Determination of p-aminohippuric acid with β-cyclodextrin sensitized fluorescence spectrometry

Alremeithi, Rashed H.; Meetani, Mohammed A.; Mousa, Muath; Saleh, Na’il; Graham, John

doi:10.1039/c6ra11742b

Cited by 8 publications

(11 citation statements)

References 23 publications

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“…Several reports have suggested the formation of 1:2 host–guest inclusion complexes with β‐CD [37–39]. Thus, hydrophobic methylated β‐CD moieties can form a relatively stable complex with phenyl groups on the surface of the stationary phase in a phenyl column to permit the column to act as a permanent methylated β‐CD‐coated chiral column.…”

Section: Resultsmentioning

confidence: 99%

Enantioseparation of phenethylamines by using high‐performance liquid chromatography column permanently coated with methylated β‐cyclodextrin

Terashima¹,

Yamamoto

Aizawa

et al. 2021

J of Separation Science

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Cyclodextrins and their derivatives have been used for chiral high‐performance liquid chromatography selectors, while they are costly to use as mobile phase additives in high‐performance liquid chromatography. Here, we report application of phenyl column coated permanently with methylated β‐cyclodextrin for chiral high‐performance liquid chromatography. A 0.1% (v/v) phosphoric acid solution containing 1 M NaCl and 0.5% (w/v) methylated β‐cyclodextrin was subjected to a phenyl column at a flow rate of 0.5 mL/min at 30°C for 2 h. Using the precoating phenyl column, all the enantiomers of the four phenethylamines (norepinephrine, epinephrine, octopamine, and synephrine) were successfully separated simultaneously by high‐performance liquid chromatography with a mobile phase without methylated β‐cyclodextrin at a flow rate of 0.2 mL/min at 30°C. The enantioseparation ability was retained for successive analyses during 1 week. It is suggested that inclusion complex of methylated β‐cyclodextrin with a phenyl group on the surface of the stationary phase could be formed and that the inclusion complex could form the ternary complex with the injected analytes. The longer retention time of (S)‐enantiomers of analytes than corresponding (R)‐enantiomers for high‐performance liquid chromatography could be explained from the higher stability of the methylated β‐cyclodextrin complexes with (S)‐enantiomers, which were confirmed by capillary electrophoresis and 1H NMR spectroscopy experiments.

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Section: Resultsmentioning

confidence: 99%

Enantioseparation of phenethylamines by using high‐performance liquid chromatography column permanently coated with methylated β‐cyclodextrin

Terashima¹,

Yamamoto

Aizawa

et al. 2021

J of Separation Science

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“…They concluded that the excimer fluorescence was attributed to formation of the 1:2 β‐CD‐drug inclusion complex. Alremeithi et al determined p ‐aminohippuric acid with β‐CD by sensitized fluorescence spectrometry 34 . The 1:2 host‐guest inclusion between β‐CD and p ‐aminohippuric acid became evident by mass spectrometry and density functional theory calculations that supported the formation of an excimer state at 355 nm.…”

Section: Resultsmentioning

confidence: 99%

“…Thus, HP‐β‐CD may form a complex with phenyl groups on the surface of the stationary phase in the column to allow a phenyl column to act as a transient chiral column. When mandelic acid was injected in the phenyl column, the ternary complex could be formed by aggregation of a phenyl group on the stationary phase, HP‐β‐CD, and a phenyl group of mandelic acid as the β‐CD inclusion complexes with two guest molecules having a phenyl group were reported 34,35 . The longer retention time for D‐mandelic acid in the chromatographic process suggests that the ternary inclusion complex with D‐mandelic acid was more stable than that with L‐mandelic acid.…”

Section: Resultsmentioning

confidence: 99%

“…Alremeithi et al determined p-aminohippuric acid with β-CD by sensitized fluorescence spectrometry. 34 The 1:2 host-guest inclusion between β-CD and p-aminohippuric acid became evident by mass spectrometry and density functional theory calculations that supported the formation of an excimer state at 355 nm. Recently, Yildiz et al has studied complexation of cinnamaldehyde with HP-β-CD and HPγ-CD and suggested formation of the 1:1 and 1:2 CDcinnamaldehyde inclusion complexes by computational molecular modeling.…”

