Separation assay of histamine and its metabolites in biological specimens

This review summarizes the determination methods for histamine and the metabolites in biological specimens by separation techniques, such as gas chromatography, liquid chromatography and capillary electrophoresis. The typical applications using these methods are also described in this review together with the characteristics of the methods. Copyright (c) 2008 John Wiley & Sons, Ltd.     

Biphenylalkoxyamine Derivatives–Histamine H3 Receptor Ligands with Butyrylcholinesterase Inhibitory Activity

Neurodegenerative diseases, e.g., Alzheimer’s disease (AD), are a key health problem in the aging population. The lack of effective therapy and diagnostics does not help to improve this situation. It is thought that ligands influencing multiple but interconnected targets can contribute to a desired pharmacological effect in these complex illnesses. Histamine H₃ receptors (H₃Rs) play an important role in the brain, influencing the release of important neurotransmitters, such as acetylcholine. Compounds blocking their activity can increase the level of these neurotransmitters. Cholinesterases (acetyl- and butyrylcholinesterase) are responsible for the hydrolysis of acetylcholine and inactivation of the neurotransmitter. Increased activity of these enzymes, especially butyrylcholinesterase (BuChE), is observed in neurodegenerative diseases. Currently, cholinesterase inhibitors: donepezil, rivastigmine and galantamine are used in the symptomatic treatment of AD. Thus, compounds simultaneously blocking H₃R and inhibiting cholinesterases could be a promising treatment for AD. Herein, we describe the BuChE inhibitory activity of H₃R ligands. Most of these compounds show high affinity for human H₃R (K_i < 150 nM) and submicromolar inhibition of BuChE (IC₅₀ < 1 µM). Among all the tested compounds, 19 (E153, 1-(5-([1,1′-biphenyl]-4-yloxy)pentyl)azepane) exhibited the most promising in vitro affinity for human H₃R, with a K_i value of 33.9 nM, and for equine serum BuChE, with an IC₅₀ of 590 nM. Moreover, 19 (E153) showed inhibitory activity towards human MAO B with an IC₅₀ of 243 nM. Furthermore, in vivo studies using the Passive Avoidance Task showed that compound 19 (E153) effectively alleviated memory deficits caused by scopolamine. Taken together, these findings suggest that compound 19 can be a lead structure for developing new anti-AD agents.     

Bed Bug Aggregation Pheromone Finally Identified

Bed bugs have become a global epidemic and current detection tools are poorly suited for routine surveillance. Despite intense research on bed bug aggregation behavior and the aggregation pheromone, which could be used as a chemical lure, the complete composition of this pheromone has thus far proven elusive. Here, we report that the bed bug aggregation pheromone comprises five volatile components (dimethyl disulfide, dimethyl trisulfide, (E)‐2‐hexenal, (E)‐2‐octenal, 2‐hexanone), which attract bed bugs to safe shelters, and one less‐volatile component (histamine), which causes their arrestment upon contact. In infested premises, a blend of all six components is highly effective at luring bed bugs into traps. The trapping of juvenile and adult bed bugs, with or without recent blood meals, provides strong evidence that this unique pheromone bait could become an effective and inexpensive tool for bed bug detection and potentially their control.     

Development of Polymeric Membrane Sensor for the Determination of Histamine: Experimental and Theoretical Study

Abstract

Some original histamine membrane sensors were prepared by incorporating thiopyrilium (TP) derivative as an excellent charged carrier. Among these sensors, TP2 shows the best response to histamine in a wide concentration range from 2.5×10^?6 to 1.0×10^?1 mol L^?1 with a slope of 55.6±0.7 mV decade^?1 and with a detection limit of 1.0 µmol L^?1 (～0.1 ppm). The interference between histamine and several amino acids and common inorganic anions was negligible as shown by the potentiometric selectivity coefficient data. The prepared electrode was used for the determination of histamine in a human serum synthetic sample. Theoretical calculations were carried out to find the best interactions between histamine and different ligands.     

