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Angewandte Chemie (International Ed. in... Jan 2017Cell adhesion is regulated by molecularly defined protein interactions and by mechanical forces, which can activate a dynamic restructuring of adhesion sites. Previous...
Cell adhesion is regulated by molecularly defined protein interactions and by mechanical forces, which can activate a dynamic restructuring of adhesion sites. Previous attempts to explore the response of cell adhesion to forces have been limited to applying mechanical stimuli that involve the cytoskeleton. In contrast, we here apply a new, oscillatory type of stimulus through push-pull azobenzenes. Push-pull azobenzenes perform a high-frequency, molecular oscillation upon irradiation with visible light that has frequently been applied in polymer surface relief grating. We here use these oscillations to address single adhesion receptors. The effect of molecular oscillatory forces on cell adhesion has been analyzed using single-cell force spectroscopy and gene expression studies. Our experiments demonstrate a reinforcement of cell adhesion as well as upregulated expression levels of adhesion-associated genes as a result of the nanoscale "tickling" of integrins. This novel type of mechanical stimulus provides a previously unprecedented molecular control of cellular mechanosensing.
Topics: Animals; Azo Compounds; Biomechanical Phenomena; Cell Adhesion; Cell Line; Integrins; Microscopy, Atomic Force; Peptides, Cyclic; Rats; Single-Cell Analysis
PubMed: 27900823
DOI: 10.1002/anie.201609483 -
Bioorganic Chemistry Jan 2020With the emergence of multi-drug resistant bacteria and hospital-acquired infections, there is an urgent need to develop new antibiotics. Here, we report the synthesis,...
With the emergence of multi-drug resistant bacteria and hospital-acquired infections, there is an urgent need to develop new antibiotics. Here, we report the synthesis, physico-chemical characterizations, and antimicrobial activity assays of four Azo compounds that differ in their alkyl chain length. The molecular mechanism of their antibacterial activity was investigated by complementary in vitro and in silico biophysical studies. The compounds with alkyl chain lengths of four or six carbons showed a low MIC against Escherichia coli and Bacillus subtilis. Our investigations into the mechanism of their action revealed that phosphatidylethanolamine in the bacterial plasma membrane plays an important role in their antibacterial activity.
Topics: Anti-Bacterial Agents; Azo Compounds; Bacillus subtilis; Dose-Response Relationship, Drug; Escherichia coli; Membrane Lipids; Microbial Sensitivity Tests; Molecular Structure; Structure-Activity Relationship; Surface-Active Agents
PubMed: 31706683
DOI: 10.1016/j.bioorg.2019.103399 -
The Journal of Physical Chemistry... Jul 2021The determination of electronic excited state (ES) properties is the cornerstone of theoretical photochemistry. Yet, traditional ES methods become impractical when...
The determination of electronic excited state (ES) properties is the cornerstone of theoretical photochemistry. Yet, traditional ES methods become impractical when applied to fairly large molecules, or when used on thousands of systems. Machine learning (ML) techniques have demonstrated their accuracy at retrieving ES properties of large molecular databases at a reduced computational cost. For these applications, nonlinear algorithms tend to be specialized in targeting individual properties. Learning fundamental quantum objects potentially represents a more efficient, yet complex, alternative as a variety of molecular properties could be extracted through postprocessing. Herein, we report a general framework able to learn three fundamental objects: the hole and particle densities, as well as the transition density. We demonstrate the advantages of targeting those outputs and apply our predictions to obtain properties, including the state character and the exciton topological descriptors, for the two bands (nπ* and ππ*) of 3427 azoheteroarene photoswitches.
Topics: Azo Compounds; Coloring Agents; Machine Learning; Models, Molecular; Molecular Conformation; Quantum Theory
PubMed: 34157226
DOI: 10.1021/acs.jpclett.1c01425 -
Molecules (Basel, Switzerland) Oct 2022Novel yellow azo pyridone dye derivatives were synthesized for use in image-sensor color filters. The synthesized compounds have a basic chemical structure composed of...
Novel yellow azo pyridone dye derivatives were synthesized for use in image-sensor color filters. The synthesized compounds have a basic chemical structure composed of azo, hydroxy, amide, and nitrile groups as well as different halide groups. New materials were evaluated on the basis of their optical, thermal, and surface properties under conditions mimicking those of a commercial device fabrication process. A comparison of their related performance revealed that, among the four prepared compounds, 5-((4,6-dichlorocyclohexa-2,4-dien-1-yl)diazenyl)-6-hydroxy-1,4-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (Cl-PAMOPC) exhibited the best performance as an image-sensor color filter material, including a solubility greater than 0.1 wt% in propylene glycol monomethyl ether acetate solvent, a high decomposition temperature of 263 °C, and stable color difference values of 4.93 and 3.88 after a thermal treatment and a solvent-resistance test, respectively. The results suggest that Cl-PAMOPC can be used as a green dye additive in an image-sensor colorant.
