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Recent articles
Publications in 2010
| Author | Title | Year | Journal/Proceedings | Reftype | DOI/URL |
|---|---|---|---|---|---|
| Rickling, S., Ghisdavu, L., Pierard, F., Gerbaux, P., Surin, M., Murat, P., Defrancq, E., Moucheron, C. and Kirsch-De Mesmaeker, A. | A Rigid Dinuclear Ruthenium(II) Complex as an Efficient Photoactive Agent for Bridging Two Guanine Bases of a Duplex or Quadruplex Oligonucleotide | 2010 | Chem. Eur. J. Vol. 16(13), pp. 3951-3961 |
article | DOI URL |
| Abstract: The rigid dinuclear [(tap)2Ru(tpac)Ru(tap)2]4+ complex (1) (TAP=1,4,5,8-tetraazaphenanthrene, TPAC=tetrapyridoacridine) is shown to be much more efficient than the mononuclear bis-TAP complexes at photodamaging oligodeoxyribonucleotides (ODNs) containing guanine (G). This is particularly striking with the G-rich telomeric sequence d(T2AG3)4. Complex 1, which interacts strongly with the ODNs as determined by surface plasmon resonance (SPR) and emission anisotropy experiments, gives rise under illumination to the formation of covalent adducts with the G units of the ODNs. The yield of photocrosslinking of the two strands of duplexes by 1 is the highest when the G bases of each strand are separated by three to four base pairs. This corresponds with each Ru(tap)2 moiety of complex 1 forming an adduct with the G base. This separation distance of the G units of a duplex could be determined thanks to the rigidity of complex 1. On the basis of results of gel electrophoresis, mass spectrometry, and molecular modelling, it is suggested that such photocrosslinking can also occur intramolecularly in the human telomeric quadruplex d(T2AG3)4. | |||||
BibTeX:
@article{PUB0242,
author = {Rickling, Stéphane and Ghisdavu, Liana and Pierard, Frédéric and Gerbaux, Pascal and Surin, Mathieu and Murat, Pierre and Defrancq, Eric and Moucheron, Cécile and Kirsch-De Mesmaeker, Andrée},
title = {A Rigid Dinuclear Ruthenium(II) Complex as an Efficient Photoactive Agent for Bridging Two Guanine Bases of a Duplex or Quadruplex Oligonucleotide},
journal = {Chem. Eur. J.},
publisher = {WILEY-VCH Verlag},
year = {2010},
volume = {16},
number = {13},
pages = {3951-3961},
url = {http://dx.doi.org/10.1002/chem.200902817},
doi = {http://dx.doi.org/10.1002/chem.200902817}
}
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| Rebarz, M., Ghesquière, J., Boisdenghien, A., Defrancq, E., Moucheron, C. and Kirsch-De Mesmaeker, A. | Photoinduced Electron Transfer from Tryptophan to RuIITAP Complexes: The Primary Process for Photo-Cross-Linking with Oligopeptides | 2010 | Inorg. Chem. Vol. 49(23), pp. 10867-10874 |
article | DOI URL |
| Abstract: The photoreaction mechanism of [Ru(TAP)2(phen)]2+ and [Ru(TAP)3]2+ (TAP = 1,4,5,8-tetraazaphenanthrene) with tryptophan (Trp), N-acetyl-Trp, and Lys-Trp-Lys is examined. The existence of a photoelectron-transfer process from the amino acid unit is demonstrated by laser flash photolysis experiments. The back electron transfer (BET) from the reduced complex to the oxidized amino acid, occurring at the microsecond time scale, corresponds approximately to an equimolecular−bimolecular process; however, it is disturbed by another reaction, originating from the oxidized Trp. Moreover, in competition with the BET, the reduced and oxidized intermediates give rise to an adduct. The latter is clearly detected by gel electrophoresis experiments in denaturing conditions, with a system composed of an oligonucleotide derivatized at the 3′ end by the RuIITAP complex and hybridized with the complementary sequence functionalized at the 5′ end by the tripeptide Lys-Trp-Lys. Thus, upon illumination, a cross-linking between the two strands is observed, which originates from the presence of a Trp residue. | |||||
BibTeX:
@article{PUB0385,
author = {Rebarz, Mateusz and Ghesquière, Jonathan and Boisdenghien, Arnaud and Defrancq, Eric and Moucheron, Cecile and Kirsch-De Mesmaeker, Andrée},
title = {Photoinduced Electron Transfer from Tryptophan to RuIITAP Complexes: The Primary Process for Photo-Cross-Linking with Oligopeptides},
journal = {Inorg. Chem.},
year = {2010},
volume = {49},
number = {23},
pages = {10867-10874},
url = {http://pubs.acs.org/doi/abs/10.1021/ic101214m},
doi = {http://dx.doi.org/10.1021/ic101214m}
}
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| Cauet, E., Bogatko, S., Mugeniwabagara, E., Fusaro, L., Kirsch-De Mesmaeker, A., Luhmer, M. and Vaeck, N. | Density Functional Theory Interpretation of the 1H Photo-Chemically Induced Dynamic Nuclear Polarization Enhancements Characterizing Photoreduced Polyazaaromatic Ru(II) Coordination Complexes | 2010 | Inorg. Chem. Vol. 49(17), pp. 7826-7831 |
article | DOI |
| Abstract: The unprotonated and protonated monoreduced forms of the polyazaaromatic Ru(II) coordination complexes [Ru(tap)3]2+ and [Ru(tap)2(phen)]2+ (tap = 1,4,5,8-tetraazaphenanthrene ; phen = 1,10-phenanthroline), that is, [Ru(tap)3]•+, [Ru(tap)2(phen)]•+, [Ru(tap)2(tap-H)]•2+, and [Ru(tap)(tap-H)(phen)]•2+, were studied by Density Functional Theory (DFT). The electron spin density of these radical cations, the isotropic Fermi-contact, and the anisotropic dipolar contributions to the hyperfine coupling constants of the H nuclei were calculated in vacuo and using a continuum model for water solvation. For [Ru(tap)2(phen)]•+, as well as for its protonated form, the DFT results show that the unpaired electron is not localized on the phen ligand. For both [Ru(tap)3]•+ and [Ru(tap)2(phen)]•+, they reveal high electron spin density in the vicinity of tap H-2 and tap H-7 (the H atoms in the ortho position of the tap non-chelating N atoms). These results are in full agreement with recent steady-state 1H photo-Chemically Induced Dynamic Nuclear Polarization (photo-CIDNP) measurements. The DFT calculations performed for the protonated species also predict major 1H photo-CIDNP enhancements at these positions. Interestingly, they indicate significantly different polarization for tap H-9,10, suggesting that the occurrence of a photoinduced electron transfer with protonation of the reduced species might be detected by high-precision photo-CIDNP experiments. | |||||
