Testing Oligothiophene Fluorophores under Physiological Conditions. Preparation and Optical Characterization of the Conjugates of Bovine Serum Albumin with Oligothiophene <i>N</i>-Hydroxysuccinimidyl Esters

Zambianchi, Massimo; Barbieri, Andrea; Ventola, Alfredo; Favaretto, Laura; Bettini, Cristian; Galeotti, Matteo; Barbarella, Giovanna

doi:10.1021/bc060332e

Cited by 19 publications

(22 citation statements)

References 18 publications

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“…[443][444][445] For the synthesis of these oligomers, 5-bromo-2-thiophenecarboxaldehyde was converted to the corresponding carboxylic acid derivative and then reacted with NHS to afford active ester-functionalized monothiophene. Repetitive bromination and Stille-type coupling reactions afforded the oligomers in good overall yields.…”

Section: Biologically Active Oligothiophenesmentioning

confidence: 99%

Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications

2009

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Amaresh Mishra (right) received his Ph.D. degree in 2000 from the Sambalpur University, India, under the coguidance of Prof. G. B. Behera and Prof. R. K. Behera, working on dye-surfactant interactions in microheterogeneous media. He started his postdoctoral research career in 1999 at the University of South Florida, Tampa, and subsequently at the University of Akron, Ohio, working with Prof. G. R. Newkome, where he gained knowledge in the area of supramolecular and dendrimer chemistry. Later, he joined the Tata Institute of Fundamental Research, Mumbai, in 2002 as a Visiting Fellow working with Prof. N. Periasamy, where he was involved in the synthesis and photophysical studies of organic light emitting materials. In 2005, he joined in the group of Prof. Peter Ba ¨uerle, University of Ulm, Germany, as an Alexander von Humboldt Fellow. His present research interests are centered on chemistry of functional oligothiophenes, donor-acceptor-based conjugated dyes, and metal complexes toward applications in solar energy conversion and molecular electronic and photonic devices. Chang-Qi Ma (left) received his bachelor's degree in chemistry from Beijing Normal University in 1998. In 2003 he obtained his Ph.D. degree at the Technical Institute of Physics and Chemistry, Chinese Academy of Sciences in Beijing with Professor B.-W. Zhang. After that he was a postdoctoral research assistant at Heriot-Watt University in Edinburgh, U.K., with Dr. G. Cooke, until he joined the research group of Prof. P. Ba ¨uerle at the University of Ulm in 2004 as an Alexander von Humboldt fellow, where he is currently a research associate. His main research interests focus on the design and synthesis of novel π-conjugated organic materials for the application in organic electronics, e.g. organic solar cells.Peter Ba ¨uerle (center) received his Ph.D. in organic chemistry from University of Stuttgart (Germany, 1985) working with Prof. F. Effenberger. After a postdoctoral year at MIT, Boston, Massachusetts, in the group of Prof. M. S. Wrighton, he carried out independent research at the University of Stuttgart and received his habilitation (1994). After being Professor of Organic Chemistry at the University of Wu ¨rzburg (Germany, 1994-95), he became Director of the Institute for Organic Chemistry II and Advanced Materials at the University of Ulm (Germany, since 1996). Current research interests of the group include development of novel organic semiconducting and conducting materials, in particular, conjugated poly-and oligothiophenes. Synthetic strategies and new reactions for their functionalization, structure-property relationships, self-assembling properties, and applications in electronic devices, in particular organic solar cells, are investigated. Results have been published in about 200 peer-reviewed scientific papers, 3 book chapters, and 7 patents. For his work in the field of plastic electronics he was awarded with the Rene ´Descartes Prize of the European Union (2000). Guest Professorships at the University of Osaka (Japan, 2002), U...

