Inclusion complex of charge transfer probe 4-amino-3-methyl benzoic acid methyl ester (AMBME) with β-CD in aqueous and non-aqueous medium: medium dependent stoichiometry of the complex and orientation of probe molecule inside β-CD nanocavity

Chakraborty, Amrita; Guchhait, Nikhil

doi:10.1007/s10847-008-9442-4

Cited by 12 publications

(2 citation statements)

References 29 publications

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“…In the aqueous phase, CyD's are amphiphilic and may interact with other chemical species that interfere with their collisional probability and hydration dynamics, leading to changes in their physical and chemical properties . These changes may be observed by various techniques to study the interactions between CyD's and guest molecules; examples include 1 H NMR, mass spectrometry, electrophoresis, UV–vis absorption spectroscopy, fluorescence spectroscopy, circular dichroism (CD) spectroscopy, X-ray crystallography, and computational calculations . Understanding the binding events of CyD's in aqueous media is crucial for employing their host–guest chemistry in sensing and controlled release systems.…”

Section: Introductionmentioning

confidence: 99%

Inclusion Complexes between Amphiphilic Phenyleneethynylene Fluorophores and Cyclodextrins in Aqueous Media

Siripornnoppakhun

Niamnont²,

Krumsri

et al. 2012

J. Phys. Chem. B

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Binding events of cyclodextrins (CyD's) in aqueous media are important for designing and explaining the host-guest chemistry applied in sensing and controlled release systems. A water-soluble tricationic compound (3N(+)) with three branches of phenyleneethynylene fluorescent moieties and its related amphiphilic compounds (3C(-), N(0)N(+), N(+), and 2N(+)) are employed as molecular probes in the systematic characterization of the supramolecular interactions with CyD's (α, β, and γ). The strong fluorescence enhancement, combined with induced circular dichroism (CD) signals and (1)H NMR data, is evidence of 1:1 static inclusion complexes of 3N(+)/γ-CyD and 2N(+)/γ-CyD. 3N(+) presents a structural design which can form inclusion complexation with γ-CyD with one of the highest binding constants of 3.0 × 10(4). The relatively moderate fluorescence enhancement, shift of (1)H NMR signals, and weak induced CD signals indicate fast exchange complexation of β-CyD with the amphiphilic guest molecules. The interaction with α-CyD is perceived only for N(0)N(+), the only nonbranched fluorescent guest model, via its strong fluorescence enhancement. However, the lack of (1)H NMR signal splitting and the lack of induced CD signals suggest the noninclusion mode of binding between N(0)N(+) and α-CyD.

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Section: Introductionmentioning

confidence: 99%

Inclusion Complexes between Amphiphilic Phenyleneethynylene Fluorophores and Cyclodextrins in Aqueous Media

Siripornnoppakhun

Niamnont²,

Krumsri

et al. 2012

J. Phys. Chem. B

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“…The ICT probes are increasingly being used in fluorescence‐probe spectroscopy of proteins and garner massive information about the structure, stability and dynamics of these biomacromolecules. Polarity changes produced on introduction in microheterogeneous media like membrane mimetic micelles (10–12), cyclodextrin nanocavities (13–15) and proteinous systems (6–8) affect the emission properties of these special fluorophores tracking which easy investigation of these systems become possible fluorimetrically.…”

Section: Introductionmentioning

confidence: 99%

Fluorescent Probing of Urea‐induced Chemical Unfolding of Bovine Serum Albumin by Intramolecular Charge Transfer Fluorescence Probe E‐3‐(4‐Dimethylamino‐Naphthalen‐1‐yl)‐Acrylic Acid

Ghosh

Guchhait

2010

Photochem & Photobiology

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Changes in polarity at the immediate binding site in protein bovine serum albumin (BSA) produces distinct changes in the solvent polarity-dependent emission band of fluorescence probe E-3-(4-dimethylamino-naphthalen-1-yl)-acrylic acid. Steady-state spectroscopy and time-resolved spectroscopy have been used to investigate this binding process. Attaching the probe to BSA and then monitoring its spectral changes with increasing urea concentration and raising temperature has also tracked the denaturation of BSA chemically and thermally. The polarity of the microenvironment was investigated employing the Reichardt E(T)(30) scale. Fluorescence anisotropy, red edge excitation shifts and acrylamide-induced quenching of fluorescence have been exploited to gain better insight into this binding process.

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Spectral modulation of a charge transfer reaction of 2-methoxy-4-(N,N-dimethylamino)benzaldehyde inside cyclodextrin nanocage

Samanta

Jana

Guchhait

2012

J Incl Phenom Macrocycl Chem

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Inclusion complex of charge transfer probe 4-amino-3-methyl benzoic acid methyl ester (AMBME) with β-CD in aqueous and non-aqueous medium: medium dependent stoichiometry of the complex and orientation of probe molecule inside β-CD nanocavity

Cited by 12 publications

References 29 publications

Inclusion Complexes between Amphiphilic Phenyleneethynylene Fluorophores and Cyclodextrins in Aqueous Media

Inclusion Complexes between Amphiphilic Phenyleneethynylene Fluorophores and Cyclodextrins in Aqueous Media

Fluorescent Probing of Urea‐induced Chemical Unfolding of Bovine Serum Albumin by Intramolecular Charge Transfer Fluorescence Probe E‐3‐(4‐Dimethylamino‐Naphthalen‐1‐yl)‐Acrylic Acid

Spectral modulation of a charge transfer reaction of 2-methoxy-4-(N,N-dimethylamino)benzaldehyde inside cyclodextrin nanocage

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