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1.
Environ Sci Pollut Res Int ; 31(22): 32664-32679, 2024 May.
Article in English | MEDLINE | ID: mdl-38658512

ABSTRACT

The adsorption property of the costless green cellulose acetate (CA) was boosted by the dual modifications: inner modification by incorporating carboxylated graphene oxide (COOH-GO) into the CA spheres and outer modification by the surface modification of the COOH-GO@CA spheres by iminodiacetic acid (IDA) for removing Pb(II). The adsorption experiments of the Pb(II) proceeded in a batch mode to evaluate the adsorption property of the COOH-GO@CA@IDA spheres. The maximal Pb(II) adsorption capacity attained 613.30 mg/g within 90 min at pH = 5. The removal of Pb(II) reached its equilibrium within 20 min, and the removal % was almost 100% after 30 min at the low Pb(II) concentration. The Pb(II) adsorption mechanism was proposed according to the kinetics and isotherms studies; in addition, the zeta potential (ZP) measurements and X-ray Photoelectron Spectroscopy (XPS) analysis defined the adsorption pathways. By comparing the XPS spectra of the authentic and used COOH-GO@CA@IDA, it was deduced that the contributed chemical adsorption pathways are Lewis acid-base, precipitation, and complexation. The zeta potential (ZP) measurements demonstrated the electrostatic interaction participation in adsorbing the cationic Pb(II) species onto the negatively charged spheres (ZP = 14.2 mV at pH = 5). The unique channel-like pores of the COOH-GO@CA@IDA spheres suggested the pore-filling mechanism of Pb(II). The promising adsorption results and the superb recyclability character of COOH-GO@CA@IDA enable it to extend of the bench scale to the industrial scale.


Subject(s)
Cellulose , Graphite , Imino Acids , Lead , Graphite/chemistry , Lead/chemistry , Adsorption , Cellulose/chemistry , Cellulose/analogs & derivatives , Imino Acids/chemistry , Porosity , Kinetics
2.
Chemistry ; 30(33): e202400680, 2024 Jun 12.
Article in English | MEDLINE | ID: mdl-38593232

ABSTRACT

Supramolecular metallogels combine the rheological properties of gels with the color, magnetism, and other properties of metal ions. Lanthanide ions such as Eu(III) can be valuable components of metallogels due to their fascinating luminescence. In this work, we combine Eu(III) and iminodiacetic acid (IDA) into luminescent hydrogels. We investigate the tailoring of the rheological properties of these gels by changes in their metal:ligand ratio. Further, we use the highly sensitive Eu(III) luminescence to obtain information about the chemical structure of the materials. In special, we take advantage of computational calculations to employ an indirect method for structural elucidation, in which the simulated luminescent properties of candidate structures are matched to the experimental data. With this strategy, we can propose molecular structures for different EuIDA gels. We also explore the usage of these gels for the loading of bioactive molecules such as OXA, observing that its aldose reductase activity remains present in the gel. We envision that the findings from this work could inspire the development of luminescent hydrogels with tunable rheology for applications such as 3D printing and imaging-guided drug delivery platforms. Finally, Eu(III) emission-based structural elucidation could be a powerful tool in the characterization of advanced materials.


Subject(s)
Europium , Hydrogels , Europium/chemistry , Hydrogels/chemistry , Luminescence , Imino Acids/chemistry , Rheology , Luminescent Agents/chemistry , Ligands , Gels/chemistry
3.
Water Sci Technol ; 89(8): 2132-2148, 2024 Apr.
Article in English | MEDLINE | ID: mdl-38678414

ABSTRACT

Given the substantial environmental pollution from industrial expansion, environmental protection has become particularly important. Nowadays, anion exchange membranes (AEMs) are widely used in wastewater treatment. With the use of polyvinyl alcohol (PVA), ethylene-vinyl alcohol (EVOH) copolymer, and methyl iminodiacetic acid (MIDA), a series of cross-linked AEMs were successfully prepared using the solvent casting technique, and the network structure was formed in the membranes due to the cross-linking reaction between PVA/EVOH and MIDA. Fourier transform infrared spectrometer, X-ray photoelectron spectroscopy, scanning electron microscopy, and transmission electron microscopy were used to analyze the prepared membranes. At the same time, its comprehensive properties which include water uptake, linear expansion rate, ion exchange capacity, thermal stability, chemical stability, and mechanical stability were thoroughly researched. In addition, diffusion dialysis performance in practical applications was also studied in detail. The acid dialysis coefficient (UH+) ranged from 10.2 to 35.6 × 10-3 m/h. Separation factor (S) value ranged from 25 to 38, which were all larger than that of the commercial membrane DF-120 (UH+: 8.5 × 10-3 m/h, S: 18.5). The prepared membranes had potential application value in acid recovery.


