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T2255

Sigma-Aldrich

Trifluorothymidine

≥99% (HPLC)

Sinonimo/i:

α,α,α-Trifluorothymidine, 2′-Deoxy-5-trifluoromethyluridine, Trifluorothymine deoxyriboside, Trifluridine

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About This Item

Formula empirica (notazione di Hill):
C10H11F3N2O5
Numero CAS:
70-00-8
Peso molecolare:
296.20
Numero CE:
200-722-8
Numero MDL:
MFCD00006534
Codice UNSPSC:
41106305
ID PubChem:
24900027
NACRES:
NA.51

Origine biologica

synthetic

Saggio

≥99% (HPLC)

Forma fisica

powder

Punto di fusione

190-193 °C (lit.)

Solubilità

water: 50 mg/mL, clear, colorless

Temperatura di conservazione

−20°C

Stringa SMILE

OC[C@H]1O[C@H](C[C@@H]1O)N2C=C(C(=O)NC2=O)C(F)(F)F

InChI

1S/C10H11F3N2O5/c11-10(12,13)4-2-15(9(19)14-8(4)18)7-1-5(17)6(3-16)20-7/h2,5-7,16-17H,1,3H2,(H,14,18,19)/t5-,6+,7+/m0/s1
VSQQQLOSPVPRAZ-RRKCRQDMSA-N

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Categorie correlate

Applicazioni

Trifluorothymidine has been used as a component of selection medium to screen thymidine kinase (TK) mutants in lymphoma cells, human lymphoblastoid TK6 cells, and L5178Y mouse lymphoma cells.

Azioni biochim/fisiol

Trifluorothymidine is a thymidine analog and is light sensitive. TFT serves as a thymidine kinase substrate to study enzyme specificity and kinetics. Incorporation of phosphorylated TFT into DNA induces damage, making it useful for DNA repair studies. TFT may also be used in the inhibition of thymidylate synthase and in screening mutant thymidine kinase gene.. It elicits antitumor activity in gastrointestinal (GI) cancers and has therapeutic potential to treat herpetic keratitis.

Confezionamento

Bottomless glass bottle. Contents are inside inserted fused cone.

Pittogrammi

Health hazard
GHS08

Avvertenze

Warning

Indicazioni di pericolo

H341,H351,H361d

Classi di pericolo

Carc. 2 - Muta. 2 - Repr. 2

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

Certificati d'analisi (COA)

Cerca il Certificati d'analisi (COA) digitando il numero di lotto/batch corrispondente. I numeri di lotto o di batch sono stampati sull'etichetta dei prodotti dopo la parola ‘Lotto’ o ‘Batch’.

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Norihiko Suzuki et al.
International journal of oncology, 39(1), 263-270 (2011-04-15)
Trifluorothymidine (TFT) is well known to be converted to TFT-monophosphate by thymidine kinase and to inhibit thymidylate synthase. In addition, TFT-triphosphate (TFT-TP) is also incorporated into DNA, resulting in cytocidal effects. However, the precise mechanism of TFT-induced DNA damage is
Irene V Bijnsdorp et al.
International journal of cancer, 126(10), 2457-2468 (2009-10-10)
Trifluorothymidine (TFT) is part of the oral drug formulation TAS-102. Both 5-fluorouracil (5-FU) and TFT can inhibit thymidylate synthase and be incorporated into DNA. TFT shows only moderate cross-resistance to 5-FU. Therefore, we examined whether mechanistic differences in cell death
I V Bijnsdorp et al.
Nucleosides, nucleotides & nucleic acids, 27(6), 699-703 (2008-07-05)
Trifluorothymidine (TFT), a potent anticancer agent, inhibits thymidylate synthase (TS) and is incorporated into the DNA, both events resulting in cell death. Cell death induction related to DNA damage often involves activation of p53. We determined the role of p53
Novel cell death mechanisms of trifluorothymidine.
Bijnsdorp IV, Kruyt F, et al.
Nucleic Acids Symposium Series, 52, 649-649 (2008)
Connie Kang et al.
Drugs, 79(14), 1583-1590 (2019-09-07)
Trifluridine/tipiracil (Lonsurf®) is a fixed-dose combination tablet comprising trifluridine, an antineoplastic nucleoside analogue, and tipiracil, a thymidine phosphorylase inhibitor. Trifluridine/tipiracil has recently been granted an additional indication in the USA for the treatment of metastatic gastric cancer, including gastroesophageal junction
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