Fluorescence quenching method for the determination of carbazochrome sodium sulfonate with aromatic amino acids

Gan, Xin; Liu, Shaopu; Liu, Zhongfang; Hu, Xiaoli; Tian, Jing; Xue, Jia-Xing

doi:10.1002/bio.2375

Cited by 16 publications

(4 citation statements)

References 6 publications

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“…In order to determine the π–π stacking between PEG-PTyr and mRNA in the micelles, we investigated the fluorescence quenching of Tyr moieties in the polymer. Tyr groups have intrinsic fluorescence (λex ~280 nm, λem ~350 nm), and π–π stacking can quench the fluorescence by electron transfer [ 33 , 34 ]. Thus, we investigated the change of fluorescence signal from the Tyr groups of PEG-PGTyr polymers after forming micelles with mRNA.…”

Section: Resultsmentioning

confidence: 99%

Block catiomers with flanking hydrolyzable tyrosinate groups enhance in vivo mRNA delivery via π–π stacking-assisted micellar assembly

Yang

Miyazaki

Nakagawa

et al. 2023

Science and Technology of Advanced Materials

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Messenger RNA (mRNA) therapeutics have recently demonstrated high clinical potential with the accelerated approval of SARS-CoV-2 vaccines. To fulfill the promise of unprecedented mRNA-based treatments, the development of safe and efficient carriers is still necessary to achieve effective delivery of mRNA. Herein, we prepared mRNA-loaded nanocarriers for enhanced in vivo delivery using biocompatible block copolymers having functional amino acid moieties for tunable interaction with mRNA. The block copolymers were based on flexible poly(ethylene glycol)-poly(glycerol) (PEG-PG) modified with glycine (Gly), leucine (Leu) or tyrosine (Tyr) via ester bonds to generate block catiomers. Moreover, the amino acids can be gradually detached from the block copolymers after ester bond hydrolyzation, avoiding cytotoxic effects. When mixed with mRNA, the block catiomers formed narrowly distributed polymeric micelles with high stability and enhanced delivery efficiency. Particularly, the micelles based on tyrosine-modified PEG-PG (PEG-PGTyr), which formed a polyion complex (PIC) and π–π stacking with mRNA, displayed excellent stability against polyanions and promoted mRNA integrity in serum. PEG-PGTyr-based micelles also increased the cellular uptake and the endosomal escape, promoting high protein expression both in vitro and in vivo . Furthermore, the PEG-PGTyr-based micelles significantly extended the half-life of the loaded mRNA after intravenous injection. Our results highlight the potential of PEG-PGTyr-based micelles as safe and effective carriers for mRNA, expediting the rational design of polymeric materials for enhanced mRNA delivery.

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Section: Resultsmentioning

confidence: 99%

Block catiomers with flanking hydrolyzable tyrosinate groups enhance in vivo mRNA delivery via π–π stacking-assisted micellar assembly

Yang

Miyazaki

Nakagawa

et al. 2023

Science and Technology of Advanced Materials

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“…At shorter wavelengths, specifically 278 and 262 nm, Tyr and Phe are also excited. 19 It has also been shown that Tyr fluorescence overlaps with Trp fluorescence at the excitation wavelength of 275 nm. 20 Furthermore, the excitation wavelength of NPX is located around 270 nm 21 , 22 and it is clear that the fluorescence of NPX alone is too strong at shorter wavelengths.…”

Section: Methodsmentioning

confidence: 98%

“…The BSA concentration is 5.0 μM for all samples. At shorter wavelengths, specifically 278 and 262 nm, Tyr and Phe are also excited . It has also been shown that Tyr fluorescence overlaps with Trp fluorescence at the excitation wavelength of 275 nm .…”

Section: Methodsmentioning

confidence: 99%

Propionic Acid Groups and Multiple Aromatic Rings Induce Binding of Ketoprofen and Naproxen to the Hydrophobic Core of Bovine Serum Albumin

