Probing the spectral response of a new class of bioactive pyrazoline derivative in homogeneous solvents and cyclodextrin nanocavities: a spectroscopic exploration appended by quantum chemical calculations and molecular docking analysis

Mati, Soumya Sundar; Sarkar, Sunandan; Rakshit, Soumyadipta; Sarkar, Arindam; Bhattacharya, Sumanta

doi:10.1039/c3ra40749g

Cited by 15 publications

(6 citation statements)

References 55 publications

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“…This clearly indicates 1 : 1 MG-CD complexation. 43 The above results indicate that MG links to only one CD molecule. To substantiate the discussion, the molecular dimensions of MG have been calculated theoretically using the DFT method (Scheme 5) with B3LYP functional and 6-31G* basis set, and the data indicates that the complete incorporation of MG inside any of the CD cavities is not possible.…”

Section: Absorption Studiesmentioning

confidence: 76%

Kinetic exploration supplemented by spectroscopic and molecular docking analysis in search of the optimal conditions for effective degradation of malachite green

et al. 2015

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The degradation of malachite green (MG) by an alkaline hydrolytic process has been explored spectrophotometrically. The kinetics of the reaction have been meticulously studied under the influence of cationic alkyltrimethylammonium bromide (DTAB, TTAB and CTAB) surfactants, a-, band gcyclodextrins (CDs) and surfactant-b-CD mixed systems applying pseudo-first order conditions at 298 K. The surfactants and cyclodextrins individually catalyze the hydrolytic rate, whereas surfactant-b-CD mixed systems exhibit both an inhibiting and catalytic influence depending on the surfactant concentrations. The kinetic results have been explained precisely based on the pseudo-phase ion exchange (PIE) model of micelles and CD-catalyzed model of CD systems. The surfactants exhibit micellar surface catalysis, while CDs accelerate the rate by forming MG-CD inclusion complexes, thereby facilitating nucleophilic attack of its ionized secondary hydroxyl group on the carbocation center of MG. The encapsulation of MG within the supramolecular host cavity of the CDs has been investigated diligently using a steady-state absorption spectroscopic technique. The result shows 1 : 1 host-guest complexation with different relative orientations of the guest (MG) inside the hosts. Studies employing density functional theory (DFT) as well as molecular docking analysis provide valuable insight on the insertion mechanism. The results reveal that quantitative analysis can be utilized to predict the optimum conditions for the fastest degradation of MG in ambient environments.Fig. 2 Plots of k obs versus [CD] 0 for the reaction of MG and À OH in aqueous medium at 298 K. [MG] 0 ¼ 1.25 Â 10 À5 M, [ À OH] 0 ¼ 1.875 mM. Inset: catalytic factor (k max obs /k w ) in different cyclodextrin systems at fixed [CD] ¼ 1.0 mM. Scheme 3 Hydrolysis of MG in aqueous solution of CD.This journal is

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Section: Absorption Studiesmentioning

confidence: 76%

Kinetic exploration supplemented by spectroscopic and molecular docking analysis in search of the optimal conditions for effective degradation of malachite green

et al. 2015

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“…On the basis of absorption spectra, Benesi-Hildebrand (B-H) relation (eqn (2)) 52 was employed to note down the association constant (K), stoichiometry, and free energy change (ΔG) due to complexation between PyHP and Zn 2+ .…”

Section: Resultsmentioning

confidence: 99%

An efficient, Schiff-base derivative for selective fluorescence sensing of Zn²⁺ions: quantum chemical calculation appended by real sample application and cell imaging study

et al. 2014

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Since zinc ions (Zn(2+)) are involved in numerous biological phenomena and go through subsequent interactions with zinc-binding proteins, we have attempted a sensitive fluorescence based detection of this second most abundant metal ion using an engineered and synthesized Schiff-base ligand, namely 2,4-bis((Z)-2-(1-(pyridin-2-yl)ethylidene)hydrazinyl)pyrimidine (PyHP). The ligand exhibits a zinc-induced fluorescence response when investigated in a MeOH-buffer (10 mM HEPES, pH = 7) (4 : 1) solvent mixture. The presence of zinc ions (λ(ex) = 410 nm, quantum yield, ϕ = 0.20) causes approximately 45 fold fluorescence enhancement at 489 nm. Formation of the metal-ligand complex was ascertained by (1)H NMR and mass spectra analysis. 1 : 1 binding affinity was ascertained according to Job's plot. Apart from this, theoretical interpretation of the experimental outcome was also obtained by applying density functional theory (DFT) to the PyHP-Zn(2+) complex formation. The practical applicability of the ligand has been tested in bacterial cells as well as in mammalian cell imaging and also by measuring and comparing the amount of Zn(2+) in some real samples such as liquid milk, tomato juice, banana stem juice and commercial fruit juice.