BibTeX:
@article{PUB0402,
author = {Cauet, Emilie and Bogatko, Stuart and Mugeniwabagara, Epiphanie and Fusaro, Luca and Kirsch-De Mesmaeker, Andrée and Luhmer, Michel and Vaeck, Nathalie},
title = {Density Functional Theory Interpretation of the 1H Photo-Chemically Induced Dynamic Nuclear Polarization Enhancements Characterizing Photoreduced Polyazaaromatic Ru(II) Coordination Complexes},
journal = {Inorg. Chem.},
year = {2010},
volume = {49},
number = {17},
pages = {7826-7831},
doi = {http://dx.doi.org/10.1021/ic100636j}
}
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| Le Gac, S., Foucart, M., Gerbaux, P., Defrancq, E., Moucheron, C. and Kirsch-De Mesmaeker, A. | Photo-reactive RuII-oligonucleotide conjugates: influence of an intercalating ligand on the inter- and intra-strand photo-ligation processes | 2010 | Dalton Trans. Vol. 39(40), pp. 9672-9683 |
article | DOI |
| Abstract: The damaging efficacy towards OligoDeoxyriboNucleotides (ODNs) of two photoreactive polyazaaromatic rutheniumII complexes, Ru(T) and Ru(D), has been evaluated. Both compounds correspond to the known [Ru(TAP)2(dppz)]2+ complex, but they are anchored differently to a guanine-containing single strand ODN (probe strand). This has allowed us to investigate the influence of the interactions existing between the tethered complexes and the single or double strand, on the photo-ligation processes. From melting temperature measurements of the duplex formed between these Ru-ODNs and their complementary sequence (target strand), it has been found that Ru(T) anchored via the TAP ligand interacts with the duplex by means of the intercalating dppz ligand (head on geometry), while Ru(D) anchored via the dppz ligand likely adopts a side on geometry without intercalation. Both single stranded Ru conjugates self-inhibit in the absence of their target ODN by forming exclusively a cyclic "seppuku" photo-adduct (intra-molecular photoreaction). In contrast, this intra-molecular photo-product is precluded in presence of the target strand, and the Ru-ODN sequence photo-crosslinks with the latter (inter-molecular photoreaction). Both intra- and inter-molecular processes with both complexes are efficient (80% yields) and lead to stable photo-adducts. Interestingly, detailed studies have revealed that the similar photo-damaging efficacy of crosslinking by Ru(T) and Ru(D) is a consequence of a cascade of events with compensatory effects, originating from the different geometry of interaction of the tethered complexes. Notably, antagonistic effects are present when the complex is intercalated, the guanine oxidation step being highly favoured and the recombination of the quenching products being hindered. | |||||
BibTeX:
@article{PUB0455,
author = {Le Gac, Stephane and Foucart, Martin and Gerbaux, Pascal and Defrancq, Eric and Moucheron, Cecile and Kirsch-De Mesmaeker, Andrée},
title = {Photo-reactive RuII-oligonucleotide conjugates: influence of an intercalating ligand on the inter- and intra-strand photo-ligation processes},
journal = {Dalton Trans.},
year = {2010},
volume = {39},
number = {40},
pages = {9672-9683},
doi = {http://dx.doi.org/10.1039/C0DT00355G}
}
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| Gauthier, N., De Winter, J., Gerbaux, P., Moucheron, C., Luhmer, M. and Kirsch-De Mesmaeker, A. | A RuII-TAP Complex, Photoreagent for Tryptophan-Containing Peptides: Structure of the Covalent Photoadduct | 2010 | Inorg. Chem. Vol. 49(15), pp. 6796-6798 |
article | DOI URL |
| Abstract: We report the first structure determination of a covalent photoadduct between a RuII-tap complex and a tryptophan-containing peptide (AlaTrpAla) by mass spectrometry and NMR spectroscopy. RuII-tap complexes could thus be exploited as photodamaging agents of Trp-containing polypeptides or proteins. | |||||
BibTeX:
@article{PUB0651,
author = {Gauthier, Nicolas and De Winter, Julien and Gerbaux, Pascal and Moucheron, Cécile and Luhmer, Michel and Kirsch-De Mesmaeker, Andrée},
title = {A RuII-TAP Complex, Photoreagent for Tryptophan-Containing Peptides: Structure of the Covalent Photoadduct},
journal = {Inorg. Chem.},
year = {2010},
volume = {49},
number = {15},
pages = {6796-6798},
url = {http://pubs.acs.org/doi/abs/10.1021/ic101151e},
doi = {http://dx.doi.org/10.1021/ic101151e}
}
|
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| Guthmuller, J., Champagne, B., Moucheron, C. and Kirsch-De Mesmaeker, A. | Investigation of the Resonance Raman Spectra and Excitation Profiles of a Monometallic Ruthenium(II) [Ru(bpy)2(HAT)]2+ Complex by Time-Dependent Density Functional Theory | 2010 | J. Phys. Chem. B Vol. 114(1), pp. 511-520 |
article | DOI URL |
| Abstract: The resonance Raman (RR) properties of the [Ru(bpy)2(HAT)]2+ (where bpy = 2,2′-bipyridine and HAT = 1,4,5,8,9,12-hexaazatriphenylene) complex have been investigated by means of time-dependent density functional theory calculations employing the hybrid B3LYP-35 XC functional and by including the effects of the solvent within the polarizable continuum model approach. Analysis of the electronic excited-state energies has demonstrated that mainly four different metal-to-ligand charge-transfer excitations contribute to the first absorption band in vacuo and water. The simulation of the absorption spectra by including the vibronic structure of the states has shown a general agreement with the experimental spectrum recorded in water. Furthermore, significant variations of the excited-state energies and compositions have been found when the effects of the solvent are included. Calculation of the short-time-approximation RR spectra has provided the vibrational signature of each contributing state and has shown that considering only one excited state is not sufficient to accurately simulate the RR spectra for excitation frequencies in resonance with the first absorption band. A comparison of the RR spectra calculated using the vibronic theory for different excitation wavelengths with the measured spectra at 514 and 458 nm has demonstrated that inclusion of the solvent effects in the simulation scheme leads to substantial improvements of the RR intensity patterns, which allow assignment of the vibrational bands. In particular, the calculations are able to reproduce the variations of the HAT and bpy RR intensities as illustrated by their RR excitation profiles, highlighting the strong dependence of the RR intensities with respect to the excitation frequency. | |||||