Subject(s)
Membranes, Artificial , Polyvinyl Alcohol , Polyvinyl Alcohol/chemistry , Imino Acids/chemistry , Diffusion , Water Purification/methods , Dialysis/methods , Ion Exchange , Anions/chemistry , Polyvinyls/chemistry
4.
Chem Commun (Camb) ; 58(96): 13298-13316, 2022 Dec 01.
Article in English | MEDLINE | ID: mdl-36382511

ABSTRACT

Organoboron compounds have a wide-range of applications in synthetic methodologies, natural products, and bioactive molecule synthesis. The sensitivity of boronic acid toward most synthetic reagents makes it necessary to introduce a protecting group before its utilization. Benchtop stable MIDA boronates have been found compatible with various common synthetic reagents which opens the doors for the synthesis of various small building blocks, natural products, and bioactive compounds. MIDA boronate compounds have been extensively utilized in Suzuki Miyaura coupling and Iterative cross-coupling reactions for the total synthesis of bioactive molecules and polymerization reactions. Different MIDA boronate compounds like vinyl, acyl, formyl, acrylic, and α-carbonyl MIDA boronates also act as novel synthetic building blocks for various synthetic transformations in organic synthesis. This paper summarizes the importance of MIDA boronate compounds in various aspects of organic chemistry.


Subject(s)
Biological Products , Imino Acids , Imino Acids/chemistry , Boronic Acids/chemistry , Chemistry Techniques, Synthetic
5.
Amino Acids ; 54(5): 687-719, 2022 May.
Article in English | MEDLINE | ID: mdl-35192062

ABSTRACT

Naturally occurring secondary amino acids, with proline as the main representative, contain an alpha-imino group in a cycle that is typically four-, five-, and six-membered. The unique ring structure exhibits exceptional properties-conformational rigidity, chemical stability, and specific roles in protein structure and folding. Many proline analogues have been used as valuable compounds for the study of metabolism of both prokaryotic and eukaryotic cells and for the synthesis of compounds with desired biological, pharmaceutical, or industrial properties. The D-forms of secondary amino acids play different roles in living organisms than the L-forms. They have different metabolic pathways, biological, physiological, and pharmacological effects, they can be indicators of changes and also serve as biomarkers of diseases. In the scientific literature, the number of articles examining D-amino acids in biological samples is increasing. The review summarises information on the occurrence and importance of D- and L-secondary amino acids-azetidic acid, proline, hydroxyprolines, pipecolic, nipecotic, hydroxypipecolic acids and related peptides containing these D-AAs, as well as the main analytical methods (mostly chromatographic) used for their enantiomeric determination in different matrices (biological samples, plants, food, water, and soil).


Subject(s)
Amino Acids , Imino Acids , Amino Acids/chemistry , Imino Acids/chemistry , Peptides , Proline/chemistry , Stereoisomerism
6.
Mikrochim Acta ; 188(12): 417, 2021 11 11.
Article in English | MEDLINE | ID: mdl-34762162

ABSTRACT

A three-step strategy is introduced to develop inherent iminodiacetic (IDA)-functionalized nanopolymer. SEM micrographs show homogenous spherical beads with a particle size of 500 nm. Further modification to COOH-functionalized 1,2-epoxy-5-hexene/DVB mesoporous nanopolymer enriches glycopeptides via hydrophilic interactions followed by their MS determination. Significantly high BET surface area 433.4336 m2 g-1 contributes to the improved surface hydrophilicity which is also shown by high concentration of ionizable carboxylic acids, 14.59 ± 0.25 mmol g-1. Measured surface area is the highest among DVB-based polymers and in general much higher in comparison to the previously reported BET surface areas of co-polymers, terpolymers, MOFs, and graphene-based composites. Thirty-one, 19, and 16 N-glycopeptides are enriched/identified by nanopolymer beads from tryptic digests of immunoglobulin G, horseradish peroxidase, and chicken avidin, respectively, without additional desalting steps. Material exhibits high selectivity (1:400 IgG:BSA), sensitivity (down to 0.1 fmol), regeneration ability up to three cycles, and batch-to-batch reproducibility (RSD > 1%). Furthermore, from 1 µL of digested human serum, 343 N-glycopeptide characteristics of 134 glycoproteins including 30 FDA-approved serum biomarkers are identified via nano-LC-MS/MS. The developed strategy to self-generate IDA on polymeric surface with improved surface area, porosity, and ordered morphology is insignia of its potential as chromatographic tool contributing to future developments in large-scale biomedical glycoproteomics studies.


