Interaction of water-soluble calix[4]arene with l-tryptophan studied by fluorescence spectroscopy

Li, Wen Ye; Li, Hui; Zhang, Guo Mei; Chao, Jian Bin; Ling, Li; Shuang, Shao Min; Dong, Chuan

doi:10.1016/j.jphotochem.2008.02.002

Cited by 13 publications

(4 citation statements)

References 26 publications

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“…Consequently, chemists have investigated the binding of water-soluble calixarenes and amino acids. For example, water-soluble calix[4]arenes may adopt different conformations to accommodate the aromatic ring of tryptophan in calix[4]arene (W. E. Li et al 2008). This article reported that molecular modeling and 1 H NMR results confirmed the possible mechanism of the binding interaction: structural effects and the electrostatic relationships between the compounds may be factors that determine the conformations.…”

Section: Introductionmentioning

confidence: 91%

Determination of Tryptophan using ap-Sulfonated Calix [4,6,8]arene Modified Gold Electrode

et al. 2014

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The ability of p-sulfonated calix[n]arenes (n ¼ 4, 6, 8) to form complexes with tryptophan was studied. The electrochemical properties of these complexes immobilized on gold surfaces were examined by cyclic voltammetry. Parameters affecting the performance of the modified electrodes including the arene concentration, scan rate, applied potential, and pH were optimized. Under the optimal conditions, the method had a linear response to tryptophan between 1 Â 10 À7 M and 1 Â 10 À5 M with a detection limit of 3 Â 10 À8 M. The interaction of the tryptophan-p-sulfonated calix[4]arene complex was more stable than the tryptophanp-sulfonated calix[6]arene and p-sulfonated calix[8]arene complexes. Molecular modeling calculations indicated that electrostatic interactions and structural matching effects were predominant stabilizing factors. The modified electrodes demonstrated good reproducibility and high selectivity, illustrating their effectiveness for analytical measurements.

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Section: Introductionmentioning

confidence: 91%

Determination of Tryptophan using ap-Sulfonated Calix [4,6,8]arene Modified Gold Electrode

et al. 2014

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“…Among amino acid residues, Trp possesses the highest UV extinction coefficient and highest quantum yield of emission. − In a polar environment, Trp fluorescence is emitted from the singlet 1 L a state because ultrafast (<100 fs) internal conversion converts a mixture with 1 L b to 1 L a . Trp is very sensitive to the polarity and dynamics of the immediate environment; spectral energy and width depend strongly on exposure to water (and/or the polarity of the electrostatic environment inside protein). , The ability to probe time-resolved fluorescence of tryptophan, which, if not already present, can often be incorporated in a peptide without significant structural changes, opens a window into peptide/protein dynamics inaccessible to other biophysical techniques. , Recently, interest in Trp has grown, as tunable ultrafast Ti:sapphire lasers have made it possible to monitor the molecular vibrational modes and femtosecond solvent relaxation. − …”

Section: Introductionmentioning

confidence: 99%

Quasi-Static Self-Quenching of Trp-X and X-Trp Dipeptides in Water: Ultrafast Fluorescence Decay

Knutson

2009

J. Phys. Chem. B

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Time-resolved fluorescence decay profiles of N-acetyl-L-tryptophan-amide (NATA) and tryptophan (Trp) dipeptides of the form Trp-X and X-Trp, where X is another aminoacyl residue, have been investigated using an ultraviolet upconversion spectrophoto fluorometer with time resolution better than 350 fs, together with a time correlated single photon counting apparatus on the 100ps to 20ns time scale. We analyzed the set of fluorescence decay profiles at multiple wavelengths using the global analysis technique. Nanosecond fluorescence transients for Trp dipeptides all show multiexponential decay, while NATA exhibits a monoexponential decay near 3 ns independent of pH. In the first 100 ps, a time constant for the water “bulk relaxation” around Trp, NATA and Trp dipeptides is seen near 1-2 ps, with an associated preexponential amplitude that is positive or negative depending on emission wavelength, as expected for a population-conserving spectral shift. The initial brightness (sub-ps) we measure for all these dipeptides is less than that of NATA, implying even faster (<200fs) intra-molecular (quasi) static quenching occurs within them. A new, third, ultrafast decay, bearing an exponential time constant of 20-30 ps with positive amplitude, has been found in many of these dipeptides. We believe it verifies our previous predictions of dipeptide QSSQ (“quasi static self quenching”) –the loss of quantum yield to sub-100ps decay process (Chen et al., Biochemistry, 1991, 30, 5184). Most important, this term is found in proteins as well (J.A.C.S., 2006, 128, 1214; Biophysical Journal 2008, 94, 546; 2009, 96, 46a), suggesting an ultrafast quenching mechanism must be common to both.

