Fluorescein Provides a Resonance Gate for FRET from Conjugated Polymers to DNA Intercalated Dyes

Wang, Shu; Gaylord, Brent S.; Bazan, Guillermo C.

doi:10.1021/ja035550m

Cited by 262 publications

(225 citation statements)

References 50 publications

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“…Therefore, the emission of FITC may be quenched by Förster resonance energy transfer (Berney and Danuser, 2003;Wang et al, 2004) to the absorbing groups in the polymer. In addition, the polymer itself shows a strong fluorescence, as can be seen in Fig.…”

Section: Confocal Fluorescence Microscopymentioning

confidence: 99%

Impedimetric immunosensors based on the conjugated polymer PPV

Cooreman

Thoelen

Manca

et al. 2005

Biosensors and Bioelectronics

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Abstract:In the work reported here, we investigated the interaction between the semiconducting polymer MDMO-PPV and antibodies against the fluorescent dyes FITC and Cy5. The antibodies are adsorbed physically onto thin polymer films on gold electrodes, as seen in AFM images of these films. By tuning the antibody concentration, the contact angle of distilled water with the film can be made to vary between 95° and 50°, showing that different surface densities of antibody can be obtained. That these biosensor films specifically bind their antigenic fluorescent molecules from PBS buffer solution is demonstrated by confocal fluorescence microscopy. Specific antigen-antibody recognition is demonstrated by lack of crosssensitivity between the two antibodies and their antigens. In a biosensor prototype based on differential impedance spectroscopy, these polymer films show a clear response to 1 ppb antigen solution, with a time constant of 2 to 3 minutes.

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Section: Confocal Fluorescence Microscopymentioning

confidence: 99%

Impedimetric immunosensors based on the conjugated polymer PPV

Cooreman

Thoelen

Manca

et al. 2005

Biosensors and Bioelectronics

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“…conjugated polymers ͉ DNA sensors ͉ time-resolved anisotropy ͉ ultrafast spectroscopy C ationic conjugated polymers (CCPs) have been demonstrated to have utility in DNA sequence detection (1)(2)(3). In the approach initially proposed by Gaylord et al (1), the luminescent conjugated polymer serves as the light-harvesting entity with subsequent energy transfer to a fluorescein (FL) molecule attached to a peptide nucleic acid (PNA) oligomer comprised of a specific sequence of bases that defines the target.…”

mentioning

confidence: 99%

The fluorescence resonance energy transfer (FRET) gate: A time-resolved study

Wang²,

Korystov³

et al. 2005

Proc. Natl. Acad. Sci. U.S.A.

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106

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The two-step energy-transfer process in a self-assembled complex comprising a cationic conjugated polymer (CCP) and a dsDNA is investigated by using pump-dump-emission spectroscopy and time-correlated single-photon counting; energy is transferred from the CCP to an ethidium bromide (EB) molecule intercalated into the dsDNA through a fluorescein molecule linked to one terminus of the DNA. Time-dependent anisotropy measurements indicate that the inefficient direct energy transfer from the CCP to the intercalated EB results from the near orthogonality of their transition moments. These measurements also show that the transition moment of the fluorescein spans a range of angular distributions and lies between that of the CCP and EB. Consequently, the fluorescein acts as a fluorescence resonance energy-transfer gate to relay the excitation energy from the CCP to the EB. conjugated polymers ͉ DNA sensors ͉ time-resolved anisotropy ͉ ultrafast spectroscopy C ationic conjugated polymers (CCPs) have been demonstrated to have utility in DNA sequence detection (1-3). In the approach initially proposed by Gaylord et al. (1), the luminescent conjugated polymer serves as the light-harvesting entity with subsequent energy transfer to a fluorescein (FL) molecule attached to a peptide nucleic acid (PNA) oligomer comprised of a specific sequence of bases that defines the target. Fluorescence resonance energy transfer (FRET) from the CCP to the PNA-FL occurs by self-assembly of the CCP and the PNA in a double helix with a complementary single-stranded DNA target. In this approach, the electrostatic interaction between the CCP and the negatively charged PNA-FL͞DNA duplex brings the donor (CCP) and the acceptor (FL) in sufficiently close proximity to enable efficient FRET. When the base sequence on the DNA is not complementary to the base sequence on the FL-labeled PNA, the PNA-FL remains as a charge-neutral single-strand oligomer. At the dilute concentrations used, the typical distance between a neutral PNA-FL and a CCP is too large for efficient FRET. By using this FRET-based biosensor, specific targeted sequences of DNA were detected at concentrations as low as 10 pM (1).Wang et al. (2) reported an alternative DNA sequencedetection scheme (Scheme 1) based on intercalation of ethidium bromide (EB) within a dsDNA. Considering that the synthesis and purification of labeled DNA is more straightforward and that both single-stranded DNA and dsDNA have good solubility in buffered water (whereas with PNA, hydrophobic interactions are important), the EB intercalation approach is attractive. However, direct FRET from the CCP to EB was found to be inefficient despite the excellent spectral overlap between the donor emission and acceptor absorption. The absence of efficient FRET was attributed to the orthogonality of the transition dipoles of the CCP and EB in the self-assembled structure (see Scheme 1). When a FL molecule is linked to one terminus of the dsDNA as shown in Scheme 1B, the EB emission is significantly enhanced after excitation...

