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Molecules 2018, 23(6), 1400; https://doi.org/10.3390/molecules23061400

Comparison of Characteristics and DNAzyme Activity of G4–Hemin Conjugates Obtained via Two Hemin Attachment Methods

Laboratory of Bioanalytical Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Umultowska 89b, 61-614 Poznań, Poland
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Received: 17 April 2018 / Revised: 30 May 2018 / Accepted: 7 June 2018 / Published: 9 June 2018
(This article belongs to the Section Bioorganic Chemistry)
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Abstract

Two conjugation methods using different linkers were applied for the investigation of the spectral characteristics and activity of G-quadruplex (G4)–hemin conjugates. For this purpose, two G-quadruplex-forming DNA sequences were selected, and then conjugated to a hemin molecule via either amine coupling or a click reaction. The products obtained via these two methods differed in their chemistry and the length of the linker between the DNA and hemin molecules. Spectral characteristics revealed that both methods produced conjugates that were more thermally stable than G4/hemin complexes. Despite similar spectral characteristics, the conjugates obtained via these two methods differed in their DNAzyme activity. G4–hemin conjugates obtained through amine coupling exhibited higher activity than conjugates obtained through a click reaction. This was potentially due to the length and chemistry of the linker, which was 30 atoms long following the click reaction, but only six atoms long following amine coupling. A longer connector favors higher flexibility, and hence, reduces the binding of hemin with G4. The aromatic groups present in the linker obtained through the click reaction can also disturb the G4–hemin interaction. However, the conjugation of G4 DNA to hemin via the click reaction was connected to a higher yield, and did not require any sophisticated synthesis equipment. View Full-Text
Keywords: G-quadruplex; hemin; click chemistry G-quadruplex; hemin; click chemistry
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Kosman, J.; Żukowski, K.; Juskowiak, B. Comparison of Characteristics and DNAzyme Activity of G4–Hemin Conjugates Obtained via Two Hemin Attachment Methods. Molecules 2018, 23, 1400.

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