Design of a new fluorescent probe: Pyrrole/imidazole hairpin polyamides with pyrene conjugation at their γ-turn.

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Abstract

Fluorophores that are conjugated with N-methylpyrrole-N-methylimidazole (Py-Im) polyamides postulates versatile applications in biological and physicochemical studies. Here, we show the design and synthesis of new types of pyrene-conjugated hairpin Py-Im polyamides (1-5). We evaluated the steady state fluorescence of the synthesized conjugates (1-5) in the presence and absence of oligodeoxynucleotides 5'-CGTATGGACTCGG-3' (ODN 1) and 5'-CCGAGTCCATACG-3' (ODN 2) and observed a distinct increase in emission at 386nm with conjugates 4 and 5. Notably, conjugate 5 that contains a β-alanine linker had a stronger binding affinity (K(D)=1.73×10(-8)M) than that of conjugate 4 (K(D)=1.74×10(-6)M). Our data suggests that Py-Im polyamides containing pyrene fluorophore with a β-alanine linker at the γ-turn NH(2) position can be developed as the competent fluorescent DNA-binding probes.

Journal

  • Bioorganic & medicinal chemistry

    Bioorganic & medicinal chemistry 21(4), 852-855, 2013-02-15

    Elsevier Ltd.

Keywords

Codes

  • NII Article ID (NAID)
    120005241442
  • NII NACSIS-CAT ID (NCID)
    AA10938083
  • Text Lang
    ENG
  • Article Type
    journal article
  • ISSN
    0968-0896
  • Data Source
    IR 
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