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1.
J Pharm Biomed Anal ; 239: 115876, 2024 Feb 15.
Article in English | MEDLINE | ID: mdl-38039872

ABSTRACT

Abnormal copper ions (Cu2+) and biothiols have potential impacts on environmental pollution and human health, so the detection of these substances with high selectivity and sensitivity has become an important research topic. In this study, we designed and synthesized two fluorescent probes (L1 and L2) based on naphthalene and anthracene derivatives that could specifically detect Cu2+ and biothiols. Owing to the paramagnetic effect of Cu2+, the strong fluorescent intensity was quenched after the addition of Cu2+. When biothiols were added to the solution (L-Cu2+), the fluorescence intensity was significantly enhanced and recovered. So, the interaction process was accompanied with "ON-OFF-ON" phenomenon in fluorescent intensity. Two complexes (L-Cu2+) showed low limit of detection for biothiols (Cys was 3.4 ×10-5 M and GSH was 2.0 ×10-5 M) and weak cytotoxicity (< 150 µg/mL). Theoretical investigation analysis revealed that the intramolecular hydrogen bond existed in the structure of probes and the roles of molecular frontier orbitals in molecular interplay. In addition, two probes also showed good applicability in actual drug Atomolan. The GSH content in the tested Atomolan reached over 99.9% of the labeling which was accord with the percentage of pharmacopoeia. Therefore, two probes have the real application value in the detection of Cu2+, biothiols and drug efficacy in various environments.


Subject(s)
Copper , Fluorescent Dyes , Humans , Copper/chemistry , Fluorescent Dyes/chemistry , Spectrometry, Fluorescence , Ions , Glutathione , Cysteine/analysis
2.
Org Lett ; 25(47): 8489-8494, 2023 Dec 01.
Article in English | MEDLINE | ID: mdl-37966853

ABSTRACT

A new electrophilic trifluoromethylselenolation reagent, N-trifluoromethylselenophthalimide (Phth-SeCF3), was developed. A strategy for the synthesis of 4-trifluoromethylselenolated isoxazoles through electrophilic trifluoromethylselenolation cyclization has been established by using Phth-SeCF3 as an electrophilic reagent. Moreover, this protocol has the features of broad substrate scope, good functional group tolerance, and high yields.

3.
J Fluoresc ; 2023 Aug 01.
Article in English | MEDLINE | ID: mdl-37526873

ABSTRACT

In order to better monitor the content of Fe3+ and H2S in the biological environment, two new fluorescent probes were designed and synthesized. With the addition of Fe3+, the strong fluorescence emission of two probes was significantly quenched due to the paramagnetic effect of Fe3+. With the further addition of S2-, the fluorescence intensity was quickly restored. Two probes showed high selectivity and strong sensitivity for the detection of Fe3+ and S2-, and the fluorescence intensity "ON-OFF-ON" was accompanied with the interaction process. At the same time, two probes displayed good anti-interference ability which was not interfered by the existence of other ions. In addition, two probes illustrated fast response time to Fe3+, S2- and small cytotoxicity to cells. Therefore, two probes can provide a potential ideal tool for detecting Fe3+ and H2S in organisms and the environment.

4.
J Org Chem ; 87(19): 13089-13101, 2022 10 07.
Article in English | MEDLINE | ID: mdl-36170059

ABSTRACT

A practical strategy for the synthesis of spiro[5.5]trienones-fused selenocyanates and spiro[4.5]trienones-fused selenocyanates through electrophilic selenocyanogen cyclization and dearomative spirocyclization is reported. This approach was conducted under mild conditions with broad substrate scope and good functional group tolerance. The utility of this procedure is exhibited in the late-stage functionalization of nature product and drug molecules.


