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Self-assembled porphyrazine-nucleoside on DNA templates: highly fluorescent chromophore arrays and sizing forensic tandem repeat sequences

DOI: 10.1002/ejoc.201800683 DOI Help

Authors: Mariia V. Ishutkina (Ivanovo State University of Chemistry and Technology) , Alice R. Berry (University of Southampton) , Rohanah Hussain (Diamond Light Source) , Olga G. Khelevina (Ivanovo State University of Chemistry and Technology) , Giuliano Siligardi (Diamond Light Source) , Eugen Stulz (University of Southampton)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: European Journal Of Organic Chemistry

State: Published (Approved)
Published: May 2018
Diamond Proposal Number(s): 13158

Abstract: The formation of chromophore arrays using a DNA templating approach leads to the creation of supramolecular assemblies, where the optical properties of the overall system can be fine‐tuned to a large extent. In particular porphyrin derivatives have shown to be versatile building blocks; mostly covalent chemistry was used for embedding the units into DNA strands. Self‐assembly of porphyrin modified nucleosides, on the other hand, has not been investigated as a simplified approach. We report on the synthesis of a magnesium(II) tetraaza porphine (MgTAP) coupled to deoxy‐uridine, and array formation on DNA templates which contain well‐defined oligo(dA) segments showing strong fluorescence enhancement which is significantly larger than with a Zn‐porphyrin. The use of the deep‐eutectic solvent glycholine is essential for successful assembly formation. The system allows for sizing of short tandem repeat markers with multiple adenosines, thus the concept could be adaptable to in vitro forensic DNA profiling with a suitable set of different chromophores on all nucleosides.

Journal Keywords: supramolecular arrays; fluorescence enhancement; porphyrinporphyrazine; STR analysis

Subject Areas: Chemistry


Instruments: B23-Circular Dichroism