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“…!-conjugated polymers with donor-acceptor architectures are currently of interest because the intramolecular charge transfer can facilitate ready manipulation of the electronic structure (HOMO/LUMO levels), leading to small band-gap semiconducting polymers [17][18][19][20]. In addition, conjugated polymers have been proven quite useful in creating highly sensi-tive fluorescent chemical sensors [21][22][23]. The conjugated polymer backbone allows efficient electron delocalization and exciton migration over large distances, thereby creating amplified sensory responses compared with small-molecule-based sensors.…”

Section: Introductionmentioning

confidence: 99%

A new conjugated polymer with donor-acceptor architectures based on alternating 1,4-divinyl-2,5-dioctyloxybenzene and 5,8-(2,3-dipyridyl)-quinoxaline: Synthesis, characterization, and photoinduced charge transfer

Chen¹,

Zhang²,

Gu³

et al. 2012

Express Polym. Lett.

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Abstract.A new conjugated polymer with donor-accepter architectures poly[1,4-dioctyloxyphenylene-2,5-diylethenylene-(2,3-dipyridine-2-ylquinoxaline-5,8-diyl)ethylene] (PPV-BD) was synthesized successfully, in which the electron-donating unit was alkoxy substituted phenyl ring, and the electron-accepting unit was a quinoxaline. The resulting polymer had a lower band-gap (1.98 eV) compared to poly[2-methoxy-5-(2-ethyl)hexoxy-phenylenevinylene] (MEH-PPV, 2.12 eV), and was characterized by infrared spectroscopy (IR), nuclear magnetic resonance (NMR), thermogravimetric analysis (TGA), gel permeation chromatography (GPC), ultraviolet-visible (UV-vis) spectroscopy, photoluminescence (PL) spectroscopy and X-ray diffraction (XRD). Its photoinduced charge transfer applications in polymer solar cell (PSC) and trinitrotoluene (TNT) detection were studied respectively, and the results indicated that this polymer might be a good candidate material for PSC or detecting TNT in solution.

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Fluorescein Provides a Resonance Gate for FRET from Conjugated Polymers to DNA Intercalated Dyes

Cited by 262 publications

References 50 publications

Impedimetric immunosensors based on the conjugated polymer PPV

Impedimetric immunosensors based on the conjugated polymer PPV

The fluorescence resonance energy transfer (FRET) gate: A time-resolved study

A new conjugated polymer with donor-acceptor architectures based on alternating 1,4-divinyl-2,5-dioctyloxybenzene and 5,8-(2,3-dipyridyl)-quinoxaline: Synthesis, characterization, and photoinduced charge transfer

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