Subject(s)
Glycopeptides/chemistry , Imino Acids/chemistry , Nanostructures/chemistry , Polymers/chemistry , Humans , Hydrophobic and Hydrophilic Interactions , Microscopy, Electron, Scanning , Nanostructures/ultrastructure , Porosity , Surface Properties
7.
ChemMedChem ; 16(20): 3231-3235, 2021 10 15.
Article in English | MEDLINE | ID: mdl-34288492

ABSTRACT

Because some of the potentially most useful boronic acids are inherently unstable in blood plasma and exhibit poor selective retention in tumours, 2-heterocyclic N-methyliminodiacetic acid (MIDA) boronates provide a stable, spacious and highly effective harbor for prodrug conjugates. Herein we report MIDA boronates in conjunction with naphthalene-based fluorophores as suitable compounds for tumour diagnosis by virtue of their remarkable specificity and uniform benchtop stability. The shielding group was found to be effective at imparting stability under physiological conditions (pH 7.4), with rapid release of the drug upon exposure to the acidic microenvironment of the tumor. This approach significantly enhanced the efficiency of drug release and was found to exhibit fewer side effects, thus indicating its great potential for precision therapeutics.


Subject(s)
Antineoplastic Agents/pharmacology , Heterocyclic Compounds/pharmacology , Hydrogen Peroxide/chemistry , Imino Acids/pharmacology , Prodrugs/pharmacology , Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/chemistry , Cell Proliferation/drug effects , Cell Survival/drug effects , Dose-Response Relationship, Drug , Drug Screening Assays, Antitumor , HeLa Cells , Heterocyclic Compounds/chemistry , Humans , Imino Acids/chemistry , Molecular Structure , Naphthalenes/chemistry , Naphthalenes/pharmacology , Prodrugs/chemical synthesis , Prodrugs/chemistry , Structure-Activity Relationship
8.
Phys Chem Chem Phys ; 23(6): 3810-3819, 2021 Feb 19.
Article in English | MEDLINE | ID: mdl-33533341

ABSTRACT

Electron paramagnetic resonance (EPR) distance measurements are making increasingly important contributions to studies of biomolecules underpinning health and disease by providing highly accurate and precise geometric constraints. Combining double-histidine (dH) motifs with CuII spin labels shows promise for further increasing the precision of distance measurements, and for investigating subtle conformational changes. However, non-covalent coordination-based spin labelling is vulnerable to low binding affinity. Dissociation constants of dH motifs for CuII-nitrilotriacetic acid were previously investigated via relaxation induced dipolar modulation enhancement (RIDME), and demonstrated the feasibility of exploiting the dH motif for EPR applications at sub-µM protein concentrations. Herein, the feasibility of using modulation depth quantitation in CuII-CuII RIDME to simultaneously estimate a pair of non-identical independent KD values in such a tetra-histidine model protein is addressed. Furthermore, we develop a general speciation model to optimise CuII labelling efficiency, depending upon pairs of identical or disparate KD values and total CuII label concentration. We find the dissociation constant estimates are in excellent agreement with previously determined values, and empirical modulation depths support the proposed model.


