Gemcitabine hydrochloride

Cat. No. 3259

Gemcitabine hydrochloride C9H11F2N3O4.HCl [122111-03-9]

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Chemical Name: (+)-2'-Deoxy-2',2'-difluorocytidine hydrochloride

Biological Activity

Deoxycytidine analog that inhibits DNA synthesis. Metabolized to form gemcitabine triphosphate (dFdCTP) and gemcitabine diphosphate (dFdCDP). dFdCTD inhibits ribonucleotide reductase causing a reduction in cellular nucleotides. dFdCTP is incorporated in DNA resulting in DNA strand termination. Displays antitumor activity in vitro and in vivo.

Technical Data

M.Wt:
299.66
Formula:
C9H11F2N3O4.HCl
Solubility:
Soluble to 100 mM in water and to 50 mM in DMSO
Purity:
>99 %
Storage:
Desiccate at +4°C
CAS No:
122111-03-9

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
All Tocris products are intended for laboratory research use only.

Certificate of Analysis / Product Datasheet / Safety Data Sheet

Heinemann et al (1995) Gemcitabine: a modulator of intracellular nucleotide and deoxynucleotide metabolism. Semin.Oncol. 22 (Suppl. 11) 11. PMID: 7481839.

Plunkett et al (1995) Preclinical characteristics of gemcitabine. Anticancer Drugs 6 (Suppl. 6) 7. PMID: 8718419.

Hertel et al (1990) Evaluation of the antitumor activity of Gemcitabine (2',2'-Difluoro-2'-deoxycytidine). Cancer Res. 50 4417. PMID: 2364394.

If you know of a relevant reference for this product please let us know.

Citations are publications that use Tocris products. Selected citations for Gemcitabine hydrochloride include:

Dolman et al (2015) DNA-Dependent Protein Kinase As Molecular Target for Radiosensitization of Neuroblastoma Cells. PLoS One 10 e0145744. PMID: 26716839.

Okita et al (2015) Contrasting Effects of the Cytotoxic Anticancer Drug Gemcitabine and the EGFR Tyrosine Kinase Inhibitor Gefitinib on NK Cell-Mediated Cytotoxicity via Regulation of NKG2D Ligand in Non-Small-Cell Lung Cancer Cells. PLoS One 10 e0139809. PMID: 26439264.

Veroli et al (2015) An automated fitting procedure and software for dose-response curves with multiphasic features. Mol Cancer Ther 5 14701. PMID: 26424192.

Bapiro et al (2014) Gemcitabine diphosphate choline is a major metabolite linked to the Kennedy pathway in pancreatic cancer models in vivo. Br J Cancer 111 318. PMID: 24874484.

Jones et al (2014) BRCA2 and RAD51 promote double-strand break formation and cell death in response to gemcitabine. PLoS One 13 2412. PMID: 25053826.

Slee et al (2014) Selective inhibition of pancreatic ductal adenocarcinoma cell growth by the mitotic MPS1 kinase inhibitor NMS-P715. Mol Cancer Ther 13 307. PMID: 24282275.

Clouser et al (2013) Characterization of permeability, stability and anti-HIV-1 activity of decitabine and gemcitabine divalerate prodrugs. Antivir Chem Chemother 23 223. PMID: 23994876.

Song et al (2013) Plk1 phosphorylation of orc2 and hbo1 contributes to gemcitabine resistance in pancreatic cancer. Mol Cancer Ther 12 58. PMID: 23188630.

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Keywords: Gemcitabine hydrochloride, supplier, DNA, synthesis, inhibitors, inhibits, Ribonucleotide, reductases, chemotherapeutics, Tocris Bioscience, DNA, RNA and Protein Synthesis Inhibitor products

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