Photophysical characterization of oligopyrene modules for DNA-based nanosystems

Photochemical and Photobiological Sciences

Volumn 8, Issue 10, 2009, Pages 1448-1454

  Galievsky, Victor A ^a   Malinovskii, Vladimir L ^b   Stasheuski, Alexander S ^a   Samain, Florent ^b   Zachariasse, Klaas A ^c   Häner, Robert ^b   Chirvony, Vladimir S ^a,d  

^a B I STEPANOV INSTITUTE OF PHYSICS   (Belarus)

^b UNIVERSITY OF BERN   (Switzerland)

^c MAX PLANCK INSTITUTE FOR BIOPHYSICAL CHEMISTRY   (Germany)

^d UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CARBOXYLPYRENE; DNA; OLIGONUCLEOTIDE; PYRENE 1,8 DICARBOXYAMIDE; PYRENE DERIVATIVE; PYRENEDICARBOXAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHROMATOPHORE; CONTROLLED STUDY; ELECTRON TRANSPORT; FLUORESCENCE SPECTROSCOPY; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; QUANTUM YIELD; ROOM TEMPERATURE; STEADY STATE;

EID: 70349782780     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b9pp00016j     Document Type: Article

References (53)

1. N. C. Seeman DNA in a material world Nature 2003 421 427 431
2. U. Feldkamp C. M. Niemeyer Rational Design of DNA Nanoarchitectures Angew. Chem., Int. Ed. 2006 45 1856 1876
3. A. Condon Designed DNA molecules: principles and applications of molecular nanotechnology Nat. Rev. Genet. 2006 7 565 575
4. M. H. Caruthers Gene synthesis machines: DNA chemistry and its uses Science 1985 230 281 285
5. K. Kinbara T. Aida Toward intelligent molecular machines: Directed motions of biological and artificial molecules and assemblies Chem. Rev. 2005 105 1377 1400
6. K. V. Gothelf T. H. Labean DNA-programmed assembly of nanostructures Org. Biomol. Chem. 2005 3 4023 4037
7. J. Wengel Nucleic acid nanotechnology - towards Angstrom-scale engineering Org. Biomol. Chem. 2004 2 277 280
8. E. R. Kay D. A. Leigh F. Zerbetto Synthetic molecular motors and mechanical machines Angew. Chem., Int. Ed. 2007 46 72 191
9. N. L. Rosi C. A. Mirkin Nanostructures in biodiagnostics Chem. Rev. 2005 105 1547 1562
10. A. Eschenmoser Searching for nucleic acid alternatives Chimia 2005 59 836 850
11. S. A. Benner Understanding nucleic acids using synthetic chemistry Acc. Chem. Res. 2004 37 784 797
12. E. Uhlmann A. Peyman Antisense Oligonucleotides - A New Therapeutic Principle Chem. Rev. 1990 90 543 584
13. A. De Mesmaeker R. Häner P. Martin H. E. Moser Antisense Oligonucleotides Acc. Chem. Res. 1995 28 366 374
14. C. J. Leumann DNA analogues: from supramolecular principles to biological properties Bioorg. Med. Chem. 2002 10 841 854
15. J. S. Jepsen M. D. Sorensen J. Wengel Locked nucleic acid: A potent nucleic acid analog in therapeutics and biotechnology Oligonucleotides 2004 14 130 146
16. P. Herdewijn Conformationally restricted carbohydrate-modified nucleic acids and antisense technology Biochim. Biophys. Acta, Gene Struct. Expression 1999 1489 167 179
17. O. Seitz Chemically Modified Antisense Oligonucleotides-Recent Improvements of RNA Binding and Ribonuclease H Recruitment Angew. Chem., Int. Ed. 1999 38 3466 3469