Subject(s)
Bacterial Proteins/chemistry , Coordination Complexes/chemistry , Copper/chemistry , Histidine/chemistry , Spin Labels , Chelating Agents/chemistry , Electron Spin Resonance Spectroscopy , Imino Acids/chemistry , Models, Chemical , Nitrilotriacetic Acid/chemistry , Streptococcus/chemistry
9.
Amino Acids ; 53(3): 347-358, 2021 Mar.
Article in English | MEDLINE | ID: mdl-33586043

ABSTRACT

L-amino acids (L-AAs) play different important roles in the physiology of all living organisms. Their chiral counterparts, D-amino acids (D-AAs) are increasingly being recognized as essential molecules in many biological systems. Secondary amino acids with cyclic structures, such as prolines, exhibit conformational rigidity and thus unique properties in the structural and protein folding. Despite their widespread occurrence, much less attention was paid to their chiral analysis, particularly when the minor, typically D-enantiomer, is present in low amounts in a complex biological matrix. In this paper, a cost-effective, chiral GC-MS method is described for capillary Chirasil-L-Val separation of nine cyclic secondary amino acid enantiomers with four-, five-, and six-membered rings, involving azetidine-2-carboxylic acid, pipecolic acid, nipecotic acid, proline, isomeric cis/trans 3-hydroxy, 4-hydroxyproline, and cis/trans-5-hydroxy-L-pipecolic acid in the excess of its enantiomeric antipode. The sample preparation involves in-situ derivatization with heptafluorobutyl chloroformate, simultaneous liquid-liquid micro-extraction into isooctane followed by amidation of the arising low-polar derivatives with methylamine, an evaporation step, re-dissolution, and final GC-MS analysis. The developed method was used for analyses of human biofluids, biologically active peptides containing chiral proline constituents, and collagen.


Subject(s)
Fluorocarbons/chemistry , Formates/chemistry , Gas Chromatography-Mass Spectrometry/methods , Imino Acids/analysis , Methylamines/chemistry , Calibration , Gas Chromatography-Mass Spectrometry/standards , Humans , Imino Acids/chemistry , Reproducibility of Results , Stereoisomerism
10.
Chem Biol Drug Des ; 97(1): 134-147, 2021 01.
Article in English | MEDLINE | ID: mdl-32844569

ABSTRACT

Prodrugs are pharmacologically attenuated derivatives of drugs that undergo bioconversion into the active compound once reaching the targeted site, thereby maximizing their efficiency. This strategy has been implemented in pharmaceuticals to overcome obstacles related to absorption, distribution, and metabolism, as well as with intracellular dyes to ensure concentration within cells. In this study, we provide the first examples of a prodrug strategy that can be applied to simple phenolic antimicrobials to increase their potency against mature biofilms. The addition of (acetoxy)methyl iminodiacetate groups increases the otherwise modest potency of simple phenols. Biofilm-forming bacteria exhibit a heightened tolerance toward antimicrobial agents, thereby accentuating the need for new antibiotics as well as those, which incorporate novel delivery strategies to enhance activity toward biofilms.


Subject(s)
Anti-Infective Agents/pharmacology , Biofilms/drug effects , Imino Acids/chemistry , Phenols/chemistry , Prodrugs/pharmacology , Anti-Infective Agents/chemistry , Microbial Sensitivity Tests , Phenols/pharmacology , Prodrugs/chemistry , Pseudomonas aeruginosa/drug effects , Pseudomonas aeruginosa/physiology , Staphylococcus epidermidis/drug effects , Staphylococcus epidermidis/physiology , Structure-Activity Relationship
11.
J Chromatogr A ; 1633: 461649, 2020 Dec 06.
Article in English | MEDLINE | ID: mdl-33166743

ABSTRACT

Different degrees of protein purity have been observed in immobilized metal affinity chromatography ranging from extremely high purity to moderate and low purity. It has been hypothesized that the host cell protein composition and the metal ligands are factors governing the purity of a protein obtained after immobilized metal affinity chromatography (IMAC). Ni nitrilotriacetic acid (NTA) has become the first choice for facile His-tagged protein purification, but alternative ligands such as iminodiacetic acid (IDA) with other immobilized metal ions such as Zn, Cu and Co are valuable options when the expected purity or binding capacity is not reached. Especially Cu and Zn are very attractive, due to their reduced environmental and safety concerns compared to Ni. Co and Zn are more selective than Ni and Cu. This increased selectivity comes at the cost of weaker binding. In this work, the influence of ligand choice on protein purity after IMAC was evaluated by several methods, including peptide mapping. His-tagged GFP was used as model protein. We found that host cell protein (HCP) content varies drastically between ligands, as IDA eluates generally showing higher HCP concentrations than NTA. The relative content of the key amino acids His, Cys and Trp in the sequence of the co-eluted protein does not suffice to explain co-eluting propensity. The co-elution of HCPs is mostly influenced by metal binding clusters on the protein surface and not by total content or surface concentration of metal interacting amino acids. Prediction of co-elution is not dependent on these clusters alone, due to protein-protein interactions, indicted by a relative low metal binding cluster score but high co-elution propensity and in a lot of cases these proteins are often part of complex such as ribosome and chaperones. The different co-eluting proteins were presented by a heatmap with a dendrogram. Ward's linkage method was used to calculate the distance between groups of co-eluting proteins. Clustering of co-eluting HCPs was observed according to ligand and by metal ions, with Zn and Co forming one cluster and Ni and Cu another. The co-elution of host cell proteins can be explained by clusters of metal interacting amino acids on the protein surface and by protein-protein interactions. While Ni NTA still appears to be highly advantageous, it might not be the cure-all for all applications.


