title: Design of a new fluorescent probe: pyrrole/imidazole hairpin polyamides with pyrene conjugation at their γ-turn.
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.
authors: Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8501, Japan.
authors: Thangavel
authors: T
authors: Vaijayanthi
authors: Toshikazu
authors: T
authors: Bando
authors: Kaori
authors: K
authors: Hashiya
authors: Ganesh N
authors: GN
authors: Pandian
authors: Hiroshi
authors: H
authors: Sugiyama
mesh_terms: D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D007093:Imidazoles / Q000737:chemistry*; D009757:Nylons / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D009838:Oligodeoxyribonucleotides / Q000737:chemistry / Q000378:metabolism; D011721:Pyrenes / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*; D013050:Spectrometry, Fluorescence
chemical_list: D005456:Fluorescent Dyes; D007093:Imidazoles; D009757:Nylons; D009838:Oligodeoxyribonucleotides; D011721:Pyrenes; D011758:Pyrroles; C029899:imidazole; C030984:pyrene