betadex and pyrene

A green synthesis method for nanoscale silver using β-cyclodextrin as both reducing agent and stabilizer was developed. β-cyclodextrin was used not only as a reducing agent but also a stabilizing agent for nano-silver, and is also an excellent detection substrate due to its special structure (inner hydrophobic and outer hydrophilic ring structure). Then, the green synthesized silver nanoparticles were used as Surface-enhanced Raman spectroscopy (SERS) enhanced substrates to detect polycyclic aromatic hydrocarbons, such as: anthracene, pyrene, chrysene and triphenylene. The SERS substrate can be used for both quantitative detection of the four polycyclic aromatic hydrocarbons and qualitative identification of mixtures of these hydrocarbons. This synthesis method is simple and convenient, having great potential in simultaneous and rapid detection of environmental organic pollutants.

Topics: Anthracenes; beta-Cyclodextrins; Chrysenes; Green Chemistry Technology; Hydrophobic and Hydrophilic Interactions; Metal Nanoparticles; Polycyclic Aromatic Hydrocarbons; Pyrenes; Silver; Spectrum Analysis, Raman

We herein report a strategy for sensitive alkaline phosphatase (ALP) fluorescent sensing based on steric hindrance regulated supramolecular assembly between β-cyclodextrin polymer (polyβ-CD) and pyrene. The fluorescence of pyrene was enhanced more than 10 times through supramolecular assembly with polyβ-CD. The 5'-phosphorylated dsDNA probe with pyrene attached on the 3'-terminal could be cleaved by λ exonuclease (λ exo), yielding pyrene attached on mononucleotides. Pyrene attached on mononucleotides could easily enter the cavity of polyβ-CD, resulting in fluorescence enhancement. When ALP was introduced, it could remove 5'-phosphate groups from dsDNA and then prevented the cleavage of dsDNA. Pyrene attached on dsDNA was difficult to enter the cavity of polyβ-CD because of steric hindrance, resulting in an inconspicuous fluorescence enhancement. Owing to the excellent fluorescence enhancement during steric hindrance regulated supramolecular assembly, excellent performance of the assay method was achieved for ALP with a detection limit of 0.04 Um L(-1). The detection limit was superior or comparable with the reported methods. Besides, this method was simple in design, avoiding double-labeling of probe.

Topics: Alkaline Phosphatase; Animals; Base Sequence; beta-Cyclodextrins; Cattle; DNA; Fluorescence; Fluorescent Dyes; Humans; Limit of Detection; Pyrenes; Spectrometry, Fluorescence

The remediation of a genuinely PAH-contaminated soil was performed, for the first time, through a new and complete investigation, including PAH extraction followed by advanced oxidation treatment of the washing solution and its recirculation, and an analysis of the impact of the PAH extraction on soil respirometry. The study has been performed on the remediation of genuine PAH-contaminated soil, in the following three steps: (i) PAH extraction with soil washing (SW) techniques, (ii) PAH degradation with an electro-Fenton (EF) process, and (iii) recirculation of the partially oxidized effluent for another SW cycle. The following criteria were monitored during the successive washing cycles: PAH extraction efficiency, PAH oxidation rates and yields, extracting agent recovery, soil microbial activity, and pH of soil. Two representative extracting agents were compared: hydroxypropyl-beta-cyclodextrin (HPCD) and a non-ionic surfactant, Tween(®) 80. Six PAH with different numbers of rings were monitored: acenaphthene (ACE), phenanthrene (PHE), fluoranthene (FLA), pyrene (PYR), benzo(a)pyrene (BaP), and benzo(g,h,i)perylene (BghiP). Tween(®) 80 showed much better PAH extraction efficiency (after several SW cycles) than HPCD, regardless of the number of washing cycles. Based on successive SW experiments, a new mathematical relation taking into account the soil/water partition coefficient (Kd*) was established, and could predict the amount of each PAH extracted by the surfactant with a good correlation with experimental results (R(2) > 0.975). More HPCD was recovered (89%) than Tween(®) 80 (79%), while the monitored pollutants were completely degraded (>99%) after 4 h and 8 h, respectively. Even after being washed with partially oxidized solutions, the Tween(®) 80 solutions extracted significantly more PAH than HPCD and promoted better soil microbial activity, with higher oxygen consumption rates. Moreover, neither the oxidation by-products nor the acidic media (pH approximately 3) of the partially oxidized solution inhibited the general soil microbial activity during the washing cycle.