Subject(s)
Chromatography, Affinity , Ions/chemistry , Ligands , Metals/chemistry , Proteomics/methods , Imino Acids/chemistry , Nitrilotriacetic Acid/chemistry
12.
J Med Chem ; 63(20): 12116-12127, 2020 10 22.
Article in English | MEDLINE | ID: mdl-32940035

ABSTRACT

Immobilized metal-ion affinity chromatography (IMAC) used to purify recombinant proteins features a resin-bound 1:1 Ni(II)-iminodiacetic acid (IDA) complex. This hemi-saturated Ni(II)-IDA system containing exchangeable sites at the metal ion is re-cast as a surrogate of a coordinatively-unsaturated metalloenzyme active site, with utility for selecting compounds with metal-binding groups from mixtures as potential metalloenzyme inhibitors. Exchanging Ni(II) for other metal ions could broaden the scope of metalloenzyme target. This work examined the performance of Cu(II)-, Fe(III)-, Ga(III)-, Ni(II)-, or Zn(II)-IMAC resins to reversibly bind experimental or clinical metalloenzyme inhibitors of Zn(II)-ACE1, Zn(II)-HDAC, Fe(II)/(III)-5-LO or Cu(II)-tyrosinase from a curated mixture (1-17). Each IMAC system gave a distinct selection profile. The Zn(II)-IMAC system selectively bound the thiol-containing Zn(II)-ACE1 inhibitors captopril and omapatrilat, and the Fe(III)-IMAC system selectively bound the Fe(II)/(III)-5-LO inhibitor licofelone, demonstrating a remarkable IMAC-metalloenzyme metal ion match. IMAC provides a simple, water-compatible platform, which could accelerate metalloenzyme inhibitor discovery.


Subject(s)
Coordination Complexes/pharmacology , Drug Discovery , Imino Acids/pharmacology , Metalloproteins/antagonists & inhibitors , Metals, Heavy/pharmacology , Chromatography, Affinity , Coordination Complexes/chemical synthesis , Coordination Complexes/chemistry , Crystallography, X-Ray , Dose-Response Relationship, Drug , Humans , Imino Acids/chemistry , Metalloproteins/metabolism , Metals, Heavy/chemistry , Models, Molecular , Molecular Structure , Structure-Activity Relationship
13.
Mikrochim Acta ; 187(8): 472, 2020 07 29.
Article in English | MEDLINE | ID: mdl-32725323

ABSTRACT

An immobilized metal affinity (IMA) adsorbent was prepared by grafting bottlebrush polymer pendant with iminodiacetic acid (IDA) from the surface of polydopamine (PDA)-coated magnetic graphene oxide (magGO), via surface-initiated atom transfer radical polymerization (SI-ATRP). Poly(hydroxyethyl methacrylate) (PHEMA) was grafted firstly from the PDA-coated magGO as the backbone, and then poly(glycidyl methacrylate) was grafted from the PHEMA chains via the second SI-ATRP to afford the bottlebrush polymer-grafted magGO Thereafter, IDA was anchored on the nanocomposites to produce the IMA adsorbent after chelating copper ions. The adsorbent was characterized by various physical and physicochemical methods. Its adsorption properties were evaluated by using histidine-rich proteins (bovine hemoglobin, BHb) and other proteins (lysozyme and cytochrome-C). The results show that its maximum adsorption capacity to BHb was 378.6 mg g-1, and the adsorption equilibrium can be quickly reached within 1 h. The adsorbent has excellent reproducibility and reusability. It has been applied to selectively purify hemoglobin from human whole blood, indicating its potential in practical applications. Graphical abstract.