BibTeX:
@article{PUB1568,
author = {Guthmuller, Julien and Champagne, Benoit and Moucheron, Cécile and Kirsch-De Mesmaeker, Andrée},
title = {Investigation of the Resonance Raman Spectra and Excitation Profiles of a Monometallic Ruthenium(II) [Ru(bpy)2(HAT)]2+ Complex by Time-Dependent Density Functional Theory},
journal = {J. Phys. Chem. B},
year = {2010},
volume = {114},
number = {1},
pages = {511-520},
note = {PMID: 19839617},
url = {http://pubs.acs.org/doi/abs/10.1021/jp908154q},
doi = {http://dx.doi.org/10.1021/jp908154q}
}
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Publications in 2011
| Author | Title | Year | Journal/Proceedings | Reftype | DOI/URL |
|---|---|---|---|---|---|
| Mattiuzzi, A., Jabin, I., Moucheron, C. and Kirsch-De Mesmaeker, A. | Ru-TAP complexes with btz and pytz ligands: novel candidates as photooxidizing agents | 2011 | Dalton Trans. Vol. 40, pp. 7395-7402 |
article | DOI URL |
| Abstract: Two ligands containing 1,2,3-triazole moieties 1 and 3 were easily prepared by a CuI-catalysed "click reaction" between commercially available (trimethylsilyl)alkynes and benzyl azide. These ligands were used in the synthesis of Ru(ii) complexes with TAP ligands, i.e. [Ru(TAP)2btz]2+2 and [Ru(TAP)2pytz]2+4. The electrochemical and photophysical properties of these complexes were investigated. The data show that both complexes should behave as highly oxidizing agents under illumination. However, complex 4 displays more attractive photophysical properties than complex 2 and constitutes thus a Ru-TAP compound that can be easily derivatized for photodamaging biomolecules. | |||||
BibTeX:
@article{PUB0858,
author = {Mattiuzzi, Alice and Jabin, Ivan and Moucheron, Cecile and Kirsch-De Mesmaeker, Andrée},
title = {Ru-TAP complexes with btz and pytz ligands: novel candidates as photooxidizing agents},
journal = {Dalton Trans.},
publisher = {The Royal Society of Chemistry},
year = {2011},
volume = {40},
pages = {7395-7402},
url = {http://dx.doi.org/10.1039/C1DT10235D},
doi = {http://dx.doi.org/10.1039/C1DT10235D}
}
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| Servaty, K., Moucheron, C. and Kirsch-De Mesmaeker, A. | Trinuclear ruthenium dendrons based on bridging PHEHAT and TPAC ligands | 2011 | Dalton Trans. Vol. 40, pp. 11704-11711 |
article | DOI URL |
| Abstract: Novel polynuclear compounds, the trinuclear precursor complex cis-[(phen)2Ru(PHEHAT)]2Ru(CH3CN)26+4 and the trinuclear TPAC (tetrapyrido[3,2-a:2[prime or minute],3[prime or minute]-c:3[prime or minute][prime or minute],2[prime or minute]-h:2[prime or minute][prime or minute][prime or minute],3[prime or minute][prime or minute][prime or minute]-j]acridine) complex [(phen)2Ru(PHEHAT)]2Ru(TPAC)6+5 have been prepared. Their electrochemistry and photophysics indicate that the 3MLCT (metal to ligand charge transfer) emissions involve the external Ru(PHEHAT) moieties for both complexes and there is no spectro-electrochemical correlation. The trinuclear dendron with the TPAC ligand represents a key compound for future constructions of much larger species thanks to the TPAC that could bridge another polynuclear precursor. For decreasing the length of preparation of these compounds, microwave assisted syntheses have been tested and used not only for the targeted complexes but also for the precursors ((phen)2RuCl2, (phen)2Ru(phendione)2+, (phen)2Ru(PHEHAT)2+ (PHEHAT = 1,10-phenanthrolino[5,6-b]1,4,5,8,9,12-hexaazatriphenylene), (DMSO)4RuCl2), and for the bridging TPAC ligand itself. The microwave method allows a drastic decrease of the preparation times, especially in the case of the TPAC, from 8 days to 60 min. | |||||
BibTeX:
@article{PUB1567,
author = {Servaty, Kathleen and Moucheron, Cecile and Kirsch-De Mesmaeker, Andree},
title = {Trinuclear ruthenium dendrons based on bridging PHEHAT and TPAC ligands},
journal = {Dalton Trans.},
publisher = {The Royal Society of Chemistry},
year = {2011},
volume = {40},
pages = {11704-11711},
url = {http://dx.doi.org/10.1039/C1DT10639B},
doi = {http://dx.doi.org/10.1039/C1DT10639B}
}
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Publications in 2012
| Author | Title | Year | Journal/Proceedings | Reftype | DOI/URL |
|---|---|---|---|---|---|
| Ghesquière, J., Gauthier, N., De Winter, J., Gerbaux, P., Moucheron, C., Defrancq, E. and Kirsch-De Mesmaeker, A. | Photocrosslinking between Peptide-Peptide or Peptide-Oligonucleotide by RuII-TAP Complexes | 2012 | Chem. Eur. J. Vol. 18(1), pp. 355-364 |
article | DOI URL |
| Abstract: RuII–TAP complexes have been shown to be very attractive compounds in the frame of developments of new anticancer drugs targeting the genetic material. This increasing interest originates from observations of covalent bond formations, triggered by photo-induced electron transfer (PET) between RuII–TAP complexes and guanine bases of DNA. This photoreaction has recently been extended to the tryptophan (Trp) amino acid for future applications involving peptides. Thus, a double photo-addition of Trp residues of peptides on RuII complexes is demonstrated by mass spectrometry with some structural issues. Such bi-adduct formations offer the possibility of photocrosslinking two Trp-containing biomolecules, which is investigated in this study. Thus, photocrosslinking between two complementary oligonucleotides (ODNs) derivatized by Trp-containing tripeptides is demonstrated by polyacrylamide gel electrophoresis (PAGE) in the presence of RuII–TAP complexes. Both PAGE and MS indicate that such photocrosslinkings arise from two reaction pathways: either via the double addition of Trp residues on the Ru complex or from dimerization of Trp radicals. The competition between these two pathways depends on the experimental conditions. Heterobridgings between guanine bases and tryptophan residues mediated by RuII–TAP complexes is also examined, opening the way to ODN–peptide photocrosslinkings. | |||||
