2-Fluoroadenine

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

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[1]
Solubility	>=10 mM in DMSO
Hazards
GHS labelling:[2]
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 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]

See also

• 5-Fluoroorotic acid (5-FOA)