Subject(s)
Graphite/chemistry , Hemoglobins/isolation & purification , Adsorption , Animals , Cattle , Copper/chemistry , Humans , Imino Acids/chemistry , Indoles/chemistry , Liquid-Liquid Extraction/methods , Magnetic Phenomena , Polyhydroxyethyl Methacrylate/chemistry , Polymers/chemistry , Polymethacrylic Acids/chemistry , Reproducibility of Results
14.
ChemMedChem ; 15(14): 1272-1282, 2020 07 20.
Article in English | MEDLINE | ID: mdl-32315115

ABSTRACT

The fungal natural product aspergillomarasmine A (AMA) has been identified as a noncompetitive inhibitor of New Delhi metallo-ß-lactamase-1 (NDM-1) that inhibits by removing ZnII from the active-site. The nonselective metal-chelating properties and difficult synthesis and derivatization of AMA have hindered the development of this scaffold into a potent and selective inhibitor of NDM-1. Iminodiacetic acid (IDA) has been identified as the metal-binding pharmacophore (MBP) core of AMA that can be leveraged for inhibitor development. Herein, we report the use of IDA for fragment-based drug discovery (FBDD) of NDM-1 inhibitors. IDA (IC50 =120 µM) was developed into inhibitor 23 f (IC50 =8.6 µM, Ki =2.6 µM), which formed a ternary complex with NDM-1, as evidenced by protein thermal-shift and native-state electrospray ionization mass spectrometry (ESI-MS) experiments. Combining mechanistic analysis with inhibitor derivatization, the use of IDA as an alternative AMA scaffold for NDM-1 inhibitor development is detailed.


Subject(s)
Coordination Complexes/pharmacology , Imino Acids/pharmacology , Zinc/pharmacology , beta-Lactamase Inhibitors/pharmacology , beta-Lactamases/metabolism , Coordination Complexes/chemical synthesis , Coordination Complexes/chemistry , Dose-Response Relationship, Drug , Humans , Imino Acids/chemical synthesis , Imino Acids/chemistry , Molecular Structure , Structure-Activity Relationship , Zinc/chemistry , beta-Lactamase Inhibitors/chemical synthesis , beta-Lactamase Inhibitors/chemistry
15.
Mikrochim Acta ; 187(3): 195, 2020 03 02.
Article in English | MEDLINE | ID: mdl-32124063

ABSTRACT

A dual functionalized magnetic nanomaterial was fabricated by combining the magnetic core, titania shell, and hydrophilic molecules (denoted as Fe3O4@TiO2-IDA). Based on the mechanism of metal oxide affinity chromatography and hydrophilic interaction liquid chromatography, the sorbent shows excellent one-step separation capacity for both glycopeptides and phosphopeptides. For phosphopeptide enrichment, Fe3O4@TiO2-IDA exhibits high sensitivity and selectivity. The concentration of ß-casein in the digests can be as low as 0.0125 ng µL-1; the mass ratio of ß-casein and BSA digest can reach 1:800. For glycopeptide enrichment, Fe3O4@TiO2-IDA also exhibits good performance. The concentration of horseradish peroxidase (HRP) in the digested sample can be as low as 0.04 ng µL-1; the mass ratio of HRP and BSA digest can reach 1:100. Following the one-step enrichment, elution, and nano LC-MS/MS analysis, 550 unique phosphopeptides and 330 glycopeptides were identified from 100 µg mouse brain sample through a single run of LC-MS/MS. Graphical abstract Multipurpose Fe3O4@TiO2-IDA nanomaterials are employed in simultaneous enrichment and separation of glycopeptides and phosphopeptides.


Subject(s)
Dicarboxylic Acids/chemistry , Glycopeptides/analysis , Imino Acids/chemistry , Magnetite Nanoparticles/chemistry , Phosphopeptides/analysis , Titanium/chemistry , Animals , Brain/metabolism , Horseradish Peroxidase/chemistry , Hydrophobic and Hydrophilic Interactions , Ligands , Mice , Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization , Tandem Mass Spectrometry
16.
Molecules ; 25(6)2020 Mar 12.
Article in English | MEDLINE | ID: mdl-32178320

