User menu

Accès à distance ? S'identifier sur le proxy UCLouvain

Towards mismatched DNA photoprobes and photoreagents: “elbow-shaped” Ru(II) complexes

Primary tabs

download
  • Open access
  • PDF
  • 1.92 M
Deraedt, Quentin [UCL] Marcélis, Lionel [UCL] Loiseau, F. [Université Grenoble-Alpes (France)] Elias, Benjamin [UCL]

Due to their potentially harmful consequences, the detection of mismatched DNA is a subject of high interest. In order to probe DNA mismatches by means of luminescent sensitive Ru(II) complexes, “elbowshaped” extended planar ligands based on an acridine or phenazine core have been synthesized (npp = naphtho[1,2-b]pyrido[3,2-f][1,7]phenanthroline and bdppz = benzo[h]dipyrido[3,2-a:2’,3’-c]phenazine). The photophysical studies revealed that [Ru(bpy)2npp]2+ (bpy = 2,2’-bipyridine) allows emission from a 3MLCTbpy/npp excited state, while the lowest 3MLCT for [Ru(bpy)2bdppz]2+ shifts from a bright 3MLCTbpy/b̲d̲p̲pz state towards a poorly luminescent 3MLCTbdpp̲z̲ state, probably due to the formation of H-bonds with water molecules in the excited state. Studies of the complexes in the presence of DNA demonstrate that they strongly bind to polynucleotides. In the presence of single base mismatched hairpin oligonucleotides, while [Ru(bpy)2npp]2+ does not show remarkable sensitivity to the nature of the mismatch site, [Ru(bpy)2bdppz]2+ exhibits noticeably differential luminescence behavior correlated to the nature and stability of the mismatch compared to the well-matched sequence. Photooxidant analogues of these complexes were prepared, replacing bpy ancillary ligands by bpz (2,2’-bipyrazine). A photo-induced electron transfer from dGMP and polynucleotides to the excited states of [Ru(bpz)2npp]2+ and [Ru(bpz)2bdppz]2+ is observed. These results emphasized the role of “elbow-shaped” Ru(II) complexes as promising candidates for the development of mismatch-sensitive DNA photoprobes.

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès libre
Publication date 2017
Language Anglais
Journal information "Inorganic Chemistry Frontiers : an international journal of inorganic chemistry" - Vol. 4, p. 91-103 (2017)
Peer reviewed yes
Publisher R S C Publications ((United Kingdom) Cambridge)
issn 2052-1553
Publication status Publié
Affiliation UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity
Links
  1. B. Alberts , A.Johnson, J.Lewis, M.Raff, K.Roberts and P.Walter, Molecular Biology of the Cell, Garland Science, New York, 5th edition, 2007
  2. Iyer Ravi R., Pluciennik Anna, Burdett Vickers, Modrich Paul L., DNA Mismatch Repair:  Functions and Mechanisms, 10.1021/cr0404794
  3. Modrich Paul, Mechanisms in Eukaryotic Mismatch Repair, 10.1074/jbc.r600022200
  4. Carell Thomas, DNA Repair, 10.1002/anie.201509770
  5. Hoeijmakers Jan H. J., 10.1038/35077232
  6. Jiricny Josef, The multifaceted mismatch-repair system, 10.1038/nrm1907
  7. Liu Peng, Li Yuxi, Wang Haiyu, Wang Zhiming, Hu Xianming, Synthesis of substituted quinolines by iron-catalyzed oxidative coupling reactions, 10.1016/j.tetlet.2012.09.090
