Photocontrolled DNA minor groove interactions of imidazole/pyrrole polyamides

Müller S, Paulus J, Mattay J, Ihmels H, Dodero VI, Sewald N (2020)
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 16: 60-70.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
Azobenzenes are photoswitchable molecules capable of generating significant structural changes upon E-to-Z photoisomerization in peptides or small molecules, thereby controlling geometry and functionality. E-to-Z photoisomerization usually is achieved upon irradiation at 350 nm (pi-pi* transition), while the Z-to-E isomerization proceeds photochemically upon irradiation at >400 nm (n-pi* transition) or thermally. Photoswitchable compounds have frequently been employed as modules, e.g., to control protein-DNA interactions. However, their use in conjunction with minor groove-binding imidazole/pyrrole (Im/Py) polyamides is yet unprecedented. Dervan-type Im/Py polyamides were equipped with an azobenzene unit, i.e., 3-(3-(aminomethyl)phenyl)azophenylacetic acid, as the linker between two Im/Py polyamide strands. Only the (Z)-azobenzene-containing polyamides bound to the minor groove of double-stranded DNA hairpins. Photoisomerization was exemplarily evaluated by H-1 NMR experiments, while minor groove binding of the (Z)-azobenzene derivatives was proven by CD titration experiments. The resulting induced circular dichroism (ICD) bands of the bound ligands, together with the photometric determination of the dsDNA melting temperature, revealed a significant stabilization of the DNA upon association with the ligand. The (Z)-azobenzene acted as a building block inducing a reverse turn, which favored hydrogen bonds between the pyrrole/imidazole amide and the DNA bases. In contrast, the E-configured polyamides did not induce any ICD characteristic for minor groove binding. The incorporation of the photoswitchable azobenzene unit is a promising strategy to obtain photoswitchable Im/Py hairpin polyamides capable of interacting with the dsDNA minor groove only in the Z-configuration.
Stichworte
azobenzene; DNA minor groove; N-methylimidazole; N-methylpyrrole; photoswitches; polyamide
Erscheinungsjahr
2020
Zeitschriftentitel
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Band
16
Seite(n)
60-70
ISSN
1860-5397
Page URI
https://pub.uni-bielefeld.de/record/2940705

Zitieren

Müller S, Paulus J, Mattay J, Ihmels H, Dodero VI, Sewald N. Photocontrolled DNA minor groove interactions of imidazole/pyrrole polyamides. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. 2020;16:60-70.
Müller, S., Paulus, J., Mattay, J., Ihmels, H., Dodero, V. I., & Sewald, N. (2020). Photocontrolled DNA minor groove interactions of imidazole/pyrrole polyamides. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 16, 60-70. doi:10.3762/bjoc.16.8
Müller, S., Paulus, J., Mattay, J., Ihmels, H., Dodero, V. I., and Sewald, N. (2020). Photocontrolled DNA minor groove interactions of imidazole/pyrrole polyamides. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 16, 60-70.
Müller, S., et al., 2020. Photocontrolled DNA minor groove interactions of imidazole/pyrrole polyamides. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 16, p 60-70.
S. Müller, et al., “Photocontrolled DNA minor groove interactions of imidazole/pyrrole polyamides”, BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, vol. 16, 2020, pp. 60-70.
Müller, S., Paulus, J., Mattay, J., Ihmels, H., Dodero, V.I., Sewald, N.: Photocontrolled DNA minor groove interactions of imidazole/pyrrole polyamides. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. 16, 60-70 (2020).
Müller, Sabrina, Paulus, Jannik, Mattay, Jochen, Ihmels, Heiko, Dodero, Veronica Isabel, and Sewald, Norbert. “Photocontrolled DNA minor groove interactions of imidazole/pyrrole polyamides”. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 16 (2020): 60-70.

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