Tsurushima,

Kurosawa,

Goto

2023

Mol. Pharmaceutics

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Ketoprofen (KP), which causes photosensitivity by interacting with serum albumin (SA), and three drugs, ibuprofen (IBP), naproxen (NPX), and diazepam (DZP), which share the same binding site, were investigated for their interaction with bovine SA (BSA). For KP, DZP, and IBP, where drugconcentration-dependent quenching of BSA-intrinsic fluorescence was observed, a modified Stern−Volmer plot showed that dynamic quenching was dominant for KP and static quenching was dominant for DZP and IBP. However, this alone cannot be compared with NPX. Therefore, by performing singular value decomposition (SVD) fluorescence spectroscopy, we were able to find the behavior of the drug-concentration-dependent Langmuir-type principal component vectors. K SVD obtained by the Langmuir equation showed a high correlation with the static extinction constant V. Therefore, K SVD indicates the association constant of the drug with BSA and it was found that NPX and IBP had higher values than KP. Finally, in the analysis of the temperature factors of amino acid residues in each drug-binding region and Trp residues, KP and NPX significantly reduced these temperature factors whereas DZP and IBP hardly changed them. This result is consistent with the dynamic and static quenching dominance in the total quenching mechanism. Summarizing the results so far, it was shown that penetration into the hydrophobic core inside BSA can be achieved not only by one of the multiple aromatic rings and propionic acid groups but also by the joint effect of both. In this study, SVD enabled us to extract information on drug adsorption to BSA from fluorescence spectra. Furthermore, the application of SVD is expected to make it possible to perform fluorescence analysis for drug binding to proteins without being limited by the fluorescence properties of the drug.

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“…As an aromatic amino acid, L-tyrosine produces endogenous fluorescence. Furthermore, L-tyrosine fluorescence quenching has previously been used in quantitative analysis [25,26].…”

mentioning

confidence: 99%

Environmentally friendly protocol for the determination of sitagliptin phosphate in pharmaceutical preparations and biological fluids using l‐tyrosine as a fluorescence probe

2023

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A responsive spectrofluorimetric method was developed for the determination of sitagliptin phosphate using L‐tyrosine as a fluorescence probe. The fluorescence intensity of L‐tyrosine was quenched with sitagliptin phosphate. The fluorescence intensity was recorded at 307 nm using a 272 nm excitation wavelength. The calibration plot between fluorescence intensity and the concentration of drug was liner in the range of 0.1 to 2.0 mM with a good correlation value of 0.997. The limit of detection and quantification were established to be 3.7 × 10‐4 and 1.23 × 10‐3 mM, respectively. Commonly used excipients did not interfere with sitagliptin phosphate measurement. The proposed method was used to measure the sitagliptin phosphate in its standard type, dosage form, and biological samples. The percent recovery were ranged from 97.41–103.36 %. The static quenching was shown to be responsible for quenching as indicated by the Stern–Volmer plot. The method was validated usin ICH guidelines and profitably applied for the content uniformity test, ensuing in a high percent recovery and small relative standard deviation. The proposed approach is effortless, susceptible, selective, economic, and provides a high precision and accuracy, and can be used to determine sitagliptin phosphate in pharmaceutical industry.

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Fluorescence quenching method for the determination of carbazochrome sodium sulfonate with aromatic amino acids

Cited by 16 publications

References 6 publications

Block catiomers with flanking hydrolyzable tyrosinate groups enhance in vivo mRNA delivery via π–π stacking-assisted micellar assembly

Block catiomers with flanking hydrolyzable tyrosinate groups enhance in vivo mRNA delivery via π–π stacking-assisted micellar assembly

Propionic Acid Groups and Multiple Aromatic Rings Induce Binding of Ketoprofen and Naproxen to the Hydrophobic Core of Bovine Serum Albumin

Environmentally friendly protocol for the determination of sitagliptin phosphate in pharmaceutical preparations and biological fluids using l‐tyrosine as a fluorescence probe

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