Section: The Possible Mechanism For Enantioseparation Of Mandelic Acid By Using Phenyl Column and Hp-β-cd As A Selectormentioning

confidence: 99%

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Direct enantioseparation of mandelic acid by high‐performance liquid chromatography using a phenyl column precoated with a small amount of cyclodextrin additive in a mobile phase

et al. 2020

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Direct enantioseparation of mandelic acid by high‐performance liquid chromatography (HPLC) with a reversed phase column and a mobile phase containing a small amount of hydroxylpropyl‐β‐cyclodextrin (HP‐β‐CD) was studied as an efficient method for saving consumption of the CD additive. As a result, it was proposed that racemic mandelic acid can be analyzed with a phenyl column by using a mobile phase composed of 10 mM ammonium acetate buffer (pH 4.2) and 0.02% (w/v) HP‐β‐CD at a flow rate of 1.0 mL/min at 40°C after the passage of 10 mM ammonium acetate buffer (pH 4.2) containing 0.1% (w/v) HP‐β‐CD as a precoating mobile phase for 60 min. It is suggested that HP‐β‐CD is bound with a phenyl group on the surface of the stationary phase to allow a phenyl column to act as a transient chiral column, and injected mandelic acid can form the ternary complex with the adsorbed HP‐β‐CD. The longer retention time of D‐mandelic acid than the L‐isomer for HPLC can be explained from the higher stability of the HP‐β‐CD complex with D‐mandelic acid, which was confirmed by CE experiment with HP‐β‐CD as a selector. The efficiency of a phenyl column compared with other stationary phases was also discussed.

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“…Formation of an inclusion complex between host and guest moieties significantly alters the solubility , and spectral properties , of the hydrophobic guest molecules. Considerable attention has been paid on the use of CDs as a means of improving aqueous solubility and spectrofluorometric methods for the identification of various analytes .…”

Section: Introductionmentioning

confidence: 99%

Supramolecular Interaction-Assisted Fluorescence and Tunable Stimuli-Responsiveness of l-Phenylalanine-Based Polymers

et al. 2017

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Supramolecular host-guest interactions between randomly methylated β-cyclodextrin (RM β-CD) and side-chain phenylalanine (Phe) and Phe-Phe dipeptide-based homopolymers have been employed for the amplification of fluorescence emission of otherwise weakly fluorescent amino acid Phe. The host-guest complex has been characterized by H andC NMR spectroscopy, two-dimensional rotating-frame overhauser spectroscopy, Fourier-transform infrared spectroscopy, UV-visible spectroscopy, and fluorescence spectroscopy. To gain insights into the origin of fluorescence in homopolymers, density functional theory calculations were performed where phenyl moieties inside the less polar core of β-CD were observed to form a π-π coupled complex resulting in an enhanced emission. Furthermore, the complex-forming ability of Phe, the guest molecule, has been employed in tuning the cloud point temperature (T) of statistical copolymers derived from side-chain Phe/Phe-Phe-based methacrylate monomers and N-isopropylacrylamide. By varying the co-monomer feed ratios in the statistical copolymer and hence the concentration of RM β-CD throughout the polymer chain, host-guest interaction-assisted broad tunability in T of the supramolecular polymeric complex has been achieved.

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Determination of p-aminohippuric acid with β-cyclodextrin sensitized fluorescence spectrometry

Abstract: Sensitive spectrofluorometric and HPLC with fluorescence detection methods have been developed for detection and determination of para-aminohippuric acid (a marker used for estimating effective renal plasma flow) in the presence of β-cyclodextrin.

Cited by 8 publications

References 23 publications

Enantioseparation of phenethylamines by using high‐performance liquid chromatography column permanently coated with methylated β‐cyclodextrin

Enantioseparation of phenethylamines by using high‐performance liquid chromatography column permanently coated with methylated β‐cyclodextrin

Direct enantioseparation of mandelic acid by high‐performance liquid chromatography using a phenyl column precoated with a small amount of cyclodextrin additive in a mobile phase

Supramolecular Interaction-Assisted Fluorescence and Tunable Stimuli-Responsiveness of l-Phenylalanine-Based Polymers

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