Subject(s)
Spiro Compounds , Cyanates , Cyclization , Molecular Structure , Selenium Compounds , Spiro Compounds/chemistry
5.
Dalton Trans ; 50(33): 11440-11445, 2021 Sep 07.
Article in English | MEDLINE | ID: mdl-34359071

ABSTRACT

A cost-effective non-noble metal bifunctional electrocatalyst towards the oxygen reduction reaction (ORR) and the oxygen evolution reaction (OER) is very important for energy-related applications. Micro/nanomaterials with core-shell structures have emerged as potential non-noble metal catalyst candidates. Herein, an efficient bifunctional oxygen electrocatalyst, S-containing Co-based metal organic framework core-shell microspheres (Co-MOF-CSMSs), has been designed and constructed by using 2,2':5',2''-terthiophene-5,5''-dicarboxylic acid as a novel ligand through a facile one-step hydrothermal method. Due to the integrated favorable structural characteristics of the core-shell structure and MOFs for electrocatalysis, Co-MOF-CSMSs are revealed as a good bifunctional electrocatalyst for the ORR and OER, including an onset potential of 0.93 V vs. RHE (reversible hydrogen electrode), a half-wave potential of 0.78 V vs. RHE and an overpotential of 0.35 V at 10 mA cm-2. This work provides a low-cost and facile method to design and construct advanced micro/nanomaterials with core-shell structures to targetedly develop high-performance bifunctional oxygen electrocatalysts.

6.
Molecules ; 25(15)2020 Jul 24.
Article in English | MEDLINE | ID: mdl-32722063

ABSTRACT

Hydrophilic ionic liquids are often used to extract the active ingredients of medicinal plants, while hydrophobic ionic liquids are rarely used to directly extract solid samples. In this paper, a simple, novel and efficient temperature-controlled hydrophobic ionic liquids-based ultrasound/heating-assisted extraction (TC-ILs-UHAE) procedure coupled with high-performance liquid chromatography (HPLC) was developed and applied to the determination of ferulic acid (FA) in Chinese herbal medicine Angelica sinensis. During the extraction procedure, hydrophobic ionic liquids (ILs) were dispersed into water to form cloudy solution (fine droplets) with the aid of ultrasound and heating simultaneous. After extraction, phase separation was easily achieved by centrifuging at 0 °C. Among all ILs used, 1-butyl-3-methylimidazolium bis(trifluoromethanesulphonyl)imide ([C4mim]NTf2) exhibited the highest extraction ability and the possible extraction mechanism was discussed. Additionally, the synergistic effect of heating and ultrasound on the extraction efficiency was investigated. Under the optimized conditions, a good linearity was observed with correlation coefficient (r) of 0.9995. The limit of detection of FA (LOD, S/N = 3) was 9.6 µg/L and the spiked recoveries of FA for real samples were in the range of 91.67 to 102.00% with relative standard deviation (RSD) lower than 3.87%. Compared with the traditional extraction methods, the proposed method gave the highest yield of FA and had the shortest extraction time. Therefore, this method is a potential simple, green and highly efficient technique and expected to be applied to the extraction of other bioactive ingredients in medicinal plants.


Subject(s)
Angelica sinensis/chemistry , Coumaric Acids/isolation & purification , Ionic Liquids/chemistry , Chromatography, High Pressure Liquid , Limit of Detection , Liquid Phase Microextraction , Plant Extracts/isolation & purification , Temperature
7.
Nanoscale Adv ; 2(5): 1878-1885, 2020 May 19.
Article in English | MEDLINE | ID: mdl-36132529

ABSTRACT

To obtain an electrode material that is capable of manifesting high Na-ion storage capacity during long-term cycling at a rapid discharge/charge rate, ternary heterophases MoSe2/MoO2/carbon are rationally designed and synthesized through a supermolecule-assisted strategy. Through using supermolecules that are constructed from MoO4 2- and polydopamine as the precursor and sulfonated polystyrene microspheres as the sacrificial template, the in situ formed ternary phases MoSe2/MoO2/carbon are fabricated into a hollow microspherical structure, which is assembled from ultrathin nanosheets with MoSe2 and MoO2 nanocrystallites strongly embedded in a nitrogen-doped carbon matrix. In the ternary phases, the MoSe2 phase contributes to a high Na-ion storage capacity by virtue of its layered crystalline structure with a wide interlayer space, while the surrounding MoO2 and porous nitrogen-doped carbon phases are conducive to rate behaviour and cycling stability of the ternary hybrids since both the two phases are beneficial for electronic transport and structural stability of MoSe2 during repeated sodiation/desodiation reaction. The as-prepared MoSe2/MoO2/carbon manifests excellent rate behaviour (a Na-ion storage capacity of 461 mA h g-1 at an extremely high current density of 70 A g-1) and outstanding cycle performance (610 mA h g-1 after 1000 cycles).

