Fluorescence properties of methyl 8-(2-anthroyl) octanoate, a solvatochromic lipophilic probe

Perochon, Etienne; Lopez, André; Tocanne, Jean‐François

doi:10.1016/0009-3084(91)90059-k

Cited by 19 publications

(6 citation statements)

References 26 publications

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“…Simple anthracene derivatives have been extensively used as fluorescent probes in biology, chemical sensors, and optoelectronic materials . For instance, Tocanne and co-workers studied methyl 8-(2-anthroyl)octanoate as a solvatochromic lipophilic probe . Coleman and Mortensen synthesized 1- and 2-anthrancenyl β-C2‘-deoxyribosides to study the dynamic properties of DNA using ultrafast photophysical techniques .…”

Section: Introductionmentioning

confidence: 99%

“…6 For instance, Tocanne and co-workers studied methyl 8-(2-anthroyl)octanoate as a solvatochromic lipophilic probe. 7 Coleman and Mortensen synthesized 1-and 2-anthrancenyl β-C2′-deoxyribosides to study the dynamic properties of DNA using ultrafast photophysical techniques. 8 Sakamoto and co-workers synthesized anthracene-linked polythiazaalkane and polythiaalkane derivatives as silver-ion-selective fluoroionophores.…”

Section: Introductionmentioning

confidence: 99%

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Long-Wavelength Analogue of PRODAN: Synthesis and Properties of Anthradan, a Fluorophore with a 2,6-Donor−Acceptor Anthracene Structure

Lord

Wang

et al. 2006

J. Org. Chem.

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We have synthesized the environment-sensitive fluorophores 2-cyano-6-dihexylaminoanthracene and 2-propionyl-6-dihexylaminoanthracene (Anthradan) starting from 2,6-diaminoanthraquinone. Anthradan is the benzologue of the well-known family of naphthalene 2-propionyl-6-dimethylaminonaphthalene (PRODAN) fluorophores. The additional spectral red shift of the anthracene avoids the autofluorescence of many biological systems and provides for more favorable excitation wavelengths for fluorescence applications. Furthermore, Anthradan exhibits polaritysensitive emission comparable to that of PRODAN and displays high quantum yields in a range of solvents. Single molecules of these anthracene-containing fluorophores have been imaged in polymer hosts as a proof-of-principle.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Long-Wavelength Analogue of PRODAN: Synthesis and Properties of Anthradan, a Fluorophore with a 2,6-Donor−Acceptor Anthracene Structure

Lord

Wang

et al. 2006

J. Org. Chem.

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“…As already mentioned, spin-label EPR measurements involve only the ground state and therefore constitute a simpler and more direct test of the different models. Finally, FIGURE 5 Stokes shifts, n a À n f (squares), for the fluorophores PRO-DAN (45), 8-AS (7), and DANSAEP (46), as function of relative dielectric permittivity, 3 r , of the solvent. Fitting the data for aprotic solvents (solid squares) by Eq.…”

Section: Figurementioning

confidence: 99%

“…Fluorescent lipid probes such as anthroyl fatty acids and LAURDAN (see Fig. 1) lack, in general, the positional precision of spin-labeled lipids, although they may be used to probe less local regional polarity (6)(7)(8). On the other hand, AEDANS [N-(iodoacetylaminoethyl)-5-napthylamine-1-sulphonic acid] fluorescent labels have been used with considerable success to determine the transmembrane polarity profiles sensed by bitopic membrane proteins (9).…”

Section: Introductionmentioning

confidence: 99%

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Reaction Fields in the Environment of Fluorescent Probes: Polarity Profiles in Membranes

Marsh

2009

Biophysical Journal

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Fluorescent probes in biological systems are sensitive to environmental polarity by virtue of their response to the reaction field created by polarization of the dielectric medium. Classically, fluorophore solvatochromism is analyzed in terms of the Lippert equation and later variants, all of which rely upon the original reaction field of Onsager. A recent survey of the solvent dependence of EPR spin-label probes, which are responsive solely to the reaction field in the ground state without the complication of excited states, shows that the reaction field of Block and Walker performs best in describing the polarity dependence. In this model, the step-function transition to the bulk dielectric medium used by Onsager is replaced by a graded transition. Analysis of the Stokes shifts for representative fluorescent membrane probes, such as PRODAN, DANSYL, and anthroyl fatty acid, reveals that, of several different reaction fields (including that of Onsager), the Block-Walker model best describes the dependence on solvent dielectric constant and refractive index for the different probes simultaneously. This is after full allowance is made for all contributions involving polarizability of the fluorophore, a point that is frequently neglected or treated incorrectly in studies using biological fluorescent probes. By using the full range of polar and apolar solvents, it is then possible to establish a common reference for the polarity dependence of different fluorophores and to relate this also to the polarity dependence of biologically relevant spin-label EPR probes. An important application is calibration of the transmembrane polarity profile recorded by fluorescent probes in terms of the high-resolution profile obtained from site-specifically spin-labeled lipid chains.

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Environmental Effects on Fluorescence Emission

2012

Molecular Fluorescence

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Fluorescence properties of methyl 8-(2-anthroyl) octanoate, a solvatochromic lipophilic probe

Cited by 19 publications

References 26 publications

Long-Wavelength Analogue of PRODAN: Synthesis and Properties of Anthradan, a Fluorophore with a 2,6-Donor−Acceptor Anthracene Structure

Long-Wavelength Analogue of PRODAN: Synthesis and Properties of Anthradan, a Fluorophore with a 2,6-Donor−Acceptor Anthracene Structure

Reaction Fields in the Environment of Fluorescent Probes: Polarity Profiles in Membranes

Environmental Effects on Fluorescence Emission

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