Bcl-2 Promoter Sequence G-Quadruplex Interactions with Three Planar and Non-Planar Cationic Porphyrins TMPyP4, TMPyP3, and TMPyP2.docVIP

Bcl-2 Promoter Sequence G-Quadruplex Interactions with Three Planar and Non-Planar Cationic Porphyrins TMPyP4, TMPyP3, and TMPyP2.doc

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Bcl-2 Promoter Sequence G-Quadruplex Interactions with Three Planar and Non-Planar Cationic Porphyrins TMPyP4, TMPyP3, and TMPyP2

Bcl-2 Promoter Sequence G-Quadruplex Interactions with Three Planar and Non-Planar Cationic Porphyrins: TMPyP4, TMPyP3, and TMPyP2 Vu H. Le , Narayana Nagesh , Edwin A. Lewis 1 2 1* 1 Department of Chemistry, Mississippi State University, Mississippi State, Mississippi, United States of America, 2 Centre for Cellular and Molecular Biology, Hyderabad, Andhra Pradesh, India Abstract The interactions of three related cationic porphyrins, TMPyP4, TMPyP3 and TMPyP2, with a WT 39-mer Bcl-2 promoter sequence G-quadruplex were studied using Circular Dichroism, ESI mass spectrometry, Isothermal Titration Calorimetry, and Fluorescence spectroscopy. The planar cationic porphyrin TMPyP4 (5, 10, 15, 20-meso- tetra (N-methyl-4-pyridyl) porphine) is shown to bind to a WT Bcl-2 G-quadruplex via two different binding modes, an end binding mode and a weaker mode attributed to intercalation. The related non-planar ligands, TMPyP3 and TMPyP2, are shown to bind to the Bcl-2 G-quadruplex by a single mode. ESI mass spectrometry experiments confirmed that the saturation stoichiometry is 4:1 for the TMPyP4 complex and 2:1 for the TMPyP2 and TMPyP3 complexes. ITC experiments determined that the equilibrium constant for formation of the (TMPyP4)1/DNA complex (K1 = 3.7 × 10 6 ) is approximately two orders of magnitude greater than the equilibrium constant for the formation of ). Porphyrin fluorescence is consistent with intercalation in the case of the (TMPyP2)1/DNA complex, (K1 = 7.0 × 10 4 the (TMPyP4)3/DNA and (TMPyP4)4/DNA complexes. The non-planar shape of the TMPyP2 and TMPyP3 molecules results in both a reduced affinity for the end binding interaction and the elimination of the intercalation binding mode. Citation: Le VH, Nagesh N, Lewis EA (2013) Bcl-2 Promoter Sequence G-Quadruplex Interactions with Three

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