8.
Sci Rep ; 9(1): 18838, 2019 12 11.
Article in English | MEDLINE | ID: mdl-31827214

ABSTRACT

A series of potential chiral compounds containing an α,ß-unsaturated ketone was developed for anion detection. The interplay of compounds and biological momentous anions (Cl-, H2PO4-, I-, AcO-, HS-, F-, and Br-) was evaluated by UV-vis experiments, fluorescence experiments, and electrochemical tests. By comparison, compound 1 had the best selectivity and compound 5 had the strongest binding ability among the five compounds. And compound 5 had the highest sensitivity to H2PO4- among the measured anions, and it also can be applied to actual samples, the content of H2PO4- tested in the potassium dihydrogen phosphate fertilizer solution reached above 97.5% of the marked content, and the recovery rates were within the range of 98.5-99.1%, attesting that this method was reliable for the test of H2PO4- in fertilizer. Through HRMS titration, circular dichroism and optical rotation experiments, the probable interacted mechanism was proved that the interaction site was the C=C of the α,ß-unsaturated ketone structure. In addition, the interacted mechanism was researched from the perspective of chirality. Furthermore, theoretical investigation analysis was introduced to reveal that the roles of molecular frontier orbitals in molecular interplay were determined. Therefore, this series of potential chiral compounds has potential application prospects in anion recognition.

9.
Sci Rep ; 8(1): 16159, 2018 11 01.
Article in English | MEDLINE | ID: mdl-30385799

ABSTRACT

A series of chemsensors (1-4) containing fluorobenzene group based on coumarin derivatives have been developed for the selective and sensitive detection of H2S. The advantages of the synthesized fluorescent probe (compound 1) were the low detection limit (4 × 10-6 mol·L-1), good selectivity and high sensitivity which had been demonstrated through UV-vis, fluorescent titration experiments. Besides cytotoxicity test of compounds (1 and 2) was studied and the results indicated that compounds (1 and 2) showed almost no cytotoxicityat at a concentration of 150 µg·mL-1. The interacted mechanism was the thiolysis reaction of dinitrophenyl ether which had been confirmed by fluorescence and HRMS titration experiment. In addition, probe 1 can also detect HS- selectively by naked eye in pure DMSO solvent.


Subject(s)
Biosensing Techniques , Coumarins/chemistry , Fluorescent Dyes/chemistry , Hydrogen Sulfide/isolation & purification , HeLa Cells , Humans , Hydrogen Sulfide/chemistry , Limit of Detection , Spectrometry, Fluorescence
10.
11.
Front Chem ; 6: 202, 2018.
Article in English | MEDLINE | ID: mdl-29988478

ABSTRACT

Owing to the role of H2S in various biochemical processes and diseases, its accurate detection is a major research goal. Three artificial fluorescent probes based on 9-anthracenecarboxaldehyde derivatives were designed and synthesized. Their anion binding capacity was assessed by UV-Vis titration, fluorescence spectroscopy, HRMS, 1HNMR titration, and theoretical investigations. Although the anion-binding ability of compound 1 was insignificant, two compounds 2 and 3, containing benzene rings, were highly sensitive fluorescent probes for HS- among the various anions studied (HS-, F-, Cl-, Br-, I-, AcO-, H2PO4- , SO32- , Cys, GSH, and Hcy). This may be explained by the nucleophilic reaction between HS- and the electron-poor C=C double bond. Due to the presence of a nitro group, compound 3, with a nitrobenzene ring, showed stronger anion binding ability than that of compound 2. In addition, compound 1 had a proliferative effect on cells, and compounds 2 and 3 showed low cytotoxicity against MCF-7 cells in the concentration range of 0-150 µg·mL-1. Thus, compounds 2 and 3 can be used as biosensors for the detection of H2S in vivo and may be valuable for future applications.

