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Abstract

N O O N COOH COOH HOOC HOOC CA Index Name Glycine, N,N 0 -[1,2-ethanediylbis(oxy-2,1-phenylene)]bis[N-(carboxymethyl)-Other Names 1,2-Bis(2-aminophenoxy)ethane-N,N,N 0 , N 0 -tetraacetic acid; 1,2-Bis(o-aminophenoxy)ethane-N,N, N 0 ,N 0 -tetraacetic acid; Ethylenedioxybis(o-phenylenenitrilo)tetraacetic acid; 2,2 0 -(Ethylenedioxy)dianiline-N,N,N 0 , N 0 -tetraacetic acid; BAPTA Merck Index Number 957 Chemical/Dye Class Aromatic Molecular Formula C 22 H 24 N 2 O 10 Molecular Weight 476.43 Physical Form Beige powder Solubility Soluble in dimethyl sulfoxide Melting Point 149-159 C Boiling Point (Calcd.) 766.6 AE 60.0 C, pressure: 760 Torr pKa (Calcd.) 1.40 AE 0.10, most acidic, temperature: 25 C; 5.96 AE 0.38, most basic, temperature 25 C Absorption (l max ) 209 nm, 254 nm, 203 nm, 274 nm Emission (l max ) 363 nm Synthesis Synthetic methods 1-3 Staining Applications Calcium ions; 1-3,6-22 zinc ions; 23,24 bone; 4 proteins 5 Biological Applications Calcium indicators; 1-3,6-22 zinc indicators; 23,24 treating acute cell death, 25 cerebral infarction, 25 myocardial infarction, 25 hepatonecrosis, 25 kidney ischemic necrosis, 25 necrotizing pancreatitis, 25 amyloidosis, 26 atherosclerosis, 26 diseases characterized by calcification and/or plaque formation, 27 osteoporosis, 28 Paget's disease, 28 heterotropic ossification, 28 hypercalcemia, 28 cancer, 29 inflammation, 29 diabetes mellitus, 30 epilepsy, 31 epithelial disorders, 32 glaucoma, 33 HIV-associated conditions, 34 respiratory disorders, 35 streptococcal infection, 36 viral diseases 37 involvement of T-type Ca 2 þ channels. J. Neurochem. 2009, 108, 676-684. 7. Flagg, T. P.; Cazorla, O.; Remedi, M. S.; Haim, T. E.; Tones, M. A.; Bahinski, A.; Numann, R. E.; Kovacs, A.; Schaffer, J. E.; Nichols, C. G.; Nerbonne, J. M. Ca 2 þ -independent alterations in diastolic sarcomere length and relaxation kinetics in a mouse model of lipotoxic diabetic cardiomyopathy. Circ. Res. 2009, 104, 95-103. 8. Yoshida, Y.; Tsuchiya, R.; Matsumoto, N.; Morita, M.; Miyakawa, H.; Kudo, Y. Ca 2 þ -dependent induction of intracellular Ca 2 þ oscillation in hippocampal astrocytes during metabotropic glutamate receptor activation. J. Pharmacol. Sci. 2005, 97, 212-218. 9. Shang, J.; Lehrman, M. A. Inhibition of mammalian RNA synthesis by the cytoplasmic Ca 2 þ buffer BAPTA: analyses of [ 3 H]uridine incorporation and stress-dependent transcription. Biochemistry 2004, 43, 9576-9582.10. Nelson, G.; Kozlova-Zwinderman, O.; Collis, A. J.; Knight, M. R.; Fincham, J. R. S.; Stanger, C. P.; Renwick, A.; Hessing, J. G. M.; Punt, P. J.; Van Den Hondel, C. A. M. J. J.; Read, N. D. Calcium measurement in living filamentous fungi expressing codon-optimized aequorin. Mol. Microbiol. 2004, 52, 1437-1450. 11. Rubart, M.; Wang, E.; Dunn, K. W.; Field, L. J. Twophoton molecular excitation imaging of Ca 2 þ transients in Langendorff-perfused mouse hearts. Am. J. Physiol. 2003, 284, C1654-C1668. 12. Rintoul, G. L.; Baimbridge, K. G. Effects of calcium buffers and calbindin-D28k upon histamine-induced calcium oscill...