Screening of allergic components mediated by H1R in homoharringtonine injection through H1R/CMC‐HPLC/MS

It has been reported that the histamine H₁ receptor (H₁R) gene is up‐regulated in patients with allergic rhinitis and H₁R expression level strongly correlates with the severity of allergy symptoms. Drugs for therapy should avoid allergy symptoms, especially for patients with over‐expressed H₁R. Therefore, screening of the components which could induce H₁R activation is urgently needed for drug safety evaluation. Homoharringtonine injection is a preparation for acute nonlymphocytic leukemia, which is approved by China Food and Drug Administration (CFDA) and US Food and Drug Administration. However, severely adverse reactions often occur with intravenous injection of the preparation. In present study, an H₁R/CMC model was applied for capturing membrane retained components which could induce H₁R activation. Retention components were enriched and analyzed by H₁R/CMC‐HPLC/MS. Homoharringtonine was recognized, separated and identified in homoharringtonine injection. Ca²⁺ flux assay and p‐IP3R expression founded that homoharringtonine retained by the H₁R/CMC model increased phosphorylation of IP3R and promoted cytosolic free Ca²⁺ elevation in a dose‐dependent manner which further verified the activity of homoharringtonine in activating the H₁R. In conclusion, homoharringtonine was screened and identified as a potential allergic factor. This provides an indication that a patient with over‐expressed H₁R should be aware of possible allergic reaction when applying homoharringtonine injection. Copyright © 2014 John Wiley & Sons, Ltd.     

Assay of Histamine in Single Mast Cells by Capillary Zone Electrophoresis with Electrochemical Detection

Histamine is one of the chemical mediators in connection with allergies. Only Pihel et al.1 reported a method for detection of histamine in isolated mast cells by high- performance liquid chromatography with electrochemical detection. In this method, single cells were removed and transferred to 300-nL microvials. A part of the supernatant from individual vials was injected into the chromatography column. The analysis of histamine in individual rat peritoneal mast cells using CZE with amp…     

Novel and Efficient Method for the Synthesis of Racemic Fexofenadine

Fexofenadine is a selective H₁-histamine receptor antagonist, which is an attractive alternative treatment for allergy symptoms. An efficient and environmentally friendly synthetic approach for the preparation of fexofenadine was developed from commercially available cumene. The method involves the Friedel–Craft's reaction, substitution, reduction, bromination, and the Grignard reaction.

Appending zinc tetraphenylporphyrin with an amine receptor at β-pyrrolic carbon for designing a selective histamine chemosensor

Adopting the rarely used β-functionalisation strategy in porphyrin-based sensor design, an amine receptive site is appended onto the zinc(II) porphyrin molecular framework affording a ditopic chemosensor 4. The assembled chemosensor interacts selectively with histamine in toluene via a ‘two-site’ binding mode. Association constant of the complex evaluated from the respective UV–vis spectra is found to be (2.32 ± 0.57) × 10⁶, which is approximately 4-fold greater than those complexes derived from 4 and nicotine/histidine. On the basis of a combined spectroscopic method and molecular modelling, the binding model of the porphyrin host and biogenic guest molecules is established. Our results clearly demonstrate the viability of the design and development of the porphyrin-based chemosensor by appending a receptor at the β-pyrrolic carbon of the porphyrin scaffold.     

高效液相色谱串联质谱法测定中药注射剂对P815细胞脱颗粒后上清液中组胺含量

建立了液相色谱-串联质谱(LC-MS/MS)检测P815细胞脱颗粒后上清液中组胺含量的方法。采用C18柱(4.6 mm×100 mm,3.5μm)进行分离,以体积比为60∶40的乙腈-0.5 mmol/L乙酸铵溶液(含0.3%甲酸)为流动相,流速0.4 mL/min;在电喷雾正离子化模式下,采用多离子反应检测方式(MRM)进行检测;检测离子对为m/z 112>95、112>68。在优化条件下,样品可在6 min内完成分析,细胞液中组胺在4.0～128.0μg/L范围内线性关系良好(r2=0.997 9)。定量下限(S/N>10)为1.2μg/L,检出限(S/N=3)为0.3μg/L。在加标水平为16、64、128μg/L时,细胞上清液中组胺的平均回收率为90%～94%,相对标准偏差(n=6)为4.1%～5.9%。该方法简便、灵敏、重复性好,可用于中药注射剂对P815细胞脱颗粒后上清液中组胺含量的测定。     

Histamine detection using functionalized porphyrin as electrochemical mediator

This study reports on deposition of asymmetrical substituted meso-phenyl porphyrin, 5-(4-carboxyphenyl)-10,15,20-triphenylporphyrin (CPTPP) thin films by matrix-assisted pulsed laser evaporation (MAPLE) on screen-printed electrodes, aiming for histamine detection. Raman spectrometry confirmed that CPTPP chemical structure was preserved in MAPLE-deposited thin films at 200 mJ/cm² laser fluence. Atomic force microscopy topography revealed that MAPLE-deposited thin films have a better coverage on the working electrode made of carbon compared to the ones obtained by dropcasting. Cyclic voltammetry demonstrated that CPTPP is an appropriate mediator for histamine detection in trichloroacetic acid solution. We proved that MAPLE serves as a soft technique in fabrication of porphyrin thin films and patterns.