BibTeX:
@article{PUB0797,
author = {Ghesquière, Jonathan and Gauthier, Nicolas and De Winter, Julien and Gerbaux, Pascal and Moucheron, Cécile and Defrancq, Eric and Kirsch-De Mesmaeker, Andrée},
title = {Photocrosslinking between Peptide-Peptide or Peptide-Oligonucleotide by RuII-TAP Complexes},
journal = {Chem. Eur. J.},
publisher = {WILEY-VCH Verlag},
year = {2012},
volume = {18},
number = {1},
pages = {355-364},
url = {http://dx.doi.org/10.1002/chem.201101458},
doi = {http://dx.doi.org/10.1002/chem.201101458}
}
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| Marcélis, L., Ghesquière, J., Garnir, K., Kirsch-De Mesmaeker, A. and Moucheron, C. | Photo-oxidizing RuII complexes and light: Targeting biomolecules via photoadditions | 2012 | Coord. Chem. Rev. Vol. 256(15-16), pp. 1569-1582 |
article | DOI URL |
| Abstract: The design of RuII complexes photoreactive with biomolecules represents an important target for the development of novel photoprobes for the study of DNA and proteins, and for the production of novel metal-based potential therapeutic agents. Luminescent RuII complexes based on π-accepting ligands were designed to allow a photoreactivity towards biomolecules, thanks to their important photo-oxidizing power. It was clearly demonstrated that this photoreactivity originates from a primary photo-induced electron transfer (PET) process from either a guanine moiety (G) or a tryptophan residue (Trp) to the excited complex. One of the consequences of this PET process is the formation of a photoadduct between the RuII complex and the G or Trp moieties of a biomolecule. In those photoadducts a covalent bond is formed linking the biomolecule to one ligand of the complex without destruction of the chelation sphere around the metal ion. These photoadducts can be exploited to photocrosslink two complementary oligonucleotides (ODNs), two peptides or even a single ODN with a peptide. Such photocrosslinking could be exploited either for diagnostic purposes or for therapeutic applications. We review in this work the advances to date in the understanding of the primary processes responsible for the photoadduct formation and we show how this photochemical behavior can be exploited for applications with DNA, peptides and proteins. |
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BibTeX:
@article{PUB0805,
author = {Lionel Marcélis and Jonathan Ghesquière and Kevin Garnir and Kirsch-De Mesmaeker, Andrée and Cécile Moucheron},
title = {Photo-oxidizing RuII complexes and light: Targeting biomolecules via photoadditions},
journal = {Coord. Chem. Rev.},
year = {2012},
volume = {256},
number = {15-16},
pages = {1569-1582},
url = {http://www.sciencedirect.com/science/article/pii/S0010854512000367},
doi = {http://dx.doi.org/10.1016/j.ccr.2012.02.012}
}
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| Ghesquière, J., Le Gac, S., Marcélis, L., Moucheron, C. and Kirsch-De Mesmaeker, A. | What Does the Future Hold for Photo-Oxidizing RuII Complexes with Polyazaaromatic Ligands in Medicinal Chemistry? | 2012 | Curr. Top. Med. Chem. Vol. 12(3), pp. 185-196 |
article | DOI URL |
| Abstract: Since the discovery of cisplatin, the search for diagnostic or therapeutic agents based on other metals, has expanded intensively owing to the numerous possibilities offered by coordination chemistry. This mini-review focuses on recent advances in the search for RuII polyazaaromatic complexes of potential interest as molecular tools applied to cellular diagnostics or as specific cellular photo-reagents for future biomedical applications. The interaction of RuII polyazaaromatic complexes with living cells is reported, as well as the photo-reaction mechanisms of photo-oxidizing RuII complexes with nucleic acids. The novel strategies currently developed to improve their reactivity and specificity towards DNA, more particularly in the gene-silencing framework, are also discussed. | |||||
BibTeX:
@article{PUB0806,
author = {Ghesquière, Jonathan and Le Gac, Stephane and Marcélis, Lionel and Moucheron, Cecile and Kirsch-De Mesmaeker, Andrée},
title = {What Does the Future Hold for Photo-Oxidizing RuII Complexes with Polyazaaromatic Ligands in Medicinal Chemistry?},
journal = {Curr. Top. Med. Chem.},
year = {2012},
volume = {12},
number = {3},
pages = {185-196},
url = {http://www.ingentaconnect.com/content/ben/ctmc/2012/00000012/00000003/art00006},
doi = {http://dx.doi.org/10.2174/156802612799079008}
}
|
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| Vanderlinden, W., Blunt, M., David, C.C., Moucheron, C., Kirsch-De Mesmaeker, A. and De Feyter, S. | Mesoscale DNA Structural Changes on Binding and Photoreaction with Ru[(TAP)2PHEHAT]2+ | 2012 | J. Am. Chem. Soc. Vol. 134(24), pp. 10214-10221 |
article | DOI URL |
| Abstract: We used scanning force microscopy (SFM) to study the binding and excited state reactions of the intercalating photoreagent Ru[(TAP)2PHEHAT]2+ (TAP = 1,4,5,8-tetraazaphenanthrene; PHEHAT = 1,10-phenanthrolino[5,6-b]1,4,5,8,9,12-hexaazatriphenylene) with DNA. In the ground state, this ruthenium complex combines a strong intercalative binding mode via the PHEHAT ligand, with TAP-mediated hydrogen bonding capabilities. After visible irradiation, SFM imaging of the photoproducts revealed both the structural implications of photocleavages and photoadduct formation. It is found that the rate of photocleaving is strongly increased when the complex can interact with DNA via hydrogen bonding. We demonstrated that the photoadduct increases DNA rigidity, and that the photo-biadduct can crosslink two separate DNA segments in supercoiled DNA. These mechanical and topological effects might have important implications in future therapeutic applications of this type of compounds. | |||||