12.
J Mol Recognit ; 31(1)2018 01.
Article in English | MEDLINE | ID: mdl-28836695

ABSTRACT

Inspired by biological related parts, Schiff base derivatives and functional groups of chemical modification can provide efficient detection method of amino acids. Therefore, we have designed and prepared 4 compounds based on Schiff base derivatives involving ─NO2 , ─OH, and naphthyl group. Results indicated that compound 4 containing 2 nitro groups showed strong sensitivity and high selectivity for arginine (Arg) among normal 18 kinds of standard amino acids (alanine, valine, leucine, isoleucine, methionine, aspartic acid, glutamic acid, arginine, glycine, serine, asparagine, phenylalanine, histidine, tryptophan, proline, lysine, glutamine, and cysteine). Theoretical investigation also approved the strong binding ability of compound 4 for Arg. In addition, compound 4 displayed high combining ability of Arg and low cytotoxicity of MCF-7 cell in the 0 to 150 µg mL-1 of concentration range; it can be used for Arg in vivo detection of fluorescent probe.


Subject(s)
Arginine/analysis , Fluorescent Dyes/chemical synthesis , Naphthalenes/chemical synthesis , Arginine/chemistry , Cell Survival/drug effects , Fluorescent Dyes/toxicity , Humans , MCF-7 Cells , Naphthalenes/toxicity
13.
Sci Rep ; 7(1): 10416, 2017 09 05.
Article in English | MEDLINE | ID: mdl-28874794

ABSTRACT

In the present study, six commonly used promoters, including cytomegalovirus major immediate-early (CMV), the CMV enhancer fused to the chicken beta-actin promoter (CAG), human elongation factor-1α (HEF-1α), mouse cytomegalovirus (mouse CMV), Chinese hamster elongation factor-1α (CHEF-1α), and phosphoglycerate kinase (PGK), a CMV promoter mutant and a CAG enhancer, were evaluated to determine their effects on transgene expression and stability in transfected CHO cells. The promoters and enhancer were cloned or synthesized, and mutation at C-404 in the CMV promoter was generated; then all elements were transfected into CHO cells. Stably transfected CHO cells were identified via screening under the selection pressure of G418. Flow cytometry, qPCR, and qRT-PCR were used to explore eGFP expression levels, gene copy number, and mRNA expression levels, respectively. Furthermore, the erythropoietin (EPO) gene was used to test the selected strong promoter. Of the six promoters, the CHEF-1α promoter yielded the highest transgene expression levels, whereas the CMV promoter maintained transgene expression more stably during long-term culture of cells. We conclude that CHEF-1α promoter conferred higher level of EPO expression in CHO cells, but the CMV promoter with its high levels of stability performs best in this vector system.

14.
Luminescence ; 32(5): 765-771, 2017 Aug.
Article in English | MEDLINE | ID: mdl-28026099

ABSTRACT

A novel Cu(II) complex chemosensor for hydrogen sulfide with azo as the colorimetric group has been synthesized. The complex and ligand crystals were obtained and the molecular structures were characterized by X-ray diffraction and Electrospray ionization High resolution mass spectrometer (ESI-HRMS). The photophysical and recognition properties were examined. The complex can recognize S2- , with an obvious color change from yellow to red based on a copper ion complex displacement mechanism. By contrast, no obvious changes were observed in the presence of other anions (AcO- , H2 PO4- , F- , Cl- , Br- and I- ). We present a simple, easily prepared, yet efficient, inorganic reaction-based sensor for the detection of S2- . The complex should have many chemical and analytical applications in the sensing of hydrogen sulfide.