18. K. H. Jung A. Marx Synthesis of 4′-C-modified 2′- deoxyribonucleoside analogues and oligonucleotides Curr. Org. Chem. 2008 12 343 354
19. R. L. Letsinger T. F. Wu Use of a Stilbenedicarboxamide Bridge in Stabilizing, Monitoring and Photochemically Altering Folded Conformations of Oligonucleotides J. Am. Chem. Soc. 1995 117 7323 7328
20. F. D. Lewis R. L. Letsinger M. R. Wasielewski Dynamics of photoinduced charge transfer and hole transport in synthetic DNA hairpins Acc. Chem. Res. 2001 34 159 170
21. W. Wang W. Wan H. H. Zhou S. Q. Niu A. D. Q. Li Alternating DNA and π-conjugated sequences. Thermophilic foldable polymers J. Am. Chem. Soc. 2003 125 5248 5249
22. S. M. Langenegger R. Häner The effect of a non-nucleosidic phenanthrene building block on DNA duplex stability Helv. Chim. Acta 2002 85 3414 3421
23. U. B. Christensen E. B. Pedersen Intercalating nucleic acids containing insertions of 1-O-(1- pyrenylmethyl)glycerol: stabilisation of dsDNA and discrimination of DNA over RNA Nucleic Acids Res. 2002 30 4918 4925
24. H. Asanuma K. Shirasuka T. Takarada H. Kashida M. Komiyama DNA-dye conjugates for controllable H* aggregation J. Am. Chem. Soc. 2003 125 2217 2223
25. C. Wagner H. A. Wagenknecht Perylene-3,4: 9,10-tetracarboxylic acid bisimide dye as an artificial DNA base surrogate Org. Lett. 2006 8 4191 4194
26. C. Beuck I. Singh A. Bhattacharya W. Heckler V. S. Parmar O. Seitz E. Weinhold Polycyclic aromatic DNA-Base surrogates: High-affinity binding to an adenine-specific base-flipping DNA methyltransferase Angew. Chem., Int. Ed. 2003 42 3958 3960
27. J. Tuma W. H. Connors D. H. Stitelman C. Richert On the effect of covalently appended quinolones on termini of DNA duplexes J. Am. Chem. Soc. 2002 124 4236 4246
28. P. Daublain K. Siegmund M. Hariharan J. Vura-Weis M. R. Wasielewski F. D. Lewis V. Shafiovich Q. Wang M. Raytchev T. Fiebig Photoinduced charge separation in pyrenedicarboxamide-linked DNA hairpins Photochem. Photobiol. Sci. 2008 7 1501 1508
29. S. M. Langenegger R. Häner A DNA Mimic Made of Non-Nucleosidic Phenanthrene Building Blocks ChemBioChem 2005 6 2149 2152
30. A. Stutz S. M. Langenegger R. Häner Phenanthrene-derived DNA hairpin mimics Helv. Chim. Acta 2003 86 3156 3163
31. S. M. Langenegger R. Häner Remarkable stabilization of duplex DNA containing an abasic site by non-nucleosidic phenanthroline and pyrene building blocks ChemBioChem 2005 6 848 851
32. S. M. Langenegger R. Häner DNA containing phenanthroline- and phenanthrene-derived, non-nucleosidic base surrogates Tetrahedron Lett. 2004 45 9273 9276
33. S. M. Langenegger R. Häner Selectivity in DNA interstrand-stacking Bioorg. Med. Chem. Lett. 2006 16 5062 5065
34. S. M. Langenegger R. Häner Excimer formation by interstrand stacked pyrenes Chem. Commun. 2004 2792 2793
35. V. L. Malinovskii F. Samain R. Häner Helical Arrangement of Interstrand Stacked Pyrenes in a DNA Framework Angew. Chem., Int. Ed. 2007 46 4464 4467
36. I. Trkulja R. Häner Triple-Helix Mediated Excimer and Exciplex Formation Bioconjugate Chem. 2007 18 289 292