BibTeX:
@article{PUB0857,
author = {Vanderlinden, Willem and Blunt, Matthew and David, Charlotte C. and Moucheron, Cécile and Kirsch-De Mesmaeker, Andrée and De Feyter, Steven},
title = {Mesoscale DNA Structural Changes on Binding and Photoreaction with Ru[(TAP)2PHEHAT]2+},
journal = {J. Am. Chem. Soc.},
year = {2012},
volume = {134},
number = {24},
pages = {10214-10221},
url = {http://pubs.acs.org/doi/abs/10.1021/ja303091q},
doi = {http://dx.doi.org/10.1021/ja303091q}
}
|
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Publications in 2013
| Author | Title | Year | Journal/Proceedings | Reftype | DOI/URL |
|---|---|---|---|---|---|
| Marcélis, L., Moucheron, C. and Kirsch-De Mesmaeker, A. | Ru–TAP complexes and DNA: from photo-induced electron transfer to gene photo-silencing in living cells | 2013 | Philosophical Transactions of the Royal Society A: Mathematical,Physical and Engineering Sciences Vol. 371(1995) |
article | DOI URL |
| Abstract: In this review, examples of applications of the photo-induced electron transfer (PET) process between photo-oxidizing Ru–TAP (TAP = 1,4,5,8-tetraazaphenanthrene) complexes and DNA or oligodeoxynucleotides (ODNs) are discussed. Applications using a free Ru–TAP complex (not chemically anchored to an ODN) are first considered. In this case, the PET gives rise to the production of an irreversible adduct of the Ru complex on a guanine (G) base, with formation of a covalent bond. After absorption of a second photon, this adduct can generate a bi-adduct, whereby the same complex binds to a second G moiety. These bi-adduct formations are responsible for photo-cross-linking between two strands of a duplex, each containing a G base, or between two G moieties of a single strand such as a telomeric sequence, as demonstrated by polyacrylamide gel electrophoresis analyses or mass spectrometry. Scanning force microscopy also allows the detection of such photobridgings with plasmid DNA. Other applications, for example with Ru–ODN, i.e. ODN with chemically anchored Ru–TAP complexes, are also discussed. It is shown that such Ru–ODN probes containing a G base in their own sequences are capable of photo-cross-linking selectively with their targeted complementary sequences, and, in the absence of such targets, they self-photo-inhibit. Such processes are applied successfully in gene photo-silencing of human papillomavirus cancer cells. | |||||
BibTeX:
@article{PUB0214,
author = {Marcélis, Lionel and Moucheron, Cécile and Kirsch-De Mesmaeker, Andrée},
title = {Ru–TAP complexes and DNA: from photo-induced electron transfer to gene photo-silencing in living cells},
journal = {Philosophical Transactions of the Royal Society A: Mathematical,Physical and Engineering Sciences},
year = {2013},
volume = {371},
number = {1995},
url = {http://rsta.royalsocietypublishing.org/content/371/1995/20120131.abstract},
doi = {http://dx.doi.org/10.1098/rsta.2012.0131}
}
|
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| Reschner, A., Bontems, S., Le Gac, S., Lambermont, J., Marcélis, L., Defrancq, E., Hubert, P., Moucheron, C., Kirsch-De Mesmaeker, A., Raes, M., Piette, J. and Delvenne, P. | Ruthenium oligonucleotides, targeting HPV16 E6 oncogene, inhibit the growth of cervical cancer cells under illumination by a mechanism involving p53
[BibTeX] |
2013 | Gene Ther. Vol. 20(4), pp. 435-443 |
article | URL |
BibTeX:
@article{PUB0856,
author = {Reschner, A. and Bontems, S. and Le Gac, S. and Lambermont, J. and Marcélis, L. and Defrancq, E. and Hubert, P. and Moucheron, C. and Kirsch-De Mesmaeker, A. and Raes, M. and Piette, J. and Delvenne, P.},
title = {Ruthenium oligonucleotides, targeting HPV16 E6 oncogene, inhibit the growth of cervical cancer cells under illumination by a mechanism involving p53},
journal = {Gene Ther.},
publisher = {Macmillan Publishers Limited},
year = {2013},
volume = {20},
number = {4},
pages = {435-443},
url = {http://dx.doi.org/10.1038/gt.2012.54}
}
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| Le Gac, S., Surin, M., Defrancq, E., Moucheron, C. and Kirsch-De Mesmaeker, A. | What Are the Parameters Controlling Inter- vs. Intra-Strand DNA Photodamage with Ru-TAP Oligonucleotides? | 2013 | Eur. J. Inorg. Chem. Vol. 2013(2), pp. 208-216 |
article | DOI URL |
| Abstract: The special photoreactivity of Ru-TAP (TAP = 1,4,5,8-tetraazaphenanthrene, phen = 1,10-phenanthroline) complexes anchored to G-containing oligodeoxyribonucleotide (ODN) probes prompted us to investigate thoroughly the parameters that influence their selectivity in two competing processes: the intermolecular photoreaction with the target complementary sequence, leading to crosslinking at G sites of the target, and the intramolecular photoreaction leading to a self-inhibition also called the Seppuku process. It is indeed particularly important to favour self-inhibition in the presence of mismatch-containing target sequences. It was found that any parameter reinforcing the association of the Ru-ODN conjugate with a sequence possessing impaired complementarity, such as a low temperature (22 °C), high sodium chloride concentration ([NaCl] = 150 mM), and the presence of an intercalating ligand in the Ru complex, led to increases in undesired photocrosslinking with the wrong target (i.e. that sequence bearing impaired complementarity). In contrast, less favorable conditions for hybridization (T = 33 °C, [NaCl] = 50 mM, a non-intercalating complex), led to a rather good selectivity; up to a 3:1 self-inhibition/photocrosslinking ratio was obtained with a target sequence containing only two mismatches. It is shown that this selectivity as well as the selectivity in the photocrosslinking sites, result from subtle changes in the probe and target interactions. These findings provide the basis for further improvements in selective DNA photoreagents (seppuku conjugates) for cancer research and elaborate the guidelines for selecting appropriate target sequences in a gene to be silenced. | |||||
