Iminocoumarin-based low affinity fluorescent Ca2+ indicators excited with visible light

Liepouri, Fotini; Foukaraki, Evangelia; Deligeorgiev, Todor; Katerinopoulos, Haralambos E.

doi:10.1054/ceca.2001.0240

Cited by 27 publications

(23 citation statements)

References 13 publications

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“…[11,12] To this end, coumarin derivative 8 with a malonate unit was synthesized according to the procedure given in Scheme 1. Briefly, 4-(benzyloxy)-2-nitrophenol (1) [13] was alkylated under typical Williamson conditions with 1-[(2-bromoethoxy)methyl]benzene to generate 4-(benzyloxy)-1-[2-(benzyloxy)ethoxy]-2-nitrobenzene (2) in 92 % yield. Then, catalytic hydrogenation of 2 resulted in the formation of aniline derivative 3, which was subsequently alkylated with methyl bromoacetate (2 equiv) to give compound 4 in 32 % yield.…”

Section: Resultsmentioning

confidence: 99%

“…Preparation of 2: K 2 CO 3 (415 mg, 3 mmol) was added to a suspension of 1 [13] (7350 mg, 3 mmol) in anhydrous DMF (60 mL). After 20 min, benzyl 2-bromomethyl ether (935 mg, 4.3 mmol, 688 mL) was added to the reaction mixture.…”

Section: Methodsmentioning

confidence: 99%

“…This compound was prepared by following a previously published procedure [13] using 3 (0.500 g, 1.43 mmol), tert-butyl bromoacetate (0.875 g, 5.72 mmol), diisopropylethylamine (0.740 g, 5.72 mmol), and sodium iodide (0.215 g, 1.43 mmol) in DMF (5 mL) as the solvent to give the product after workup and purification (0.215 g, 30 %). UV/Vis (CH 2 …”

Section: Preparation Ofmentioning

confidence: 99%

“…This compound was prepared according to a previously described method [13] using 4 (0.215 g, 0.45 mmol) and phosphoryl chloride (0.064 mL, 0.70 mmol) in DMF (5 mL) to give the product after workup and purification (0.175 g, 72 %). UV/Vis (CH 2 Preparation of 6: This compound was prepared according to a previously described method [13] using compound 5 ( 0.175 g, 0.33 mmol), 10 % Pd/C (0.02 g) as the hydrogenation catalyst and ethyl acetate (10 mL) as the solvent to give the product after workup and purification (0.112 g, 98 % …”

Section: Preparation Ofmentioning

confidence: 99%

“…UV/Vis (CH 2 Preparation of 6: This compound was prepared according to a previously described method [13] using compound 5 ( 0.175 g, 0.33 mmol), 10 % Pd/C (0.02 g) as the hydrogenation catalyst and ethyl acetate (10 mL) as the solvent to give the product after workup and purification (0.112 g, 98 % …”

Section: Preparation Ofmentioning

confidence: 99%

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Fullerene–Coumarin Dyad as a Selective Metal Receptor: Synthesis, Photophysical Properties, Electrochemistry and Ion Binding Studies

Pagona

Economopoulos

Tsikalas

et al. 2010

Chemistry A European J

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A coumarin derivative with a malonate unit has been synthesized and used for the preparation of a fullerene-coumarin dyad through the Bingel cyclopropanation method. The newly synthesized dyad is soluble in organic solvents and has been fully characterized with traditional spectroscopic techniques. Electronic interactions between the two components of the dyad were probed with the aid of UV/Vis spectroscopy, fluorescence emission, and electrochemistry measurements. Our studies clearly show the presence of electronic interactions between C(60) and modified coumarin in the ground state; efficient electron-transfer quenching of the singlet excited state of the coumarin moiety by the appended fullerene sphere was also observed. Time-resolved fluorescence measurements revealed lifetimes for the coumarin-C(60) dyad at a maximum of 50 ps, while the quantum yield was reaching unity. Additionally, the redox potentials of the C(60)-coumarin dyad were determined and the energetics of the electron-transfer processes were evaluated. Finally, after alkaline treatment of C(60)-coumarin, which resulted in the deprotection of carboxylate units, the dyad was tested as a metal receptor for divalent metal cations; ion competition studies and fluorescence experiments showed binding selectivity for lead ions.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Preparation Ofmentioning

confidence: 99%

Section: Preparation Ofmentioning

confidence: 99%

Section: Preparation Ofmentioning

confidence: 99%

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Fullerene–Coumarin Dyad as a Selective Metal Receptor: Synthesis, Photophysical Properties, Electrochemistry and Ion Binding Studies

Pagona

Economopoulos

Tsikalas

et al. 2010

Chemistry A European J

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B

2010

Handbook of Biological Dyes and Stains

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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...

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Copper‐Catalyzed Three‐Component Synthesis of 2‐Iminodihydrocoumarins and 2‐Iminocoumarins

et al. 2010

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An efficient synthesis of N-sulfonyl-substituted 2-imino-3,4-dihydrocoumarins and 2-iminocoumarins via a copper-catalyzed multicomponent reaction of sulfonyl azides with terminal alkynes and b-(ortho-hydroxyphenyl)-a,b-unsaturated ketones or ortho-hydroxyphenylpropiolates has been developed. The cascade process involves trapping the keteimine by a nucleophilic addition and an intramolecular Michael addition. This methodology could well be extended to the concise synthesis of the polysubstituted piperidine scaffold.

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Iminocoumarin-based low affinity fluorescent Ca2+ indicators excited with visible light

Cited by 27 publications

References 13 publications

Fullerene–Coumarin Dyad as a Selective Metal Receptor: Synthesis, Photophysical Properties, Electrochemistry and Ion Binding Studies

Fullerene–Coumarin Dyad as a Selective Metal Receptor: Synthesis, Photophysical Properties, Electrochemistry and Ion Binding Studies

B

Copper‐Catalyzed Three‐Component Synthesis of 2‐Iminodihydrocoumarins and 2‐Iminocoumarins

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