Kinetic studies on visible-light-switchable photochromic fluorophores based on diarylethenes

Seefeldt B, Altenhöner K, Tosic O, Geisler T, Sauer M, Mattay J (2011)
Photochemical & Photobiological Sciences 10(9): 1488-1495.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
We present three recently developed photochromic fluorophores that are based on diarylethenes with elongated conjugated p-systems. The diarylethenes 1 and 3 can be switched from their open to their closed form with visible light. The diarylethenes 1 and 2 are covalently coupled to a standard rhodamine B-based fluorophore and act as photoswitchable resonance energy acceptors. By controlling their switching state, the fluorescence intensity of the dye can be modulated. The third compound 3 is a diarylethene that shows photoswitchable inherent fluorescence due to its stilbazolium-like structure. Ensemble experiments demonstrate that diarylethene-based photoswitches show superior characteristics regarding their switching performance, thermal stability and fatigue resistance. These attributes make them promising candidates for super-resolution imaging methods that are based on the determinate fluorescence switching of fluorophores between an off- and an on-state.
Erscheinungsjahr
2011
Zeitschriftentitel
Photochemical & Photobiological Sciences
Band
10
Ausgabe
9
Seite(n)
1488-1495
ISSN
1474-905X
eISSN
1474-9092
Page URI
https://pub.uni-bielefeld.de/record/2394701

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Seefeldt B, Altenhöner K, Tosic O, Geisler T, Sauer M, Mattay J. Kinetic studies on visible-light-switchable photochromic fluorophores based on diarylethenes. Photochemical & Photobiological Sciences. 2011;10(9):1488-1495.
Seefeldt, B., Altenhöner, K., Tosic, O., Geisler, T., Sauer, M., & Mattay, J. (2011). Kinetic studies on visible-light-switchable photochromic fluorophores based on diarylethenes. Photochemical & Photobiological Sciences, 10(9), 1488-1495. https://doi.org/10.1039/c1pp05051f
Seefeldt, B., Altenhöner, K., Tosic, O., Geisler, T., Sauer, M., and Mattay, J. (2011). Kinetic studies on visible-light-switchable photochromic fluorophores based on diarylethenes. Photochemical & Photobiological Sciences 10, 1488-1495.
Seefeldt, B., et al., 2011. Kinetic studies on visible-light-switchable photochromic fluorophores based on diarylethenes. Photochemical & Photobiological Sciences, 10(9), p 1488-1495.
B. Seefeldt, et al., “Kinetic studies on visible-light-switchable photochromic fluorophores based on diarylethenes”, Photochemical & Photobiological Sciences, vol. 10, 2011, pp. 1488-1495.
Seefeldt, B., Altenhöner, K., Tosic, O., Geisler, T., Sauer, M., Mattay, J.: Kinetic studies on visible-light-switchable photochromic fluorophores based on diarylethenes. Photochemical & Photobiological Sciences. 10, 1488-1495 (2011).
Seefeldt, Britta, Altenhöner, Kai, Tosic, Oliver, Geisler, Thomas, Sauer, Markus, and Mattay, Jochen. “Kinetic studies on visible-light-switchable photochromic fluorophores based on diarylethenes”. Photochemical & Photobiological Sciences 10.9 (2011): 1488-1495.

3 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Single-wavelength-controlled in situ dynamic super-resolution fluorescence imaging for block copolymer nanostructures via blue-light-switchable FRAP.
Gong WL, Yan J, Zhao LX, Li C, Huang ZL, Tang BZ, Zhu MQ., Photochem Photobiol Sci 15(11), 2016
PMID: 27739551
Nondestructive photoluminescence read-out by intramolecular electron transfer in a perylene bisimide-diarylethene dyad.
Berberich M, Natali M, Spenst P, Chiorboli C, Scandola F, Würthner F., Chemistry 18(43), 2012
PMID: 22969018
Reversible photoswitching of dye-doped core-shell nanoparticles.
Genovese D, Montalti M, Prodi L, Rampazzo E, Zaccheroni N, Tosic O, Altenhöner K, May F, Mattay J., Chem Commun (Camb) 47(39), 2011
PMID: 21909549

40 References

Daten bereitgestellt von Europe PubMed Central.


Abbe, Arch. Mikrosk. Anat. 9(), 1873

Gustafsson, J. Microsc. 198(2), 2000
Precise nanometer localization analysis for individual fluorescent probes.
Thompson RE, Larson DR, Webb WW., Biophys. J. 82(5), 2002
PMID: 11964263
Myosin V walks hand-over-hand: single fluorophore imaging with 1.5-nm localization.
Yildiz A, Forkey JN, McKinney SA, Ha T, Goldman YE, Selvin PR., Science 300(5628), 2003
PMID: 12791999
Imaging intracellular fluorescent proteins at nanometer resolution.
Betzig E, Patterson GH, Sougrat R, Lindwasser OW, Olenych S, Bonifacino JS, Davidson MW, Lippincott-Schwartz J, Hess HF., Science 313(5793), 2006
PMID: 16902090
Sub-diffraction-limit imaging by stochastic optical reconstruction microscopy (STORM).
Rust MJ, Bates M, Zhuang X., Nat. Methods 3(10), 2006
PMID: 16896339
Ultra-high resolution imaging by fluorescence photoactivation localization microscopy.
Hess ST, Girirajan TP, Mason MD., Biophys. J. 91(11), 2006
PMID: 16980368
Subdiffraction imaging through the selective donut-mode depletion of thermally stable photoswitchable fluorophores: numerical analysis and application to the fluorescent protein Dronpa.
Dedecker P, Hotta J, Flors C, Sliwa M, Uji-i H, Roeffaers MB, Ando R, Mizuno H, Miyawaki A, Hofkens J., J. Am. Chem. Soc. 129(51), 2007
PMID: 18047340
Far-field optical nanoscopy.
Hell SW., Science 316(5828), 2007
PMID: 17525330
Super-resolution microscopy by nanoscale localization of photo-switchable fluorescent probes.
Bates M, Huang B, Zhuang X., Curr Opin Chem Biol 12(5), 2008
PMID: 18809508

