Sigma-Aldrich Gemcitabine HCl 1pc X 50mg

Assay

≥99% (HPLC)

Quality Level

100

Form

powder

Manufacturer/Tradename

Calbiochem^®

Storage Condition

OK to freeze
desiccated (hygroscopic)
protect from light

Color

white

Solubility

water: 25 mg/mL

Storage Temp.

2-8°C

Inchi

1S/C9H11F2N3O4.ClH/c10-9(11)6(16)4(3-15)18-7(9)14-2-1-5(12)13-8(14)17;/h1-2,4,6-7,15-16H,3H2,(H2,12,13,17);1H/t4-,6-,7-;/m1./s1

Inchi Key

OKKDEIYWILRZIA-OSZBKLCCSA-N

General 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 (IC₅₀= 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).

Biochem/Physiol Actions

Cell permeable: yesPrimary Target
DNAReversible: noSecondary Target
DNA polymerase

Packaging

Packaged under inert gas

Warning

Toxicity: Carcinogenic / Teratogenic (D)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Other Notes

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.CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, GermanyGHS08H360P201 - P202 - P280 - P308 + P313 - P405 - P501