A unique boronic acid functionalized monolithic capillary for specific capture, separation and immobilization of cis-diol biomolecules

Liu, Yunchun; Ren, Lianbing; Liu, Zhen

doi:10.1039/c0cc05675h

Cited by 173 publications

(114 citation statements)

References 20 publications

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“…The relatively low recoveries of Pseu and C can be attributed to their super hydrophilic properties, which reduce their affinities toward boronate. 20 Therefore, Fe 3 O 4 @SiO 2 @PEI-FPBA can be applied to enrich the ribose conjugates for subsequent qualitative and quantitative analyses.…”

mentioning

confidence: 99%

Facile Synthesis of Boronate-Decorated Polyethyleneimine-Grafted Hybrid Magnetic Nanoparticles for the Highly Selective Enrichment of Modified Nucleosides and Ribosylated Metabolites

Shan

Qiao

et al. 2013

Anal. Chem.

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Ribosylated metabolites, especially modified nucleosides, have been extensively evaluated as cancer-related biomarkers. Boronate adsorbents are considered to be promising materials for extracting them from complex matrices. However, the enrichment of ribosylated metabolites in low abundance is still a challenge due to the limited capacity and selectivity of the existing boronate adsorbents. In this study, a novel type of magnetic nanoparticles named Fe 3 O 4 @ SiO 2 @PEI-FPBA was synthesized by grafting polyethyleneimine (PEI) onto the surface of Fe 3 O 4 @SiO 2 before modification by boronate groups. The high density of the amino groups on the PEI chains supplied a large number of binding sites for boronate groups. Thus, the adsorption capacity (1.34 ± 0.024 mg/g) of the nanoparticles, which is 6-to 7-fold higher than that of analogous materials, was greatly improved. The unreacted secondary amines and tertiary amines of the PEI enhanced the aqueous solubility of the nanoparticles, which could efficiently reduce nonspecific adsorption. The nanoparticles were able to capture 1,2 cis-diol nucleosides from 1000-fold interferences. Moreover, the flexible chains of PEI were favorable for effective enrichment and quick equilibration (<2 min). Finally, 60 ribose conjugates were enriched from human urine using the nanoparticles. Among them, 43 were identified to be nucleosides and other ribosylated metabolites. Nine low abundance modified nucleosides were detected for the first time. In conclusion, Fe 3 O 4 @SiO 2 @PEI-FPBA is an attractive candidate material for the highly selective enrichment of 1,2-cis-diol compounds.R ibonucleic acids (RNA) play crucial roles in many fundamental bioprocesses, and modifications in their bases or ribose are closely correlated with bioactivity. 1 Ribonucleosides as end products directly reflect the degradation rate of the RNA. Due to the lack of phosphorylases in cells, modified nucleosides cannot be reused as normal nucleosides for RNA synthesis and are thus excreted from the cell into the biofluids. 2 In tumor cells, the impaired tRNA metabolism usually leads to abnormal levels of modified nucleosides. 3 Therefore, modified nucleosides have been extensively studied in the search for cancer-related biomarkers. 4−6 Previous research has focused mainly on the detection of several common modified nucleosides in urine through chromatography or capillary electrophoresis coupled with mass spectrometry (MS) or UV detection. 7−11 Detection of potentially unknown modified nucleosides is significant for discovering new cancer biomarkers. However, the low concentrations and serious matrix interferences in the biological samples set great obstacles for their detection. Therefore, appropriate pretreatment approaches are necessary for the comprehensive analysis of nucleosides.Online solid phase extraction (SPE) purification by aprotic boronic acid chromatography (ApBAC) encounters an incompatibility issue between the loading solvents and the separation solvents. 12,13 For offline purif...

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confidence: 99%

Facile Synthesis of Boronate-Decorated Polyethyleneimine-Grafted Hybrid Magnetic Nanoparticles for the Highly Selective Enrichment of Modified Nucleosides and Ribosylated Metabolites

Shan

Qiao

et al. 2013

Anal. Chem.

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“…Boronic acid functionalized monoliths have recently gained rising attentions [30][31][32][33][34][35][36][37][38][39][40][41][42][43][44][45][46], and a lots of attempts have been made to design boronate affinity monolith with desired properties for glycoproteomic researches. A variety of boronate affinity monoliths have been developed for specific capture of glycopeptides and glycoproteins [38][39][40][41][42][43][44].…”

Section: Introductionmentioning

confidence: 99%

“…A variety of boronate affinity monoliths have been developed for specific capture of glycopeptides and glycoproteins [38][39][40][41][42][43][44]. Different from regular polymer-based boronate affinity monoliths, an inorganic-organic hybrid boronate affinity monolith synthesized via a "one-pot" process was brought into sight by Lin [44], and the monolith was successfully applied to isolation and enrichment of glycoproteins.…”