Topics: 2-Hydroxypropyl-beta-cyclodextrin; Benzo(a)pyrene; beta-Cyclodextrins; Environmental Pollution; Environmental Restoration and Remediation; Phenanthrenes; Polycyclic Aromatic Hydrocarbons; Polysorbates; Pyrenes; Soil; Soil Pollutants; Solutions; Surface-Active Agents

Nowadays, enzyme-free nucleic acid-based signal amplification strategies are frequently utilized in the design of biosensors due to their excellent sensitivity. Developing more extended analytical methods is fundamental for basic studies in the biological and biomedical fields. Herein, we introduce an enzyme-free amplified detection strategy for the small molecule adenosine. The approach is based on adenosine-aptamer binding triggered catalyzed hairpin assembly and host-guest interactions between β-cyclodextrin polymer (β-CDP) and pyrene. Two hairpin probes (probe H1 and probe H2) and an aptamer-trigger/inhibitor duplex probe were employed in the system and the pyrene-labeled probe H1 was chosen as the signal unit. In the absence of adenosine, the aptamer-trigger was inhibited by the inhibitor strand. The hairpin probes were in the closed hairpin formation without activation of the trigger strand. Pyrene labeled at the 5'-termini of the single-stranded stem of probe H1 could be easily trapped in the hydrophobic cavity of β-CDP because of weak steric hindrance, leading to a significant fluorescence enhancement. Once the hairpin assembly was catalyzed by the adenosine-aptamer binding event, a hybridized DNA duplex H1/H2 was created continuously. Pyrene labeled at the 5'-termini of the DNA duplex H1/H2 finds it difficult to enter the cavity of β-CDP due to steric hindrance, leading to a weaker fluorescence signal. Thus, the target could be detected by this simple mix-and-detect amplification method without a need for expensive and perishable protein enzymes. As low as 42 nM of adenosine was detected by this assay, which is comparable to that of some reported colorimetric methods. Meanwhile, the proposed method was further successfully applied to detect adenosine in human serum samples, showing great potential for adenosine detection from complex fluids.

Topics: Adenosine; beta-Cyclodextrins; Biosensing Techniques; Catalysis; DNA Probes; Humans; Inverted Repeat Sequences; Limit of Detection; Pyrenes; Spectrometry, Fluorescence

The present study was conducted to evaluate the effect of two non ionic surfactants (Tween 80 and Triton X-100), a biosurfactant (Lecithin), and randomly methylated-β-cyclodextrins (RAMEB) on the remediation of pyrene from soil planted with tall fescue (Festuca arundinacea). Soils with pyrene concentration of about 243 mg kg(-1) was grown with tall fescue and were individually amended with 0, 200, 600, 1000, and 1500 mg kg(-1) of Tween 80, Triton X-100, biosurfactant, and RAMEB. The results show that all surfactants significantly increased plant biomass compared to unamended soil. Dehydrogenase activity was also stimulated as a result of surfactant addition. Only 3.9 and 3.2 % of pyrene was decreased in the uncovered and covered abiotic sterile control, suggesting that microbial degradation was the main removal mechanism of pyrene from soil. In the planted treatment receiving no surfactant, the remediation of pyrene was 45 % which is significantly higher than that of corresponding unplanted control soil, suggesting that the cultivation of tall fescue alone could enhance the overall remediation of pyrene in soil. All surfactants had significantly higher rates of pyrene remediation compared to the unamended planted soil. Generally, RAMEB displayed the highest remediation rates, i.e., 64.4-79.1 % followed by the Triton X-100, i.e., 60.1-74.8 %. The positive impact of surfactants on pyrene remediation could possibly be because of their capacities to increase its bioavailability in soil. The evidence from this study suggests that the addition of surfactants could enhance phytoremediation of PAHs polluted soil.

