Synthesis and spectral properties of polymethine-cyanine dye–nitroxide radical hybrid compounds for use as fluorescence probes to monitor reducing species and radicals

Sato, Shingo; Tsunoda, Minoru; Suzuki, Minoru; Kutsuna, Masahiro; Takido-uchi, Kiyomi; Shindo, Mitsuru; Mizuguchi, Hitoshi; Obara, Heitaro; Ohya, Hiroaki

doi:10.1016/j.saa.2008.07.045

Cited by 30 publications

(20 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The fluorescence intensity of these hybrid compounds was restored after the addition of excess AsA, For the hybrid compound 7-O- [2,2,6,6-tetramethylpiperidine-Noxyl (TEMPO)-4-carbonyl]umbelliferone, adding excess AsA increased the fluorescence intensity 9.1-fold [7]. Similarly, for 5.5′-bis- [2,2,5,5-tetramethylpyrrolidine-N-oxyl (PROXYL)-3-aminocarbonyl]Cy3 and 5.5′-bis-(PROXYL-3-aminocarbonyl)Cy5, the increase in fluorescence intensity was 5.1-fold and 1.8-fold, respectively [8]. Fluorophores bearing a nitroxide radical show weak fluorescence; however, after reduction of the radical, the fluorescence is restored significantly.…”

Section: Introductionmentioning

confidence: 86%

“…Since we previously found that the increase in fluorescence intensity was greater for hybrids bearing a TEMPO group than for those with a PROXYL group [7], we used TEMPO as a nitroxide radical in the present study. We designed a hybrid compound wherein the TEMPO group was bonded to the phenol residue of the xanthene moiety as in our previous study [7,8]. The desired compound 4 was synthesized in 39% yield (Scheme 3) by direct condensation of fluorescein and 4-carboxy-TEMPO.…”

Section: Synthesismentioning

confidence: 99%

“…Using fluorescence techniques it is possible to both detect and quantify radicals or radical-reducing species such as ascorbic acid (AsA) [5,6]. We have also designed and synthesized several new hybrid compounds consisting of a nitroxide radical and well-known fluorophores, such as umbelliferone [7] and polymethine-cyanine dyes (Cy3 and Cy5) [8], and measured the increase in fluorescence of these hybrid compounds upon radical reduction, with the goal of developing a probe to monitor reducing species or radicals in biological systems. The fluorescence intensity of these hybrid compounds was restored after the addition of excess AsA, For the hybrid compound 7-O- [2,2,6,6-tetramethylpiperidine-Noxyl (TEMPO)-4-carbonyl]umbelliferone, adding excess AsA increased the fluorescence intensity 9.1-fold [7].…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis and fluorescence properties of six fluorescein-nitroxide radical hybrid-compounds

Sato

Endo

Kurokawa

et al. 2016

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

Self Cite

View full text Add to dashboard Cite

Section: Introductionmentioning

confidence: 86%

Section: Synthesismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and fluorescence properties of six fluorescein-nitroxide radical hybrid-compounds

Sato

Endo

Kurokawa

et al. 2016

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

Self Cite

View full text Add to dashboard Cite

“…7 Emerging biological applications demanded the synthesis of new fluorophore-nitroxide acceptor-donor molecules. New probes included various nitroxide moieties (nitronyl-, 8 pyrrolidine-, 9 piperidine-5 ) coupled to diverse fluorophores (acridine, 10 cyanine dye, 11 dansyl, 5,6 fluorescamine, 12 BODIPY, 8,13 Nile-red, 13 CdSe quantum dots 14 and naphthalimides 15,16 ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and potential use of 1,8-naphthalimide type 1O2 sensor molecules

Kálai

Hideg

Ayaydin

et al. 2013

Photochem Photobiol Sci

View full text Add to dashboard Cite

New double (fluorescent and spin) sensor molecules (4 and 7) were synthesized and their responses to ROS in vitro are reported with perspectives of plant physiology use in vivo.Please check this proof carefully. Our staff will not read it in detail after you have returned it.Translation errors between word-processor files and typesetting systems can occur so the whole proof needs to be read. Please pay particular attention to: tabulated material; equations; numerical data; figures and graphics; and references. If you have not already indicated the corresponding author(s) please mark their name(s) with an asterisk. Please e-mail a list of corrections or the PDF with electronic notes attached -do not change the text within the PDF file or send a revised manuscript.Please bear in mind that minor layout improvements, e.g. in line breaking, table widths and graphic placement, are routinely applied to the final version.We will publish articles on the web as soon as possible after receiving your corrections; no late corrections will be made.Please return your final corrections, where possible within 48 hours of receipt, by e-mail to: pps@rsc.org Reprints-Electronic (PDF) reprints will be provided free of charge to the corresponding author. Enquiries about purchasing paper reprints should be addressed via: http://www.rsc.org/publishing/journals/guidelines/paperreprints/. Costs for reprints are below: Please check the proofs of your paper carefully, paying particular attention to the numerical data, tables, figures and references.When answering the queries below please ensure that any changes required are clearly marked on the proof. There is no need to e-mail your answers to the queries separately from the rest of your proof corrections.

show abstract

“…Various hybrid compounds comprised of two types of nitroxide radicals and either a pentamethine (Cy5) or trimethine cyanine (Cy3) were synthesized by Sato and co-workers [32]. These compounds seem to be promising fluorescent chemosensors for the measurement of reducing species such as Fe 2+ , ascorbic acid, and hydroxyl radicals.…”

Section: Introductionmentioning

confidence: 99%

Long-Wavelength Probes and Labels Based on Cyanines and Squaraines

Patsenker

Tatarets

Terpetschnig³

2010

Springer Series on Fluorescence

View full text Add to dashboard Cite

In this review, we make an attempt to compare the characteristics and applications of red and near infrared cyanine and squaraine dyes used for biological research, biomedical assays, and high-throughput screening. While the favorable photophysical properties of cyanine dyes makes them predestined as covalent labels, the environmentally sensitive squaraine dyes are utilizable as both florescent probes and labels. Reducing the aggregation tendencies of these dyes in aqueous media seems to be one of the most promising ways to improve their brightness, fluorescence lifetimes, and photostability. Indolenine-based squaraines including ring-substituted squaraines exhibit great potential for the design of bright and sensitive fluorescent probes and labels with increased photostability.

show abstract

Synthesis and spectral properties of polymethine-cyanine dye–nitroxide radical hybrid compounds for use as fluorescence probes to monitor reducing species and radicals

Cited by 30 publications

References 27 publications

Synthesis and fluorescence properties of six fluorescein-nitroxide radical hybrid-compounds

Synthesis and fluorescence properties of six fluorescein-nitroxide radical hybrid-compounds

Synthesis and potential use of 1,8-naphthalimide type 1O2 sensor molecules

Long-Wavelength Probes and Labels Based on Cyanines and Squaraines

Contact Info

Product

Resources

About