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Submit ReviewGemcitabine hydrochloride
Description: DNA synthesis inhibitor
Chemical Name: (+)-2'-Deoxy-2',2'-difluorocytidine hydrochloride
Purity: ≥99% (HPLC)
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. Inhibits replication of MERS-CoV and SARS-CoV in vitro (EC50 values are 1,2 16 and 4.957 μM, respectively).
Compound Libraries
Gemcitabine hydrochloride is also offered as part of the Tocriscreen 2.0 Max and Tocriscreen FDA-Approved Drugs. 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 the degree 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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Product Datasheets
References
References are publications that support the biological activity of the product.
Hertel et al (1990) Evaluation of the antitumor activity of gemcit. (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 gemcit. Anticancer Drugs 6 7 PMID: 8718419
Dyall et al (2014) Repurposing of clinically developed drugs for treatment of Middle East Respiratory Syndrome coronavirus infection. Antimicrob.Agents.Chemother. 58 4885 PMID: 24841273
If you know of a relevant reference for Gemcitabine hydrochloride, please let us know.
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14 Citations for Gemcitabine hydrochloride
Citations are publications that use Tocris products. Selected citations for Gemcitabine hydrochloride include:
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
Li et al (2016) Plk1 inhibition enhances the efficacy of gemcit. in human pancreatic cancer. Cell Cycle 15 711 PMID: 26890815
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
Jones et al (2014) BRCA2 and RAD51 promote double-strand break formation and cell death in response to gemcit. PLoS One 13 2412 PMID: 25053826
Marchetti et al (2018) Targeting Multiple Effector Pathways in Pancreatic Ductal Adenocarcinoma with a G-Quadruplex-Binding Small Molecule. J Med Chem 61 2500 PMID: 29356532
Viotti et al (2018) SUV420H2 is an epigenetic regulator of epithelial/mesenchymal states in pancreatic cancer. J Cell Biol 217 763 PMID: 29229751
Veroli et al (2015) An automated fitting procedure and software for dose-response curves with multiphasic features. Mol Cancer Ther 5 14701 PMID: 26424192
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
Song et al (2013) Plk1 phosphorylation of orc2 and hbo1 contributes to gemcit. 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 decit. and gemcit. divalerate prodrugs. Antivir Chem Chemother 23 223 PMID: 23994876
Okita et al (2015) Contrasting Effects of the Cytotoxic Anticancer Drug gemcit. and the EGFR Tyrosine Kinase Inhibitor gefi. 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
Do you know of a great paper that uses Gemcitabine hydrochloride from Tocris? Please let us know.
Reviews for Gemcitabine hydrochloride
Average Rating: 5 (Based on 2 Reviews.)
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Great product.
By
Anonymous on 07/28/2019
Assay Type: In Vitro
Species: Human
Cell Line/Tissue: Jurkat Cells
The compound was used as a control in a study where we determined the effect of our compounds on ribonucleotide reductase enzyme.
The concentration used was 20uM.
Gemcitabine effectively kills growth of melanoma cell line in vitro.
By
Anonymous on 02/14/2019
Assay Type: In Vitro
Species: Human
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.
Literature in this Area
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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