Reversible photoswitching of the DNA-binding properties of styrylquinolizinium derivatives through photochromic [2+2] cycloaddition and cycloreversion

Koelsch S, Ihmels H, Mattay J, Sewald N, Patrick BO (2020)
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 16: 111-124.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Autor*in
Koelsch, Sarah; Ihmels, Heiko; Mattay, JochenUniBi; Sewald, NorbertUniBi ; Patrick, Brian O.
Abstract / Bemerkung
It was demonstrated that styrylquinolizinium derivatives may be applied as photoswitchable DNA ligands. At lower ligand:DNA ratios (<= 1.5), these compounds bind to duplex DNA by intercalation, with binding constants ranging from K-b = 4.1 x 10(4) M to 2.6 x 10(5) M (four examples), as shown by photometric and fluorimetric titrations as well as by CD and LD spectroscopic analyses. Upon irradiation at 450 nm, the methoxy-substituted styrylquinolizinium derivatives form the corresponding syn head-to-tail cyclobutanes in a selective [2 + 2] photocycloaddition, as revealed by X-ray diffraction analysis of the reaction products. These photodimers bind to DNA only weakly by outside-edge association, but they release the intercalating monomers upon irradiation at 315 nm in the presence of DNA. As a result, it is possible to switch between these two ligands and likewise between two different binding modes by irradiation with different excitation wavelengths.
Stichworte
azoniahetarenes; DNA ligands; photodimerization; photoswitches
Erscheinungsjahr
2020
Zeitschriftentitel
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Band
16
Seite(n)
111-124
ISSN
1860-5397
Page URI
https://pub.uni-bielefeld.de/record/2941247

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Koelsch S, Ihmels H, Mattay J, Sewald N, Patrick BO. Reversible photoswitching of the DNA-binding properties of styrylquinolizinium derivatives through photochromic [2+2] cycloaddition and cycloreversion. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. 2020;16:111-124.
Koelsch, S., Ihmels, H., Mattay, J., Sewald, N., & Patrick, B. O. (2020). Reversible photoswitching of the DNA-binding properties of styrylquinolizinium derivatives through photochromic [2+2] cycloaddition and cycloreversion. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 16, 111-124. doi:10.3762/bjoc.16.13
Koelsch, S., Ihmels, H., Mattay, J., Sewald, N., and Patrick, B. O. (2020). Reversible photoswitching of the DNA-binding properties of styrylquinolizinium derivatives through photochromic [2+2] cycloaddition and cycloreversion. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 16, 111-124.
Koelsch, S., et al., 2020. Reversible photoswitching of the DNA-binding properties of styrylquinolizinium derivatives through photochromic [2+2] cycloaddition and cycloreversion. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 16, p 111-124.
S. Koelsch, et al., “Reversible photoswitching of the DNA-binding properties of styrylquinolizinium derivatives through photochromic [2+2] cycloaddition and cycloreversion”, BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, vol. 16, 2020, pp. 111-124.
Koelsch, S., Ihmels, H., Mattay, J., Sewald, N., Patrick, B.O.: Reversible photoswitching of the DNA-binding properties of styrylquinolizinium derivatives through photochromic [2+2] cycloaddition and cycloreversion. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. 16, 111-124 (2020).
Koelsch, Sarah, Ihmels, Heiko, Mattay, Jochen, Sewald, Norbert, and Patrick, Brian O. “Reversible photoswitching of the DNA-binding properties of styrylquinolizinium derivatives through photochromic [2+2] cycloaddition and cycloreversion”. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 16 (2020): 111-124.

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