Topics: beta-Cyclodextrins; Biodegradation, Environmental; Biomass; Festuca; Octoxynol; Polysorbates; Pyrenes; Rhizosphere; Soil; Surface-Active Agents

Herein, we proposed an enzyme-free strategy for the amplified detection of DNA by combining the efficient fluorescence enhancement capability of a β-cyclodextrin-tethered cationic polymer (cationic polyβ-CD) to pyrene with the amplification capability of target DNA triggered hybridization chain reaction (HCR). Cationic polyβ-CD with positive charge was synthesized. Two hairpin probes, H1 and H2, were employed in the system and the pyrene-labelled H2 was chosen as the signal unit. The pyrene attached on the sticky end of H2 was flexible and there was strong electrostatic interaction between cationic polyβ-CD and negatively-charged H2, so pyrene could easily enter the cavity of CD that is tethered on the cationic polymer, accompanied by significant fluorescence enhancement. Once target DNA was introduced, HCR was triggered to form a rigid long dsDNA polymer with pyrene attached on it. The pyrene was hardly able to enter the cavity of cationic polyβ-CD because of steric hindrance, leading to a weak fluorescent signal. Owing to the efficient pyrene fluorescence enhancement of cationic polyβ-CD and the amplified capability of HCR, an enzyme-free sensitive detection of target DNA was achieved with a detection limit of 0.1 nM and high selectivity.

Topics: beta-Cyclodextrins; DNA; Limit of Detection; Nucleic Acid Hybridization; Polymers; Pyrenes; Spectrometry, Fluorescence

A multiple amplification strategy has been developed for nucleic acid detection based on host-guest interaction between the β-cyclodextrin polymer (β-CDP) and pyrene. Briefly, the detection system consists of three parts: the polymerase and nicking enzyme-assisted isothermal strand displacement amplification (SDA) activated by a target DNA or microRNA; the exonuclease III-aided cyclic enzymatic amplification (CEA); and the fluorescence enhancement effect based on host-guest interaction between β-CDP and pyrene. This strategy showed a good positive linear correlation with target DNA concentrations in the range from 75 fM to 1 pM with a detection limit of 41 fM. Significantly, our amplification platform was further validated and evaluated successfully by assaying miRNA-21 in human serum. The proposed assay has great potential as a nucleic acid quantification method for use in biomedical research, clinical analysis and disease diagnostics.

Topics: beta-Cyclodextrins; Cellulose; Cyclodextrins; DNA; Humans; Limit of Detection; MicroRNAs; Nucleic Acid Amplification Techniques; Pyrenes

pH-responsive supramolecular amphiphilic micelles based on benzimidazole-terminated poly(ethylene glycol) (PEG-BM) and β-cyclodextrin-modified poly(L-lactide) (CD-PLLA) were developed by exploiting the host-guest interaction between benzimidazole (BM) and β-cyclodextrin (β-CD). The dissociation of the supramolecular micelles was triggered in acidic environments. An antineoplastic drug, doxorubicin (DOX), was loaded into the supramolecular micelles as a model drug. The release of DOX from the supramolecular micelles was clearly accelerated as the pH was reduced from 7.4 to 5.5. The DOX-loaded PEG-BM/CD-PLLA supramolecular micelles displayed an enhanced intracellular drug-release rate in HepG2 cells compared to the pH-insensitive DOX-loaded PEG-b-PLLA counterpart. After intravenous injection into nude mice bearing HepG2 xenografts by the tail vein, the DOX-loaded supramolecular micelles exhibited significantly higher tumor inhibition efficacy and reduced systemic toxicity compared to free DOX. Furthermore, the DOX-loaded supramolecular micelles showed a blood clearance rate markedly lower than that of free DOX and comparable to that of the DOX-loaded PEG-b-PLLA micelles after intravenous injection into rats. Therefore, the pH-responsive PEG-BM/CD-PLLA supramolecular micelles hold potential as a smart nanocarrier for anticancer drug delivery.