Section: Introductionmentioning

confidence: 99%

“…A lowered binding pH not only is favorable for protecting the hybrid monolith, but also can avoid the risk of protein degradation when applied monolith to separations of glycoproteins. A number of strategies have been proposed to reduce the binding pH [34,35,41,42], and the resulted boronate affinity monoliths exhibit excellent specificity toward cis-diol-containing biomolecules under neutral conditions. A hybrid boronate affinity monolith was subsequently reported by Liu [45], which exhibited selectivity of cis-diol containing compounds under neutral pH conditions.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of boronate-silica hybrid affinity monolith via a one-pot process for specific capture of glycoproteins at neutral conditions

Yang

Mao

et al. 2013

Anal Bioanal Chem

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In this study, a boronate-silica hybrid affinity monolith was prepared for specific capture of glycoproteins at neutral pH condition. The monolith was synthesized via a facile one-pot procedure in a stainless steel column by concurrently mixing hydrolyzed alkoxysilanes tetramethoxysilane and vinyltrimethoxysilane, organic monomer 3-acrylamidophenylboronic acid and initiator 2,2′-azobisisobutyronitrile together. The polycondensation of alkoxysilanes and copolymerization of organic monomer and vinyl-silica monolith were carried out successively by reacting at different temperatures. After optimizing the preparation conditions, the resulting hybrid affinity monolith was systematically characterized and exhibited excellent affinity to both cis-diol-containing small molecules and glycoproteins at neutral and physiological pH, including adenosine, horseradish peroxidase, transferrin and ovalbumin. The binding capacity of ovalbumin on monolith was measured to be 2.5 mg g −1 at pH 7.0. Furthermore, the hybrid affinity monolith was applied to the separation of transferrin from bovine serum sample at a physiological condition. Good repeatability was obtained and the relative standard deviations of retention time were 1.15 and 4.77 % (n=5) for run-torun and column-to-column, respectively.

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“…The majority of the reported monolithic columns for separation and analysis of glycans are organic polymer-based [82][83][84][85][86][87]89,90,[92][93][94][95][97][98][99][100][101][102][103][104][107][108][109][110][111][112]114,115,[118][119][120][121]123,[144][145][146]. This may be due to the straightforward approach in the preparation and the availability of a variety of functional monomers to obtain desired functionality of the surface.…”

Section: Monolithic Columns Can Easily Be Prepared In-situmentioning

confidence: 99%

Development of Monolithic Column Materials for the Separation and Analysis of Glycans

Alla

Stine

2015

Chromatography

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Monolithic column materials offer great advantages as chromatographic media in bioseparations and as solid-supports in biocatalysis. These single-piece porous materials have an interconnected ligament structure that limits the void volume inside the column, thus increasing the efficiency without sacrificing the permeability. The preparation of monolithic materials is easy, reproducible and has available a wide range of chemistries to utilize. Complex, heterogeneous and isobaric glycan structures require preparation methods that may include glycan release, separation and enrichment prior to a comprehensive and site-specific glycosylation analysis. Monolithic column materials aid that demand, as shown by the results reported by the research works presented in this review. These works include selective capture of glycans and glycoproteins via their interactions with lectins, boronic acids, hydrophobic, and hydrophilic/polar functional groups on monolith surfaces. It also includes immobilization of enzymes trypsin and PNGase F on monoliths to digest and deglycosylate glycoproteins and glycopeptides, respectively. The use of monolithic capillary columns for glycan separations through nano-liquid chromatography (nano-LC) and capillary electrochromatography (CEC) and coupling these columns to MS instruments to create multidimensional systems show the potential in the development of miniaturized, high-throughput and automated systems of glycan separation and analysis.

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A unique boronic acid functionalized monolithic capillary for specific capture, separation and immobilization of cis-diol biomolecules

Abstract: We report a sulfonyl substituted phenylboronic acid containing monolith capillary that exhibited not only a strong boronate affinity at neutral pH but also secondary separation capability to cis-diol biomolecules.

Cited by 173 publications

References 20 publications

Facile Synthesis of Boronate-Decorated Polyethyleneimine-Grafted Hybrid Magnetic Nanoparticles for the Highly Selective Enrichment of Modified Nucleosides and Ribosylated Metabolites

Facile Synthesis of Boronate-Decorated Polyethyleneimine-Grafted Hybrid Magnetic Nanoparticles for the Highly Selective Enrichment of Modified Nucleosides and Ribosylated Metabolites

Synthesis of boronate-silica hybrid affinity monolith via a one-pot process for specific capture of glycoproteins at neutral conditions

Development of Monolithic Column Materials for the Separation and Analysis of Glycans

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