37. I. Trkulja R. Häner Monomeric and Heterodimeric Triple Helical DNA Mimics J. Am. Chem. Soc. 2007 129 7982 7989
38. F. Samain V. L. Malinovskii S. M. Langenegger R. Häner Spectroscopic properties of pyrene-containing DNA mimics Bioorg. Med. Chem. 2008 16 27 33
39. R. Häner F. Samain V. L. Malinovskii DNA-Assisted Self-Assembly of Pyrene Foldamers Chem.-Eur. J. 2009 15 5701 5708
40. P. J. Hrdlicka B. R. Babu M. D. Sorensen N. Harrit J. Wengel Multilabeled pyrene-functionalized 2′-amino-LNA probes for nucleic acid detection in homogeneous fluorescence assays J. Am. Chem. Soc. 2005 127 13293 13299
41. E. Mayer-Enthart H. A. Wagenknecht Structure-Sensitive and Self-Assembled Helical Pyrene Array Based on DNA Architecture Angew. Chem., Int. Ed. 2006 45 3372 3375
42. M. Kosuge M. Kubota A. Ono Multiple-pyrene residues arrayed along DNA backbone exhibit significant excimer fluorescence Tetrahedron Lett. 2004 45 3945 3947
43. M. Nakamura Y. Ohtoshi K. Yamana Helical pyrene-array along the outside of duplex RNA Chem. Commun. 2005 5163 5165
44. N. N. Kruk B. M. Dzhagarov V. A. Galievsky V. S. Chirvony P. Y. Turpin Photophysics of the cationic 5,10,15,20-tetrakis(4-N-methylpyridyl) porphyrin bound to DNA, [poly(dA-dT)](2) and [poly(dG-dC)](2): interaction with molecular oxygen studied by porphyrin triplet-triplet absorption and singlet oxygen luminescence J. Photochem. Photobiol., B 1998 42 181 190
45. J. N. Demas G. A. Crosby Measurement of Photoluminescence Quantum Yields - Review J. Phys. Chem. 1971 75 991 1024
46. S. I. Druzhinin V. A. Galievsky K. A. Zachariasse Photoproduct formation with 4-aminobenzonitriles in acetonitrile and its effect on photophysical measurements J. Phys. Chem. A 2005 109 11213 11223
47. A. C. Benniston A. Harriman S. L. Howell C. A. Sams Y. G. Zhi Intramolecular excimer formation and delayed fluorescence in sterically constrained pyrene dimers Chem.-Eur. J. 2007 13 4665 4674
48. O. Taratula J. Rochford P. Piotrowiak E. Galoppini R. A. Carlisle G. J. Meyer Pyrene-terminated phenylenethynylene rigid linkers anchored to metal oxide nanoparticles J. Phys. Chem. B 2006 110 15734 15741
49. J. B. Birks, Photophysics of Aromatic Molecules, Wiley, New York, 1970
50. P. G. Hoertz R. A. Carlisle G. J. Meyer D. Wang P. Piotrowiak E. Galoppini Organic rigid-rod linkers for coupling chromophores to metal oxide nanoparticles Nano Lett. 2003 3 325 330
51. M. Manoharan K. L. Tivel M. Zhao K. Nafisi T. L. Netzel Base-Sequence Dependence of Emission Lifetimes for DNA Oligomers and Duplexes Covalently Labeled with Pyrene - Relative Electron-Transfer Quenching Efficiencies of A-Nucleoside, G-Nucleoside, C-Nucleoside, and T-Nucleoside Toward Pyrene J. Phys. Chem. 1995 99 17461 17472
52. H. Bittermann D. Siegemund V. L. Malinovskii R. Häner Dialkynylpyrenes: strongly fluorescent, environment-sensitive DNA building blocks J. Am. Chem. Soc. 2008 130 15285 15287
53. S. Werder V. L. Malinovskii R. Häner Triazolylpyrenes: Synthesis, fluorescence properties, and incorporation into DNA Org. Lett. 2008 10 2011 2014