ABSTRACT

The mixed-ligand copper(II) iminodiacetates [Cu(ida)(2-mim)(H2O)2]·H2O (1), [Cu(ida)(2-mim)2]·2H2O (2), [Cu(ida)(2-mim)(H2O)]n·4.5nH2O (3), and [Cu2(ida)2(2-mim)2]n·nH2O (4) (H2ida = iminodiacetic acid, 2-mim = 2-methylimidazole) were obtained from neutral or alkaline solutions at different temperatures. The novel complex 4 contains very small holes with diameters of 2.9 Å, which can adsorb O2 selectively and reversibly between 1.89 to 29.90 bars, compared with the different gases of N2, H2, CO2, and CH4. This complex is stable up to 150 °C based on thermal analyses and XRD patterns. The four complexes show catalytic activities that facilitate the conversion of cyclohexane to cyclohexanol and cyclohexanone with hydrogen peroxide in a solution. The total conversion is 31% for 4.


Subject(s)
Coordination Complexes/chemistry , Cyclohexanes/chemistry , Imidazoles/chemistry , Imino Acids/chemistry , Adsorption , Catalysis , Copper/chemistry , Crystallography, X-Ray , Ligands , Oxidation-Reduction/drug effects , Oxygen/chemistry
17.
Int J Biol Macromol ; 148: 1072-1083, 2020 Apr 01.
Article in English | MEDLINE | ID: mdl-31981664

ABSTRACT

Novel anionic adsorbent microbeads were fabricated based on surface functionalization of p-benzoquinone-carboxymethyl cellulose (CMC-PBQ) activated microbeads with iminodiacetic acid (IDA). The developed IDA@CMC-PBQ microbeads were characterized by FT-IR, TGA, SEM, XPS and zeta potential analysis tools. Ion exchange capacity measurements proved the successful generation of extra carboxylic groups on the surface of IDA@CMC-PBQ microbeads with a maximum value reached 3.984 meq/g compared to 1.32 meq/g for neat CMC microbeads. The fabricated microbeads were tested for the removal of cationic crystal violet (CV) dye from aqueous solutions under various adsorption conditions. The results clarified that the removal percent of CV dye was augmented and reached a maximum value of 91.56% with increasing IDA concentration up to 0.15 M. Moreover, the experimental data were well-fitted both Langmuir and Freundlich isotherms with a maximum adsorption capacity of 107.52 mg/g. while the adsorption process was obeyed the pseudo-second order kinetic model. The developed adsorbent displayed respectable reusability after five sequential cycles and exhibited higher adsorption ability towards cationic CV dye compared to cationic methylene blue (MB) and anionic methyl orange (MO) dyes. Therefore, IDA@CMC-PBQ adsorbent could be effectually used as a convenient and reusable adsorbent for removing cationic dyes from their aqueous solutions.


Subject(s)
Carboxymethylcellulose Sodium/chemistry , Cations/chemistry , Gentian Violet/chemistry , Imino Acids/chemistry , Microspheres , Adsorption , Hydrogen-Ion Concentration , Molecular Structure , Spectroscopy, Fourier Transform Infrared , Thermogravimetry , Water Pollutants, Chemical/chemistry , X-Ray Diffraction
18.
Proc Natl Acad Sci U S A ; 117(5): 2449-2455, 2020 02 04.
Article in English | MEDLINE | ID: mdl-31949004

ABSTRACT

NMR sensitivity-enhancement methods involving hyperpolarized water could be of importance for solution-state biophysical investigations. Hyperpolarized water (HyperW) can enhance the 1H NMR signals of exchangeable sites by orders of magnitude over their thermal counterparts, while providing insight into chemical exchange and solvent accessibility at a site-resolved level. As HyperW's enhancements are achieved by exploiting fast solvent exchanges associated with minimal interscan delays, possibilities for the rapid monitoring of chemical reactions and biomolecular (re)folding are opened. HyperW NMR can also accommodate heteronuclear transfers, facilitating the rapid acquisition of 2-dimensional (2D) 15N-1H NMR correlations, and thereby combining an enhanced spectral resolution with speed and sensitivity. This work demonstrates how these qualities can come together for the study of nucleic acids. HyperW injections were used to target the guanine-sensing riboswitch aptamer domain (GSRapt) of the xpt-pbuX operon in Bacillus subtilis Unlike what had been observed in proteins, where residues benefited of HyperW NMR only if/when sufficiently exposed to water, these enhancements applied to every imino resonance throughout the RNA. The >300-fold enhancements observed in the resulting 1H NMR spectra allowed us to monitor in real time the changes that GSRapt undergoes upon binding hypoxanthine, a high-affinity interaction leading to conformational refolding on a ∼1-s timescale at 36 °C. Structural responses could be identified for several nucleotides by 1-dimensional (1D) imino 1H NMR as well as by 2D HyperW NMR spectra acquired upon simultaneous injection of hyperpolarized water and hypoxanthine. The folding landscape revealed by this HyperW strategy for GSRapt, is briefly discussed.


