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

Lu, Zhiyuan; Lord, Samuel J.; Wang, Hui; Moerner, W. E.; Twieg, Robert J.

doi:10.1021/jo0616660

Cited by 80 publications

(69 citation statements)

References 36 publications

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“…Unlike the merocyanine derivatives, PRODAN is excited at wavelengths below 400 nm and has an appreciably smaller extinction coefficient. A report of a conjugation-extended analogue of PRODAN showed enhancement of these properties by shifting the excitation wavelength to around 460 nm [12]. …”

Section: Solvatochromic Fluorophores Commonly Used In Biological Studiesmentioning

confidence: 99%

Monitoring protein interactions and dynamics with solvatochromic fluorophores

Loving

Sainlos

Imperiali

2010

Trends in Biotechnology

266

196

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Solvatochromic fluorophores possess emission properties that are sensitive to the nature of the local microenvironment. These dyes have been exploited in applications ranging from the study of protein structural dynamics to the detection of protein-binding interactions. While the solvatochromic indole fluorophore of tryptophan has been utilized extensively for in vitro studies to advance our understanding of basic protein biochemistry, the emergence of new extrinsic synthetic dyes with improved properties in conjunction with recent developments in site-selective methods to incorporate these chemical tools into proteins now open the way for studies in more complex systems. Herein we discuss recent technological advancements and their application in the design of powerful reporters, which serve critical roles in modern cell biology and assay development.

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Section: Solvatochromic Fluorophores Commonly Used In Biological Studiesmentioning

confidence: 99%

Monitoring protein interactions and dynamics with solvatochromic fluorophores

Loving

Sainlos

Imperiali

2010

Trends in Biotechnology

266

196

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“…But apart from functionalization at the meso positions (C9, C10) 78,85 the synthesis of such anthracene derivatives, especially with donor and acceptor functionalities in the lateral positions, is a rather elaborate project. [86][87][88][89][90] In contrast, the pyridinium unit within the benzo[b]quinolizinium already constitutes an intrinsic acceptor functionality, so that already the introduction of a single electron donating substituent in a "conjugated" position (i.e. position 2, 4, 6, 7, 9 or 11) establishes a donoracceptor system.…”

Section: Photophysical Propertiesmentioning

confidence: 99%

The benzo[b]quinolizinium ion as a water-soluble platform for the fluorimetric detection of biologically relevant analytes

Granzhan¹,

Ihmels²,

Tian³

2015

Arkivoc

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In this Account our efforts are described to establish the benzo[b]quinolizinium ion, also known as acridizinium or 4a-azoniaanthracene, as a water-soluble surrogate of anthracene for the development of selective fluorescent probes. It is demonstrated with selected examples that especially the 9-aminobenzo[b]quinolizinium is a donor-acceptor dye with favorable absorption and emission properties and may be used as a versatile building block for fluorescent light-up probes and ratiometric probes.

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“…ANTHRADAN, an analog of PRODAN (27) possessing an anthracene core rather than naphthalene, is one particular example where increased conjugation resulted in an approximate 100 nm bathochromic shift of absorption and emission spectra compared with PRODAN. 29 While extremely useful, this strategy can also be limiting due to reduced brightness of the dye associated with the presence of additional nonradiative relaxation modes and more pronounced perturbations in systems being studied resulting from the increasing size of the probe. We have demonstrated that changes to the substitution pattern of the naphthalene ring produce longer absorption and emissions wavelengths without proportionate increases in molecular size or decreases in quantum yield.…”

Section: Accounts Of Chemical Researchmentioning

confidence: 99%

Intramolecular Didehydro-Diels–Alder Reaction and Its Impact on the Structure–Function Properties of Environmentally Sensitive Fluorophores.

Brummond

Kocsis

2015

Acc. Chem. Res.

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Reaction discovery plays a vital role in accessing new chemical entities and materials possessing important function.1 In this Account, we delineate our reaction discovery program regarding the [4 + 2] cycloaddition reaction of styrene-ynes. In particular, we highlight our studies that lead to the realization of the diverging reaction mechanisms of the intramolecular didehydro-Diels-Alder (IMDDA) reaction to afford dihydronaphthalene and naphthalene products. Formation of the former involves an intermolecular hydrogen atom abstraction and isomerization, whereas the latter is formed via an unexpected elimination of H2. Forming aromatic compounds by a unimolecular elimination of H2 offers an environmentally benign alternative to typical oxidation protocols. We also include in this Account ongoing work focused on expanding the scope of this reaction, mainly its application to the preparation of cyclopenta[b]naphthalenes. Finally, we showcase the synthetic utility of the IMDDA reaction by preparing novel environmentally sensitive fluorophores. The choice to follow this path was largely influenced by the impact this reaction could have on our understanding of the structure-function relationships of these molecular sensors by taking advantage of a de novo construction and functionalization of the aromatic portion of these compounds. We were also inspired by the fact that, despite the advances that have been made in the construction of small molecule fluorophores, access to rationally designed fluorescent probes or sensors possessing varied and tuned photophysical, spectral, and chemical properties are still needed. To this end, we report our studies to correlate fluorophore structure with photophysical property relationships for a series of solvatochromic PRODAN analogs and viscosity-sensitive cyanoacrylate analogs. The versatility of this de novo strategy for fluorophore synthesis was demonstrated by showing that a number of functional groups could be installed at various locations, including handles for eventual biomolecule attachment or water-solubilizing groups. Further, biothiol sensors were designed, and we expect these to be of general utility for the study of lipid dynamics in cellular membranes and for the detection of protein-binding interactions, ideal applications for these relatively hydrophobic fluorophores. Future studies will be directed toward expanding this chemistry-driven approach to the rational preparation of fluorophores with enhanced photophysical and chemical properties for application in biological systems.

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

Cited by 80 publications

References 36 publications

Monitoring protein interactions and dynamics with solvatochromic fluorophores

Monitoring protein interactions and dynamics with solvatochromic fluorophores

The benzo[b]quinolizinium ion as a water-soluble platform for the fluorimetric detection of biologically relevant analytes

Intramolecular Didehydro-Diels–Alder Reaction and Its Impact on the Structure–Function Properties of Environmentally Sensitive Fluorophores.

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