  8. Chen Yongxin, Li Kangning, Zhao Mingming, Li Yuanjiao, Chen Baohua, Cu(II)-catalyzed synthesis of quinoxalines from o-phenylenediamines and nitroolefins, 10.1016/j.tetlet.2012.11.127
  9. Gill Martin R., Thomas Jim A., Ruthenium(ii) polypyridyl complexes and DNA—from structural probes to cellular imaging and therapeutics, 10.1039/c2cs15299a
  10. McKinley Andrew W., Lincoln Per, Tuite Eimer M., Environmental effects on the photophysics of transition metal complexes with dipyrido[2,3-a:3′,2′-c]phenazine (dppz) and related ligands, 10.1016/j.ccr.2011.06.012
  11. Komor Alexis C., Barton Jacqueline K., The path for metal complexes to a DNA target, 10.1039/c3cc00177f
  12. Elias Benjamin, Herman Leslie, Moucheron Cécile, Kirsch-De Mesmaeker Andrée, Dinuclear RuIIPHEHAT and -TPAC Complexes:  Effects of the Second RuIICenter on Their Spectroelectrochemical Properties, 10.1021/ic070224j
  13. Herman Leslie, Elias Benjamin, Pierard Frédéric, Moucheron Cécile, Kirsch-De Mesmaeker Andrée, Effects of Protonation on the Spectroscopic Properties of Tetrapyridoacridine (TPAC) Mono- and Dinuclear Ru(II) Complexes in Their Ground and3MLCT Excited States, 10.1021/jp072782p
  14. Kobayashi Katsuaki, Ohtsu Hideki, Nozaki Koichi, Kitagawa Susumu, Tanaka Koji, Photochemical Properties and Reactivity of a Ru Compound Containing an NAD/NADH-Functionalized 1,10-Phenanthroline Ligand, 10.1021/acs.inorgchem.5b02390
  15. Ortmans Isabelle, Elias Benjamin, Kelly John M., Moucheron Cécile, Kirsch-DeMesmaeker Andrée, [Ru(TAP)2(dppz)]2+: a DNA intercalating complex, which luminesces strongly in water and undergoes photo-induced proton-coupled electron transfer with guanosine-5′-monophosphate, 10.1039/b313213g
  16. Smith Jayden A., George Michael W., Kelly John M., Transient spectroscopy of dipyridophenazine metal complexes which undergo photo-induced electron transfer with DNA, 10.1016/j.ccr.2011.04.007
  17. Keane Páraic M., Poynton Fergus E., Hall James P., Sazanovich Igor V., Towrie Michael, Gunnlaugsson Thorfinnur, Quinn Susan J., Cardin Christine J., Kelly John M., Reversal of a Single Base-Pair Step Controls Guanine Photo-Oxidation by an Intercalating Ruthenium(II) Dipyridophenazine Complex, 10.1002/anie.201502608
  18. Cloonan Suzanne M., Elmes Robert B. P., Erby MariaLuisa, Bright Sandra A., Poynton Fergus E., Nolan Derek E., Quinn Susan J., Gunnlaugsson Thorfinnur, Williams D. Clive, Detailed Biological Profiling of a Photoactivated and Apoptosis Inducing pdppz Ruthenium(II) Polypyridyl Complex in Cancer Cells, 10.1021/acs.jmedchem.5b00451
  19. Elias Benjamin, Creely Caitriona, Doorley Gerard W., Feeney Martin M., Moucheron Cécile, Kirsch-DeMesmaeker Andrée, Dyer Joanne, Grills David C., George Michael W., Matousek Pavel, Parker Anthony W., Towrie Michael, Kelly John M., Photooxidation of Guanine by a Ruthenium Dipyridophenazine Complex Intercalated in a Double-Stranded Polynucleotide Monitored Directly by Picosecond Visible and Infrared Transient Absorption Spectroscopy, 10.1002/chem.200700564
  20. Sentagne, J. Photochem. Photobiol., B, 26, 165 (1994)
