Spiropyran photoswitches in the context of DNA: Synthesis and photochromic properties

Chemistry - A European Journal

Volumn 19, Issue 46, 2013, Pages 15726-15734

  Brieke, Clara ^a,b   Heckel, Alexander ^a  

^a GOETHE UNIVERSITY   (Germany)

^b MAX PLANCK INSTITUTE FOR MEDICAL RESEARCH   (Germany)

Author keywords

DNA; nucleic acid hybridization; photochromism; photoswitching; spiropyrans

Indexed keywords

FLUORESCENCE QUENCHING; NUCLEIC ACID HYBRIDIZATION; PHOTOCHEMICAL PROPERTIES; PHOTOCHROMIC PROPERTIES; PHOTOSWITCHING; SOLID PHASE SYNTHESIS; SPIROPYRAN DERIVATIVES; SPIROPYRANS;

BIOMOLECULES; DESIGN; DNA; EXCITED STATES; LIGHT; OLIGONUCLEOTIDES; SWITCHING; SYNTHESIS (CHEMICAL); ULTRAVIOLET VISIBLE SPECTROSCOPY;

PHOTOCHROMISM;

BENZOPYRAN DERIVATIVE; DNA; INDOLE DERIVATIVE; MEROCYANINE; NITRO DERIVATIVE; SPIROPYRAN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEIC ACID HYBRIDIZATION; PHOTOCHEMISTRY; PHOTOCHROMISM; PHOTOSWITCHING; SPIROPYRANS; SYNTHESIS;

DNA; NUCLEIC ACID HYBRIDIZATION; PHOTOCHROMISM; PHOTOSWITCHING; SPIROPYRANS;

BENZOPYRANS; DNA; INDOLES; MOLECULAR STRUCTURE; NITRO COMPOUNDS; NUCLEIC ACID HYBRIDIZATION; PHOTOCHEMICAL PROCESSES;

EID: 84887024621     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201302640     Document Type: Article

References (47)

