Gemcitabine 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.
Compound Libraries
Gemcitabine hydrochloride is also offered as part of the Tocriscreen Plus and Tocriscreen Library of FDA-Approved Compounds. Find out more about compound libraries available from Tocris.
Technical Data
| M. Wt | 299.66 |
| Formula | C9H11F2N3O4.HCl |
| Storage | Desiccate at +4°C |
| Purity | ≥99% (HPLC) |
| CAS Number | 122111-03-9 |
| PubChem ID | 69101485 |
| InChI Key | OKKDEIYWILRZIA-OSZBKLCCSA-N |
| Smiles | OC[C@@H]1[C@@H](O)C(F)(F)[C@H](N2C(N=C(N)C=C2)=O)O1.Cl |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| water | 29.97 | 100 | |
| DMSO | 5.99 | 20 |
Preparing Stock Solutions
The following data is based on the product molecular weight 299.66. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 3.34 mL | 16.69 mL | 33.37 mL |
| 5 mM | 0.67 mL | 3.34 mL | 6.67 mL |
| 10 mM | 0.33 mL | 1.67 mL | 3.34 mL |
| 50 mM | 0.07 mL | 0.33 mL | 0.67 mL |
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References
References are publications that support the biological activity of the product.
Hertel et al (1990) Evaluation of the antitumor activity of Gemcitabine (2',2'-Difluoro-2'-deoxycytidine). Cancer Res. 50 4417 PMID: 2364394
Heinemann et al (1995) Gemcitabine: a modulator of intracellular nucleotide and deoxynucleotide metabolism. Semin.Oncol. 22 11 PMID: 7481839
Plunkett et al (1995) Preclinical characteristics of gemcitabine. Anticancer Drugs 6 7 PMID: 8718419
If you know of a relevant reference for Gemcitabine hydrochloride, please let us know.
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Keywords: Gemcitabine hydrochloride, Gemcitabine hydrochloride supplier, DNA, synthesis, inhibitors, inhibits, Ribonucleotide, reductases, chemotherapeutics, DNA,, RNA, and, Protein, Synthesis, Reductase, 3259, Tocris Bioscience
12 Citations for Gemcitabine hydrochloride
Citations are publications that use Tocris products. Selected citations for Gemcitabine hydrochloride include:
Song et al (2013) Plk1 phosphorylation of orc2 and hbo1 contributes to gemcitabine resistance in pancreatic cancer. Mol Cancer Ther 12 58 PMID: 23188630
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
Li et al (2016) Plk1 inhibition enhances the efficacy of gemcitabine in human pancreatic cancer. Cell Cycle 15 711 PMID: 26890815
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
Truman et al (2015) Quantitative proteomics of the yeast Hsp70/Hsp90 interactomes during DNA damage reveal chaperone-dependent regulation of ribonucleotide reductase. J Proteomics 112 285 PMID: 25452130
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
Dolman et al (2015) DNA-Dependent Protein Kinase As Molecular Target for Radiosensitization of Neuroblastoma Cells. PLoS One 10 e0145744 PMID: 26716839
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
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
Mayor-López et al (2014) Comparative Study of 17-AAG and NVP-AUY922 in Pancreatic and Colorectal Cancer Cells: Are There Common Determinants of Sensitivity? Transl Oncol 7 590 PMID: 25389454
Veroli et al (2015) An automated fitting procedure and software for dose-response curves with multiphasic features. Mol Cancer Ther 5 14701 PMID: 26424192
Chan et al (2013) A simple high-content cell cycle assay reveals frequent discrepancies between cell number and ATP and MTS proliferation assays. PLoS One 8 e63583 PMID: 23691072
Do you know of a great paper that uses Gemcitabine hydrochloride from Tocris? Please let us know.
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Gemcitabine was used at a 20 uM concentration for in vitro culture with SK-MEL-28 and cell viability was monitored over time with live imaging. Arrow indicates when compound was added to media.
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Cancer Research Product Guide
A collection of over 750 products for cancer research, the guide includes research tools for the study of:
- Cancer Metabolism
- Epigenetics in Cancer
- Receptor Signaling
- Cell Cycle and DNA Damage Repair
- Angiogenesis
- Invasion and Metastasis
