Spiropyrans as molecular optical switches

Seefeldt B, Kasper R, Beining M, Mattay J, Arden-Jacob J, Kemnitzer N, Drexhage KH, Heilemann M, Sauer M (2010)
PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES 9(2): 213-220.

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Abstract
Optical microscopes use visible light and an arrangement of lenses to provide us with magnified images of small samples. Combined with efficient fluorescent probes and highly sensitive fluorescence detection techniques they allow the non-invasive 3D study of subcellular structures even in living cells or tissue. However, optical microscopes are subject to diffraction of light which limits optical resolution to approximately 200 nm in the imaging plane. In the recent past, powerful methods emerged that enable fluorescence microscopy with subdiffraction optical resolution. Since most of these methods are based on the temporal control of fluorescence emission of fluorophores, photochromic molecules that can be switched reversibly between a fluorescent on- and a non-fluorescent off-state are the key for super-resolution imaging methods. Here, we present our approach to use spiropyran-fluorophore conjugates as efficient molecular optical switches (photoswitches). In these photochromic conjugates fluorescence emission of the fluorophore is controlled by the state of the spiropyran, which can be switched reversibly between a colorless spiropyran and a colored merocyanine form upon irradiation with light. Thus, the efficiency of energy transfer from the fluorophore to the spiropyran can be modulated by the irradiation conditions. We present ensemble data of the switching process of various spiropyrans and spiropyran-fluorophore conjugates and demonstrate photoswitching at the single-molecule level. Our data suggest that spiropyrans have to be immobilized in polymers to stabilize the merocyanine form in order to be useful for super-resolution fluorescence imaging based on precise localization of individual emitters. Special emphasis is put on photobleaching of donor fluorophores due to UV irradiation, i.e. photoswitching of the photochromic acceptor. Furthermore, we present a water soluble switchable spiropyran derivative and demonstrate the first intermolecular single-molecule photoswitching experiments in polymers.
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Seefeldt B, Kasper R, Beining M, et al. Spiropyrans as molecular optical switches. PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES. 2010;9(2):213-220.
Seefeldt, B., Kasper, R., Beining, M., Mattay, J., Arden-Jacob, J., Kemnitzer, N., Drexhage, K. H., et al. (2010). Spiropyrans as molecular optical switches. PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 9(2), 213-220.
Seefeldt, B., Kasper, R., Beining, M., Mattay, J., Arden-Jacob, J., Kemnitzer, N., Drexhage, K. H., Heilemann, M., and Sauer, M. (2010). Spiropyrans as molecular optical switches. PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES 9, 213-220.
Seefeldt, B., et al., 2010. Spiropyrans as molecular optical switches. PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 9(2), p 213-220.
B. Seefeldt, et al., “Spiropyrans as molecular optical switches”, PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, vol. 9, 2010, pp. 213-220.
Seefeldt, B., Kasper, R., Beining, M., Mattay, J., Arden-Jacob, J., Kemnitzer, N., Drexhage, K.H., Heilemann, M., Sauer, M.: Spiropyrans as molecular optical switches. PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES. 9, 213-220 (2010).
Seefeldt, Britta, Kasper, Robert, Beining, Mirco, Mattay, Jochen, Arden-Jacob, Jutta, Kemnitzer, Norbert, Drexhage, Karl Heinz, Heilemann, Mike, and Sauer, Markus. “Spiropyrans as molecular optical switches”. PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES 9.2 (2010): 213-220.
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45 References

Data provided by Europe PubMed Central.

Photochromism: Non-Linear Picosecond Kinetics and 3D Computer Memory
Dvornikov, Molecular Crystals and Liquid Crystals 246(1), 1994
A stroboscopic approach for fast photoactivation-localization microscopy with Dronpa mutants.
Flors C, Hotta J, Uji-i H, Dedecker P, Ando R, Mizuno H, Miyawaki A, Hofkens J., J. Am. Chem. Soc. 129(45), 2007
PMID: 17956094
Synthesis and characterization of photoswitchable fluorescent silica nanoparticles.
Folling J, Polyakova S, Belov V, van Blaaderen A, Bossi ML, Hell SW., Small 4(1), 2008
PMID: 18064615
Switchable Fluorescent and Solvatochromic Molecular Probes Based on 4-Amino-N-methylphthalimide and a Photochromic Diarylethene
Yan, European Journal of Organic Chemistry 2008(15), 2008
Subdiffraction-Resolution Fluorescence Imaging with Conventional Fluorescent Probes
Heilemann, Angewandte Chemie International Edition 47(33), 2008
Fluorescence nanoscopy by ground-state depletion and single-molecule return.
Folling J, Bossi M, Bock H, Medda R, Wurm CA, Hein B, Jakobs S, Eggeling C, Hell SW., Nat. Methods 5(11), 2008
PMID: 18794861
Beiträge zur Theorie des Mikroskops und der mikroskopischen Wahrnehmung
Abbe, Archiv für Mikroskopische Anatomie 9(1), 1873
Photoswitching microscopy with standard fluorophores
Linde, Applied Physics B 93(4), 2008
Superresolution microscopy on the basis of engineered dark states.
Steinhauer C, Forthmann C, Vogelsang J, Tinnefeld P., J. Am. Chem. Soc. 130(50), 2008
PMID: 19053449
Precise nanometer localization analysis for individual fluorescent probes.
Thompson RE, Larson DR, Webb WW., Biophys. J. 82(5), 2002
PMID: 11964263
Photoswitches: Key molecules for subdiffraction-resolution fluorescence imaging and molecular quantification
Heilemann, Laser & Photonics Review 3(1-2), 2009
Multicolor photoswitching microscopy for subdiffraction-resolution fluorescence imaging.
van de Linde S, Endesfelder U, Mukherjee A, Schuttpelz M, Wiebusch G, Wolter S, Heilemann M, Sauer M., Photochem. Photobiol. Sci. 8(4), 2009
PMID: 19337659
Single-molecule photophysics of oxazines on DNA and its application in a FRET switch.
Vogelsang J, Cordes T, Tinnefeld P., Photochem. Photobiol. Sci. 8(4), 2009
PMID: 19337662
Advances in the speed and resolution of light microscopy.
Ji N, Shroff H, Zhong H, Betzig E., Curr. Opin. Neurobiol. 18(6), 2008
PMID: 19375302
Controlling the fluorescence of ordinary oxazine dyes for single-molecule switching and superresolution microscopy.
Vogelsang J, Cordes T, Forthmann C, Steinhauer C, Tinnefeld P., Proc. Natl. Acad. Sci. U.S.A. 106(20), 2009
PMID: 19433792
Super-Resolution Imaging with Small Organic Fluorophores
Heilemann, Angewandte Chemie International Edition 48(37), 2009
Real-time computation of subdiffraction-resolution fluorescence images.
Wolter S, Schuttpelz M, Tscherepanow M, VAN DE Linde S, Heilemann M, Sauer M., J Microsc 237(1), 2010
PMID: 20055915

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