Chemistry:2-Fluoroadenine

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2-Fluoroadenine (2-FA) is a toxic adenine antimetabolite which can be used in laboratory biological research for counterselection of wildtype bacterial[1] or eukaryotic (i.e. animals,[2] yeast,[3] plants,[4] diatoms,[5] brown algae[6]) 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.[7]  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.[8] 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.[9]

See also

References

  1. ↑ Riley, Lauren A.; Guss, Adam M. (2021-01-25). "Approaches to genetic tool development for rapid domestication of non-model microorganisms". Biotechnology for Biofuels (Springer Science and Business Media LLC) 14 (1): 30. doi:10.1186/s13068-020-01872-z. ISSN 1754-6834. PMID 33494801. 
  2. ↑ 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. doi:10.1073/pnas.87.21.8675. PMID 2236079. Bibcode: 1990PNAS...87.8675S. 
  3. ↑ 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 (Elsevier BV) 180 (1): 81–87. doi:10.1016/0027-5107(87)90069-8. ISSN 0027-5107. PMID 3306356. 
  4. ↑ Schaff, Dennis A. (1994). "The adenine phosphoribosyltransferase (APRT) selectable marker system". Plant Science (Elsevier BV) 101 (1): 3–9. doi:10.1016/0168-9452(94)90159-7. ISSN 0168-9452. 
  5. ↑ 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 (Springer Science and Business Media LLC) 9 (1): 3924. doi:10.1038/s41467-018-06378-9. ISSN 2041-1723. PMID 30254261. Bibcode: 2018NatCo...9.3924S. 
  6. ↑ Badis, Yacine; Scornet, Delphine; Harada, Minori; Caillard, Céline; Godfroy, Olivier; Raphalen, Morgane; Gachon, Claire M. M.; Coelho, Susana M. et al. (2021-07-10). "Targeted CRISPR-Cas9-based gene knockouts in the model brown alga Ectocarpus". New Phytologist (Wiley) 231 (5): 2077–2091. doi:10.1111/nph.17525. ISSN 0028-646X. PMID 34076889. https://hal-cnrs.archives-ouvertes.fr/hal-03356727/file/Ectocarpus_CRISPR_paper_25may21.pdf. 
  7. ↑ Salehi Marzijarani, Nastaran; Snead, David R.; McMullen, Jonathan P.; Lévesque, François; Weisel, Mark; Varsolona, Richard J.; Lam, Yu-hong; Liu, Zhijian et al. (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. https://pubs.acs.org/doi/10.1021/acs.oprd.9b00178. 
  8. ↑ 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. https://pubs.acs.org/doi/abs/10.1021/jm00303a605. 
  9. ↑ 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. PMID 30633420. 



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