Journal
JOURNAL OF PHYSICAL CHEMISTRY B
Volume 115, Issue 46, Pages 13701-13712Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jp207265s
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- Wake Forest University
- U.S. National Institutes of Health [CA101880]
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The interactions of a newly synthesized platinum-modified perylene derivative, compound 7 ([{Pt(dien)}(2)-(mu-4-S,S')](NO(3))(4) (then = diethylenetriamine, 4 = N,N'-bis-(1-(2-aminoethyl)-1,3-dimethylthiourea)-3,4,9,10-perylenete-tracarboxylic acid diimide), with the human telomeric repeat were studied using various model oligo(deoxy)ribonucleotides to mimic the polymorphic nature of the telomeric G-quadruplex. UV/visible spectroscopy, CD spectropolarimetry, electrospray mass spectrometry (ES-MS), and isothermal titration calorimetry (ITC) were used to demonstrate that compound 7 selectively recognizes the antiparallel form of the unimolecular telomeric G-quadruplex formed by the sequence d(TTAGGG)(4) (dG-24), to which it binds with a 2:1 stoichiometry and nanomolar affinity. Compared with telomeric DNA, the first binding event of compound 7 in titrations with the RNA quadruplex formed by r(UUAGGG)(4) (rG-24) is 1 order of magnitude weaker. Compound 7 does not induce the antiparallel G-quadruplex RNA, which invariably exists in a parallel form and dimerizes in solution. On the basis of the cumulative experimental data, two distinct mechanisms are proposed for the recognition of G-quadruplex DNA and RNA by compound 7. Potential biomedical and biochemical applications of the platinum-perylene technology are discussed.
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