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Chemical Compound Review

SureCN8647866     2-[[2-[2-[2- (bis(carboxymethyl)amino)- 4...

Synonyms: AC1Q5WIA, AR-1D0258, LS-187468, AC1L3X1S, 4,4'-Fbapta, ...
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Disease relevance of Glycine, N,N'-(1,2-ethanediylbis(oxy(5-fluoro-2,1-phenylene)))bis(N-(carboxymethyl)-

  • We used ion-selective electrodes, nuclear magnetic resonance spectroscopy, and the four-electrode method to perform four series of experiments in the isolated blood-perfused rabbit heart loaded with 5F-BAPTA during 30 to 35 minutes of no-flow ischemia [1].
  • We explored the role of intracellular free calcium in the pathophysiology and pathogenesis of ventricular fibrillation in perfused ferret hearts loaded with the Ca2+ indicator 5F-BAPTA [2].
  • To elucidate the mechanism of contractile dysfunction in postischemic ("stunned") myocardium, time-resolved measurements of intracellular free Ca2+ concentration ([Ca2+]i) were made using gated 19F nuclear magnetic resonance in seven perfused ferret hearts loaded with the fluorinated Ca2+ indicator 5F-BAPTA [3].
  • The effects of the heavy-metal ions Cd2+ and Zn2+ on the homoeostasis of intracellular free Ca2+ in E367 neuroblastoma cells were examined using 19F-NMR spectroscopy with the fluorinated chelator probe 1,2-bis-(2-amino-5-fluorophenoxy)ethane-N,N,N', N'-tetra-acetic acid (5F-BAPTA) [4].
  • In other NMR studies, where 5F-BAPTA was not used, metabolic toxicity was modulated by three glutamate receptor antagonists: dizocilpine, NBQX and kynurenic acid [5].

High impact information on Glycine, N,N'-(1,2-ethanediylbis(oxy(5-fluoro-2,1-phenylene)))bis(N-(carboxymethyl)-

  • 19F NMR in combination with 1,2-bis(2-amino-5-fluorophenoxy)ethane-N,N,N',N'-tetraacetic acid (5F-BAPTA) was used to simultaneously measure [Ca2+]i and intracellular free Pb2+ concentration ([Pb2+]i) in the rat osteoblastic bone cell line ROS 17/2 [6].
  • Developed pressure recovers to only 50% of control values during reflow, indicating that the presence of 5F-BAPTA in the cytosol does not protect against stunning, at least when the extracellular calcium concentration has been raised to 8 mM [7].
  • Although the nonlinear response of 5F-BAPTA to [Ca2+] leads to underestimation of the true time-averaged [Ca2+]i, the measured alterations of intracellular Ca2+ homeostasis during ischemia are large compared with the likely errors in quantification [7].
  • Several lines of evidence are presented to show that loading with the acetoxymethyl ester of 5F-BAPTA is not significantly complicated by accumulation of partially de-esterified metabolites, compartmentalization into mitochondria, or disproportionate uptake into endothelial cells [7].
  • In this study, 1,2-bis(2-amino-5-fluorophenoxy)ethane N,N,N',N'-tetraacetic acid (5F-BAPTA) was used to buffer Pb2+ and Ca2+ concentrations in the PKC reaction mixture [8].

Anatomical context of Glycine, N,N'-(1,2-ethanediylbis(oxy(5-fluoro-2,1-phenylene)))bis(N-(carboxymethyl)-

  • Using 19F-NMR spectroscopy of rat cortical synaptosomes loaded with the fluorinated chelator 1,2-bis(2-amino-5-fluorophenoxy)ethane-N,N,N',N'- tetraacetic acid (5F-BAPTA), we have determined unambiguously that MeHg increases the free intrasynaptosomal Zn2+ concentration ([Zn2+]i) [9].
  • The intracellular free calcium ion concentration ([Ca2+]i) of the neuroblastoma x glioma hybrid cell line, NG108-15, was measured using the 19F-nuclear magnetic resonance divalent cation indicator, 1,2-bis(2-amino-5-fluorophenoxy)ethane-N,N,N',N'-tetra-acetic acid (5F-BAPTA) [10].

