2-Fluoroadenine

2-Fluoroadenine
Names
	IUPAC name 2-Fluoro-7H-purin-6-amine
	Other names 2-FA
Identifiers
CAS Number	700-49-2;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:72457;
ChEMBL	ChEMBL580404;
ChemSpider	12264;
ECHA InfoCard	100.152.774
EC Number	624-159-6;
PubChem CID	12790;
UNII	2C8H3H4EBG;
CompTox Dashboard (EPA)	DTXSID80220264 ;
	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−1
Solubility in water	< 0.5 mM
Solubility	>=10 mM in DMSO
Hazards
	GHS labelling:
Pictograms
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 [77 °F], 100 kPa). Infobox references

2-Fluoroadenine (2-FA) is a toxic adenine antimetabolite which can be used in laboratory biological research for counterselection of wildtype bacterial^[3] or eukaryotic (i.e. animals,^[4] yeast,^[5] plants,^[6] diatoms,^[7] brown algae^[8]) 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.^[9] 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.^[10] 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.^[11]

References

^ 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-Fluoroadenine". pubchem.ncbi.nlm.nih.gov. Retrieved 4 May 2022.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

[Kayushin_Tokunova_Fateev_Arnautova_p=539-1] 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.

[Riley_Guss_p.-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.

[Schaff_Jarrett_Dlouhy_Ponniah_p.-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.

[Sahota_Ranjekar_Alfonzo_Lewin_1987_pp._81–87-5] 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.

[Schaff_1994_pp._3–9-6] 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.

[Serif_Dubois_Finoux_Teste_p.-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.

[Badis_Scornet_Harada_Caillard_pp._2077–2091-8] 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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See also

References