Photoswitchable DNA-binding properties of a photochromic spirooxazine derivative

Ihmels H, Mattay J, May F, Thomas L (2013)
Organic & Biomolecular Chemistry 11(31): 5184-5188.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
Download
Es wurden keine Dateien hochgeladen. Nur Publikationsnachweis!
Autor*in
Ihmels, Heiko; Mattay, JochenUniBi; May, Florian; Thomas, Laura
Abstract / Bemerkung
An N-methylphenanthrolinium-annelated spirooxazine derivative 2(SO) whose DNA-intercalating properties are reversibly changed by a photochromic reaction was prepared. Upon irradiation at 350 nm the spirooxazine is transformed to the corresponding photomerocyanine 2(PM) that binds to DNA. After irradiation with visible light the spirooxazine 2(SO), which exhibits no significant DNA-binding properties, is regained. The association of 2(PM) with DNA was examined by CD and absorption spectroscopy, fluorescent intercalator displacement and viscometric titration.
Erscheinungsjahr
2013
Zeitschriftentitel
Organic & Biomolecular Chemistry
Band
11
Ausgabe
31
Seite(n)
5184-5188
ISSN
1477-0520
eISSN
1477-0539
Page URI
https://pub.uni-bielefeld.de/record/2636056

Zitieren

Ihmels H, Mattay J, May F, Thomas L. Photoswitchable DNA-binding properties of a photochromic spirooxazine derivative. Organic & Biomolecular Chemistry. 2013;11(31):5184-5188.
Ihmels, H., Mattay, J., May, F., & Thomas, L. (2013). Photoswitchable DNA-binding properties of a photochromic spirooxazine derivative. Organic & Biomolecular Chemistry, 11(31), 5184-5188. doi:10.1039/c3ob40930a
Ihmels, Heiko, Mattay, Jochen, May, Florian, and Thomas, Laura. 2013. “Photoswitchable DNA-binding properties of a photochromic spirooxazine derivative”. Organic & Biomolecular Chemistry 11 (31): 5184-5188.
Ihmels, H., Mattay, J., May, F., and Thomas, L. (2013). Photoswitchable DNA-binding properties of a photochromic spirooxazine derivative. Organic & Biomolecular Chemistry 11, 5184-5188.
Ihmels, H., et al., 2013. Photoswitchable DNA-binding properties of a photochromic spirooxazine derivative. Organic & Biomolecular Chemistry, 11(31), p 5184-5188.
H. Ihmels, et al., “Photoswitchable DNA-binding properties of a photochromic spirooxazine derivative”, Organic & Biomolecular Chemistry, vol. 11, 2013, pp. 5184-5188.
Ihmels, H., Mattay, J., May, F., Thomas, L.: Photoswitchable DNA-binding properties of a photochromic spirooxazine derivative. Organic & Biomolecular Chemistry. 11, 5184-5188 (2013).
Ihmels, Heiko, Mattay, Jochen, May, Florian, and Thomas, Laura. “Photoswitchable DNA-binding properties of a photochromic spirooxazine derivative”. Organic & Biomolecular Chemistry 11.31 (2013): 5184-5188.

8 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Recent developments in reversible photoregulation of oligonucleotide structure and function.
Lubbe AS, Szymanski W, Feringa BL., Chem Soc Rev 46(4), 2017
PMID: 28128377
Copper(II)-Controlled Molecular Glue for Mismatched DNA.
Kotera N, Guillot R, Teulade-Fichou MP, Granzhan A., Chembiochem 18(7), 2017
PMID: 28106332
DNA-ligand interactions gained and lost: light-induced ligand redistribution in a supramolecular cascade.
Berdnikova DV, Aliyeu TM, Paululat T, Fedorov YV, Fedorova OA, Ihmels H., Chem Commun (Camb) 51(23), 2015
PMID: 25704787
Enhancement in intramolecular interactions and in vitro biological activity of a tripodal tetradentate system upon complexation.
Tyagi N, Viji M, Karunakaran SC, Varughese S, Ganesan S, Priya S, Saneesh Babu PS, Nair AS, Ramaiah D., Dalton Trans 44(35), 2015
PMID: 26244289
Recent advances in small organic molecules as DNA intercalating agents: synthesis, activity, and modeling.
Rescifina A, Zagni C, Varrica MG, Pistarà V, Corsaro A., Eur J Med Chem 74(), 2014
PMID: 24448420
DNA-binding properties of amidine-substituted spiropyran photoswitches.
Hammarson M, Nilsson JR, Li S, Lincoln P, Andréasson J., Chemistry 20(48), 2014
PMID: 25302848

32 References

Daten bereitgestellt von Europe PubMed Central.

