2009
Abstract: Aiming at the development of new benzopyran-based photocleavable protecting groups, novel chloromethylated and hydroxymethylated 2-oxo-2H-benzo[h]benzopyran derivatives bearing a methoxy substituent were designed and used in the synthesis of a series of fluorescent bioconjugates, by linking through an ester or urethane bond to several model neurotransmitter amino acids (glycine, alanine, beta-alanine and gamma-aminobutyric acid, GABA). The resulting fluorescent bioconjugates with emission in the visible range …
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Cited by 27 publications
(17 citation statements)
References 27 publications
(17 reference statements)
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“…The expected cleavage alcohol product, Bbp-OH, was found to decay monoexponentially [Φ F determined as 0.45 in both ethanol and methanol/HEPES (80:20)]. [18] This allowed the estimation of the radiative and nonradiative rate constants (k r and k nr ) of 5.2 ϫ 10 7 and 6.3 ϫ 10 7 s -1 , respectively, in methanol/ HEPES and 4.6 ϫ 10 7 and 9.4 ϫ 10 7 s -1 in acetonitrile/ HEPES (Φ F = 0.45 and 0.33 for the two solvent systems, respectively). [23] With the exception of 3a, which decayed biexponentially, the sum of three exponential components was required to fit the decay data (see Supporting Information), indicating the presence of different coumarin species.…”
Section: Resultsmentioning
confidence: 99%
“…The expected cleavage alcohol product, Bbp-OH, was found to decay monoexponentially [Φ F determined as 0.45 in both ethanol and methanol/HEPES (80:20)]. [18] This allowed the estimation of the radiative and nonradiative rate constants (k r and k nr ) of 5.2 ϫ 10 7 and 6.3 ϫ 10 7 s -1 , respectively, in methanol/ HEPES and 4.6 ϫ 10 7 and 9.4 ϫ 10 7 s -1 in acetonitrile/ HEPES (Φ F = 0.45 and 0.33 for the two solvent systems, respectively). [23] With the exception of 3a, which decayed biexponentially, the sum of three exponential components was required to fit the decay data (see Supporting Information), indicating the presence of different coumarin species.…”
Section: Resultsmentioning
confidence: 99%
“…Cleavage kinetic data obtained by HPLC/UV monitoring was also collected and time-resolved fluorescence measurements were used to elucidate the dynamics. [18] (1) was treated with N-(benzyloxycarbonyl)-l-valine (2a) or N-(benzyloxycarbonyl)-l-phenylalanine (2b) in the presence of potassium fluoride in DMF at room temperature [20] to give N-(benzyloxycarbonyl)-l-valine (6-methoxy-2-oxo-2H-naphtho[1,2-b]pyran-4-yl)methyl ester (3a) and N-(benzyloxycarbonyl)-l-phenylalanine (6-methoxy-2-oxo-2H-naphtho[1,2-b]pyran-4-yl)methyl ester (3b), respectively, in good yields (Scheme 1). In order to compare the release of the model amino acids in their N-protected 2a and 2b and free forms 5a and 5b under irradiation, the N-benzyloxycarbonyl protecting group was removed by acidolysis with hydrobromic acid in acetic acid to give 4a and 4b bearing the amino acid and the photosensitive tag (Scheme 1).…”
Section: Introductionmentioning
confidence: 97%
“…Our strategy was to identify the key subunit required for activity using various substituents. Further, essential substituents like, ‐CH 3 (electron donating), ‐OCH 3 (electron releasing), Br, Cl, F (halogen), t‐Bu and benzo groups were varied on the coumarin ring to get the optimum results.A fused benzo substituent was also present in our synthesized compounds, since this fused benzogroup to coumarins have been described in their electronic along with their photo‐physical characteristics have resulted in promising biological applications and photocleavage studies …”
Section: Resultsmentioning
confidence: 99%
“…Carboxylic acid containing molecules (amino acids, including neurotransmitters) have been effectively protected by a variety of PRPGs, such as 1-pyrenylmethyl (Fernandes et al 2007(Fernandes et al , 2008a, quinolones (Fonseca et al 2010), benzoxazoles (Soares et al 2010a), as well as 2-oxo-benzopyrans (trivially known as coumarins) (Fonseca et al 2007(Fonseca et al , 2010, and 2-oxo-benzobenzopyrans (benzocoumarins, Piloto et al 2006;Fernandes et al 2008a, b;Soares et al 2010b). Their behaviour towards photocleavage under UV irradiation was studied at different wavelengths, in simulated physiological environment in mixtures of aqueous buffer and different organic solvents.…”
Section: Introductionmentioning
confidence: 99%
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