688008-85-7

Basic information

• Product Name: 5'-O-L-phenylalanylgemcitabine
• Synonyms: 5'-O-L-phenylalanylgemcitabine
• CAS NO: 688008-85-7
• Molecular Weight: 410.377
• Mol File: 688008-85-7.mol

Chemical Properties

• CAS DataBase Reference: 5'-O-L-phenylalanylgemcitabine(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-L-phenylalanylgemcitabine(688008-85-7)
• EPA Substance Registry System: 5'-O-L-phenylalanylgemcitabine(688008-85-7)

Safety Data

• Hazardous Substances Data: 688008-85-7(Hazardous Substances Data)

Upstream product

• 250698-51-2 (2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4,4-difluoro-2-(hydroxymethyl)tetrahydrofuran-3-yl tert-butyl carbonate 
• 1609205-97-1 4-allyloxycarbonylamino-1-[(2R,4R,5R)-4-allyloxycarbonyloxy-3,3-difluoro-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one 
• 95058-81-4 gemcitabine 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 849814-02-4 C₂₃H₂₈F₂N₄O₇ 

Relevant articles and documents

Design, characterization, and in vitro antiproliferative efficacy of gemcitabine conjugates based on carboxymethyl glucan

Gemcitabine (GEM) is widely used in clinical practice in the treatment of cancer and several other solid tumors. Nevertheless, the antitumor effect of GEM is partially prevented by some limitations including short half life, and lack of tumor localizing. Carboxymethyl glucan (CMG), a carboxymethylated derivative of β-(1-3)-glucan, shows biocompatibility and biodegradability as well as a potential anticarcinogenic effect. To enhance the antiproliferative activity of GEM, four water soluble conjugates of GEM bound to CMG via diverse amino acid linkers were designed and synthesized. 1H NMR, FT IR, elementary analysis and RP-HPLC chromatography were employed to verify the correct achievement of the conjugates. In vitro release study indicated that conjugates presented slower release in physiological buffer (pH 7.4) than acidic buffer (pH 5.5) mimicking the acidic tumor microenvironment. Moreover, A549, HeLa and Caco-2 cancer cell lines were used to evaluate the in vitro cytotoxicity of conjugates and the results showed that binding GEM to CMG significantly enhanced antiproliferative activity of GEM on A549 cells. Therefore, these conjugates may be potentially useful as a delivery vehicle in cancer therapy and worthy of further study on structure-activity relationship and antiproliferative activity in vitro and in vivo, especially for lung tumor.

Regioselective synthesis of 5′-amino acid esters of some nucleosides via orthogonal protecting protocol

Amino acid esters of nucleosides at 5′-position, as peptidomimetic prodrugs, which could be actively transported by the intestinal oligopeptide transporters 1 (PepT1), bear improved oral bioavailability. We established here a regioselective synthesis of the 5′-esters of some nucleosides via an orthogonal protecting protocol with triphenylmethyl (Tr) and allyloxycarbonyl (AOC) protecting groups. A series of 5′-esters of cytarabine and gemcitabine were selectively synthesized in over 36.0% total yields. This efficient and robust methodology will be examplified for the further study of the prodrugs of large number of antiviral and anticancer nucleosides.

Prodrug composition

A prodrug composition is provided which includes a pharmaceutical species and an amino acid having a covalent bond to the pharmaceutical species. The pharmaceutical species is characterized by bioavailability of 30% or less and a molecular weight in the r