Versatile click cyanine amino acid conjugates showing one-atom-influenced eecognition of DNA/RNA secondary structure and mitochondrial localisation in living cells

Tamara Šmidlehner, Atanas Kurutos, Jakov Slade, Robert Belužić, Dale L. Ang, Alison Rodger, Ivo Piantanida*

*Corresponding author for this work

    Research output: Contribution to journalArticle

    10 Citations (Scopus)

    Abstract

    By a simple click CuAAC (copper(I)-catalysed azide alkyne cycloaddition) procedure several cyanine dye analogues have been attached to the side-chain of an amino acid to yield chromophore amino acid conjugates with the potential to fluoresce upon binding to a target. Due to the availabiltiy of the amino acid C and N termini for peptide coupling, these conjugates are suitable for easy incorporation into the backbone of peptides. The novel amino acid dyes prepared in this work, although intrinsically non-fluorescent, gave rise to strong fluorimetric responses upon binding to double-stranded (ds) DNA or RNA, the emission response to various polynucleotide secondary structures being controlled either by linker length or a halogen atom located on the cyanine part of the molecule. Molecular modelling confirmed the mode of binding to different polynucleotides, which was responsible for the recognition. Interestingly, cell localisation experiments showed that the dyes were specifically localised in mitochondria at variance with the localisation of the parent dyes, which accumulate in cell nuclei, which suggests that the amino acid tail (containing a triazole ring) might function as a novel mitochondria-directing appendage.

    Original languageEnglish
    Pages (from-to)1682-1692
    Number of pages11
    JournalEuropean Journal of Organic Chemistry
    Volume2018
    Issue number14
    DOIs
    Publication statusPublished - 17 Apr 2018

    Keywords

    • Fluorescence
    • Amino acids
    • DNA recognition
    • Circular dichroism
    • DNA
    • Biological activity

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