Heilemann, Angew. Chem., Int. Ed. 47(33), 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

Heilemann, Angew. Chem., Int. Ed. 48(37), 2009
Live-cell super-resolution imaging with trimethoprim conjugates.
Wombacher R, Heidbreder M, van de Linde S, Sheetz MP, Heilemann M, Cornish VW, Sauer M., Nat. Methods 7(9), 2010
PMID: 20693998
Live-cell dSTORM with SNAP-tag fusion proteins.
Klein T, Loschberger A, Proppert S, Wolter S, van de Linde S, Sauer M., Nat. Methods 8(1), 2011
PMID: 21191367
Fluorescence microscopy with diffraction resolution barrier broken by stimulated emission.
Klar TA, Jakobs S, Dyba M, Egner A, Hell SW., Proc. Natl. Acad. Sci. U.S.A. 97(15), 2000
PMID: 10899992
Make them blink: probes for super-resolution microscopy.
Vogelsang J, Steinhauer C, Forthmann C, Stein IH, Person-Skegro B, Cordes T, Tinnefeld P., Chemphyschem 11(12), 2010
PMID: 20632356
The effect of photoswitching kinetics and labeling densities on super-resolution fluorescence imaging.
van de Linde S, Wolter S, Heilemann M, Sauer M., J. Biotechnol. 149(4), 2010
PMID: 20176060

Shannon, Proc. Inst. Radio Eng. 37(), 1949
Spiropyrans as molecular optical switches.
Seefeldt B, Kasper R, Beining M, Mattay J, Arden-Jacob J, Kemnitzer N, Drexhage KH, Heilemann M, Sauer M., Photochem. Photobiol. Sci. 9(2), 2010
PMID: 20126797
Regulated fast nucleocytoplasmic shuttling observed by reversible protein highlighting.
Ando R, Mizuno H, Miyawaki A., Science 306(5700), 2004
PMID: 15550670
Reversible single-molecule photoswitching in the GFP-like fluorescent protein Dronpa.
Habuchi S, Ando R, Dedecker P, Verheijen W, Mizuno H, Miyawaki A, Hofkens J., Proc. Natl. Acad. Sci. U.S.A. 102(27), 2005
PMID: 15972810
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
A photoactivatable GFP for selective photolabeling of proteins and cells.
Patterson GH, Lippincott-Schwartz J., Science 297(5588), 2002
PMID: 12228718
EosFP, a fluorescent marker protein with UV-inducible green-to-red fluorescence conversion.
Wiedenmann J, Ivanchenko S, Oswald F, Schmitt F, Rocker C, Salih A, Spindler KD, Nienhaus GU., Proc. Natl. Acad. Sci. U.S.A. 101(45), 2004
PMID: 15505211

Sheng, Nanotechnology 18(), 2007
Diarylethenes for Memories and Switches.
Irie M., Chem. Rev. 100(5), 2000
PMID: 11777416
Organic chemistry: a digital fluorescent molecular photoswitch.
Irie M, Fukaminato T, Sasaki T, Tamai N, Kawai T., Nature 420(6917), 2002
PMID: 12490936
Digital photoswitching of fluorescence based on the photochromism of diarylethene derivatives at a single-molecule level.
Fukaminato T, Sasaki T, Kawai T, Tamai N, Irie M., J. Am. Chem. Soc. 126(45), 2004
PMID: 15535710
Spiropyrans and Spirooxazines for Memories and Switches.
Berkovic G, Krongauz V, Weiss V., Chem. Rev. 100(5), 2000
PMID: 11777418
Fulgides for Memories and Switches.
Yokoyama Y., Chem. Rev. 100(5), 2000
PMID: 11777417
Photochromic dithienylethenes with extended pi-systems.
Tosic O, Altenhoner K, Mattay J., Photochem. Photobiol. Sci. 9(2), 2009
PMID: 20126784
Practical synthetic route to functionalized rhodamine dyes.
Nguyen T, Francis MB., Org. Lett. 5(18), 2003
PMID: 12943398
Synthesis and photoisomerization of dithienylethene-bridged diporphyrins.
Osuka A, Fujikane D, Shinmori H, Kobatake S, Irie M., J. Org. Chem. 66(11), 2001
PMID: 11375015

Carsky, Liebigs Ann. Chem. 1980(), 1980
Mechanism of cis/trans equilibration of alkenes via iodine catalysis.
Hepperle SS, Li Q, East AL., J Phys Chem A 109(48), 2005
PMID: 16331941
Revealing competitive Forster-type resonance energy-transfer pathways in single bichromophoric molecules.
Hofkens J, Cotlet M, Vosch T, Tinnefeld P, Weston KD, Ego C, Grimsdale A, Mullen K, Beljonne D, Bredas JL, Jordens S, Schweitzer G, Sauer M, De Schryver F., Proc. Natl. Acad. Sci. U.S.A. 100(23), 2003
PMID: 14583594

Zheng, Tetrahedron Lett. 50(14), 2009

Coe, Adv. Funct. Mater. 12(), 2002

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