Topics: Acetates; Amides; Azo Compounds; Color; Coloring Agents; Dihydropyridines; Inorganic Chemicals; Nitriles; Pyridones; Solvents
PubMed: 36235139
DOI: 10.3390/molecules27196601 -
Nature Communications Jul 2018Paraquat, as one of the most widely used herbicides globally, is highly toxic to humans, and chronic exposure and acute ingestion leads to high morbidity and mortality...
Paraquat, as one of the most widely used herbicides globally, is highly toxic to humans, and chronic exposure and acute ingestion leads to high morbidity and mortality rates. Here, we report user-friendly, photo-responsive paraquat-loaded supramolecular vesicles, prepared via one-pot self-assembly of amphiphilic, ternary host-guest complexes between cucurbit[8]uril, paraquat, and an azobenzene derivative. In this vesicle formulation, paraquat is only released upon UV or sunlight irradiation that converts the azobenzene derivative from its trans- to its cis- form, which in turn dissociates the ternary host-guest complexations and the vesicles. The cytotoxicity evaluation of this vesicle formulation of paraquat on in vitro cell models, in vivo zebrafish models, and mouse models demonstrates an enhanced safety profile. Additionally, the PQ-loaded vesicles' herbicidal activity against a model of invasive weed is nearly identical to that of free paraquat under natural sunlight. This study provides a safe yet effective herbicide formulation.
Topics: Animals; Azo Compounds; COS Cells; Chlorocebus aethiops; Female; Herbicides; Humans; Kidney; Liver; Mice; Mice, Inbred C57BL; Models, Animal; Paraquat; Zebrafish
PubMed: 30054483
DOI: 10.1038/s41467-018-05437-5 -
Ecotoxicology and Environmental Safety Jun 2022This study aimed to exploit the potential of Enterococcus faecalis R1107 in the bioremediation of azo dyes. The maximal decolorization of Congo Red (CR), Reactive Black...
This study aimed to exploit the potential of Enterococcus faecalis R1107 in the bioremediation of azo dyes. The maximal decolorization of Congo Red (CR), Reactive Black 5 (RB5), and Direct Black 38 (DB38) were 90.17%, 96.82%, and 81.95%, respectively, with the bacterial treatment for 48 h. 65.57% of CR and 72.64% of RB5 could be decolorized by E. faecalis R1107 within 48 h when the concentration of azo dyes increased up to 1000 mg/L. FTIR analysis confirmed that E. faecalis R1107 could effectively break down the chemical structures of three azo dyes. E. faecalis R1107 alleviated the phytotoxicity of azo dyes and improved seed germination, which contributed to the increase in the lengths of roots, stems, and leaves of Vigna radiata seedlings. Transcriptomic analysis suggested that the gene regulatory networks in E. faecalis R1107 synergistically improved the degradation and detoxification of RB5, including the major metabolic pathways, the secondary metabolism, the transport system, the amino acid metabolic pathways, and the signal transduction systems. Simulated textile effluent (STE) was used to mimic real textile effluent to evaluate the bioremediation potential of E. faecalis R1107, and 72.79% STE can be decolorized after E. faecalis R1107 treatment for 48 h. In summary, our study demonstrated that E. faecalis R1107 might be well suitable for potential applications in the bioremediation of textile effluent.
Topics: Azo Compounds; Biodegradation, Environmental; Coloring Agents; Congo Red; Enterococcus faecalis; Textile Industry; Textiles
PubMed: 35526458
DOI: 10.1016/j.ecoenv.2022.113577 -
Journal of the American Chemical Society Jun 2023Supramolecular synthetic transporters are crucial to understand and activate the passage across lipid membranes of hydrophilic effector molecules. Herein, we introduce...