Associations of Glycine, N,N'-(1,2-ethanediylbis(oxy(5-fluoro-2,1-phenylene)))bis(N-(carboxymethyl)- with other chemical compounds


Analytical, diagnostic and therapeutic context of Glycine, N,N'-(1,2-ethanediylbis(oxy(5-fluoro-2,1-phenylene)))bis(N-(carboxymethyl)-

  • We conclude that 5F-BAPTA provides useful measurements that reveal that time-averaged [Ca2+]i rises during ischemia and returns to control levels soon after reperfusion [7].


  1. Correlation of ischemia-induced extracellular and intracellular ion changes to cell-to-cell electrical uncoupling in isolated blood-perfused rabbit hearts. Experimental Working Group. Owens, L.M., Fralix, T.A., Murphy, E., Cascio, W.E., Gettes, L.S. Circulation (1996) [Pubmed]
  2. Cell calcium in the pathophysiology of ventricular fibrillation and in the pathogenesis of postarrhythmic contractile dysfunction. Koretsune, Y., Marban, E. Circulation (1989) [Pubmed]
  3. Excitation-contraction coupling in postischemic myocardium. Does failure of activator Ca2+ transients underlie stunning? Kusuoka, H., Koretsune, Y., Chacko, V.P., Weisfeldt, M.L., Marban, E. Circ. Res. (1990) [Pubmed]
  4. Study of the interactions of cadmium and zinc ions with cellular calcium homoeostasis using 19F-NMR spectroscopy. Benters, J., Flögel, U., Schäfer, T., Leibfritz, D., Hechtenberg, S., Beyersmann, D. Biochem. J. (1997) [Pubmed]
  5. 19F NMR calcium changes, edema and histology in neonatal rat brain slices during glutamate toxicity. Espanol, M.T., Litt, L., Xu, Y., Chang, L.H., James, T.L., Weinstein, P.R., Chan, P.H. Brain Res. (1994) [Pubmed]
  6. Lead increases free Ca2+ concentration in cultured osteoblastic bone cells: simultaneous detection of intracellular free Pb2+ by 19F NMR. Schanne, F.A., Dowd, T.L., Gupta, R.K., Rosen, J.F. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
  7. Quantification of [Ca2+]i in perfused hearts. Critical evaluation of the 5F-BAPTA and nuclear magnetic resonance method as applied to the study of ischemia and reperfusion. Marban, E., Kitakaze, M., Koretsune, Y., Yue, D.T., Chacko, V.P., Pike, M.M. Circ. Res. (1990) [Pubmed]
  8. Lead activation of protein kinase C from rat brain. Determination of free calcium, lead, and zinc by 19F NMR. Long, G.J., Rosen, J.F., Schanne, F.A. J. Biol. Chem. (1994) [Pubmed]
  9. Methylmercury-induced elevations in intrasynaptosomal zinc concentrations: an 19F-NMR study. Denny, M.F., Atchison, W.D. J. Neurochem. (1994) [Pubmed]
  10. Effect of lead on intracellular free calcium ion concentration in a presynaptic neuronal model: 19F-NMR study of NG108-15 cells. Schanne, F.A., Moskal, J.R., Gupta, R.K. Brain Res. (1989) [Pubmed]
  11. Alterations of intracellular calcium homeostasis and myocardial energetics in acute adriamycin-induced heart failure. Kusuoka, H., Futaki, S., Koretsune, Y., Kitabatake, A., Suga, H., Kamada, T., Inoue, M. J. Cardiovasc. Pharmacol. (1991) [Pubmed]
  12. Determination of intracellular calcium in vivo via fluorine-19 nuclear magnetic resonance spectroscopy. Song, S.K., Hotchkiss, R.S., Neil, J., Morris, P.E., Hsu, C.Y., Ackerman, J.J. Am. J. Physiol. (1995) [Pubmed]
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