BIOMAT Database Logo BIOMAT Database Logo

Determination of the antimetabolite Gemcitabine (2',2'-difluoro-2'-deoxycytidine) and of 2',2'-difluoro-2'-deoxyuridine by 19F nuclear magnetic resonance spectroscopy. 1993

H T Edzes, and G J Peters, and P Noordhuis, and J B Vermorken
Department of Physical and Theoretical Chemistry, Vrije Universiteit Amsterdam, The Netherlands.

The analysis of the new antimetabolite 2',2'-difluoro-2'-deoxycytidine (Gemcitabine, Eli Lilly Corp.) and of its metabolic deamination product, 2',2'-difluoro-2'-deoxyuridine, in urine and plasma by means of 19F NMR is described. Both compounds show AB-type NMR spectra which are characterized as a function of pH at a magnetic field strength of 9.4 T. In the physiological pH range the spectra of both compounds are distinct, despite the fact that both compounds have almost identical average 19F shifts. A linear relation between NMR intensity and concentration in urine has been established. The NMR method does not require sample pretreatment and allows for rapid, nondestructive analysis of Gemcitabine concentrations over 0.01 mM. Separation of the two compounds in vivo by 19F NMR spectroscopy is difficult to achieve.

UI MeSH Term Description Entries
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D003841 Deoxycytidine A nucleoside component of DNA composed of CYTOSINE and DEOXYRIBOSE. Cytosine Deoxyribonucleoside,Cytosine Deoxyriboside,Deoxyribonucleoside, Cytosine,Deoxyriboside, Cytosine
D005461 Fluorine A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries. Fluorine-19,Fluorine 19
D005467 Floxuridine An antineoplastic antimetabolite that is metabolized to fluorouracil when administered by rapid injection; when administered by slow, continuous, intra-arterial infusion, it is converted to floxuridine monophosphate. It has been used to treat hepatic metastases of gastrointestinal adenocarcinomas and for palliation in malignant neoplasms of the liver and gastrointestinal tract. FUdR,Fluorodeoxyuridine,5-FUdR,5-Fluorodeoxyuridine,5 Fluorodeoxyuridine
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000093542 Gemcitabine A deoxycytidine antimetabolite used as an antineoplastic agent. 2',2'-Difluoro-2'-Deoxycytidine,2',2'-Difluorodeoxycytidine,2'-Deoxy-2',2''-Difluorocytidine-5'-O-Monophosphate,2'-Deoxy-2'-Difluorocytidine,Gemcitabine Hydrochloride,Gemcitabine, (D-threo-pentafuranosyl)-Isomer,Gemcitabine, (alpha-D-threo-pentofuranosyl)-Isomer,Gemcitabine, (beta-D-threo-pentafuranosyl)-Isomer,Gemicitabine,2',2'-DFDC,Gemzar,LY 188011,LY-188011,dFdCyd,188011, LY,2' Deoxy 2' Difluorocytidine,2' Deoxy 2',2'' Difluorocytidine 5' O Monophosphate,Hydrochloride, Gemcitabine
D000964 Antimetabolites, Antineoplastic Antimetabolites that are useful in cancer chemotherapy. Antineoplastic Antimetabolites

Related Publications

H T Edzes, and G J Peters, and P Noordhuis, and J B Vermorken
Gemcitabine (2',2'-difluoro-2'-deoxycytidine), an antimetabolite that poisons topoisomerase I.
August 2002, Clinical cancer research : an official journal of the American Association for Cancer Research,
H T Edzes, and G J Peters, and P Noordhuis, and J B Vermorken
Inhibition of thymidylate synthase by 2',2'-difluoro-2'-deoxycytidine (Gemcitabine) and its metabolite 2',2'-difluoro-2'-deoxyuridine.
March 2015, The international journal of biochemistry & cell biology,
H T Edzes, and G J Peters, and P Noordhuis, and J B Vermorken
Evaluation of the antitumor activity of gemcitabine (2',2'-difluoro-2'-deoxycytidine).
July 1990, Cancer research,
H T Edzes, and G J Peters, and P Noordhuis, and J B Vermorken
[19F]fluorine nuclear-magnetic-resonance study of the interaction of difluoro-oxaloacetate with aspartate transaminase.
May 1977, The Biochemical journal,
H T Edzes, and G J Peters, and P Noordhuis, and J B Vermorken
Toxicity on human hemopoietic progenitors of 2'-2'-difluoro-2'deoxycytidine (gemcitabine).
January 1998, Anticancer research,
H T Edzes, and G J Peters, and P Noordhuis, and J B Vermorken
The role of apoptosis in 2',2'-difluoro-2'-deoxycytidine (gemcitabine)-mediated radiosensitization.
February 2001, Clinical cancer research : an official journal of the American Association for Cancer Research,
H T Edzes, and G J Peters, and P Noordhuis, and J B Vermorken
Protein structure determination by nuclear magnetic resonance spectroscopy.
January 1990, Biotechnology (Reading, Mass.),
H T Edzes, and G J Peters, and P Noordhuis, and J B Vermorken
Induction of in vivo resistance against gemcitabine (dFdC, 2',2'-difluoro-deoxycytidine).
January 1998, Advances in experimental medicine and biology,
H T Edzes, and G J Peters, and P Noordhuis, and J B Vermorken
Measurement of free intracellular calcium in the brain by 19F-nuclear magnetic resonance spectroscopy.
October 1988, Journal of neurochemistry,
H T Edzes, and G J Peters, and P Noordhuis, and J B Vermorken
Concentration and time dependent growth inhibition and metabolism in vitro by 2',2'-difluoro-deoxycytidine (gemcitabine).
January 1991, Advances in experimental medicine and biology,
Copied contents to your clipboard!