2′-Deoxy-2′-fluoroadenosine

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].

Product Specifications

CAS Number

[64183-27-3]

UNSPSC

12352005

Hazard Statement

H302, H315, H319, H335

Target

Nucleoside Antimetabolite/Analog

Type

Oligonucleotides

Related Pathways

Cell Cycle/DNA Damage

Applications

Cancer-programmed cell death

Field of Research

Cancer; Infection

Assay Protocol

https://www.medchemexpress.com/2-deoxy-2-fluoroadenosine.html

Purity

99.71

Solubility

DMSO : 50 mg/mL (ultrasonic)

Smiles

OC[C@@H]1[C@@H](O)[C@@H](F)[C@H](N2C(N=CN=C3N)=C3N=C2)O1

Molecular Formula

C10H12FN5O3

Molecular Weight

269.24

Precautions

H302, H315, H319, H335

References & Citations

[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.|[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.|[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.