110988-86-8
Chemical Structure
Gemcitabine triphosphate
Synonym(s): dFdCTP
- CAS No.: 110988-86-8
- Formula:C9H14F2N3O13P3
- Molecular Weight:503.14
IUPAC Name: ((2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4,4-difluoro-3-hydroxytetrahydrofuran-2-yl)methyl tetrahydrogen triphosphate
InChIKey: YMOXEIOKAJSRQX-QPPQHZFASA-N
SMILES: NC(C=CN1[C@H]2C(F)(F)[C@H](O)[C@@H](COP(OP(OP(O)(O)=O)(O)=O)(O)=O)O2)=NC1=O
Biological Activity: Gemcitabine triphosphate (dFdCTP) is the active metabolite of Gemcitabine (HY-17026). The mechanism of Gemcitabine triphosphate cell-killing is its competition with cytidine triphosphate during DNA replication, which results in the inhibition of chain elongation. Gemcitabine triphosphate shows a Ki of 11.2 μM against DNA polymerase α and 14.4 μM against DNA polymerase ε. Gemcitabine triphosphate partially inhibits dCMP deaminase and acts as a substrate for DNA synthesis to incorporate into cellular DNA and RNA. Gemcitabine triphosphate disrupts DNA and RNA synthesis, arrests cell cycle in G0/G1 and S phases, triggers apoptosis, reduces tumor cell proliferation. Gemcitabine triphosphate can be used for the research of pancreatic cancer and non-small cell lung cancer[1][2][3][4].
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Gemcitabine triphosphate | Gemcitabine triphosphate (dFdCTP) is the active metabolite of Gemcitabine (HY-17026). The mechanism of Gemcitabine triphosphate cell-killing is its competition with cytidine triphosphate during DNA replication, which results in the inhibition of chain elongation. Gemcitabine triphosphate shows a Ki of 11.2 μM against DNA polymerase α and 14.4 μM against DNA polymerase ε. Gemcitabine triphosphate partially inhibits dCMP deaminase and acts as a substrate for DNA synthesis to incorporate into cellular DNA and RNA. Gemcitabine triphosphate disrupts DNA and RNA synthesis, arrests cell cycle in G0/G1 and S phases, triggers apoptosis, reduces tumor cell proliferation. Gemcitabine triphosphate can be used for the research of pancreatic cancer and non-small cell lung cancer. | |||||||||||||||||||||
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References
- [1]. Shewach DS, et al. Gemcitabine and radiosensitization in human tumor cells. Invest New Drugs. 1996;14(3):257-263. [Content Brief]
- [2]. Matsumoto T, et al. A Liposomal Gemcitabine, FF-10832, Improves Plasma Stability, Tumor Targeting, and Antitumor Efficacy of Gemcitabine in Pancreatic Cancer Xenograft Models. Pharm Res. 2021;38(6):1093-1106. [Content Brief]
- [3]. Zhang Y, et al. Systemic delivery of gemcitabine triphosphate via LCP nanoparticles for NSCLC and pancreatic cancer therapy. Biomaterials. 2013;34(13):3447-3458. [Content Brief]
- [4]. Rizzuto I, et al. Pharmacological factors affecting accumulation of gemcitabine's active metabolite, gemcitabine triphosphate. Pharmacogenomics. 2017;18(9):911-925. [Content Brief]
