Synthesis and properties of some 7‐dimethylamino‐1,4‐benzoxazin‐2‐ones

Bris, M.-T. Le

doi:10.1002/jhet.5570220526

Cited by 31 publications

(13 citation statements)

References 9 publications

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“…In addition, molecular orbital analysis indicates a π – π * transition for these molecules. These results are consistent with those previously reported for benzoxazole derivatives and structurally related compounds such as benzoxazinones and coumarins .…”

Section: Resultssupporting

confidence: 93%

Solvent and Media Effects on the Photophysics of Naphthoxazole Derivatives

Curitol

Ragàs

Nonell

et al. 2013

Photochem & Photobiology

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The photophysical properties of 2-phenyl-naphtho[1,2-d][1,3]oxazole, 2(4-N,N-dimethylaminophenyl)naphtho[1,2-d][1,3]oxazole and 2(4-N,N-diphenylaminophenyl) naphtho[1,2-d][1,3]oxazole were studied in a series of solvents. UV-Vis absorption spectra are insensitive to solvent polarity whereas the fluorescence spectra in the same solvent set show an important solvatochromic effect leading to large Stokes shifts. Linear solvation energy relationships were employed to correlate the position of fluorescence spectra maxima with microscopic empirical solvent parameters. This study indicates that important intramolecular charge transfer takes place during the excitation process. In addition, an analysis of the solvatochromic behavior of the UV-Vis absorption and fluorescence spectra in terms of the Lippert-Mataga equation shows a large increase in the excited-state dipole moment, which is also compatible with the formation of an intramolecular charge-transfer excited state. We propose both naphthoxazole derivatives as suitable fluorescent probes to determine physicochemical microproperties in several systems and as dyes in dye lasers; consequence of their high fluorescence quantum yields in most solvents, their large molar absorption coefficients, with fluorescence lifetimes in the range 1-3 ns as well as their high photostability.

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Section: Resultssupporting

confidence: 93%

Solvent and Media Effects on the Photophysics of Naphthoxazole Derivatives

Curitol

Ragàs

Nonell

et al. 2013

Photochem & Photobiology

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“…This small molecule is not symmetrical, and the dipole moment in the excited state is much larger than in the ground state. 57 The slight structure differences between coumarin and 7-dimethylamino-1,4-benzoxazin-2-one, make the latter have a longer wavelength. Therefore, we introduced a simple aldehyde group to this molecule and developed a novel fluorescent chemodosimeter T1 which displayed absorption ratiometric and fluorescence enhanced responses to Cys/Hcy based on cyclization of mercapto biomolecules with aldehydes.…”

mentioning

confidence: 99%

Fluorescent chemodosimeter for Cys/Hcy with a large absorption shift and imaging in living cells

Fan

et al. 2011

Org. Biomol. Chem.

121

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A novel molecule T1 with efficient intramolecular charge transfer was designed as a fluorescent chemodosimeter for cysteine (Cys) and homocysteine (Hcy). Upon addition of Cys/Hcy, T1 exhibited greatly enhanced fluorescence intensity as well as a large absorption peak shift (70 nm), and can be used for bioimaging of Cys/Hcy in living cells and detection in human plasma by visual color change. The detection mechanism was proved by (1)H NMR, mass spectrometry analysis and Gaussian calculations.

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“…Benzoxazinone derivatives [5,6] appear to be an interesting class of fuorescent dyes suitable for use in flow cytometry in conjunction with fluorescein derivatives. Benzoxazinone derivatives have a high molar absorbance (~M-39500; [6]) = 488 nm (one of the main excitation wavelengths, from Hg lamp and Ar laser) and a large Stokes shift leading to a very low fluorescence intensity at 520 nm (the maximum wavelength of fluorescein derivative emission) and a large fluorescence intensity above 550 rim.…”

Section: Resultsmentioning

confidence: 99%

“…However, these fluorescent proteins have a high molecular weight (M r = 240000) and are quite expensive. Recently, Valeur et al [5] described the synthesis and the fluorescent characteristics [6] of a new benzoxazinone derivative, 7-dimethylamino 3-(p-formylstyryl) 1,4.benzoxazin 2-one which can be excited at 488 nm and which fuoresces at 590 nm. In the p~esent paper, we show that this compound can be used in flow cytometry to render microorganisms or animal cells fluorescent.…”

Section: Introductionmentioning

confidence: 99%

Benzoxazinone derivatives: new fluorescent probes for two-color flow cytometry analysis using one excitation wavelength

Monsigny

1989

Biology of the Cell

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A new class of fluorescent dye which upon excitation at 488 nm turns red is shown to be probe-suitable for using in flow cytometry alone or in conjunction with fluorescein derivatives. 7-dimethylamino 3-(p-formylstyryl) 1,4 benzoxazin 2-one is suitable for rendering microorganisms, such as Plasmodium merozoites and cells detectable by flow cytometry, allowing a dual fluorescence analysis when the cells are labelled with suitable fluoresceinylated ligands such as fluorescein labeled neoglycoproteins or antibodies. The synthesis of the new benzoxazinone derivatives is described: p-[beta-(7-dimethylamino 1,4 benzoxazin 2-one 3-yl)-vinyl]-phenylpropenoic acid can be easily activated as a hydroxysuccinimide derivative and linked to amino groups of polypeptides. Hydrophilic polypeptides such as poly-L-lysine or glycosylated polymers combined with this new fluorescent dye are shown to be helpful in analyzing cell surface receptors, in dual fluorescence flow cytometry analysis, using a single excitation wavelength and two sets of compounds labeled with the new benzoxazinone derivative and with fluorescein isothiocyanate, respectively. The new benzoxazinone derivative has a high molar absorbance, a good quantum yield fluorescence when it is bound to hydrophilic polypeptides and its fluorescence intensity is not dependent on pH in the physiological pH range.

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Synthesis and properties of some 7‐dimethylamino‐1,4‐benzoxazin‐2‐ones

Cited by 31 publications

References 9 publications

Solvent and Media Effects on the Photophysics of Naphthoxazole Derivatives

Solvent and Media Effects on the Photophysics of Naphthoxazole Derivatives

Fluorescent chemodosimeter for Cys/Hcy with a large absorption shift and imaging in living cells

Benzoxazinone derivatives: new fluorescent probes for two-color flow cytometry analysis using one excitation wavelength

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