BibTeX:
@article{PUB1021,
author = {Le Gac, Stéphane and Surin, Mathieu and Defrancq, Eric and Moucheron, Cécile and Kirsch-De Mesmaeker, Andrée},
title = {What Are the Parameters Controlling Inter- vs. Intra-Strand DNA Photodamage with Ru-TAP Oligonucleotides?},
journal = {Eur. J. Inorg. Chem.},
publisher = {WILEY-VCH Verlag},
year = {2013},
volume = {2013},
number = {2},
pages = {208-216},
url = {http://dx.doi.org/10.1002/ejic.201201019},
doi = {http://dx.doi.org/10.1002/ejic.201201019}
}
|
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| Ramlot, D., Rebarz, M., Volker, L., Ovaere, M., Beljonne, D., Dehaen, W., Van Meervelt, L., Moucheron, C. and Kirsch-De Mesmaeker, A. | An Experimental and Theoretical Approach to the Photophysical Properties of Some Rh and Ir Complexes Incorporating the Dipyrromethene Ligand | 2013 | Eur. J. Inorg. Chem. Vol. 2013(12), pp. 2031-2040 |
article | DOI URL |
| Abstract: Rh and Ir complexes that contain meso-(p-methoxyphenyl)dipyrromethene (dipy) and phenylpyridine (ppy) ligands i.e., [Rh(dipy)3], [Rh(ppy)2(dipy)] and [Ir(ppy)2(dipy)] have been prepared and their electrochemical and luminescence behaviour are discussed and compared to results of theoretical calculations. The oxidation and reduction potentials, in agreement with the time-dependent (TD)-DFT calculations, indicate clearly that the HOMO–LUMO transitions are governed by the dipy ligand, which controls also the triplet excited-state emission. However, in luminescence, the two Rh complexes exhibit, in addition to a dipy-centred triplet emission, luminescence from the singlet excited state, which predominates at room temperature, due to a less important influence of the heavy-metal effect in Rh than in Ir complexes. Although the TD-DFT results are in very good agreement with the experimental emission spectra from the dipy-centred triplet excited state, this is not the case for the absorption spectra of the complexes and free dipy ligand. | |||||
BibTeX:
@article{PUB1045,
author = {Ramlot, Diane and Rebarz, Mateusz and Volker, Leen and Ovaere, Margriet and Beljonne, David and Dehaen, Wim and Van Meervelt, Luc and Moucheron, Cécile and Kirsch-De Mesmaeker, Andrée},
title = {An Experimental and Theoretical Approach to the Photophysical Properties of Some Rh and Ir Complexes Incorporating the Dipyrromethene Ligand},
journal = {Eur. J. Inorg. Chem.},
publisher = {WILEY-VCH Verlag},
year = {2013},
volume = {2013},
number = {12},
pages = {2031--2040},
url = {http://dx.doi.org/10.1002/ejic.201201427},
doi = {http://dx.doi.org/10.1002/ejic.201201427}
}
|
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| Reschner, A., Shim, Y.H., Dubois, P., Delvenne, P., Evrard, B., Marcélis, L., Moucheron, C., Kirsch-De Mesmaeker, A., Defrancq, E., Raes, M., Piette, J., Collard, L. and Piel, G. | Evaluation of a New Biocompatible Poly(N-(Morpholino Ethyl Methacrylate)-Based Copolymer for the Delivery of Ruthenium Oligonucleotides, Targeting HPV16 E6 Oncogene | 2013 | J. Biomed. Nanotechnol. Vol. 9(8), pp. 1432-1440 |
article | DOI URL |
| Abstract: This study investigates the use of a new biocompatible block copolymer poly(2-(dimethylamino)ethyl methacrylate-N-(morpholino)ethyl methacrylate (PDMAEMA-b-PMEMA) for the delivery of a particular antisense oligonucleotide targeting E6 gene from human papilloma virus. This antisense oligonucleotide was derivatized with a polyazaaromatic Ru complex which, under visible illumination, is able to produce an irreversible crosslink with the complementary targeted sequence. The purpose of this study is to determine whether by the use of a suitable transfection agent, it is possible to increase the efficiency of the antisense oligonucleotide targeting E6 gene, named Ru-P-4. In a recent study, we showed that Oligofectamine transfected Ru-P-4 antisense oligonucleotide failed to inhibit efficiently the growth of cervical cancer cell line SiHa, contrarily to the Ru-P-6 antisense oligonucleotide, another sequence also targeting the E6 gene. The ability of PDMAEMA-b-PMEMA to form polyplexes with optimal physicochemical characteristics was investigated first. Then the ability of the PDMAEMA--PMEMA/Ru-P-4 antisense oligonucleotide polyplexes to transfect two keratinocyte cell lines (SiHa and HaCat) and the capacity of polyplexes to inhibit HPV16 + cervical cancer cell growth was evaluated. PDMAEMA-b-PMEMA base polyplexes at the optimal molar ratio of polymer nitrogen atoms to DNA phosphates (N/P), were able to deliver Ru-P-4 antisense oligonucleotide and to induce a higher growth inhibition in human cervical cancer SiHa cells, compared to other formulations based on Oligofectamine. | |||||
BibTeX:
@article{PUB1252,
author = {Reschner, Anca and Shim, Yong Ho and Dubois, Philippe and Delvenne, Philippe and Evrard, Brigitte and Marcélis, Lionel and Moucheron, Cecile and Kirsch-De Mesmaeker, Andrée and Defrancq, Eric and Raes, Martine and Piette, Jacques and Collard, Laurence and Piel, Geraldine},
title = {Evaluation of a New Biocompatible Poly(N-(Morpholino Ethyl Methacrylate)-Based Copolymer for the Delivery of Ruthenium Oligonucleotides, Targeting HPV16 E6 Oncogene},
journal = {J. Biomed. Nanotechnol.},
year = {2013},
volume = {9},
number = {8},
pages = {1432-1440},
url = {http://www.ingentaconnect.com/content/asp/jbn/2013/00000009/00000008/art00016},
doi = {http://dx.doi.org/10.1166/jbn.2013.1634}
}
|
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| Mattiuzzi, A., Marcélis, L., Jabin, I., Moucheron, C. and Kirsch-De Mesmaeker, A. | Synthesis and Electrochemical and Photophysical Properties of Calixarene-Based Ruthenium(II) Complexes as Potential Multivalent Photoreagents | 2013 | Inorg. Chem. Vol. 52(19), pp. 11228-11236 |
article | DOI URL |
