Beilstein J. Org. Chem.2020,16, 2795–2806, doi:10.3762/bjoc.16.230
-forming repeat unit from the “insulin-linked polymorphic region” (ILPR) [50], that was also shown to bind quadruplex ligands [51].
Results
Synthesis
As the Cu-catalyzed click reaction between azides and alkynes is a well-established method for the variable functionalization of G4-DNA ligands [52], the
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Graphical Abstract
Scheme 1:
The structures and numbering of berberine (1a) and the alkyl-substituted derivatives 1an–en and the...
Beilstein J. Org. Chem.2014,10, 2963–2974, doi:10.3762/bjoc.10.314
Darinka Dzubiel Heiko Ihmels Mohamed M. A. Mahmoud Laura Thomas Department Chemie-Biologie, Universität Siegen, Adolf-Reichwein-Str. 2, 57068 Siegen, Germany 10.3762/bjoc.10.314 Abstract The interactions of the ILPR sequence (ILPR = "insulin-linked polymorphic region") a2 [d(ACAG4TGTG4ACAG4TGTG4
-b′′′]tetraquinolizinium (5) and thiazole orange (6) were studied. It is demonstrated with absorption, fluorescence and CD spectroscopy that all investigated ligands bind with relatively high affinity to the ILPR-quadruplex DNA a2 (0.2–5.5 × 106 M−1) and that in most cases the binding parameters of
ligand-ILPR complexes are different from the ones observed with other native quadruplex-forming DNA sequences.
Keywords: DNA ligands; fluorescent probes; ILPR; nucleic acids; quadruplex DNA; Introduction
The “insulin-linked polymorphic region” (ILPR) is a physiologically relevant G-rich DNA sequence
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Graphical Abstract
Scheme 1:
Equilibrium between single-stranded ILPR-DNA a2 and its parallel and antiparallel quadruplex form.