Topics: Antineoplastic Agents; Benzimidazoles; beta-Cyclodextrins; Cell Death; Doxorubicin; Drug Delivery Systems; Flow Cytometry; HeLa Cells; Hep G2 Cells; Humans; Hydrogen-Ion Concentration; Lactates; Micelles; Polyethylene Glycols; Pyrenes; Spectrometry, Fluorescence

The detection of nucleic acids is fundamental for studying their functions and for the development of biological studies and medical diagnostics. Herein, we report a new strategy for nucleic acid amplified detection by combining target-catalyzed dynamic assembly with host-guest interaction between β-cyclodextrin polymer (β-CDP) and pyrene. In this strategy, a metastable pyrene-labeled hairpin DNA probe (probe H1) and a metastable unlabeled hairpin DNA probe (probe H2) were elaborately designed as the assembly components, which were kinetically handicapped from cross-opening in the absence of target DNA. In this state, pyrene labled at the 5'-termini of single-stranded stem of probe H1 would be easily trapped into the hydrophobic cavity of β-CDP because of weak steric hindrance, leading to significant fluorescence enhancement. Once the dynamic assembly was catalyzed by target DNA, a hybridized DNA duplex H1-H2 would be created continuously. In this state, it is difficult for pyrene to enter the cavity of β-CDP due to steric hindrance and weak-binding interaction, leading to a weak fluorescent signal. Thus, target DNA could be detected by this simple mix-and-detect amplification method without the need of expensive and perishable protein enzymes. As low as 10 pM of the target DNA was detected by this assay, which was comparable to that of some reported enzyme-dependent amplification methods. Meanwhile, the proposed method was further successfully applied to detect DNA in cell lysate samples, showing great potential for target detection from complex fluids. In addition, as a novel transformation of dynamic DNA assembly technology into enzyme-free signal-amplification analytical application, the proposed strategy has shown great potential for applications in a wide range of fields, such as aptamer-based non-nucleic acid target sensing, biomedicine and bioimaging.

Topics: beta-Cyclodextrins; Catalysis; DNA; DNA Probes; Fluorescence; Nucleic Acid Amplification Techniques; Polymers; Pyrenes

Bioavailability of organic pollutants in soil is currently a much-debated issue in risk assessment of contaminated sites. Ecorisk of an organic pollutant in soil is strongly influenced by the properties of the soil and its contamination history. To evaluate the effect of aging on the availability of pyrene, earthworm (Eisenia fetida) accumulation and chemical extraction by exhaustive and nonexhaustive techniques in soil spiked with a range of pyrene levels (1.07, 9.72, 88.4, 152, and 429 μg g⁻¹ dry soil) were measured in this study using both unaged (i.e., 0 days) and aged (i.e., 69, 150, and 222 days) soil samples. The results showed that the amount of pyrene accumulated by earthworms did not change greatly with aging time under different high-dose contamination levels, but changed significantly at lower concentrations. Moreover, aging (after 222 days) significantly decreased biological and chemical availability of pyrene. Furthermore, the relationship between earthworm bioaccumulation, hydroxypropyl-β-cyclodextrin (HPCD), and organic solvent extraction was investigated in order to find a suitable and rapid method to predict pyrene bioavailability. Results showed that, at different levels of pyrene, the mean values of earthworm uptake and HPCD extractability were 10-40% and 10-65%, respectively. Correlation (r² = 0.985) and extraction results for pyrene suggested that mild HPCD extraction was a better method to predict bioavailability of pyrene in soil compared with organic solvent extraction.