1. Molecular Switches (Eds.:, B.L. Feringa, W.R. Browne,), 2 nd ed., Wiley-VCH, Weinheim, 2011.
2. C. Brieke, F. Rohrbach, A. Gottschalk, G. Mayer, A. Heckel, Angew. Chem. 2012, 124, 8572-8604
3. Angew. Chem. Int. Ed. 2012, 51, 8446-8476.
4. T. Fehrentz, M. Schoenberger, D. Trauner, Angew. Chem. 2011, 123, 12362-12390
5. Angew. Chem. Int. Ed. 2011, 50, 12156-12182.
6. M. Bossi, V. Belov, S. Polyakova, S. W. Hell, Angew. Chem. 2006, 118, 7623-7627
7. Angew. Chem. Int. Ed. 2006, 45, 7462-7465.
8. Y. Yan, M. E. Marriott, C. Petchprayoon, G. Marriott, Biochem. J. 2011, 433, 411-422.
9. E. Friedrichs, F. C. Simmel, in Molecular Switches (Eds.:, B.L. Feringa, W.R. Browne,), Wiley-VCH, Weinheim, 2011, pp. 227-256.
10. R. P. Goodman, Science 2005, 310, 1661-1665.
11. I. E. Catrina, S. A. E. Marras, D. P. Bratu, ACS Chem. Biol. 2012, 7, 1586-1595.
12. M. M. Rozenman, D. R. Liu, ChemBioChem 2006, 7, 253-256.
13. Y. N. Teo, E. T. Kool, Chem. Rev. 2012, 112, 4221-4245.
14. G. H. Clever, C. Kaul, T. Carell, Angew. Chem. 2007, 119, 6340-6350
15. Angew. Chem. Int. Ed. 2007, 46, 6226-6236.
16. E. Stulz, G. Clever, M. Shionoya, C. Mao, Chem. Soc. Rev. 2011, 40, 5633.
17. S. Ogasawara, M. Maeda, Angew. Chem. 2008, 120, 8971-8974
18. Angew. Chem. Int. Ed. 2008, 47, 8839-8842.
19. H. Asanuma, T. Ito, T. Yoshida, X. Liang, M. Komiyama, Angew. Chem. 1999, 111, 2547-2549
20. Angew. Chem. Int. Ed. 1999, 38, 2393-2395.
21. H. Asanuma, D. Tamaru, A. Yamazawa, M. Liu, M. Komiyama, ChemBioChem 2002, 3, 786-789.
22. M. Zhou, X. Liang, T. Mochizuki, H. Asanuma, Angew. Chem. 2010, 122, 2213-2216
23. Angew. Chem. Int. Ed. 2010, 49, 2167-2170.
24. J. Manchester, D. M. Bassani, J.-L. H. A. Duprey, L. Giordano, J. S. Vyle, Z. Zhao, J. H. R. Tucker, J. Am. Chem. Soc. 2012, 134, 10791-10794.
25. H. Cahová, A. Jäschke, Angew. Chem. 2013, 125, 3268-3272
26. Angew. Chem. Int. Ed. 2013, 52, 3186-3190.
27. S. Barrois, H.-A. Wagenknecht, Beilstein J. Org. Chem. 2012, 8, 905-914.
28. H. Asanuma, K. Shirasuka, T. Yoshida, T. Takarada, X. Liang, M. Komiyama, Chem. Lett. 2001, 108-109.
29. C. Beyer, H.-A. Wagenknecht, Synlett 2010, 1371-1376.
30. T. Stafforst, D. Hilvert, Chem. Commun. 2009, 287-288.
31. J. Andersson, S. Li, P. Lincoln, J. Andrasson, J. Am. Chem. Soc. 2008, 130, 11836-11837.
32. D. D. Young, A. Deiters, ChemBioChem 2008, 9, 1225-1228.
33. Y. Shiraishi, M. Itoh, T. Hirai, Phys. Chem. Chem. Phys. 2010, 12, 13737-13745.
34. S. V. Paramonov, V. Lokshin, O. A. Fedorova, J. Photochem. Photobiol. C 2011, 12, 209-236.
35. F. M. Raymo, M. Tomasulo, Chem. Soc. Rev. 2005, 34, 327-336.
36. E. Leete, J. Am. Chem. Soc. 1959, 81, 6023-6026.
37. J. G. Rodríguez, A. Urrutia, J. Heterocycl. Chem. 1999, 36, 129-135.
38. I. Gruda, R. M. Leblanc, Can. J. Chem. 1976, 54, 576-580.
39. L. Eggers, V. Buss, Angew. Chem. 1997, 109, 885-887
40. Angew. Chem. Int. Ed. Engl. 1997, 36, 881-883.
41. H. Görner, Phys. Chem. Chem. Phys. 2001, 3, 416-423.
42. J. Buback, P. Nuernberger, M. Kullmann, F. Langhojer, R. Schmidt, F. Wrthner, T. Brixner, J. Phys. Chem. A 2011, 115, 3924-3935.
43. J. Kohl-Landgraf, M. Braun, C. Oezcoban, D. P. N. Goncalves, A. Heckel, J. Wachtveitl, J. Am. Chem. Soc. 2012, 134, 14070-14077.
44. C. Boulègue, M. Löweneck, C. Renner, L. Moroder, ChemBioChem 2007, 8, 591-594.
45. G. Marriott, S. Mao, T. Sakata, J. Ran, D. K. Jackson, C. Petchprayoon, T. J. Gomez, E. Warp, O. Tulyathan, H. L. Aaron, E. Y. Isacoff, Y. Yan, Proc. Natl. Acad. Sci. USA 2008, 105, 17789-17794.
46. R. Sureshbabu, R. Balamurugan, A. K. Mohanakrishnan, Tetrahedron 2009, 65, 3582-3591.
47. R. A. Daines, P. A. Chambers, I. Pendrak, D. R. Jakas, H. M. Sarau, J. J. Foley, D. B. Schmidt, W. D. Kingsbury, J. Med. Chem. 1993, 36, 3321-3332.