2016
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Mitochondria-Targeted Triphenylamine Derivatives Activatable by Two-Photon Excitation for Triggering and Imaging Cell Apoptosis Article de journal Rahima Chennoufi; Houcine Bougherara; Nathalie Gagey-Eilstein; Blaise Dumat; Etienne Henry; Frédéric Subra; Stéphanie Bury-Moné; Florence Mahuteau-Betzer; Patrick Tauc; Marie-Paule Teulade-Fichou; Eric Deprez Scientific Reports, 6 (January), p. 21458-21458, 2016. @article{Chennoufi:2016,
title = {Mitochondria-Targeted Triphenylamine Derivatives Activatable by Two-Photon Excitation for Triggering and Imaging Cell Apoptosis},
author = {Rahima Chennoufi and Houcine Bougherara and Nathalie {Gagey-Eilstein} and Blaise Dumat and Etienne Henry and Fr\'{e}d\'{e}ric Subra and St\'{e}phanie {Bury-Mon\'{e}} and Florence {Mahuteau-Betzer} and Patrick Tauc and Marie-Paule {Teulade-Fichou} and Eric Deprez},
doi = {10.1038/srep21458},
year = {2016},
date = {2016-01-01},
journal = {Scientific Reports},
volume = {6},
number = {January},
pages = {21458-21458},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
|
2015
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Development of Bright Fluorescent Quadracyclic Adenine Analogues: TDDFT-Calculation Supported Rational Design Article de journal Anders Foller Larsen; Blaise Dumat; Moa S Wranne; Christopher P Lawson; Søren Preus; Mattias Bood; Henrik Gradén; L Marcus Wilhelmsson; Morten Grøtli Scientific Reports, 5 , p. 12653-12653, 2015. @article{FollerLarsen:2015,
title = {Development of Bright Fluorescent Quadracyclic Adenine Analogues: TDDFT-Calculation Supported Rational Design},
author = {Anders Foller Larsen and Blaise Dumat and Moa S Wranne and Christopher P Lawson and S\oren Preus and Mattias Bood and Henrik Grad\'{e}n and L Marcus Wilhelmsson and Morten Gr\otli},
doi = {10.1038/srep12653},
year = {2015},
date = {2015-07-01},
journal = {Scientific Reports},
volume = {5},
pages = {12653-12653},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
|
Second-Generation Fluorescent Quadracyclic Adenine Analogues: Environment-Responsive Probes with Enhanced Brightness Article de journal Blaise Dumat; Mattias Bood; Moa S Wranne; Christopher P Lawson; Anders Foller Larsen; Søren Preus; Jens Streling; Henrik Gradén; Eric Wellner; Morten Grøtli; Marcus L Wilhelmsson Chemistry - A European Journal, 21 (10), p. 4039-4048, 2015. @article{Dumat:2015,
title = {Second-Generation Fluorescent Quadracyclic Adenine Analogues: Environment-Responsive Probes with Enhanced Brightness},
author = {Blaise Dumat and Mattias Bood and Moa S Wranne and Christopher P Lawson and Anders Foller Larsen and S\oren Preus and Jens Streling and Henrik Grad\'{e}n and Eric Wellner and Morten Gr\otli and Marcus L Wilhelmsson},
doi = {10.1002/chem.201405759},
year = {2015},
date = {2015-03-01},
journal = {Chemistry - A European Journal},
volume = {21},
number = {10},
pages = {4039-4048},
abstract = {Fluorescent base analogues comprise a group of increasingly important molecules for the investigation of nucleic acid structure, dynamics, and interactions with other molecules. Herein, we report on the quantum chemical calculation aided design, synthesis, and characterization of four new putative quadracyclic adenine analogues. The compounds were efficiently synthesized from a common intermediate through a two-step pathway with the Suzuki-Miyaura coupling as the key step. Two of the compounds, qAN1 and qAN4, display brightnesses ($epsilonPhi$F ) of 1700 and 2300, respectively, in water and behave as wavelength-ratiometric pH probes under acidic conditions. The other two, qAN2 and qAN3, display lower brightnesses but exhibit polarity-sensitive dual-band emissions that could prove useful to investigate DNA structural changes induced by DNA-protein or -drug interactions. The four qANs are very promising microenvironment-sensitive fluorescent adenine analogues that display considerable brightness for such compounds.