  21. Vicendo Patricia, Mouysset Serge, Paillous Nicole, Comparative Study of Ru(bpz)32+Ru(bipy)32+and Ru(bpz)2CI2as Photosensitizers of DNA Cleavage and Adduct Formation, 10.1111/j.1751-1097.1997.tb01906.x
  22. Lim Mi Hee, Song Hang, Olmon Eric D., Dervan Elizabeth E., Barton Jacqueline K., Sensitivity of Ru(bpy)2dppz2+Luminescence to DNA Defects, 10.1021/ic900407n
  23. Rüba Eva, Hart Jonathan R., Barton Jacqueline K., [Ru(bpy)2(L)]Cl2: Luminescent Metal Complexes That Bind DNA Base Mismatches, 10.1021/ic0499291
  24. McConnell Anna J., Lim Mi Hee, Olmon Eric D., Song Hang, Dervan Elizabeth E., Barton Jacqueline K., Luminescent Properties of Ruthenium(II) Complexes with Sterically Expansive Ligands Bound to DNA Defects, 10.1021/ic3019524
  25. Deraedt Quentin, Marcélis Lionel, Auvray Thomas, Hanan Garry S., Loiseau Frédérique, Elias Benjamin, Design and Photophysical Studies of Acridine-Based RuIIComplexes for Applications as DNA Photoprobes : Design and Photophysical Studies of Acridine-Based RuIIComplexes for Applications as DNA Photoprobes, 10.1002/ejic.201600468
  26. Juris A., Balzani V., Barigelletti F., Campagna S., Belser P., von Zelewsky A., Ru(II) polypyridine complexes: photophysics, photochemistry, eletrochemistry, and chemiluminescence, 10.1016/0010-8545(88)80032-8
  27. Amouyal Edmond, Homsi Abdulrazzak, Chambron Jean-Claude, Sauvage Jean-Pierre, Synthesis and study of a mixed-ligand ruthenium(II) complex in its ground and excited states: bis(2,2′-bipyridine)(dipyrido[3,2-a : 2′,3′-c]phenazine-N4N5)ruthenium(II), 10.1039/dt9900001841
  28. Crutchley R. J., Lever A. B. P., Poggi A., Bis(bipyrazine)ruthenium(II) complexes: characterization, spectroscopy, and electrochemistry, 10.1021/ic00160a038
  29. Sentagne Christiane, Chambron Jean-Claude, Sauvage Jean-Pierre, Paillous Nicole, Tuning the mechanism of DNA cleavage photosensitized by ruthenium dipyridophenazine complexes by varying the structure of the two non intercalating ligands, 10.1016/1011-1344(94)07031-8
  30. Olofsson Johan, Wilhelmsson L. Marcus, Lincoln Per, Effects of Methyl Substitution on Radiative and Solvent Quenching Rate Constants of [Ru(phen)2dppz]2+in Polyol Solvents and Bound to DNA, 10.1021/ja047166a
  31. Pourtois Geoffrey, Beljonne David, Moucheron Cécile, Schumm Stephan, Kirsch-De Mesmaeker Andrée, Lazzaroni Roberto, Brédas Jean-Luc, Photophysical Properties of Ruthenium(II) Polyazaaromatic Compounds:  A Theoretical Insight, 10.1021/ja034444h
  32. Olofsson Johan, Önfelt Björn, Lincoln Per, Three-State Light Switch of [Ru(phen)2dppz]2+:  Distinct Excited-State Species with Two, One, or No Hydrogen Bonds from Solvent, 10.1021/jp037967k
  33. Gicquel Etienne, Souchard Jean-Pierre, Magnusson Fay, Chemaly Jad, Calsou Patrick, Vicendo Patricia, Role of intercalation and redox potential in DNA photosensitization by ruthenium(ii) polypyridyl complexes: assessment using DNA repair protein tests, 10.1039/c3pp50070e
  34. Hager G. D., Crosby G. A., Charge-transfer exited states of ruthenium(II) complexes. I. Quantum yield and decay measurements, 10.1021/ja00857a013