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Section: Biologically Active Oligothiophenesmentioning

confidence: 99%

Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications

2009

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“…[45][46][47][48][49] These features, along with their favorable binding to oligonucleotides and proteins, make oligothiophene-based biomarkers useful as fluorescent dyes in DNA and proteins. 48,49 As shown in Fig. 1, these oligothiophene derivatives can be chemically modified to create various push-pull systems.…”

Section: Introductionmentioning

confidence: 99%

Absorption and fluorescence properties of oligothiophene biomarkers from long-range-corrected time-dependent density functional theory

Wong

Piacenza

Sala

2009

Phys. Chem. Chem. Phys.

159

151

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The absorption and fluorescence properties in a class of oligothiophene push-pull biomarkers are investigated with a long-range-corrected (LC) density functional method. Using linear response timedependent density functional theory (TDDFT), we calculate excitation energies, fluorescence energies, oscillator strengths, and excited-state dipole moments. To benchmark and assess the quality of the LC-TDDFT formalism, an extensive comparison is made between LC-BLYP excitation energies and approximate coupled cluster singles and doubles (CC2) calculations. When using a properly-optimized value of the range parameter, , we find that the LC technique provides an accurate description of charge-transfer excitations as a function of biomarker size and chemical functionalization. In contrast, we find that re-optimizing the fraction of Hartree Fock exchange in conventional hybrid functionals still yields an inconsistent description of excitation energies and oscillator strengths for the two lowest excited states in our series of biomarkers. The results of the present study emphasize the importance of a distance-dependent contribution of exchange in TDDFT for investigating excited-state properties.2

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“…Uptake experiments were performed at pH 4.5 and 7.0 with both the TF (Fig. 1) and its albumin conjugate (BSA‐TF) 28, 29. TF is hydrophobic and pH‐insensitive, whereas its conjugate with BSA is pH‐sensitive and its charge is correlated to the isoelectric point of the protein (p I 4.7) 43.…”

Section: Resultsmentioning

confidence: 99%

“…5″‐Methylsulfanyl‐[2,2′,5′,2″]terthiophene‐5‐carboxylic acid 2,5‐Dioxopyrrolidin‐1‐yl Ester (TF, Fig. 1),28 and its bovine serum albumin conjugate (BSA‐TF)29 were used as received, and their chemical and optical properties, as well as their synthetic procedure are reported elsewhere 28, 29…”

Section: Methodsmentioning

confidence: 99%

“…To evaluate the nanogel uptake behavior at two different expansion states, two incubation solutions were prepared at different pH values (Solution a, pH 4.5 and Solution b , pH 7.0). The incubation solution was prepared by mixing nanogel (0.1 g/L), TF (3.66 × 10 −3 g/L), and Tween 20 (0.1%, w/v)29 in a 1.0 m M borate buffer. The volume for each sample was 0.5 mL.…”

Section: Methodsmentioning

confidence: 99%

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Nanogels of poly(acrylic acid): Uptake and release behavior with fluorescent oligothiophene‐labeled bovine serum albumin

Argentiere

Blasi

Ciccarella

et al. 2010

J of Applied Polymer Sci

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Nanometer-sized poly(acrylic acid) (PAA) hydrogels were synthesized by emulsion polymerization of methyl acrylate and subsequent acidic hydrolysis. The nanohydrogel was characterized by spectroscopic methods (FTIR and 1 H-NMR) and scanning probe techniques, and their pH-dependent swelling behavior was studied by dynamic light scattering. To determine the suitability of PAA nanogels as pH-sensitive carriers for biomedical applications, uptake and release of an oligothiophene fluorophore and its albumin conjugated from PAA nanogels were investigated as a function of pH by absorption and photoluminescence measurements. It was observed that uptake and release processes of both the oligothiophene and its conjugate could be controlled by changing the pH of the external solution.

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Testing Oligothiophene Fluorophores under Physiological Conditions. Preparation and Optical Characterization of the Conjugates of Bovine Serum Albumin with Oligothiophene N-Hydroxysuccinimidyl Esters

Cited by 19 publications

References 18 publications

Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications

Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications

Absorption and fluorescence properties of oligothiophene biomarkers from long-range-corrected time-dependent density functional theory

Nanogels of poly(acrylic acid): Uptake and release behavior with fluorescent oligothiophene‐labeled bovine serum albumin

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