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Fluorescent base analogues comprise a group of increasingly important molecules for the investigation of nucleic acid structure, dynamics, and interactions with other molecules. Herein, we report on the quantum chemical calculation aided design, synthesis, and characterization of four new putative quadracyclic adenine analogues. The compounds were efficiently synthesized from a common intermediate through a two-step pathway with the Suzuki-Miyaura coupling as the key step. Two of the compounds, qAN1 and qAN4, display brightnesses ($epsilonPhi$F ) of 1700 and 2300, respectively, in water and behave as wavelength-ratiometric pH probes under acidic conditions. The other two, qAN2 and qAN3, display lower brightnesses but exhibit polarity-sensitive dual-band emissions that could prove useful to investigate DNA structural changes induced by DNA-protein or -drug interactions. The four qANs are very promising microenvironment-sensitive fluorescent adenine analogues that display considerable brightness for such compounds. |
Differential Behaviour of Cationic Triphenylamine Derivatives in Fixed and Living Cells: Triggering and Imaging Cell Death Article de journal R Chennoufi; H Bougherara; N Gagey-Eilstein; B Dumat; E Henry; F Subra; F Mahuteau-Betzer; P Tauc; M -P Teulade-Fichou; E Deprez Chemical Communications, 51 (80), p. 14881-14884, 2015. @article{Chennoufi:2015,
title = {Differential Behaviour of Cationic Triphenylamine Derivatives in Fixed and Living Cells: Triggering and Imaging Cell Death},
author = {R Chennoufi and H Bougherara and N {Gagey-Eilstein} and B Dumat and E Henry and F Subra and F {Mahuteau-Betzer} and P Tauc and M -P {Teulade-Fichou} and E Deprez},
doi = {10.1039/C5CC05970D},
year = {2015},
date = {2015-01-01},
journal = {Chemical Communications},
volume = {51},
number = {80},
pages = {14881-14884},
abstract = {Nuclear staining by cationic triphenylamines is spontaneous in fixed cells while a cytoplasm\textendashnucleus translocation is strictly dependent on light illumination in living cells and concomitant to a fast cell death process.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Nuclear staining by cationic triphenylamines is spontaneous in fixed cells while a cytoplasm–nucleus translocation is strictly dependent on light illumination in living cells and concomitant to a fast cell death process. |
2013
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DNA Switches on the Two-Photon Efficiency of an Ultrabright Triphenylamine Fluorescent Probe Specific of AT Regions Article de journal Blaise Dumat; Guillaume Bordeau; Elodie Faurel-Paul; Florence Mahuteau-Betzer; Nicolas Saettel; Germain Metge; Céline Fiorini-Debuisschert; Fabrice Charra; Marie-Paule Teulade-Fichou Journal of the American Chemical Society, 135 (34), p. 12697-12706, 2013. @article{Dumat:2013,
title = {DNA Switches on the Two-Photon Efficiency of an Ultrabright Triphenylamine Fluorescent Probe Specific of AT Regions},
author = {Blaise Dumat and Guillaume Bordeau and Elodie {Faurel-Paul} and Florence {Mahuteau-Betzer} and Nicolas Saettel and Germain Metge and C\'{e}line {Fiorini-Debuisschert} and Fabrice Charra and Marie-Paule {Teulade-Fichou}},
doi = {10.1021/ja404422z},
year = {2013},
date = {2013-08-01},
journal = {Journal of the American Chemical Society},
volume = {135},
number = {34},
pages = {12697-12706},
abstract = {We report on the design and synthesis of two-photon fluorescent triphenylamines bearing two or three vinyl branches terminated by a N-methyl benzimidazolium moiety. The new compounds (TP-2Bzim, TP-3Bzim) are light-up fluorescent DNA probes with a long wavelength emission ($>$580 nm). Compared to their pyridinium models, the TP-Bzim dyes exhibit a remarkable improvement of both their DNA affinity and fluorescence quantum yield, especially for the two-branch derivative (TP-2Bzim: $Phi$F = 0.54},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
