". Journal of Medicinal Chemistry. 12 (3): 498–504. doi:10.1021/jm00303a605. ISSN 0022-2623.
  11. 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. doi:10.1002/hed.25627. ISSN 1097-0347. PMC 6531318. PMID 30633420.
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