Topics: 2-Hydroxypropyl-beta-cyclodextrin; Animals; beta-Cyclodextrins; Biodegradation, Environmental; Environmental Monitoring; Oligochaeta; Pyrenes; Soil; Soil Pollutants; Solvents

TiO(2) nanoparticles were synthesized by hydrolysis of tetraisopropyl orthotitanate in an aqueous solution of cyclodextrin. The β-cyclodextrin-modified spherical TiO(2) nanoparticles were water-dispersible and had an average particle diameter of 4.4 ± 1 nm. Pyrene fluorescence was enhanced by increasing the concentration of β-cyclodextrin-modified TiO(2) nanoparticle and the sensitization effect was triply stronger than the case of the β-cyclodextrin only. The increase in a concentration of host (β-cyclodextrin) changes its microenvironment for guest (pyrene), that is, the interaction of pyrene with apolar cavity of β-cyclodextrin increases, resulting in enhancement of fluorescence. The sensitization behavior of pyrene fluorescence in the presence of TiO(2) nanoparticles occurs from the increase in the extinction coefficient of pyrene, demonstrating the charge transfer between pyrene and metal oxide nanoparticle.

Topics: beta-Cyclodextrins; Fluorescence; Nanoparticles; Particle Size; Pyrenes; Solutions; Surface Properties; Titanium; Water

Synchronous fluorescence spectroscopy (SFS) was directly applied to rapidly quantify selected polycyclic aromatic hydrocarbons (PAHs: benzo[a]pyrene and pyrene) in aqueous hydroxypropyl-beta-cyclodextrin (HPCD) soil extract solutions from a variety of aged contaminated soils containing four different PAHs. The method was optimized and validated. The results show that SFS can be used to analyse benzo[a]pyrene and pyrene in HPCD based soil extracts with high sensitivity and selectivity. The linear calibration ranges were 4.0x10(-6)-1.0x10(-3)mM for benzo[a]pyrene and 6.0x10(-6)-1.2x10(-3)mM for pyrene in 10mM HPCD aqueous solution alone. The detection limits according to the error propagation theory for benzo[a]pyrene and pyrene were 3.9x10(-6) and 5.4x10(-6)mM, respectively. A good agreement between SFS and HPLC was reached for both determinations of PAHs in HPCD alone and in soil HPCD extracts. Hence, SFS is a potential means to simplify the present non-exhaustive hydroxypropyl-beta-cyclodextrin (HPCD)-based extraction technique for the evaluation of PAH bioavailability in soil.

Topics: 2-Hydroxypropyl-beta-cyclodextrin; Benzo(a)pyrene; beta-Cyclodextrins; Environmental Monitoring; Polycyclic Aromatic Hydrocarbons; Pyrenes; Soil Pollutants; Spectrometry, Fluorescence

There is currently considerable scientific interest in finding a chemical technique capable of predicting bioavailability; non-exhaustive extraction techniques (NEETs) offer such potential. Hydroxypropyl-beta-cyclodextrin (HPCD), a NEET, is further validated through the investigation of concentration ranges, differing soil types, and the presence of co-contaminants. This is the first study to demonstrate the utility of the HPCD-extraction technique to predict the microbial availability to phenanthrene across a wide concentration range and independent of soil-contaminant contact time (123 d). The efficacy of the HPCD-extraction technique for the estimation of PAH microbial availability in soil is demonstrated in the presence of co-contaminants that have been aged for the duration of the experiment together in the soil. Desorption dynamics are compared in co-contaminant and single-PAH contaminated spiked soils to demonstrate the occurrence of competitive displacement. Overall, a single HPCD-extraction technique proved accurate and reproducible for the estimation of PAH bioavailability from soil.