We report on the design and synthesis of two-photon fluorescent triphenylamines bearing two or three vinyl branches terminated by a N-methyl benzimidazolium moiety. The new compounds (TP-2Bzim, TP-3Bzim) are light-up fluorescent DNA probes with a long wavelength emission ($>$580 nm). Compared to their pyridinium models, the TP-Bzim dyes exhibit a remarkable improvement of both their DNA affinity and fluorescence quantum yield, especially for the two-branch derivative (TP-2Bzim: $Phi$F = 0.54 |
2012
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Vinyl-Triphenylamine Dyes, a New Family of Switchable Fluorescent Probes for Targeted Two-Photon Cellular Imaging: From DNA to Protein Labeling Article de journal Blaise Dumat; Guillaume Bordeau; Ana I Aranda; Florence Mahuteau-Betzer; Yara El Harfouch; Germain Metgé; Fabrice Charra; Céline Fiorini-Debuisschert; Marie-Paule Teulade-Fichou Organic & Biomolecular Chemistry, 10 (30), p. 6054-6054, 2012. @article{Dumat:2012,
title = {Vinyl-Triphenylamine Dyes, a New Family of Switchable Fluorescent Probes for Targeted Two-Photon Cellular Imaging: From DNA to Protein Labeling},
author = {Blaise Dumat and Guillaume Bordeau and Ana I Aranda and Florence {Mahuteau-Betzer} and Yara El Harfouch and Germain Metg\'{e} and Fabrice Charra and C\'{e}line {Fiorini-Debuisschert} and Marie-Paule {Teulade-Fichou}},
doi = {10.1039/c2ob25515d},
year = {2012},
date = {2012-08-01},
journal = {Organic & Biomolecular Chemistry},
volume = {10},
number = {30},
pages = {6054-6054},
abstract = {On the basis of our previous work on vinyl-triphenylamine derived DNA fluorophores we explored the structure space around this core by coupling it to diverse cationic, anionic and zwitterionic groups in the aim of targeting different classes of biomolecules. In parallel core modifications were performed to optimize the photophysical properties (quantum yield, two-photon absorption). The resulting water soluble $pi$-conjugated molecules are called TP dyes and display an exceptional combination of optical properties: high two-photon absorption cross-section, high photostability, no self-quenching, and switchable fluorescence emission when bound to a biopolymer matrix. The linear and nonlinear optical properties of the TP dyes were studied in vitro in presence of DNA and in presence of a model protein (human serum albumin) using complementary absorption and fluorescence spectroscopy characterization tools. Structure modifications enabled to switch from DNA probes (cationic TP-pyridinium series) to protein probes (anionic TP-rhodanine series) without affecting the optical properties. Finally most TP compounds appear cell-permeant and show an intracellular localization consistent with their in vitro target specificity.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
On the basis of our previous work on vinyl-triphenylamine derived DNA fluorophores we explored the structure space around this core by coupling it to diverse cationic, anionic and zwitterionic groups in the aim of targeting different classes of biomolecules. In parallel core modifications were performed to optimize the photophysical properties (quantum yield, two-photon absorption). The resulting water soluble $pi$-conjugated molecules are called TP dyes and display an exceptional combination of optical properties: high two-photon absorption cross-section, high photostability, no self-quenching, and switchable fluorescence emission when bound to a biopolymer matrix. The linear and nonlinear optical properties of the TP dyes were studied in vitro in presence of DNA and in presence of a model protein (human serum albumin) using complementary absorption and fluorescence spectroscopy characterization tools. Structure modifications enabled to switch from DNA probes (cationic TP-pyridinium series) to protein probes (anionic TP-rhodanine series) without affecting the optical properties. Finally most TP compounds appear cell-permeant and show an intracellular localization consistent with their in vitro target specificity. |
2011