  35. Caspar Jonathan V., Kober Edward M., Sullivan B. Patrick, Meyer Thomas J., Application of the energy gap law to the decay of charge-transfer excited states, 10.1021/ja00366a051
  36. Caspar Jonathan V., Meyer Thomas J., Photochemistry of tris(2,2'-bipyridine)ruthenium(2+) ion (Ru(bpy)32+). Solvent effects, 10.1021/ja00355a009
  37. Coates Colin G., Jacquet Luc, McGarvey John J., Bell Steven E. J., Al-Obaidi Ala H. R., Kelly John M., Resonance Raman Probing of the Interaction between Dipyridophenazine Complexes of Ru(II) and DNA, 10.1021/ja970064i
  38. Hartshorn Richard M., Barton Jacqueline K., Novel dipyridophenazine complexes of ruthenium(II): exploring luminescent reporters of DNA, 10.1021/ja00041a002
  39. Bhasikuttan Achikanath C., Suzuki Masaya, Nakashima Satoru, Okada Tadashi, Ultrafast Fluorescence Detection in Tris(2,2‘-bipyridine)ruthenium(II) Complex in Solution:  Relaxation Dynamics Involving Higher Excited States, 10.1021/ja026135h
  40. Cannizzo Andrea, van Mourik Frank, Gawelda Wojciech, Zgrablic Goran, Bressler Christian, Chergui Majed, Broadband Femtosecond Fluorescence Spectroscopy of [Ru(bpy)3]2+, 10.1002/anie.200600125
  41. Olson E. J. C., Hu D., Hörmann A., Jonkman A. M., Arkin M. R., Stemp E. D. A., Barton J. K., Barbara P. F., First Observation of the Key Intermediate in the “Light-Switch” Mechanism of [Ru(phen)2dppz]2+, 10.1021/ja971151d
  42. Lincoln Per, Broo Anders, Nordén Bengt, Diastereomeric DNA-Binding Geometries of Intercalated Ruthenium(II) Trischelates Probed by Linear Dichroism:  [Ru(phen)2DPPZ]2+and [Ru(phen)2BDPPZ]2+, 10.1021/ja953363l
  43. Sun Yujie, Joyce Lauren E., Dickson Nicole M., Turro Claudia, Efficient DNA photocleavage by [Ru(bpy)2(dppn)]2+ with visible light, 10.1039/b925574e
  44. Marcélis Lionel, Ghesquière Jonathan, Garnir Kevin, Kirsch-De Mesmaeker Andrée, Moucheron Cécile, Photo-oxidizing RuII complexes and light: Targeting biomolecules via photoadditions, 10.1016/j.ccr.2012.02.012
  45. Marcelis L., Moucheron C., Kirsch-De Mesmaeker A., Ru-TAP complexes and DNA: from photo-induced electron transfer to gene photo-silencing in living cells, 10.1098/rsta.2012.0131
  46. Turro Claudia, Bossmann Stefan H., Jenkins Yonchu, Barton Jacqueline K., Turro Nicholas J., Proton Transfer Quenching of the MLCT Excited State of Ru(phen)2dppz2+ in Homogeneous Solution and Bound to DNA, 10.1021/ja00140a020
  47. Onfelt B., Lincoln P., Norden B., Baskin J. S., Zewail A. H., Femtosecond linear dichroism of DNA-intercalating chromophores: Solvation and charge separation dynamics of [Ru(phen)2dppz]2+ systems, 10.1073/pnas.100127397
  48. Moucheron Cécile, Kirsch-De Mesmaeker Andrée, Choua Sylvia, Photophysics of Ru(phen)2(PHEHAT)2+:  A Novel “Light Switch” for DNA and Photo-oxidant for Mononucleotides, 10.1021/ic9609315
  49. McGhee James D., von Hippel Peter H., Theoretical aspects of DNA-protein interactions: Co-operative and non-co-operative binding of large ligands to a one-dimensional homogeneous lattice, 10.1016/0022-2836(74)90031-x