Subject(s)
Imino Acids/chemistry , Nuclear Magnetic Resonance, Biomolecular/methods , RNA/chemistry , Water/chemistry , Aptamers, Nucleotide/chemistry , RNA Folding , Riboswitch
19.
Mikrochim Acta ; 187(2): 121, 2020 01 12.
Article in English | MEDLINE | ID: mdl-31927641

ABSTRACT

Monodisperse porous silica microspheres were functionalized with the iminodiacetic acid/copper(II) complex and then evaluated as a group-specific peroxidase-mimicking nanozyme for colorimetric determination of histidine-tagged (His-tagged) proteins. The green fluorescent protein (GFP) was selected as a typical His-tagged protein. The specificity for GFP and the peroxidase-like activity for the selected substrate were obtained by immobilizing the complex on the porous microspheres. The modified microspheres were also evaluated as a group specific immobilized metal affinity chromatography (IMAC) sorbent for the purification of GFP from Escherichia coli extract. The peroxidase-like activity of the microspheres was inhibited by the GFP adsorbed onto the microspheres due to the interaction of His-tagged protein with the immobilized Cu(II) complex. Ortho-phenylenediamine is used as a substrate for the enzyme mimic. The photometric response (measured at 416 nm) is linear in the 9.0-92 µg·mL-1 GFP concentration range in E. coli lysate. The limit of detection is 6.9 µg·mL-1. Graphical abstractSchematic representation of metal affinity chromatography-based colorimetric determination of histidine-tagged proteins using silica microspheres functionalized with iminodiacteic acid/copper (II) complex as a peroxidase mimic.


Subject(s)
Colorimetry/methods , Microspheres , Peroxidases/metabolism , Proteins/analysis , Silicon Dioxide , Chromatography, Affinity/methods , Copper/chemistry , Histidine , Imino Acids/chemistry , Molecular Mimicry , Proteins/chemistry , Silicon Dioxide/chemistry
20.
Appl Biochem Biotechnol ; 191(2): 810-823, 2020 Jun.
Article in English | MEDLINE | ID: mdl-31863350

ABSTRACT

Iminodiacetic acid (IDA) is one of the chelating ligands most frequently employed in immobilized metal-ion affinity chromatography (IMAC) due to its ability to act as electron-pair donor, forming stable complexes with intermediate and borderline Lewis metal ions (electron acceptor). Thus, IDA can also be employed in ion exchange chromatography to purify positively charged proteins at neutral pH values. This study aimed to evaluate IDA as an ionogenic group (ion exchanger) immobilized on poly (ethylene vinyl alcohol) (PEVA) hollow fiber membranes for immunoglobulin G1 (IgG1) monoclonal antibody (MAb) purification. IDA-PEVA membranes showed considerable promise for MAb purification, since IgG1 was recovered in eluted fractions with traces of contaminants as confirmed by Western blotting and ELISA analysis. Quantification of IgG1 showed that a purity of 94.2% was reached in the elution step. Breakthrough curve and batch adsorption experiments showed that the MAb dynamic binding capacity (DBC) of 3.10 mg g-1 and the maximum adsorption capacity of 70 mg g-1 were of the same order of magnitude as those found in the literature. The results obtained showed that the IDA-PEVA hollow fiber membrane could be a powerful adsorbent for integrating large-scale processes for purification of MAb from cell culture supernatant.


Subject(s)
Antibodies, Monoclonal/chemistry , Chromatography, Affinity/methods , Imino Acids/chemistry , Immunoglobulin G/chemistry , Membranes, Artificial , Adsorption , Animals , Antibodies, Monoclonal/isolation & purification , Chelating Agents/chemistry , Hydrogen-Ion Concentration , Immunoglobulin G/isolation & purification , Ions , Ligands , Metals/chemistry , Mice
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