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N-Phenyl-Carbazole-Based Two-Photon Fluorescent Probes: Strong Sequence Dependence of the Duplex vs Quadruplex Selectivity Article de journal B Dumat; G Bordeau; E Faurel-Paul; F Mahuteau-Betzer; N Saettel; M Bombled; G Metgé; F Charra; C Fiorini-Debuisschert; M-P Teulade-Fichou Biochimie, 93 (8), p. 1209-1218, 2011. @article{Dumat:2011,
title = {N-Phenyl-Carbazole-Based Two-Photon Fluorescent Probes: Strong Sequence Dependence of the Duplex vs Quadruplex Selectivity},
author = {B Dumat and G Bordeau and E {Faurel-Paul} and F {Mahuteau-Betzer} and N Saettel and M Bombled and G Metg\'{e} and F Charra and C {Fiorini-Debuisschert} and M-P {Teulade-Fichou}},
doi = {10.1016/j.biochi.2011.05.035},
year = {2011},
date = {2011-08-01},
journal = {Biochimie},
volume = {93},
number = {8},
pages = {1209-1218},
abstract = {Herein we report on the synthesis and DNA recognition properties of a series of three N-phenyl carbazole-based light-up probes initially designed for two-photon absorption. The vinylic derivatives (Cbz-2Py, Cbz-3Py) display strong fluorescence enhancement when bound to various duplex- and quadruplex-forming oligonucleotides whereas the oxazole derivative is not fluorescent in DNA. Determination of affinity constants by fluorimetric titrations evidenced that Cbz-2Py has a clear preference for AT-rich duplex structures. Circular Dichroism (CD) measurements confirmed the sequence-dependent binding of this compound and suggest insertion in the minor groove as shown by a strong induced CD (ICD) signal and further supported by molecular modeling. Altogether the data indicate that duplex vs quadruplex selectivity of the dyes is strongly dependent on the sequence of the duplex. Finally, the dyes exhibit high two-photon absorption cross-sections (up to 540GM in glycerol) and allow a fine and bright staining of nuclear DNA with low background fluorescence as shown by one and two-photon confocal microscopy imaging of fixed cells.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Herein we report on the synthesis and DNA recognition properties of a series of three N-phenyl carbazole-based light-up probes initially designed for two-photon absorption. The vinylic derivatives (Cbz-2Py, Cbz-3Py) display strong fluorescence enhancement when bound to various duplex- and quadruplex-forming oligonucleotides whereas the oxazole derivative is not fluorescent in DNA. Determination of affinity constants by fluorimetric titrations evidenced that Cbz-2Py has a clear preference for AT-rich duplex structures. Circular Dichroism (CD) measurements confirmed the sequence-dependent binding of this compound and suggest insertion in the minor groove as shown by a strong induced CD (ICD) signal and further supported by molecular modeling. Altogether the data indicate that duplex vs quadruplex selectivity of the dyes is strongly dependent on the sequence of the duplex. Finally, the dyes exhibit high two-photon absorption cross-sections (up to 540GM in glycerol) and allow a fine and bright staining of nuclear DNA with low background fluorescence as shown by one and two-photon confocal microscopy imaging of fixed cells. |
2009
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Synthesis of N-Functionalized 2,2$'$-Dipyridylamine Ligands, Complexation to Ruthenium (II) and Anchoring of Complexes to Papain from Papaya Latex Article de journal Pierre Haquette; Blaise Dumat; Barisa Talbi; Shararé Arbabi; Jean-Luc Renaud; Gérard Jaouen; Mich`ele Salmain Journal of Organometallic Chemistry, 694 (6), p. 937-941, 2009. @article{Haquette:2009,
title = {Synthesis of N-Functionalized 2,2$'$-Dipyridylamine Ligands, Complexation to Ruthenium (II) and Anchoring of Complexes to Papain from Papaya Latex},
author = {Pierre Haquette and Blaise Dumat and Barisa Talbi and Sharar\'{e} Arbabi and Jean-Luc Renaud and G\'{e}rard Jaouen and Mich{`e}le Salmain},
doi = {10.1016/j.jorganchem.2008.11.052},
year = {2009},
date = {2009-03-01},
journal = {Journal of Organometallic Chemistry},
volume = {694},
number = {6},
pages = {937-941},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
|