Supramolecular synthetic transporters are crucial to understand and activate the passage across lipid membranes of hydrophilic effector molecules. Herein, we introduce photoswitchable calixarenes for the light-controlled transport activation of cationic peptide cargos across model lipid bilayers and inside living cells. Our approach was based on rationally designed -sulfonatocalix[4]arene receptors equipped with a hydrophobic azobenzene arm, which recognize cationic peptide sequences at the nM range. Activation of membrane peptide transport is confirmed, in synthetic vesicles and living cells, for calixarene activators featuring the azobenzene arm in the configuration. Therefore, this method allows the modulation of the transmembrane transport of peptide cargos upon - photoisomerization of functionalized calixarenes using 500 nm visible light. These results showcase the potential of photoswitchable counterion activators for the light-triggered delivery of hydrophilic biomolecules and pave the way for potential applications in remotely controlled membrane transport and photopharmacology applications of hydrophilic functional biomolecules.
Topics: Calixarenes; Azo Compounds; Lipid Bilayers; Biological Transport
PubMed: 37289668
DOI: 10.1021/jacs.3c01829 -
Journal of Cancer Research and... 2016Certain anthraquinone compounds are effectively used for treatment of cancer. The present study describes the inhibitory activity of lac dye, a mixture of polyhydroxy...
OBJECTIVE
Certain anthraquinone compounds are effectively used for treatment of cancer. The present study describes the inhibitory activity of lac dye, a mixture of polyhydroxy anthraquinone compounds (Laccaic acid A, B, C, D and E), produced by the Indian lac insect, Kerria lacca (Kerr).
MATERIALS AND METHODS
In vitro testing for anticancer activity of lac dye was done at four concentrations (10, 20, 40, 80 μg/ml) on ten human malignant cell lines including six human leukemia cell lines, U973, Raji, K562, Jurkat, MOLT 4 and HL60 using SRB assay.
RESULTS AND CONCLUSION
Both crimson and yellow lac dye inhibits proliferation of Human leukemia cell lines, Raji, U937, K562, HL60 and Jurkat, therefore can be considered as a potential anticancer agent for leukemia.
Topics: Antineoplastic Agents; Azo Compounds; Cell Line, Tumor; Cell Proliferation; Humans
PubMed: 27461693
DOI: 10.4103/0973-1482.155975 -
Advanced Science (Weinheim,... May 2022In this work, a real-time precise electrical method to directly monitor the stochastic binding dynamics of a single supramolecule based on the host-guest interaction...
In this work, a real-time precise electrical method to directly monitor the stochastic binding dynamics of a single supramolecule based on the host-guest interaction between a cyclodextrin and an azo compound is reported. Different intermolecular binding states during the binding process are distinguished by conductance signals detected from graphene-molecule-graphene single-molecule junctions. In combination with theoretical calculations, the reciprocating and unidirectional motions in the trans form as well as the restrained reciprocating motion in the cis form due to the steric hindrance is observed, which could be reversibly switched by visible and UV irradiation. The integration of individual supramolecules into nanocircuits not only offers a facile and effective strategy to probe the dynamic process of supramolecular systems, but also paves the way to construct functional molecular devices toward real applications such as switches, sensors, and logic devices.
Topics: Azo Compounds; Cyclodextrins; Graphite; Nanotechnology; Ultraviolet Rays
PubMed: 35233985
DOI: 10.1002/advs.202200022 -
Journal of Industrial Microbiology &... Dec 2009The capability of Lactobacillus acidophilus and Lactobacillus fermentum to degrade azo dyes was investigated. The bacteria were incubated under anaerobic conditions in...
The capability of Lactobacillus acidophilus and Lactobacillus fermentum to degrade azo dyes was investigated. The bacteria were incubated under anaerobic conditions in the presence of 6 microg/ml Methyl Red, Ponceau BS, Orange G, Amaranth, Orange II, and Direct Blue 15; 5 microg/ml Sudan I and II; or 1.5 microg/ml Sudan III and IV in deMann-Rogosa-Sharpe broth at 37 degrees C for 36 h, and reduction of the dyes was monitored. Both bacteria were capable of degrading all of the water-soluble azo dyes to some extent. They were also able to completely reduce the oil-soluble diazo dyes Sudan III and IV but were unable to reduce the oil-soluble monoazo dyes Sudan I and II to any significant degree in the concentrations studied. Growth of the bacteria was not significantly affected by the presence of the Sudan azo dyes. Metabolites of the bacterial degradation of Sudan III and IV were isolated and identified by liquid chromatography electrospray ionization tandem mass spectrometry analyses and compared with authentic standards. Aniline and o-toluidine (2-methylaniline), both potentially carcinogenic aromatic amines, were metabolites of Sudan III and IV, respectively.
Topics: Azo Compounds; Coloring Agents; Lactobacillus acidophilus; Limosilactobacillus fermentum; Oils; Water
PubMed: 19727875
DOI: 10.1007/s10295-009-0633-9