3'-Fluoro-3'-deoxythymidine

3'-Fluoro-3'-deoxythymidine

IUPAC Name:	1-[(2R,5S)-5-(2-Fluoro-5-hydroxymethyl-tetrahydro-furan-2-yl)pyrimidine-2,4-dione
Other Names:	FLT
Identifiers
CAS Number
PubChem
ChemSpider
SMILES
InChI
InChIKey
StdInChI
StdInChIKey
Properties
Chemical formula	CHNO
Appearance
Density
Melting Point
Boiling Point
Solubility
Hazards
Main Hazards
Flash Point
Autoignition Temperature

3'-Fluoro-3'-deoxythymidine (FLT) is a nucleoside analog used primarily in the imaging of proliferation in cancer cells with positron emission tomography (PET). It is a synthetic analog of thymidine. FLT is transported into cells via nucleoside transporters and is subsequently phosphorylated by thymidine kinase 1 (TK1), an enzyme whose activity correlates with cell proliferation. This phosphorylation traps FLT within cells, allowing it to be used as a marker of tissue metabolism and cell proliferation.

Chemistry

3'-Fluoro-3'-deoxythymidine belongs to the class of compounds known as nucleoside analogs, which are molecules that mimic the structure of natural nucleosides but contain modifications that alter their biochemical properties. In the case of FLT, the 3' hydroxyl group of thymidine is replaced by a fluorine atom, which prevents the normal enzymatic degradation of the nucleoside, thereby enhancing its stability and uptake in proliferating cells.

Mechanism of Action

FLT is used in PET imaging to assess tumor cell proliferation by exploiting its uptake and retention in proliferating cells. After entering the cell, FLT is phosphorylated by thymidine kinase 1, an enzyme that is upregulated in rapidly dividing cells. The phosphorylated form of FLT, FLT-monophosphate, is not further incorporated into DNA but is trapped within the cell, allowing it to accumulate in proliferative tissues. The level of FLT uptake in tissues can thus be used as an indirect marker of cellular proliferation.

Clinical Applications

The primary application of 3'-Fluoro-3'-deoxythymidine is in the field of oncology, where it is used to evaluate the effectiveness of cancer therapies by measuring changes in the proliferation rate of tumor cells. FLT-PET imaging can provide valuable information on the responsiveness of cancer to treatment, helping in the adjustment of treatment plans and in the prediction of patient outcomes.

Safety and Efficacy

As with all radiopharmaceuticals, the safety and efficacy of FLT for use in humans depend on the proper preparation, dosage, and administration of the compound. Clinical trials are essential to determine the optimal conditions for its use in various types of cancers and to assess its potential risks and benefits.

See Also

• Thymidine kinase
• Positron emission tomography
• Nucleoside analogs
• Cancer