Subject(s)
Colorimetry/methods , Coordination Complexes/chemistry , Copper/chemistry , Fluorescent Dyes/chemistry , Fluorometry/methods , Hydrogen Sulfide/analysis , Anions , Coordination Complexes/chemical synthesis , Crystallography, X-Ray , Dimethyl Sulfoxide/chemistry , Fluorescent Dyes/chemical synthesis , Spectrometry, Mass, Electrospray Ionization , Spectrophotometry, Ultraviolet , Sulfides/analysis , X-Ray Diffraction
15.
Sensors (Basel) ; 15(11): 28166-76, 2015 Nov 06.
Article in English | MEDLINE | ID: mdl-26561816

ABSTRACT

The synthesis of four symmetrical compounds containing urea/thiourea and anthracene/nitrobenzene groups was optimized. N,N'-Di((anthracen-9-yl)-methylene) thio-carbonohydrazide showed sensitive and selective binding ability for acetate ion among the studied anions. The presence of other competitive anions including F(-), H2PO4(-), Cl(-), Br(-) and I(-) did not interfere with the strong binding ability. The mechanism of the host-guest interaction was through multiple hydrogen bonds due to the conformational complementarity and higher basicity. A theoretical investigation explained that intra-molecular hydrogen bonds existed in the compound which could strengthen the anion binding ability. In addition, molecular frontier orbitals in molecular interplay were introduced in order to explain the red-shift phenomenon in the host-guest interaction process. Compounds based on thiourea and anthracene derivatives can thus be used as a chemosensor for detecting acetate ion in environmental and pharmaceutical samples.


Subject(s)
Chemistry Techniques, Analytical/methods , Thiourea/chemistry , Acetates/analysis , Acetates/chemistry , Anions/analysis , Anions/chemistry , Anthracenes/chemistry , Models, Molecular , Thiourea/chemical synthesis
16.
Acta Chim Slov ; 62(1): 35-44, 2015.
Article in English | MEDLINE | ID: mdl-25830958

ABSTRACT

New phenanthroline derivatives (1, 2, 3, 4) containing phenol groups have been synthesized and optimized. The nano-material of compound 2 was also developed. Their binding properties were evaluated for various biological anions (F(-), Cl(-), Br(-), I(-), AcO(-) and H(2)PO(4)(-)) by theoretical investigation, UV-vis, fluorescence, (1)HNMR titration experiments and these compounds all showed strong binding ability for AcO(-) without the interference of other anions tested. The anion binding ability could be regularized by electron push-pull properties of the ortho- or para- substituent on benzene. Theoretical investigation analysis revealed the effect of intramolecular hydrogen bond existed between -OH and other atoms in the structure of these compounds.


Subject(s)
Acetates/chemistry , Nanostructures/chemistry , Phenanthrolines/chemistry , Quantum Theory , Anions/chemistry , Molecular Structure , Particle Size , Phenanthrolines/chemical synthesis , Surface Properties
17.
Mater Sci Eng C Mater Biol Appl ; 51: 279-86, 2015 Jun.
Article in English | MEDLINE | ID: mdl-25842136

ABSTRACT

Inspired from biological counterparts, chemical modification of azo derivatives with function groups may provide a highly efficient method to detect amino acid. Herein, we have designed and prepared a series of azo nano-materials involving -NO2, -COOH, -SO3H and naphthyl group, which showed high response for Arginine (Arg) among normal twenty kinds of (Alanine, Valine, Leucine, Isoleucine, Methionine, Aspartic acid, Glutamic acid, Arginine, Glycine, Serine, Threonine, Asparagine, Phenylalanine, Histidine, Tryptophan, Proline, Lysine, Glutamine, Tyrosine and Cysteine). Furthermore, theoretical investigation further illustrated the possible binding mode in the host-guest interaction and the roles of molecular frontier orbitals in molecular interplay. In addition, nano-material 3 exhibited high binding ability for Arg and low cytotoxicity to KYSE450 cells over a concentration range of 5-50µmol·L(-1) which may be used a biosensor for the Arg detection in vivo.


