The Unusual Fluorescence Quenching of Coumarin 314 by β-Cyclodextrin and the Effect of β-Cyclodextrin on its Binding with Calf Thymus DNA

Chandrasekaran, Sowrirajan; Yousuf, Sameena; Enoch, Israel V.M.V.

doi:10.1071/ch13364

Cited by 31 publications

(4 citation statements)

References 27 publications

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“…The most common cyclodextrin, β-CD, is known to alter the fluorescence emission of complexed guest molecules. Fluorescence enhancement is the most observed property on such host–guest complex formation, whereas quenching of fluorescence also is scarcely reported. − …”

Section: Introductionmentioning

confidence: 99%

Differential Metal Ion Sensing by an Antipyrine Derivative in Aqueous and β-Cyclodextrin Media: Selectivity Tuning by β-Cyclodextrin

Selvan¹,

Poomalai²,

Ramasamy³

et al. 2018

Anal. Chem.

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β-Cyclodextrin (β-CD) is a nontoxic cyclic oligosachcharide that can encapsulate all or part of organic molecules of appropriate size and specific shape through noncovalent interaction. Herein, we report the influence of β-CD complex formation of an antipyrine derivative on its metal ion sensing behavior. In aqueous solution, the antipyrine shows a turn-on fluorescence sensing of vanadyl ion, and in cyclodextrin medium it senses aluminum ion. The compound shows an unusual fluorescence quenching on binding with β-cyclodextrin (log K SV = 2.34 ± 0.02). The differential metal ion sensing is due to the partial blocking of the chelating moiety by the cyclodextrin molecule. The structure of the antipyrine− cyclodextrin complex is optimized by two-dimensional rotating-frame Overhauser effect spectroscopy. The binding constant is determined by isothermal titration calorimetry (log K = 2.09 ± 0.004). The metal ion binding site is optimized by quanutm mechanical calculations. The lower limit of detection of vanadyl and aluminum ions, respectively, are 5 × 10 −8 and 5 × 10 −7 mol dm −3 . This is the first report of selectivity of two different cations by a chemosensor in water and in β-CD.

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Section: Introductionmentioning

confidence: 99%

Differential Metal Ion Sensing by an Antipyrine Derivative in Aqueous and β-Cyclodextrin Media: Selectivity Tuning by β-Cyclodextrin

Selvan¹,

Poomalai²,

Ramasamy³

et al. 2018

Anal. Chem.

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“…Further evidence for intercalative binding is discussed in the section on molecular docking. A double reciprocal plot was used to determine the binding constant of the H 2 acacnn–DNA binding using the following equation:

\frac{A_{0}}{A - {normalA}_{0}} = \frac{ɛ_{normalH 2 acacnn}}{ɛ_{normalH 2 acacnn - β - CD} - ɛ_{H 2 acacnn}} + \frac{ɛ_{H 2 acacnn}}{((), ɛ_{H 2 acacnn - β - CD} - ɛ_{normalH 2 acacnn}) 𝐾_{b} ([], DNA)}

…”

Section: Resultsmentioning

confidence: 99%

Picking Out Logic Operations in a Naphthalene β‐Diketone Derivative by Using Molecular Encapsulation, Controlled Protonation, and DNA Binding

Yousuf

Paulraj

et al. 2015

ChemistryOpen

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On–off switching and molecular logic in fluorescent molecules are associated with what chemical inputs can do to the structure and dynamics of these molecules. Herein, we report the structure of a naphthalene derivative, the fashion of its binding to β-cyclodextrin and DNA, and the operation of logic possible using protons, cyclodextrin, and DNA as chemical inputs. The compound crystallizes out in a keto-amine form, with intramolecular N−H⋅⋅⋅O bonding. It shows stepwise formation of 1:1 and 1:2 inclusion complexes with β-cyclodextrin. The aminopentenone substituents are encapsulated by β-cyclodextrin, leaving out the naphthalene rings free. The binding constant of the β-cyclodextrin complex is 512 m−1. The pKa value of the guest molecule is not greatly affected by the complexation. Dual input logic operations, based on various chemical inputs, lead to the possibility of several molecular logic gates, namely NOR, XOR, NAND, and Buffer. Such chemical inputs on the naphthalene derivative are examples of how variable signal outputs based on binding can be derived, which, in turn, are dependent on the size and shape of the molecule.

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“…β-Cyclodextrin (β-CD) is a doughnut-shaped cyclic oligosachcharide containing a hydrophobic cavity capable of accommodating guest molecules of appropriate size [9]. The biological activities of chromenones have been well-documented [10] and the bindings of native chromenones to β-CD and duplex DNA have been reported by our research group [10][11][12][13][14][15][16]. This article provides the possible modes and strengths of binding of the chromenones viz., 2'-Hydroxyflavanone (2'HF), Hesperidin (HP), Naringin (NR), 7-aminoflavone (7AF), Baicalein (BC), Coumarin153 (C153) and Coumarin314 (C314) loaded, aminoethylamino-modified dextran-coated iron oxide nanoparticles to β-CD and DNA.…”

Section: Introductionmentioning

confidence: 96%

Chromenone-conjugated magnetic iron oxide nanoparticles. Toward conveyable DNA binders

Yousuf

Enoch

Paulraj

et al. 2015

Colloids and Surfaces B: Biointerfaces

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The Unusual Fluorescence Quenching of Coumarin 314 by β-Cyclodextrin and the Effect of β-Cyclodextrin on its Binding with Calf Thymus DNA

Cited by 31 publications

References 27 publications

Differential Metal Ion Sensing by an Antipyrine Derivative in Aqueous and β-Cyclodextrin Media: Selectivity Tuning by β-Cyclodextrin

Differential Metal Ion Sensing by an Antipyrine Derivative in Aqueous and β-Cyclodextrin Media: Selectivity Tuning by β-Cyclodextrin

Picking Out Logic Operations in a Naphthalene β‐Diketone Derivative by Using Molecular Encapsulation, Controlled Protonation, and DNA Binding

Chromenone-conjugated magnetic iron oxide nanoparticles. Toward conveyable DNA binders

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