Thiophene-based fluorescent markers for the efficient labeling of monoclonal antibodies and oligonucleotides

Barbarella, Giovanna; Zambianchi, Massimo; Sotgiu, Giovanna; Ventola, Alfredo; Galeotti, Matteo; Gigli, Giuseppe; Cazzato, A.; Capobianco, Massimo L.

doi:10.1016/j.jnoncrysol.2006.02.076

Cited by 7 publications

(7 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[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%

“…Recently, Barbarella et al synthesized a series of oligothiophenes 2.381 − 2.383 bearing N -succinimidyl ester groups as markers for monoclonal antibodies and oligonucleotides (Chart ). − 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: Functionalized Linear Oligothiophenesmentioning

confidence: 99%

See 1 more Smart Citation

Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications

2009

View full text Add to dashboard Cite

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...

show abstract

Section: Biologically Active Oligothiophenesmentioning

confidence: 99%

Section: Functionalized Linear Oligothiophenesmentioning

confidence: 99%

Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications

2009

View full text Add to dashboard Cite

show abstract

“…Later, Sotgiu et al 50 verified that oligothiophenes functionalized with the N-succinimidyl ester (39 and 40, Figure 4) reacted under mild conditions with both monoclonal antibodies and -NH 2 -terminated oligonucleotides to produce bioconjugates that were photochemically and chemically very…”

Section: Fluorophores Based On Sulfur Heterocyclesmentioning

confidence: 99%

“…Later, Sotgiu et al verified that oligothiophenes functionalized with the N -succinimidyl ester ( 39 and 40 , Figure ) reacted under mild conditions with both monoclonal antibodies and −NH 2 -terminated oligonucleotides to produce bioconjugates that were photochemically and chemically very stable and could be used for cellular imaging and fluorescence resonance energy transfer experiments, respectively. The maximum emission wavelengths of the fluorescent conjugates of 39 with monoclonal antibodies anti-CD3 and 40 with the oligonucleotide functionalized with an amine terminal group at the 3′ position occurred at 425 ( 39 ) and 480 nm ( 40 ), respectively.…”

Section: Organic Labels With Emission Up To 500 Nmmentioning

confidence: 99%

Fluorescent Labeling of Biomolecules with Organic Probes

2008

View full text Add to dashboard Cite

“…To increase the fixation rate, a succinimidyl ester active group was introduced onto azo thiazole–OH , resulting in the synthesis of azo thiazole-NHS , whose synthetic process is shown in Scheme . Succinimidyl esters are usually used in fluorescent labeling proteins. , This functional group may react with the amino groups in wool fibers, thus enhancing the bonding force between the dyestuff and the wool fibers. To our surprise, although the dyeing performance of azo thiazole-NHS was not better than that of azo thiazole-N(CH 3 ) 2 , the fixation rate for azo thiazole-NHS reached 100%; by comparison, that of azo thiazole-N(CH 3 ) 2 reached 45.5% (SI Table S4).…”

Section: Resultsmentioning

confidence: 99%

Constructing of Dyes Suitable for Eco-friendly Dyeing Wool Fibers in Supercritical Carbon Dioxide

Xue-jun

et al. 2018

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

Compared with traditional water dyeing, supercritical carbon dioxide (scCO2) dyeing is more environmentally benign. scCO2 is widely used as a green solvent in dyeing synthetic fibers. However, studies involving dyeing natural fibers in scCO2 are scarce. The commonly used methods result in corrosion of the dyeing equipment. Thus, the development of new special dyes suitable for scCO2 dyeing is necessary; in addition, insight into the dyeing mechanism is important in promoting the design and synthesis of dyes for wool fibers in scCO2. On the basis of our previous work, a possible dyeing mechanism in which the dyes exhibit hydrophobic interaction with keratins is proposed. The NN bond twisting in azo dyes promotes the dyes embedding into the spaces of the alpha helices in proteins. According to the proposed mechanism, two new azo disperse dyes (azo thiazole-N(CH3)2 and azo thiazole-OCH3 ) were synthesized; these dyes enable the dyeing of wool fibers in scCO2. Meanwhile, the introduction of a succinimidyl ester group results in the fixation rate of the new reactive disperse dyes azo thiazole-NHS and azo-NHS reaching 100%. The byproduct of azo thiazole-NHS and azo-NHS reacting with the amino group of wool keratin is not corrosive to the dyeing equipment, thus enabling an eco-friendly dyeing process for wool fibers. Our strategy of introducing a succinimidyl ester reactive group will promote the development of new functional disperse dyes suitable for dyeing wool fibers in scCO2.

show abstract

Thiophene-based fluorescent markers for the efficient labeling of monoclonal antibodies and oligonucleotides

Cited by 7 publications

References 13 publications

Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications

Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications

Fluorescent Labeling of Biomolecules with Organic Probes

Constructing of Dyes Suitable for Eco-friendly Dyeing Wool Fibers in Supercritical Carbon Dioxide

Contact Info

Product

Resources

About