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“…Several expensive theoretical approaches based on wave function have also been used to accurately study the excited states of fluorescent probes. A relatively inexpensive ab initio method for excited‐state calculations is configuration interaction with single excitation (CIS), which was a good choice at a time when excited‐state optimization could not be performed by TDDFT . Recently, higher level methods have also been applied to obtain VTEs, in order to confirm the results of TDDFT calculations, such as the multi‐configuration second‐order perturbation theory, the internally contracted multi‐reference second‐order perturbation theory, and the second‐order approximate coupled cluster singles and doubles model (CC2) .…”

Section: Methodsmentioning

confidence: 99%

“…A relatively inexpensive ab initio method for excited-state calculations is configuration interaction with single excitation (CIS), which was a good choice at a time when excited-state optimization could not be performed by TDDFT. 63,[89][90][91][92] Recently, higher level methods have also been applied to obtain VTEs, in order to confirm the results of TDDFT calculations, such as the multi-configuration second-order perturbation theory, 93 the internally contracted multireference second-order perturbation theory, 94 and the second-order approximate coupled cluster singles and doubles model (CC2). 20,79 However, the computational costs of these methods are so expensive for fluorescent probe systems that no sensing mechanisms can be deduced by using these methods alone.…”

Section: Excited-state Calculations Based On Wave Functionmentioning

confidence: 99%

The sensing mechanism studies of the fluorescent probes with electronically excited state calculations

Han

2017

WIREs Comput Mol Sci

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Recent research has indicated that fluorescent probes have tremendous potential for the selective detection of chemical and biological species. Over the past decade, researchers have proposed a series of fluorescence‐based sensing mechanisms of such probes by the calculation of their electronic excited states. Investigations of sensing mechanisms have been based on deep insights into the interactions between probe molecules and their target species, as well as their fluorescence properties. Advances in calculation methods, modeling software, and computational power have enabled researchers to use excited‐state theoretical calculations to reproduce experimental fluorescence phenomena and then provide molecular‐level explanations thereof. In this advanced review, we describe the evolution of theoretical studies on excited‐state sensing mechanisms for fluorescent probes that respond to target species. Focusing on calculation methods that facilitate investigation of the photophysical properties and excited‐state dynamics of probes, we emphasize sensing mechanisms mainly reported by our group. Most of these studies have been supported by theoretical predictions based on time‐dependent density functional theory. For this most popular excited‐state calculation method, vertical excitation energy, excited‐state geometrical optimization and a scan of the excited‐state potential energy surface should be noted in the calculation of electronic and molecular differences between the excited‐state probe and its reaction product with the target analyte. These state‐of‐the‐art calculations are of great importance for unraveling details of fluorescence‐based sensing mechanisms, including photochemical reactions (such as twist intramolecular charge transfer and excited‐state proton transfer) and excited‐state electronic processes (such as intramolecular charge transfer and photoinduced electron transfer). These studies have generated new and inspirational mechanistic proposals and have provided a systematic approach for the development of efficient fluorescent sensors. WIREs Comput Mol Sci 2018, 8:e1351. doi: 10.1002/wcms.1351 This article is categorized under: Structure and Mechanism > Computational Biochemistry and Biophysics Theoretical and Physical Chemistry > Spectroscopy

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Probing the spectral response of a new class of bioactive pyrazoline derivative in homogeneous solvents and cyclodextrin nanocavities: a spectroscopic exploration appended by quantum chemical calculations and molecular docking analysis

Cited by 15 publications

References 55 publications

Kinetic exploration supplemented by spectroscopic and molecular docking analysis in search of the optimal conditions for effective degradation of malachite green

Kinetic exploration supplemented by spectroscopic and molecular docking analysis in search of the optimal conditions for effective degradation of malachite green

An efficient, Schiff-base derivative for selective fluorescence sensing of Zn²⁺ions: quantum chemical calculation appended by real sample application and cell imaging study

The sensing mechanism studies of the fluorescent probes with electronically excited state calculations

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Probing the spectral response of a new class of bioactive pyrazoline derivative in homogeneous solvents and cyclodextrin nanocavities: a spectroscopic exploration appended by quantum chemical calculations and molecular docking analysis

Cited by 15 publications

References 55 publications

Kinetic exploration supplemented by spectroscopic and molecular docking analysis in search of the optimal conditions for effective degradation of malachite green

Kinetic exploration supplemented by spectroscopic and molecular docking analysis in search of the optimal conditions for effective degradation of malachite green

An efficient, Schiff-base derivative for selective fluorescence sensing of Zn2+ions: quantum chemical calculation appended by real sample application and cell imaging study

The sensing mechanism studies of the fluorescent probes with electronically excited state calculations

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An efficient, Schiff-base derivative for selective fluorescence sensing of Zn²⁺ions: quantum chemical calculation appended by real sample application and cell imaging study