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504594
Sigma-AldrichGemcitabine, HCl - CAS 122111-03-9 - Calbiochem
A bioavailable, moderately toxic, deoxyctytidine analog with anti-metabolite and anti-tumor properties. Shown to be effective against a variety of tumors and blocks the growth of cancer cells in culture (IC 50 = 8.7, 57, 3.7, and 36 nM for L1210, CEM, Caco2, and HeLa cells, respectively). Following its uptake into cells by nucleoside transporters it is phosphorylated to its mono (dFdCMP), di (dFdCDP), and triphosphorylated (dFdCTP) forms by deoxycytidine kinase. dFdCDP and dFdCTP are reported to inhibit the activity of ribonucleotide reductase and impede DNA synthesis and repair mechanisms and induce cell death. Blocks the progression of cells through the G1/S phase. The dFdCTP is shown to compete with endogenous deoxycytidine triphosphate (dCTP) for incorporation into DNA and against CTP into RNA. Gemcitabine is also shown to block mitochondrial DNA polymerase γ. Works synergistically with other chemotherapeutic agents to enhance their cytotoxicity. Its half life is reported to be 42 to 94 min (depending upon the age and sex of the individual).
Catalogue Number
504594
Brand Family
Calbiochem®
Synonyms
Ribonucleotide Reductase Inhibitor II, RNR Inhibitor II, 2ʹ,2ʹ-Difluoro-2ʹ-deoxycytidine, HCl, 2ʹ-Deoxy-2ʹ,2ʹ-difluorocytidine, HCl, 4-Amino-1-((2R,5S)-3,3-difluoro-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one, HCl, LY188011, dFdC, dFdCyd
References
References
Hung, S.W., et al. 2012. Cancer Lett.320, 138. Fowler, J.D., et al. 2008. J. Biol. Chem.283, 15339. Mackey, J.R., et al. 1998. Cancer Res.58, 4349. Eda, H., et al. 1998. Cancer Res.58, 1165. Burris III, H.A., et al. 1997. J. Clin. Oncol.15, 2403. Heinemann, V., et al. 1992. Cancer Res.52, 533. Hertel, L.W., et al. 1990. Cancer Res.50, 4417.
Gemcitabine, HCl - CAS 122111-03-9 - Calbiochem Certificates of Analysis
Title
Lot Number
504594
References
Reference overview
Hung, S.W., et al. 2012. Cancer Lett.320, 138. Fowler, J.D., et al. 2008. J. Biol. Chem.283, 15339. Mackey, J.R., et al. 1998. Cancer Res.58, 4349. Eda, H., et al. 1998. Cancer Res.58, 1165. Burris III, H.A., et al. 1997. J. Clin. Oncol.15, 2403. Heinemann, V., et al. 1992. Cancer Res.52, 533. Hertel, L.W., et al. 1990. Cancer Res.50, 4417.
Data Sheet
Note that this data sheet is not lot-specific and is representative of the current specifications for this product. Please consult the vial label and the certificate of analysis for information on specific lots. Also note that shipping conditions may differ from storage conditions.
Revision
01-July-2013 JSW
Synonyms
Ribonucleotide Reductase Inhibitor II, RNR Inhibitor II, 2ʹ,2ʹ-Difluoro-2ʹ-deoxycytidine, HCl, 2ʹ-Deoxy-2ʹ,2ʹ-difluorocytidine, HCl, 4-Amino-1-((2R,5S)-3,3-difluoro-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one, HCl, LY188011, dFdC, dFdCyd
Description
A bioavailable, moderately toxic, deoxyctytidine analog with anti-metabolite and anti-tumor properties. Shown to be effective against a variety of tumors and blocks the growth of cancer cells in culture (IC 50 = 8.7, 57, 3.7, and 36 nM for L1210, CEM, Caco2, and HeLa cells, respectively). Following its uptake into cells by nucleoside transporters it is phosphorylated to its mono (dFdCMP), di (dFdCDP), and triphosphorylated (dFdCTP) forms by deoxycytidine kinase. dFdCDP and dFdCTP are reported to inhibit the activity of ribonucleotide reductase and impede DNA synthesis and repair mechanisms and induce cell death. Blocks the progression of cells through the G1/S phase. The dFdCTP is shown to compete with endogenous deoxycytidine triphosphate (dCTP) for incorporation into DNA and against CTP into RNA. Gemcitabine is also shown to block mitochondrial DNA polymerase γ. Works synergistically with other chemotherapeutic agents to enhance their cytotoxicity. Its half life is reported to be 42 to 94 min (depending upon the age and sex of the individual).
Form
White powder
Intert gas (Yes/No)
Packaged under inert gas
CAS number
122111-03-9
Chemical formula
C₉H₁₁F₂N₃O₄ • HCl
Purity
≥99% by HPLC
Solubility
H₂O (25 mg/ml)
Storage
Protect from light +2°C to +8°C Hygroscopic
Do Not Freeze
Ok to freeze
Special Instructions
Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.
Toxicity
Carcinogenic / Teratogenic
References
Hung, S.W., et al. 2012. Cancer Lett.320, 138. Fowler, J.D., et al. 2008. J. Biol. Chem.283, 15339. Mackey, J.R., et al. 1998. Cancer Res.58, 4349. Eda, H., et al. 1998. Cancer Res.58, 1165. Burris III, H.A., et al. 1997. J. Clin. Oncol.15, 2403. Heinemann, V., et al. 1992. Cancer Res.52, 533. Hertel, L.W., et al. 1990. Cancer Res.50, 4417.