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“…In recent years, chemists often explore the host-guest binding interaction of water-soluble calixarenes and amino acids in several aspects. The properties of amino acids have been studied by various methods such as spectrofluorometry, 19 1 H NMR spectroscopy, 20 microcalorimetry, 21 reverse-phase high-performance liquid chromatography, 22 voltammetry 23 and other electrochemical methods. [24][25][26][27] Tryptophan, as one of most basic amino acids, plays an important role in the growth, development, and metabolism of humans and animals and has been attracting much attention in medicine.…”

Section: Introductionmentioning

confidence: 99%

Supramolecular p-sulfonated calix[4,6,8]arene for tryptophan detection

et al. 2014

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Numerous techniques have focused on the ability of p-sulfonated calix[n]arene to form complexes with tryptophan. Scanning electron microscopy and Fourier transform infrared spectroscopy were utilized to study the organization and molecular structure of different layers of the electrode surface. Scanning electron microscopy results showed that SC4A displayed a cubic structure whereas SC6A and SC8A displayed dendrite structures. The electrochemical properties and potential complex formation between SCnA and tryptophan were characterized by cyclic voltammetry and electrochemical impedance spectroscopy. Cyclic voltammetry experiments showed that the gold electrode was successfully functionalized by self-assembled cysteamine and SC4A. Electrochemical impedance spectroscopy results showed the observation of the tryptophan-SCnA interaction and indicated that SC4A had the highest sensitivity to tryptophan and allowed 2.04 g L −1 tryptophan to be detected. Electrochemical impedance spectroscopy analysis and molecular modeling calculation confirmed that SC4A has higher tryptophan sensitivity than SC6A and SC8A.Résumé : De nombreuses techniques ont été axées sur la capacité des calix[n]arènes p-sulfonés à former des complexes avec le tryptophane. La microscopie électronique à balayage et la spectroscopie infrarouge à transformée de Fourier ont été utilisées pour étudier l'organisation et la structure moléculaire de différentes couches de la surface de l'électrode. Les résultats de la microscopie électronique à balayage ont montré que SC4A présentait une structure cubique alors que SC6A et SC8A possédaient des structures dendritiques. Les propriétés électrochimiques et la formation possible d'un complexe entre SCnA et le tryptophane ont été caracté-risées par voltammétrie cyclique et spectroscopie d'impédance électrochimique. Les expériences de voltammétrie cyclique ont montré que l'électrode en or était fonctionnalisée avec succès par autoassemblage de cystéamine et de SC4A. Les résultats de la spectroscopie d'impédance électrochimique ont permis d'observer l'interaction tryptophane-SCnA et ont révélé que SC4A avait une sensibilité élevée au tryptophane et qu'une concentration en tryptophane de 2,04 g L −1 pouvait être détectée de cette technique d'analyse. Les calculs de modélisation moléculaire et les résultats de la spectroscopie d'impédance électrochimique ont confirmé que SC4A présentait une plus grande sensibilité au tryptophane que SC6A et SC8A. [Traduit par la Rédaction] Mots-clés : spectroscopie infrarouge à transformée de Fourier, calculs de modélisation moléculaire, voltammétrie cyclique, spectroscopie d'impédance électrochimique, microscopie électronique à balayage.

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Interaction of water-soluble calix[4]arene with l-tryptophan studied by fluorescence spectroscopy

Cited by 13 publications

References 26 publications

Determination of Tryptophan using ap-Sulfonated Calix [4,6,8]arene Modified Gold Electrode

Determination of Tryptophan using ap-Sulfonated Calix [4,6,8]arene Modified Gold Electrode

Quasi-Static Self-Quenching of Trp-X and X-Trp Dipeptides in Water: Ultrafast Fluorescence Decay

Supramolecular p-sulfonated calix[4,6,8]arene for tryptophan detection

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