Organic photoresponse materials and devices.
Dong H, Zhu H, Meng Q, Gong X, Hu W., Chem Soc Rev 41(5), 2011
PMID: 22158983

Akita, Organometallics 30(), 2011
Azobenzene photoswitches for biomolecules.
Beharry AA, Woolley GA., Chem Soc Rev 40(8), 2011
PMID: 21483974
Photocontrolling peptide alpha helices.
Woolley GA., Acc. Chem. Res. 38(6), 2005
PMID: 15966715

Fehrentz, Angew. Chem., Int. Ed. 50(), 2011
A chiroptical photoswitchable DNA complex.
Mammana A, Carroll GT, Areephong J, Feringa BL., J Phys Chem B 115(40), 2011
PMID: 21879715
Photoswitched DNA-binding of a photochromic spiropyran.
Andersson J, Li S, Lincoln P, Andreasson J., J. Am. Chem. Soc. 130(36), 2008
PMID: 18698779
Influence of DNA-binding on the photochromic equilibrium of a chromene derivative.
Paramonov SV, Lokshin V, Ihmels H, Fedorova OA., Photochem. Photobiol. Sci. 10(8), 2011
PMID: 21556394

Dohno, Eur. J. Org. Chem. (), 2009
Photoswitchable molecular glue for DNA.
Dohno C, Uno SN, Nakatani K., J. Am. Chem. Soc. 129(39), 2007
PMID: 17850087

Caamaño, Angew. Chem., Int. Ed. 39(), 2000

Basak, Chem. Commun. (), 2008

Lokshin, Russ. Chem. Rev. 71(), 2002

Barton, J. Am. Chem. Soc. 106(), 1984
Metal complexes as DNA intercalators.
Liu HK, Sadler PJ., Acc. Chem. Res. 44(5), 2011
PMID: 21446672

Pozzo, J. Chem. Soc., Perkin Trans. 2 (), 1993

Paquette, Chem. Commun. (), 2009
Improved curve fitting procedures to determine equilibrium binding constants.
Stootman FH, Fisher DM, Rodger A, Aldrich-Wright JR., Analyst 131(10), 2006
PMID: 17003863
Steric effects on the intercalation of aromatic cations to deoxyribonucleic acid.
Gabbay EJ, Scofield RE, Baxter CS., J. Am. Chem. Soc. 95(23), 1973
PMID: 4759035
The interactions between the fluorescent dye thiazole orange and DNA.
Nygren J, Svanvik N, Kubista M., Biopolymers 46(1), 1998
PMID: 9612138
Influence of the amino substituents in the interaction of ethidium bromide with DNA.
Garbett NC, Hammond NB, Graves DE., Biophys. J. 87(6), 2004
PMID: 15465858
Criteria for the mode of binding of DNA binding agents.
Suh D, Chaires JB., Bioorg. Med. Chem. 3(6), 1995
PMID: 7582950

Cohen, Biopolymers 8(), 1969
Chemical control of the DNA light switch: cycling the switch ON and OFF.
Liu Y, Chouai A, Degtyareva NN, Lutterman DA, Dunbar KR, Turro C., J. Am. Chem. Soc. 127(31), 2005
PMID: 16076162

Tuite, J. Am. Chem. Soc. 116(), 1994
Supramolecular DNA recognition.
Hannon MJ., Chem Soc Rev 36(2), 2006
PMID: 17264930
Noncovalent interactions with DNA: an overview.
Strekowski L, Wilson B., Mutat. Res. 623(1-2), 2007
PMID: 17445837

Ihmels, Top. Curr. Chem. 258(), 2005
Export

Markieren/ Markierung löschen
Markierte Publikationen

Open Data PUB

Web of Science

Dieser Datensatz im Web of Science®
Quellen

PMID: 23824474
PubMed | Europe PMC

Suchen in

Google Scholar