64183-27-3
Chemical Structure
2′-Deoxy-2′-fluoroadenosine
- CAS No.: 64183-27-3
- Formula:C10H12FN5O3
- Molecular Weight:269.24
IUPAC Name: (2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol
InChIKey: ZGYYPTJWJBEXBC-QYYRPYCUSA-N
SMILES: OC[C@@H]1[C@@H](O)[C@@H](F)[C@H](N2C(N=CN=C3N)=C3N=C2)O1
Biological Activity: 2′-Deoxy-2′-fluoroadenosine is a fluorinated deoxyadenosine with antitumor and antiviral activity, able to interfere with viral or cancer cell replication by being incorporated into DNA. 2′-Deoxy-2′-fluoroadenosine can be used for the synthesis of 2′-Deoxy-2′-fluoro-modified oligonucleotides hybridized with RNA. 2′-Deoxy-2′-fluoroadenosine can be cleaved efficiently by E. coli purine nucleoside phosphorylase (PNP) to the toxic agent 2-fluoroadenine (FAde). 2′-Deoxy-2′-fluoroadenosine shows excellent in vivo activity against tumors expressing E. coli PNP[1][2][3].
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2′-Deoxy-2′-fluoroadenosine | 99.71% | 2′-Deoxy-2′-fluoroadenosine is a fluorinated deoxyadenosine with antitumor and antiviral activity, able to interfere with viral or cancer cell replication by being incorporated into DNA. 2′-Deoxy-2′-fluoroadenosine can be used for the synthesis of 2′-Deoxy-2′-fluoro-modified oligonucleotides hybridized with RNA. 2′-Deoxy-2′-fluoroadenosine can be cleaved efficiently by E. coli purine nucleoside phosphorylase (PNP) to the toxic agent 2-fluoroadenine (FAde). 2′-Deoxy-2′-fluoroadenosine shows excellent in vivo activity against tumors expressing E. coli PNP. | ||||||||||||||||||||
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References
- [1]. A E Hassan, et al. A convenient synthesis of 2'-deoxy-2-fluoroadenosine; a potential prodrug for suicide gene therapy. Nucleosides Nucleotides Nucleic Acids. 2000 Mar;19(3):559-65. [Content Brief]
- [2]. Parker WB, et al. Antitumor activity of 2-fluoro-2'-deoxyadenosine against tumors that express Escherichia coli purine nucleoside phosphorylase. Cancer Gene Ther. 2003 Jan;10(1):23-9. [Content Brief]
- [3]. Wright JM, et al. Susceptibility in vitro of clinically metronidazole-resistant Trichomonas vaginalis to nitazoxanide, toyocamycin, and 2-fluoro-2'-deoxyadenosine. Parasitol Res. 2010 Sep;107(4):847-53. [Content Brief]