| Abstract: The grafting of photoreactive and photooxidizing RuII(TAP) (TAP = 1,4,5,8-tetraazaphenanthrene) complexes on calix[4 or 6]arene molecular platforms is reported. Thus, either [Ru(TAP)2(phen)]2+ (phen = 1,10-phenanthroline) or [Ru(TAP)2(pytz)]2+ [pytz = 2-(1,2,3-triazol-4-yl)pyridine] complexes are anchored to the calixarenes. The data in electrochemistry, combined with those in emission under steady state and pulsed illumination and the determination of the associated photophysical rate constants, indicate the presence of intramolecular luminescence quenching by the phenol moieties of calixarene. From transient absorption studies under pulsed laser irradiation, it is concluded that the quenching originates from a par proton-coupled electron transfer (PCET) process. Such an intramolecular quenching is absent when the phenol groups of the calixarene platform are derivatized by azido arms. | |||||
BibTeX:
@article{PUB1361,
author = {Mattiuzzi, Alice and Marcélis, Lionel and Jabin, Ivan and Moucheron, Cécile and Kirsch-De Mesmaeker, A},
title = {Synthesis and Electrochemical and Photophysical Properties of Calixarene-Based Ruthenium(II) Complexes as Potential Multivalent Photoreagents},
journal = {Inorg. Chem.},
year = {2013},
volume = {52},
number = {19},
pages = {11228-11236},
url = {http://pubs.acs.org/doi/abs/10.1021/ic401468t},
doi = {http://dx.doi.org/10.1021/ic401468t}
}
|
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| Servaty, K., Cauet, E., Thomas, F., Lambermont, J., Gerbaux, P., De Winter, J., Ovaere, M., Volker, L., Vaeck, N., Van Meervelt, L., Dehaen, W., Moucheron, C. and Kirsch-De Mesmaeker, A. | Peculiar properties of homoleptic Cu complexes with dipyrromethene derivatives | 2013 | Dalton Trans. Vol. 42, pp. 14188-14199 |
article | DOI URL |
| Abstract: In view of preparing Cu polynuclear complexes with dipyrromethene ligands, the mononuclear complexes [Cu(ii)(dipy)2] (dipyH = 5-phenyldipyrromethene) and [Cu(ii)(dpdipy)2] (dpdipyH = 1,5,9-triphenyldipyrromethene) have been prepared and characterized by X-ray crystallography, mass spectrometry and EPR spectroscopy. Their peculiar redox and spectroscopic (absorption/emission) behaviours are discussed. In contrast to CuII complexes of 1,1[prime or minute]-bidypyrrin, the reduction electrolysis of [Cu(ii)(dpdipy)2] leads to decomposition products on a time scale of a few hours. Moreover in relation to this observation, [Cu(i)(dpdipy)2]- could not be synthesized in spite of the CuI core protection by the phenyl substituents in ortho position of the nitrogen atoms. Theoretical calculations provide some explanations for this instability. Interestingly [Cu(ii)(dipy)2] and [Cu(ii)(dpdipy)2] display weak luminescence at room temperature, attributed to a ligand centered emission. | |||||
| Troian-Gautier, L., De Winter, J., Gerbaux, P. and Moucheron, C. | A Direct Method for Oxidizing Quinoxaline, Tetraazaphenanthrene, and Hexaazatriphenylene Moieties Using Hypervalent λ3-Iodinane Compounds | 2013 | J. Org. Chem. Vol. 78(21), pp. 11096-11101 |
article | DOI URL |
| Abstract: An efficient oxidation reaction of various electron-poor quinoxaline-core-containing compounds, such as quinoxalines, 1,4,5,8-tetraazaphenanthrenes, and 1,4,5,8,9,12-hexaazatriphenylene, using [bis(trifluoroacetoxy)iodo]benzene is reported. These compounds are converted into the corresponding quinoxalinediones in good to high yields at room temperature using an acetonitrile/water solvent mixture. This unprecedented reaction should enable the synthesis of a wide variety of compounds useful in several fields of chemistry. | |||||
BibTeX:
@article{PUB1383,
author = {Troian-Gautier, Ludovic and De Winter, Julien and Gerbaux, Pascal and Moucheron, Cécile},
title = {A Direct Method for Oxidizing Quinoxaline, Tetraazaphenanthrene, and Hexaazatriphenylene Moieties Using Hypervalent λ3-Iodinane Compounds},
journal = {J. Org. Chem.},
year = {2013},
volume = {78},
number = {21},
pages = {11096-11101},
url = {http://pubs.acs.org/doi/abs/10.1021/jo401872e},
doi = {http://dx.doi.org/10.1021/jo401872e}
}
|
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BibTeX:
@article{PUB1384,
author = {Servaty, Kathleen and Cauet, Emilie and Thomas, Fabrice and Lambermont, Javiera and Gerbaux, Pascal and De Winter, Julien and Ovaere, Margriet and Volker, Leen and Vaeck, Nathalie and Van Meervelt, Luc and Dehaen, Wim and Moucheron, Cecile and Kirsch-De Mesmaeker, Andree},
title = {Peculiar properties of homoleptic Cu complexes with dipyrromethene derivatives},
journal = {Dalton Trans.},
publisher = {The Royal Society of Chemistry},
year = {2013},
volume = {42},
pages = {14188-14199},
url = {http://dx.doi.org/10.1039/C3DT51541A},
doi = {http://dx.doi.org/10.1039/C3DT51541A}
}
|
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Publications in 2014
| Author | Title | Year | Journal/Proceedings | Reftype | DOI/URL |
|---|---|---|---|---|---|
| Marcélis, L., Vanderlinden, W. and Kirsch-De Mesmaeker, A. | Probing DNA using metal complexes
[BibTeX] |
2014 | Inorganic Chemical Biology: Principles, Techniques and Applications | inbook | |
BibTeX:
@inbook{BOOK013,
author = {Marcélis, L and Vanderlinden, W. and Kirsch-De Mesmaeker, A.},
title = {Probing DNA using metal complexes},
booktitle = {Inorganic Chemical Biology: Principles, Techniques and Applications},
publisher = {John Wiley & Sons, Ltd, UK},
year = {2014}
}
|
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| Rebarz, M., Marcélis, L., Menand, M., Cornut, D., Moucheron, C., Jabin, I. and Kirsch-De Mesmaeker, A. | Revisited Photophysics and Photochemistry of a Ru-TAP Complex Using Chloride Ions and a Calix[6]crypturea | 2014 | Inorg. Chem. Vol. 53(5), pp. 2635–2644 |
article | DOI URL |
