Interactions of a photochromic spiropyran with liposome model membranes

Langmuir

Volumn 29, Issue 7, 2013, Pages 2099-2103

  Jonsson, Fabian ^a   Beke Somfai, Tamás ^a   Andréasson, Joakim ^a   Nordén, Bengt ^a  

^a CHALMERS UNIVERSITY OF TECHNOLOGY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING GEOMETRIES; DNA-BINDING; ISOMERIC FORMS; LINEAR DICHROISM SPECTROSCOPIES; LIPID MEMBRANES; LIPOSOME MEMBRANES; MEMBRANE INTERACTIONS; MODEL MEMBRANES; PHOTOSWITCH; SPECTRAL CHARACTERISTICS; SPIROPYRANS; THERMAL ISOMERIZATIONS; UV/VIS ABSORPTIONS;

LIPOSOMES; SHEAR FLOW; WATER ABSORPTION;

PHOTOCHROMISM;

BENZOPYRAN DERIVATIVE; INDOLE DERIVATIVE; LIPOSOME; NITRO DERIVATIVE; SPIROPYRAN;

ARTICLE; ARTIFICIAL MEMBRANE; CHEMISTRY; SPECTROSCOPY; THEORETICAL MODEL;

BENZOPYRANS; INDOLES; LIPOSOMES; MEMBRANES, ARTIFICIAL; MODELS, THEORETICAL; NITRO COMPOUNDS; SPECTRUM ANALYSIS;

EID: 84874033612     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la304867d     Document Type: Article

References (27)

1. Paul, A.; Bhattacharya, S. Chemistry and biology of DNA-binding small molecules Curr. Sci. 2012, 102, 212-231
2. Dervan, P. B. Molecular recognition of DNA by small molecules Bioorg. Med. Chem. 2001, 9, 2215-2235
3. Nelson, S. M.; Ferguson, L. R.; Denny, W. A. Non- covalent ligand/DNA interactions: minor groove binding agents Mutat. Res. 2007, 623, 24-40
4. Dass, C. R.; Choong, P. F. M. Targeting of small molecule anticancer drugs to the tumour and its vasculature using cationic liposomes: lessons from gene therapy. Cancer Cell Int. 2006, 6.
5. Berdnikova, D.; Fedorova, O.; Gulakova, E.; Ihmels, H. Photoinduced in situ generation of a DNA-binding benzothiazoloquinolinium derivative Chem. Commun. 2012, 48, 4603-4605
6. Di Pietro, M. L.; Puntoriero, F.; Tuyeras, F.; Ochsenbein, P.; Laine, P. P.; Campagna, S. Photochemically driven intercalation of small molecules into DNA by in situ irradiation Chem. Commun. 2010, 46, 5169-5171
7. Brieke, C.; Rohrbach, F.; Gottschalk, A.; Mayer, G.; Heckel, A. Light-Controlled Tools Angew. Chem., Int. Ed. 2012, 51, 8446-8476
8. Mammana, A.; Carroll, G. T.; Areephong, J.; Feringa, B. L. A; Chiroptical Photoswitchable, D. N. A. Complex J. Phys. Chem. B 2011, 115, 11581-11587
9. Mayer, G.; Heckel, A. Biologically active molecules with a ″light switch″ Angew. Chem., Int. Ed. 2006, 45, 4900-4921
10. Paramonov, S. V.; Lokshin, V.; Ihmels, H.; Fedorova, O. A. Influence of DNA-binding on the photochromic equilibrium of a chromene derivative Photochem. Photobiol. Sci. 2011, 10, 1279-1282
11. Willner, I. Photoswitchable biomaterials: En route to optobioelectronic systems Acc. Chem. Res. 1997, 30, 347-356
12. Andersson, J.; Li, S. M.; Lincoln, P.; Andréasson, J. Photoswitched DNA-binding of a photochromic spiropyran J. Am. Chem. Soc. 2008, 130, 11836-11837
13. Hammarson, M.; Andersson, J.; Li, S. M.; Lincoln, P.; Andréasson, J. Molecular AND-logic for dually controlled activation of a DNA-binding spiropyran Chem. Commun. 2010, 46, 7130-7132
14. Nilsson, J. R.; Li, S. M.; Önfelt, B.; Andréasson, J. Light-induced cytotoxicity of a photochromic spiropyran Chem. Commun. 2011, 47, 11020-11022
15. Lasic, D. D.; Lipowsky, R.;; Sackmann, E. Applications of liposomes. In Handbook of Biological Physics; North-Holland: Amsterdam, 1995; p 491-519.
16. Nordén, B.; Rodger, A.; Dafforn, T. Linear Dichroism and Circular Dichroism. A Textbook on Polarized-Light Spectroscopy; The Royal Society of Chemistry: Cambridge, 2010.
17. Hicks, M. R.; Kowalski, J.; Rodger, A. LD spectroscopy of natural and synthetic biomaterials Chem. Soc. Rev. 2010, 39, 3380-3393
18. Adachi, R.; Yamaguchi, K.; Yagi, H.; Sakurai, K.; Naiki, H.; Goto, Y. Flow-induced alignment of amyloid protofilaments revealed by linear dichroism J. Biol. Chem. 2007, 282, 8978-8983
19. Dafforn, T. R.; Rajendra, J.; Halsall, D. J.; Serpell, L. C.; Rodger, A. Protein fiber linear dichroism for structure determination and kinetics in a low-volume, low-wavelength couette flow cell Biophys. J. 2004, 86, 404-410
20. Ardhammar, M.; Mikati, N.; Nordén, B. Chromophore orientation in liposome membranes probed with flow dichroism J. Am. Chem. Soc. 1998, 120, 9957-9958
21. Rajendra, J.; Damianoglou, A.; Hicks, M.; Booth, P.; Rodger, P. M.; Rodger, A. Quantitation of protein orientation in flow-oriented unilamellar liposomes by linear dichroism Chem. Phys. 2006, 326, 210-220
22. Ardhammar, M.; Lincoln, P.; Nordén, B. Invisible liposomes: Refractive index matching with sucrose enables flow dichroism assessment of peptide orientation in lipid vesicle membrane Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 15313-15317
23. Frisch, M. J. et al. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford CT, 2004.
24. Wohl, C. J.; Helms, M. A.; Chung, J. O.; Kuciauskas, D. Phospholipid bilayer free volume analysis employing the thermal ring-closing reaction of merocyanine molecular switches J. Phys. Chem. B 2006, 110, 22796-22803
25. Reichardt, C. Solvatochromic dyes as solvent polarity indicators Chem. Rev. 1994, 94, 2319-2358
26. Rosario, R.; Gust, D.; Hayes, M.; Springer, J.; Garcia, A. A. Solvatochromic study of the microenvironment of surface-bound spiropyrans Langmuir 2003, 19, 8801-8806
27. Görner, H. Photochromism of nitrospiropyrans: effects of structure, solvent and temperature Phys. Chem. Chem. Phys. 2001, 3, 416-423