  50. Srishailam A., Kumar Yata Praveen, Venkat Reddy P., Nambigari Navaneetha, Vuruputuri Uma, Singh Surya S., Satyanarayana S., Cellular uptake, cytotoxicity, apoptosis, DNA-binding, photocleavage and molecular docking studies of ruthenium(II) polypyridyl complexes, 10.1016/j.jphotobiol.2014.02.003
  51. Boynton Adam N., Marcélis Lionel, Barton Jacqueline K., [Ru(Me4phen)2dppz]2+, a Light Switch for DNA Mismatches, 10.1021/jacs.6b02022
  52. Jackson Brian A., Barton Jacqueline K., Recognition of DNA Base Mismatches by a Rhodium Intercalator, 10.1021/ja972489a
  53. Jackson Brian A., Alekseyev Viktor Y., Barton Jacqueline K., A Versatile Mismatch Recognition Agent:  Specific Cleavage of a Plasmid DNA at a Single Base Mispair†, 10.1021/bi990255t
  54. Jackson Brian A., Barton Jacqueline K., Recognition of Base Mismatches in DNA by 5,6-Chrysenequinone Diimine Complexes of Rhodium(III):  A Proposed Mechanism for Preferential Binding in Destabilized Regions of the Double Helix†, 10.1021/bi9927033
  55. Steenken Steen, Jovanovic Slobodan V., How Easily Oxidizable Is DNA? One-Electron Reduction Potentials of Adenosine and Guanosine Radicals in Aqueous Solution, 10.1021/ja962255b
  56. Zeglis Brian M, Barton Jacqueline K, DNA base mismatch detection with bulky rhodium intercalators: synthesis and applications, 10.1038/nprot.2007.22
  57. Boyle Kelsey M., Barton Jacqueline K., Targeting DNA mismatches with rhodium metalloinsertors, 10.1016/j.ica.2016.01.021
  58. Weidmann A. G., Komor A. C., Barton J. K., Biological effects of simple changes in functionality on rhodium metalloinsertors, 10.1098/rsta.2012.0117
  59. SantaLucia John, Hicks Donald, The Thermodynamics of DNA Structural Motifs, 10.1146/annurev.biophys.32.110601.141800
  60. Riesgo Elvira C., Jin Xiaoqing, Thummel Randolph P., Introduction of Benzo[h]quinoline and 1,10-Phenanthroline Subunits by Friedländer Methodology, 10.1021/jo952164h
  61. Villa Stefania, Cignarella Giorgio, Barlocco Daniela, Gervasoni Marco, Carcassola Gabriella, Giannino Laura, Mantegazza Paolo, Congo red analogues as potential anti-prion agents, 10.1016/s0014-827x(03)00151-4
  62. Travis Will, Knapp Caroline E., Savory Christopher N., Ganose Alex M., Kafourou Panagiota, Song Xingchi, Sharif Zainab, Cockcroft Jeremy K., Scanlon David O., Bronstein Hugo, Palgrave Robert G., Hybrid Organic–Inorganic Coordination Complexes as Tunable Optical Response Materials, 10.1021/acs.inorgchem.5b02749
  63. Castanheira Elisabete MS, Carvalho Maria Solange D, Rodrigues Ana Rita O, Calhelha Ricardo C, Queiroz Maria-João RP, New potential antitumoral fluorescent tetracyclic thieno[3,2-b]pyridine derivatives: interaction with DNA and nanosized liposomes, 10.1186/1556-276x-6-379
  64. DIXIT Ritu B., DNA-Binding Interaction Studies of Microwave Assisted Synthesized Sulfonamide Substituted 8-Hydroxyquinoline Derivatives, 10.3797/scipharm.1102-16
Bibliographic reference Deraedt, Quentin ; Marcélis, Lionel ; Loiseau, F. ; Elias, Benjamin. Towards mismatched DNA photoprobes and photoreagents: “elbow-shaped” Ru(II) complexes. In: Inorganic Chemistry Frontiers : an international journal of inorganic chemistry, Vol. 4, p. 91-103 (2017)
Permanent URL http://hdl.handle.net/2078.1/186301