| Abstract: The effects of the nonprotonated and protonated calix[6]crypturea 1/1•H+ on the PF6– and Cl– salts of a luminescent Ru-TAP complex (TAP = 1,4,5,8-tetraazaphenanthrene) were investigated. Thus, the phototriggered basic properties of this complex were examined with 1•H+ in acetonitrile (MeCN) and butyronitrile (BuCN). The Ru excited complex was shown to be able to extract a proton from the protonated calixarene, accompanied by a luminescence quenching in both solvents. However, in BuCN, the Cl– salt of the complex exhibited a surprising behavior in the presence of 1/1•H+. Although an emission decrease was observed with the protonated calixarene, an emission increase was evidenced in the presence of nonprotonated 1. As the Cl– ions were shown to inhibit the luminescence of the complex in BuCN, this luminescence increase by nonprotonated 1 was attributed to the protection effect of 1 by encapsulation of the Cl– anions into the tris-urea binding site. The study of the luminescence lifetimes of the Ru-TAP complex in BuCN as a function of temperature for the PF6– and Cl– salts in the absence and presence of 1 led to the following conclusions. In BuCN, in contrast to MeCN, in addition to ion pairing, because of the poor solvation of the ions, the luminescent metal-to-ligand charge transfer (3MLCT) state could reach two metal-centered (3MC) states, one of which is in equilibrium with the 3MLCT state during the emission lifetime. The reaction of Cl– with this latter 3MC state would be responsible for the luminescence quenching, in agreement with the formation of photosubstitution products. | |||||
BibTeX:
@article{PUB1622,
author = {Rebarz, Mateusz and Marcélis, Lionel and Menand, Mickaël and Cornut, Damien and Moucheron, Cécile and Jabin, Ivan and Kirsch-De Mesmaeker, Andrée},
title = {Revisited Photophysics and Photochemistry of a Ru-TAP Complex Using Chloride Ions and a Calix[6]crypturea},
journal = {Inorg. Chem.},
year = {2014},
volume = {53},
number = {5},
pages = {2635–2644},
url = {http://pubs.acs.org/doi/abs/10.1021/ic403024z},
doi = {http://dx.doi.org/10.1021/ic403024z}
}
|
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| Troian-Gautier, L. and Moucheron, C. | RutheniumII Complexes bearing Fused Polycyclic Ligands: From Fundamental Aspects to Potential Applications [BibTeX] |
2014 | Molecules Vol. 19(4), pp. 5028-5087 |
article | DOI URL |
BibTeX:
@article{PUB1680,
author = {Troian-Gautier, Ludovic and Moucheron, Cécile},
title = {RutheniumII Complexes bearing Fused Polycyclic Ligands: From Fundamental Aspects to Potential Applications},
journal = {Molecules},
year = {2014},
volume = {19},
number = {4},
pages = {5028--5087},
url = {http://www.mdpi.com/1420-3049/19/4/5028},
doi = {http://dx.doi.org/10.3390/molecules19045028}
}
|
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| Marcélis, L., Surin, M., Lartia, R., Moucheron, C., Defrancq, E. and Kirsch-De Mesmaeker, A. | Specificity of Light-Induced Covalent Adduct Formation between RuII Oligonucleotide Conjugates and Target Sequences for Gene Silencing Applications | 2014 | European Journal of Inorganic Chemistry Vol. 2014(19), pp. 3016-3022 |
article | DOI URL |
| Abstract: Under irradiation, Ru–TAP (TAP = 1,4,5,8-tetraazaphenanthrene) complexes tethered to oligonucleotides (Ru–ODN) hybridized to their complementary target sequences produce irreversible adducts with guanine (G) bases. The interesting feature is that the G bases that react in the double strand (DS) topology belong exclusively to the complementary strand; thus, no G base of the Ru–ODN strand participates in the production of these adducts. This highly specific photoreaction in the DS topology is demonstrated by gel electrophoresis analyses of different duplex sequences in which the positions of the G bases are varied. Atomistic molecular modelling simulations indicate that this specificity is due to important steric constraints for the intrastrand adduct formation in the duplex. Luminescence lifetime measurements furnish more detailed information on these different duplex systems. | |||||
BibTeX:
@article{PUB1696,
author = {Marcélis, Lionel and Surin, Mathieu and Lartia, Rémy and Moucheron, Cécile and Defrancq, Eric and Kirsch-De Mesmaeker, Andrée},
title = {Specificity of Light-Induced Covalent Adduct Formation between RuII Oligonucleotide Conjugates and Target Sequences for Gene Silencing Applications},
journal = {European Journal of Inorganic Chemistry},
publisher = {WILEY-VCH Verlag},
year = {2014},
volume = {2014},
number = {19},
pages = {3016-3022},
url = {http://dx.doi.org/10.1002/ejic.201402189},
doi = {http://dx.doi.org/10.1002/ejic.201402189}
}
|
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| Marcélis, L., Van Overstraeten-Schlögel, N., Lambermont, J., Bontems, S., Spinelli, N., Defrancq, E., Moucheron, C., Kirsch-De Mesmaeker, A. and Raes, M. | Light-Triggered Green Fluorescent Protein Silencing in Human Keratinocytes in Culture Using Antisense Oligonucleotides Coupled to a Photoreactive Ruthenium(II) Complex | 2014 | ChemPlusChem Vol. 79(11), pp. 1597-1604 |
article | DOI URL |
| Abstract: A photoreactive ruthenium(II) complex that contains two tetraazaphenanthrene (TAP) and one phenanthroline (phen) ligands was synthesized and then tethered to (antisense) oligonucleotides (Ru–ASO) to target a destabilized GFP (dGFP). The specificity of the photoreaction of this Ru–ASO conjugate was studied in vitro by polyacrylamide gel electrophoresis (PAGE) experiments in denaturing conditions. Other nonspecific Ru–ASO conjugates were also prepared and evaluated with human keratinocytes that expressed dGFP. An illumination-dependent cytotoxicity was observed for most Ru–ASO conjugates that varied from 10 to almost 40 %, but only the specific Ru–ASO conjugate was able to significantly reduce GFP expression in illuminated cells. | |||||
BibTeX:
@article{PUB1707,
author = {Marcélis, Lionel and Van Overstraeten-Schlögel, Nancy and Lambermont, Javiera and Bontems, Sébastien and Spinelli, Nicolas and Defrancq, Eric and Moucheron, Cécile and Kirsch-De Mesmaeker, Andrée and Raes, Martine},
title = {Light-Triggered Green Fluorescent Protein Silencing in Human Keratinocytes in Culture Using Antisense Oligonucleotides Coupled to a Photoreactive Ruthenium(II) Complex},
journal = {ChemPlusChem},
publisher = {WILEY-VCH Verlag},
year = {2014},
volume = {79},
number = {11},
pages = {1597--1604},
url = {http://dx.doi.org/10.1002/cplu.201402212},
doi = {http://dx.doi.org/10.1002/cplu.201402212}
}
|
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