DNA binding studies of a solvatochromic fluorescence probe 3-methoxybenzanthrone

Yang, Xin; Liu, Wanhui; Weijun, Jin; Shen, Guo‐Li; Yu, Ru‐Qin

doi:10.1016/s1386-1425(99)00161-4

Cited by 57 publications

(21 citation statements)

References 23 publications

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“…In our work no manipulation of the data was performed other than to subtract the background fluorescence of the ligand in the absence of fibrils followed by fitting of the data using nonlinear regression methods to a single-site binding model. In contrast, Agdeppa et al (8) analyzed their raw data using a more complex series of calculations to determine, first, the free concentration of ligand (17) and then to use those values to construct Scatchard plots from which the binding constants were determined.…”

Section: Discussionmentioning

confidence: 99%

Delineation of Positron Emission Tomography Imaging Agent Binding Sites on β-Amyloid Peptide Fibrils

Liang

Morgenstern

Gee

et al. 2005

Journal of Biological Chemistry

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A range of imaging agents for use in the positron emission tomography of Alzheimer's disease is currently under development. Each of the main compound classes, derived from thioflavin T (PIB), Congo Red (BSB), and aminonaphthalene (FDDNP) are believed to bind to mutually exclusive sites on the ␤-amyloid (A␤) peptide fibrils. We recently reported the presence of three classes of binding sites (BS1, BS2, BS3) on the A␤ fibrils for thioflavin T derivatives and now extend these findings to demonstrate that these sites are also able to accommodate ligands from the other chemotype classes. The results from competition assays using [3H]Me-BTA-1 (BS3 probe) indicated that both PIB and FDDNP were able to displace the radioligand with K i values of 25 and 42 nM, respectively. BSB was unable to displace the radioligand tracer from the A␤ fibrils. In contrast, each of the compounds examined were able to displace thioflavin T (BS1 probe) from the A␤ fibrils when evaluated in a fluorescence competition assay with K i values for PIB, FDDNP, and BSB of 1865, 335, and 600 nM, respectively. Finally, the K d values for FDDNP and BSB binding to A␤ fibrils were directly determined by monitoring the increases in the ligand intrinsic fluorescence, which were 290 and 104 nM, respectively. The results from these assays indicate that (i) the three classes of thioflavin T binding sites are able to accommodate a wide range of chemotype structures, (ii) BSB binds to two sites on the A␤ fibrils, one of which is BS2, and the other is distinct from the thioflavin T derivative binding sites, and (iii) there is no independent binding site on the fibrils for FDDNP, and the ligand binds to both the BS1 and BS3 sites with significantly lower affinities than previously reported.The development of imaging agents to detect the senile plaques and neurofibrillary tangles associated with Alzheimer disease (AD) 1 is a rapidly emerging and important field for both preclinical and clinical drug development (1). Three main structural classes or chemotypes of positron emission tomography imaging agents are currently under development and are derived from thioflavin T (PIB (2), IMPY (3), TZDM (4)), Congo Red/styrylbenzene (ISB (4), BSB (5), X34 (6), stilbene (7)) and aminonaphthalene (FDDNP, FENE (8)) backbones. These ligands are primarily believed to target the polymeric form of ␤-amyloid (A␤) peptide associated with the senile plaques and may in addition bind to neurofibrillary tangles, which are composed of tau protein polymers (1).Because the number of compounds under development has increased, a somewhat confusing picture has emerged with respect to the interaction of members of the different chemotype classes with the A␤ fibrils. Initial findings, which were based on radioligand binding assays, indicated an independent binding site on the A␤ fibrils for each of the three chemotypes. For example, Agdeppa et al. (9) demonstrated that [ 18 F]FDDNP was not displaced from A␤ fibrils by either Congo Red or thioflavin T. In addition, data from Zhuang et al. (4...

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Section: Discussionmentioning

confidence: 99%

Delineation of Positron Emission Tomography Imaging Agent Binding Sites on β-Amyloid Peptide Fibrils

Liang

Morgenstern

Gee

et al. 2005

Journal of Biological Chemistry

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“…3b). The blue shift would tend to indicating that the 4g enters CT-DNA-stacking region with lower polarity rather than the bulk solution of CT-DNA 24 and implying that the 4g more easily inserts into CT-DNA than 4a. Based on the Scatchard method, 18,19 two following Eqs.…”

Section: Dna-binding Studiesmentioning

confidence: 99%

5-Non-amino aromatic substituted naphthalimides as potential antitumor agents: Synthesis via Suzuki reaction, antiproliferative activity, and DNA-binding behavior

Xie

Cui

Qian

et al. 2011

Bioorganic & Medicinal Chemistry

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“…The main importance of TXNHCH 2 COOH is the broad, intense absorption spectrum which extends from the UV to the red region [53] The intrinsic binding constant K b for TXNHCH 2 COOH is found to be 6x10 5 M -1 by the ratio of slope to the intercept (Fig.2). This K b value indicates the strong binding affinity of TXNHCH 2 COOH towards ct-DNA and intercalation mode between TXNHCH 2 COOH and ct-DNA are considered to be most indicative binding [48,56,57].…”

Section: 1absorption Propertiesmentioning

confidence: 96%

Studies of the binding mode of TXNHCH 2 COOH with calf thymus DNA by spectroscopic methods

Ataci

Arsu

2016

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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DNA binding studies of a solvatochromic fluorescence probe 3-methoxybenzanthrone

Cited by 57 publications

References 23 publications

Delineation of Positron Emission Tomography Imaging Agent Binding Sites on β-Amyloid Peptide Fibrils

Delineation of Positron Emission Tomography Imaging Agent Binding Sites on β-Amyloid Peptide Fibrils

5-Non-amino aromatic substituted naphthalimides as potential antitumor agents: Synthesis via Suzuki reaction, antiproliferative activity, and DNA-binding behavior

Studies of the binding mode of TXNHCH 2 COOH with calf thymus DNA by spectroscopic methods

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