Subject(s)
Arginine/analysis , Azo Compounds/chemistry , Biosensing Techniques/methods , Nanostructures/chemistry , Neoplasms, Experimental/pathology , Arginine/chemistry , Azo Compounds/toxicity , Binding Sites , Cell Line, Tumor , Cell Survival/drug effects , Computer Simulation , Humans , Materials Testing , Models, Chemical , Nanostructures/toxicity , Neoplasms, Experimental/physiopathology , Reproducibility of Results , Sensitivity and Specificity , Spectrometry, Fluorescence/methods
18.
Mater Sci Eng C Mater Biol Appl ; 38: 101-6, 2014 May 01.
Article in English | MEDLINE | ID: mdl-24656358

ABSTRACT

Two nano-material-containing azo groups have been designed and developed, and the binding ability of nano-materials with various amino acids has been characterized by UV-vis and fluorescence titrations. Results indicated that two nano-materials showed the strongest binding ability for homocysteine among twenty normal kinds of amino acids (alanine, valine, leucine, isoleucine, methionine, aspartic acid, glutamic acid, arginine, glycine, serine, threonine, asparagine, phenylalanine, histidine, tryptophan, proline, lysine, glutamine, tyrosine and homocysteine). The reason for the high sensitivity for homocysteine was that two nano-materials containing an aldehyde group reacted with SH in homocysteine and afforded very stable thiazolidine derivatives. Theoretical investigation further illustrated the possible binding mode in host-guest interaction and the roles of molecular frontier orbitals in molecular interplay. Thus, the two nano-materials can be used as optical sensors for the detection of homocysteine.


Subject(s)
Amino Acids/metabolism , Azo Compounds/metabolism , Models, Molecular , Nanostructures/chemistry , Amino Acids/chemistry , Azo Compounds/chemical synthesis , Azo Compounds/chemistry , Kinetics , Molecular Conformation , Nanostructures/ultrastructure , Spectrometry, Fluorescence , Spectrophotometry, Ultraviolet
19.
Molecules ; 18(12): 14840-8, 2013 Dec 03.
Article in English | MEDLINE | ID: mdl-24300118

ABSTRACT

A fluorescent and colorimetric molecular probe containing phenol groups has been designed and synthesized. The anion binding ability was evaluated for biolgically important anions (F-, Cl-, Br-, I-, AcO- and H2PO4-) by theoretical investigation, UV-Vis and fluorescence spectroscopy and 1H-NMR titration experiments. Results indicated the probe showed strong binding ability for H2PO4- without the interference of other anions tested and the interaction process was accompanied by color changes. Theoretical investigation analysis revealed that intramolecular hydrogen bonds existed in the structure of the probe and the roles of molecular frontier orbitals in molecular interplay were determined.


Subject(s)
Coloring Agents/chemistry , Molecular Probes/chemistry , Phenanthrolines/chemistry , Anions/chemistry , Coloring Agents/chemical synthesis , Hydrogen Bonding , Models, Chemical , Models, Molecular , Molecular Conformation , Molecular Probes/chemical synthesis , Nuclear Magnetic Resonance, Biomolecular , Phenanthrolines/chemical synthesis
20.
Spectrochim Acta A Mol Biomol Spectrosc ; 103: 276-81, 2013 Feb 15.
Article in English | MEDLINE | ID: mdl-23261623

ABSTRACT

Based on thiourea moiety, three colorimetric and fluorescent anion probes have been synthesized. Results indicated the probe 1 containing p-NO(2) group showed the strongest binding ability for AcO(-) among the anions tested (F(-), AcO(-), H(2)PO(4)(-), Cl(-), Br(-), I(-)), which was not influenced by the existence of other anions. The interaction of host-guest was accompanied with a dramatic color change from colorless to orange. However, the addition of various anions did not cause noticeable spectral response of the probes (2 and 3) containing o, m-NO(2) groups. Theoretical investigation demonstrated the electron transition of the highest LUMO aroused the red-shift phenomenon in UV-vis spectra of 1-anion.


Subject(s)
Acetates/analysis , Anions/analysis , Coloring Agents/chemistry , Thiourea/chemistry , Colorimetry/methods , Fluorescence , Fluorescent Dyes/chemistry , Models, Molecular , Spectrophotometry, Ultraviolet
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