Enantiospecific recognition of DNA sequences by a proflavine Tröger base.
The DNA interaction of a chiral Tröger base derived from proflavine was investigated by DNA melting temperature measurements and complementary biochemical assays. DNase I footprinting experiments demonstrate that the binding of the proflavine-based Tröger base is both enantio- and sequence-specific. The (+)-isomer poorly interacts with DNA in a non-sequence-selective fashion. In sharp contrast, the corresponding (-)-isomer recognizes preferentially certain DNA sequences containing both A. T and G. C base pairs, such as the motifs 5'-GTT. AAC and 5'-ATGA. TCAT. This is the first experimental demonstration that acridine-type Tröger bases can be used for enantiospecific recognition of DNA sequences.
Bailly
C
C
INSERM U-524 et Laboratoire de Pharmacologie du Centre Oscar Lambret, Institut de Recherches sur le Cancer, Place de Verdun, Lille, 59045, France. bailly@lille.inserm.fr
Laine
W
W
Demeunynck
M
M
Lhomme
J
J
D000818:Animals; D020029:Base Pairing; D001483:Base Sequence; D001665:Binding Sites; D001952:Bridged-Ring Compounds / Q000737:chemistry / Q000378:metabolism; D002417:Cattle; D004247:DNA / Q000737:chemistry / Q000235:genetics / Q000378:metabolism*; D018983:DNA Footprinting; D066298:In Vitro Techniques; D011370:Proflavine / Q000737:chemistry* / Q000378:metabolism*; D013237:Stereoisomerism
D001952:Bridged-Ring Compounds; D004247:DNA; D011370:Proflavine