Topics: 2-Hydroxypropyl-beta-cyclodextrin; Adsorption; Bacteria; beta-Cyclodextrins; Biodegradation, Environmental; Environmental Monitoring; Phenanthrenes; Poaceae; Polycyclic Aromatic Hydrocarbons; Pyrenes; Soil Microbiology; Soil Pollutants; Time; Trees

It is well known that the limited aqueous solubilities of polycyclic aromatic hydrocarbons (PAH) often reduce their bioavailability to bacterial populations. The objective of this study was to test the impact of a solubility-enhancement reagent, hydroxypropyl-beta-cyclodextrin (HPCD), on the bioavailability and biodegradation of pyrene. No measurable loss of pyrene occurred for the control vials throughout the first 22 weeks of the experiment, indicating the absence of mass loss via abiotic transformation and volatilization. The vials containing pyrene and the degrader isolate (Burkholderia CRE 7), but no HPCD, also exhibited no measurable loss of pyrene throughout the experiment. Conversely, biodegradation of pyrene appears to have been initiated after approximately 15 weeks for the vials containing 10(4) mg l(-1) HPCD. By the end of the experiment, approximately 14% (w/w) of the pyrene was biodegraded in the presence of HPCD. These results indicate that HPCD may be useful for enhancing the bioavailability and biodegradation of pyrene and other PAHs.

Topics: 2-Hydroxypropyl-beta-cyclodextrin; beta-Cyclodextrins; Biodegradation, Environmental; Fluorescent Dyes; Pyrenes; Solubility; Volatilization

Recent epidemiological studies revealed inhibitors of the hydroxymethylglutaryl-coenzyme A reductase, so-called statins, to be effective in lowering the prevalence of Alzheimer's disease (AD). In vitro, statins strongly reduced the cellular amyloid beta-protein load by modulating the processing of the amyloid beta precursor protein. Both observations are probably linked to cellular cholesterol homeostasis in brain. So far, little is known about brain effects of statins. Recently, we could demonstrate that treatment of mice with the lipophilic compound lovastatin resulted in a discrete reduction of brain membrane cholesterol levels. To follow up these findings, we subsequently carried out a further in vivo study including lovastatin and simvastatin as lipophilic agents, as well as pravastatin as a hydrophilic compound, focussing on their efficiency to affect subcellular membrane cholesterol pools in synaptosomal plasma membranes of mice. In contrast to the hydrophilic pravastatin, the lipophilic lovastatin and simvastatin strongly reduced the levels of free cholesterol in SPM. Interestingly, lovastatin and pravastatin but not simvastatin significantly reduced cholesterol levels in the exofacial membrane leaflet. These changes were accompanied by modified membrane bulk fluidity. All three statins reduced the expression of the raft marker protein flotillin. Alterations in transbilayer cholesterol distribution have been suggested as the underlying mechanism that forces amyloidogenic processing of APP in AD. Thus, our data give some first insight in the mode of action of statins to reduce the prevalence of AD in clinical trials.

Topics: Animals; Anisotropy; beta-Cyclodextrins; Brain; Cell Membrane; Cholesterol; Cyclodextrins; Diphenylhexatriene; Female; Fluorescent Dyes; Gene Expression; Lovastatin; Membrane Proteins; Mice; Mice, Inbred C57BL; Pyrenes; Simvastatin; Synaptosomes; Trinitrobenzenesulfonic Acid

The influence of achiral modifiers on the chiral separation of propranolol is examined by cyclodextrin modified capillary zone electrophoresis. The improved chiral separation of propranolol is by molecules previously identified in our group as forming ternary complexes with cyclodextrin and pyrene. The polarity, chain size and heteroatom composition of the functional groups on the comodifiers was systematically varied in order to study the influence of these variables on the separation of propranolol. The improved chiral separation is accompanied by a decrease in retention time. The decrease in retention time is suggestive of a decrease in the association of beta-cyclodextrin (beta-CD) with propranolol which was verified by calculation of apparent association constants using fluorometric methods.

Topics: beta-Cyclodextrins; Cyclodextrins; Electrophoresis, Capillary; Propranolol; Pyrenes