Fluorescence, anisotropy and docking studies of proteins through excited state intramolecular proton transfer probe molecules

Maity, Suman Kalyan; Samanta, Subhodip; Sardar, Pinki Saha; Pal, Anirban; Dasgupta, Swagata; Ghosh, Sanjib

doi:10.1016/j.chemphys.2008.10.020

Cited by 19 publications

(31 citation statements)

References 41 publications

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“…The broad stokes shifted emission at E500 nm 1 (pÀ p n ) has been ascribed to the emission from an enol tautomer (anionic T-form, Scheme 1) generated by the ESIPT from hydroxyl groups to the carbonyl oxygen of the 3HNA [23]. Our observation of significant higher quantum yield of the ESIPT emission of 3HNA in PVP-water mixture compared to that in aqueous phosphate buffer (pH 7) [27,28] at 298 K prompted us to study the interaction of 3HNA with PVP using both steady state and time resolved techniques (including anisotropy). As a control experiment we also studied the interaction of 3HNA with the monomer N-vinyl 2-pyrrolidone and acryl amide and the other water soluble polymers.…”

Section: Introductionmentioning

confidence: 57%

“…toluene and DCM) consists of only a single emission from locally excited lowest 1 (p Àp n ) state at $ 398-420 nm [23,[27][28]. In polar solvents (e.g.…”

Section: Steady State Emission Spectra Of 3hna In Different Solvents mentioning

confidence: 99%

“…The concentration of PVP (M r $ 40 000) in water used in this study is much lower compared to other studies mentioned [18]. We have used a low concentration (20 mM) of 3HNA to prevent any polymerization of 3HNA [23][24][25][26][27][28]. The molecule 3HNA is known for its dual emission: the normal and the ESIPT emissions having emission maxima around 418 and 495-515 nm regions, respectively.…”

Section: Introductionmentioning

confidence: 96%

“…As a control experiment we also studied the interaction of 3HNA with the monomer N-vinyl 2-pyrrolidone and acryl amide and the other water soluble polymers. The binding constant of the probe with PVP has been measured and the results have been compared with our recent studies of the interaction of 3HNA with bovine serum albumin (BSA) and human serum albumin (HSA) [27,28]. In order to understand the enhancement of the ESIPT emission in PVP-water mixture and to assess the micro-polarity and micro-viscosity of the probe in the complex, the ESIPT emission of 3HNA has been also explored in detail using time resolved technique in various mixed solvents at different temperatures.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Interaction of the excited state intramolecular proton transfer probe 3-hydroxy-2-naphthoic acid with poly N-vinyl-2-pyrrolidone polymer in water: An insight into the water structure in the binding region

Pal

Maity

Samanta

et al. 2010

Journal of Luminescence

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Section: Introductionmentioning

confidence: 57%

“…toluene and DCM) consists of only a single emission from locally excited lowest 1 (p Àp n ) state at $ 398-420 nm [23,[27][28]. In polar solvents (e.g.…”

Section: Steady State Emission Spectra Of 3hna In Different Solvents mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Interaction of the excited state intramolecular proton transfer probe 3-hydroxy-2-naphthoic acid with poly N-vinyl-2-pyrrolidone polymer in water: An insight into the water structure in the binding region

Pal

Maity

Samanta

et al. 2010

Journal of Luminescence

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“…The computed free energy for a number of PDB ligand-receptor complexes was studied and compared with experimental binding affinity. A substantial degree of correlation between the computed free energy and experimental binding affinity was found, which suggests that PEARLS may be useful in facilitating the energetic analysis of ligand-protein, ligand-nucleic acid, and protein-nucleic acid interactions (Han et al, 2006;Sperandio et al, 2006;Ghosh et al, 2007;Vijjulatha and Kanth, 2007;Maity et al, 2008;Caceres et al, 2008;Pauli et al, 2008).…”

Section: Calculation Of Ligand-protein Interaction Energymentioning

confidence: 91%

Binding dynamics and energetic insight into the molecular forces driving nucleotide binding by guanylate kinase

Kandeel

Kitade

2010

J of Molecular Recognition

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Plasmodium deoxyguanylate pathways are an attractive area of investigation for future metabolic and drug discovery studies due to their unique substrate specificities. We investigated the energetic contribution to guanylate kinase substrate binding and the forces underlying ligand recognition. In the range from 20 to 35°C, the thermodynamic profiles displayed marked decrease in binding enthalpy, while the free energy of binding showed little changes. GMP produced a large binding heat capacity change of -356 cal mol(-1) K(-1), indicating considerable conformational changes upon ligand binding. Interestingly, the calculated ΔCp was -32 cal mol(-1) K(-1), indicating that the accessible surface area is not the central change in substrate binding, and that other entropic forces, including conformational changes, are more predominant. The thermodynamic signature for GMP is inconsistent with rigid-body association, while dGMP showed more or less rigid-body association. These binding profiles explain the poor catalytic efficiency and low affinity for dGMP compared with GMP. At low temperature, the ligands bind to the receptor site under the effect of hydrophobic forces. Interestingly, by increasing the temperature, the entropic forces gradually vanish and proceed to a nonfavorable contribution, and the interaction occurs mainly through bonding, electrostatic forces, and van der Waals interactions.

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Spectroscopic investigations and hydrogen bond interactions of 8-aza analogues of xanthine, theophylline and caffeine: a theoretical study

Karthika¹,

Kanakaraju²,

Lakshmipathi

2013

J Mol Model

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The structure, spectral properties and the hydrogen bond interactions of 8-aza analogues of xanthine, theophylline and caffeine have been studied by using quantum chemical methods. The time-dependent density functional theory (TD-DFT) and the singly excited configuration interaction (CIS) methods are employed to optimize the excited state geometries of isolated 8-azaxanthine, 8-azatheophylline tautomers and 8-azacaffeine in both the gas and solvent phases. The solvent phase calculations are performed using the polarizable continuum model (PCM). The absorption and emission spectra are calculated using the time-dependent density functional theory (TD-DFT) method. The results from the TD-DFT calculations reveal that the excitation spectra are red shifted relative to absorption in aqueous medium. These changes in the transition energies are qualitatively comparable to the experimental data. The examination of molecular orbital reveals that the molecules with a small H→L energy gap possess maximum absorption and emission wavelength. The relative stability and hydrogen bonded interactions of mono and heptahydrated 8-azaxanthine, 8-azatheophylline tautomers and 8-azacaffeine have been studied using the density functional theory (DFT) and Møller Plesset perturbation theory (MP2) implementing the 6-311++G(d,p) basis set. The formation of strong N-H...O bond has resulted in the highest interaction energy among the monohydrates. Hydration does not show any significant impact on the stability of heptahydrated complexes. The atoms in molecule (AIM) and natural bonding orbital (NBO) analyses have been performed to elucidate the nature of the hydrogen bond interactions in these complexes.

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Fluorescence, anisotropy and docking studies of proteins through excited state intramolecular proton transfer probe molecules

Cited by 19 publications

References 41 publications

Interaction of the excited state intramolecular proton transfer probe 3-hydroxy-2-naphthoic acid with poly N-vinyl-2-pyrrolidone polymer in water: An insight into the water structure in the binding region

Interaction of the excited state intramolecular proton transfer probe 3-hydroxy-2-naphthoic acid with poly N-vinyl-2-pyrrolidone polymer in water: An insight into the water structure in the binding region

Binding dynamics and energetic insight into the molecular forces driving nucleotide binding by guanylate kinase

Spectroscopic investigations and hydrogen bond interactions of 8-aza analogues of xanthine, theophylline and caffeine: a theoretical study

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