Gemcitabine-5'-triphosphate

2'-Deoxy-2',2'-difluorocytidine-5'-triphosphate, dFdCTP

Gemcitabine triphosphate is supplied as the triethylammonium salt in aqueous solution with the amount and concentration written on the label. This is the most stable form for di and triphosphates. For a quotation for larger quantities or for a custom synthesis of any nucleoside mono, di or triphosphate, please inquire.

Orders can be placed online, by telephone or by email

$148/1mg (1.1 µmole)
$472/5mg (5.5 µmole)
$843/10mg (11 µmole)

The 2D structure of Gemcitabine triphosphate (dFdCTP) is:

 

Selected references:

McCluskey et al. Biophysical Analysis of Bacterial CTP Synthase Filaments Formed in the Presence of the hemotherapeutic Metabolite Gemcitabine-5'-triphosphate. J Mol Biol. 2018 Apr 13;430(8):1201-1217.

Rizzuto et al. Pharmacological factors affecting accumulation of gemcitabine's active metabolite, gemcitabine triphosphate.Pharmacogenomics. 2017 Jun;18(9):911-925.

McCluskey et al. Exploring the Potent Inhibition of CTP Synthase by Gemcitabine-5'-Triphosphate. Chembiochem. 2016 Dec 2;17(23):2240-2249.

Kamčeva et al. Liquid chromatography/tandem mass spectrometry method for simultaneous quantification of eight endogenous nucleotides and the intracellular gemcitabine metabolite dFdCTP in human peripheral blood mononuclear cells. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Sep 15;1001:212-20.

Tham et al. Erratum to: does saturable formation of gemcitabine triphosphate occur in patients? Cancer Chemother Pharmacol. 2015 Mar;75(3):657.

Khatri et al. SLC28A3 genotype and gemcitabine rate of infusion affect dFdCTP metabolite disposition in patients with solid tumours. Br J Cancer. 2014 Jan 21;110(2):304-12.

Zhang et al. Systemic delivery of gemcitabine triphosphate via LCP nanoparticles for NSCLC and pancreatic cancer therapy. Biomaterials. 2013 Apr;34(13):3447-58.

Bapiro et al. A novel method for quantification of gemcitabine and its metabolites 2',2'-difluorodeoxyuridine and gemcitabine triphosphate in tumour tissue by LC-MS/MS: comparison with (19)F NMR spectroscopy. Cancer Chemother Pharmacol. 2011 Nov;68(5):1243-53.

Battaglia et al. Pharmacokinetic∕pharmacodynamic modelling of intracellular gemcitabine triphosphate accumulation: translating in vitro to in vivo. IET Syst Biol. 2011 Jan;5(1):34.

Lohman et al. Inactivation of Lactobacillus leichmannii ribonucleotide reductase by 2',2'-difluoro-2'-deoxycytidine 5'-triphosphate: covalent modification. Biochemistry. 2010 Feb 23;49(7):1404-17. .

Lohman et al. Inactivation of Lactobacillus leichmannii ribonucleotide reductase by 2',2'-difluoro-2'-deoxycytidine 5'-triphosphate: adenosylcobalamin destruction and formation of a nucleotide-based radical. Biochemistry. 2010 Feb 23;49(7):1396-403.

Risbood et al. Synthesis of gemcitabine triphosphate (dFdCTP) as a tris(triethylammonium) salt. Bioorg Med Chem Lett. 2008 May 1;18(9):2957-8.

Tham et al. Does saturable formation of gemcitabine triphosphate occur in patients? Cancer Chemother Pharmacol. 2008 Dec;63(1):55-64.

Veltkamp et al. Quantitative analysis of gemcitabine triphosphate in human peripheral blood mononuclear cells using weak anion-exchange liquid chromatography coupled with tandem mass spectrometry. J Mass Spectrom. 2006 Dec;41(12):1633-42.

Nishi et al. A new, simple method for quantifying gemcitabine triphosphate in cancer cells using isocratic high-performance liquid chromatography. Cancer Sci. 2006 Nov;97(11):1274-8.

Buesa et al. Phase I clinical trial of fixed-dose rate infusional gemcitabine and dacarbazine in the treatment of advanced soft tissue sarcoma, with assessment of gemcitabine triphosphate accumulation. Cancer. 2004 Nov 15;101 (10):2261-9.

Sparidans et al. Isocratic ion-exchange chromatographic assay for the nucleotide gemcitabine triphosphate in human white blood cells. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Nov 25;780(2):423-30.

Patel et al. Phase II clinical investigation of gemcitabine in advanced soft tissue sarcomas and window evaluation of dose rate on gemcitabine triphosphate accumulation. J Clin Oncol. 2001 Aug 1;19(15):3483-9. .

Smid et al. Interference of gemcitabine triphosphate with the measurements of deoxynucleotides using an optimized DNA polymerase elongation assay. Int J Oncol. 2001 Jul;19(1):157-62.

Silva et al. Gemcitabine 5'-triphosphate is a stoichiometric mechanism-based inhibitor of Lactobacillus leichmannii ribonucleoside triphosphate reductase: evidence for thiyl radical-mediated nucleotide radical formation. Biochemistry. 1998 Apr 21;37(16):5528-35.