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1.
Pak J Pharm Sci ; 37(1(Special)): 173-184, 2024 Jan.
Article En | MEDLINE | ID: mdl-38747267

Hydrazones 1-6, azo-pyrazoles 7-9 and azo-pyrimidines 10-15 are compounds that exhibit antibacterial activity. The mode of action and structures of these derivatives have been previously confirmed as antibacterial. In this investigation, biological screening and molecular docking studies were performed for derivatives 1-15, with compounds 2, 7, 8, 14 and 15 yielding the best energy scores (from -20.7986 to -10.5302 kcal/mol). Drug-likeness and in silico ADME prediction for the most potent derivatives, 2, 7, 8, 14 and 15, were predicted (from 84.46 to 96.85%). The latter compounds showed good recorded physicochemical properties and pharmacokinetics. Compound 8 demonstrated the strongest inhibition, which was similar to the positive control (eflornithine) against Trypanosoma brucei brucei (WT), with an EC50 of 25.12 and 22.52µM, respectively. Moreover, compound 14 exhibited the best activity against Leishmania mexicana promastigotes and Leishmania major promastigotes (EC50 =46.85; 40.78µM, respectively).


Molecular Docking Simulation , Pyrazoles , Pyrimidines , Trypanocidal Agents , Trypanosoma brucei brucei , Pyrimidines/pharmacology , Pyrimidines/chemistry , Pyrimidines/chemical synthesis , Trypanosoma brucei brucei/drug effects , Pyrazoles/pharmacology , Pyrazoles/chemistry , Trypanocidal Agents/pharmacology , Trypanocidal Agents/chemistry , Trypanocidal Agents/chemical synthesis , Leishmania mexicana/drug effects , Leishmania major/drug effects , Antiprotozoal Agents/pharmacology , Antiprotozoal Agents/chemistry , Computer Simulation , Azo Compounds/pharmacology , Azo Compounds/chemistry , Azo Compounds/chemical synthesis , Structure-Activity Relationship , Parasitic Sensitivity Tests
2.
Sci Rep ; 14(1): 10419, 2024 05 06.
Article En | MEDLINE | ID: mdl-38710746

The present work elicits a novel approach to combating COVID-19 by synthesizing a series of azo-anchored 3,4-dihydroimidazo[4,5-b]indole derivatives. The envisaged methodology involves the L-proline-catalyzed condensation of para-amino-functionalized azo benzene, indoline-2,3-dione, and ammonium acetate precursors with pertinent aryl aldehyde derivatives under ultrasonic conditions. The structures of synthesized compounds were corroborated through FT-IR, 1H NMR, 13C NMR, and mass analysis data. Molecular docking studies assessed the inhibitory potential of these compounds against the main protease (Mpro) of SARS-CoV-2. Remarkably, in silico investigations revealed significant inhibitory action surpassing standard drugs such as Remdesivir, Paxlovid, Molnupiravir, Chloroquine, Hydroxychloroquine (HCQ), and (N3), an irreversible Michael acceptor inhibitor. Furthermore, the highly active compound was also screened for cytotoxicity activity against HEK-293 cells and exhibited minimal toxicity across a range of concentrations, affirming its favorable safety profile and potential suitability. The pharmacokinetic properties (ADME) of the synthesized compounds have also been deliberated. This study paves the way for in vitro and in vivo testing of these scaffolds in the ongoing battle against SARS-CoV-2.


Antiviral Agents , COVID-19 Drug Treatment , Coronavirus 3C Proteases , Indoles , Molecular Docking Simulation , Protease Inhibitors , SARS-CoV-2 , Humans , Antiviral Agents/pharmacology , Antiviral Agents/chemistry , Antiviral Agents/chemical synthesis , SARS-CoV-2/drug effects , Coronavirus 3C Proteases/antagonists & inhibitors , Coronavirus 3C Proteases/metabolism , Coronavirus 3C Proteases/chemistry , Indoles/pharmacology , Indoles/chemistry , Indoles/chemical synthesis , HEK293 Cells , Protease Inhibitors/pharmacology , Protease Inhibitors/chemistry , Protease Inhibitors/chemical synthesis , Imidazoles/pharmacology , Imidazoles/chemistry , Imidazoles/chemical synthesis , Computer Simulation , COVID-19/virology , Azo Compounds/pharmacology , Azo Compounds/chemistry , Azo Compounds/chemical synthesis
3.
Anal Chem ; 96(19): 7723-7729, 2024 May 14.
Article En | MEDLINE | ID: mdl-38695281

Accurate detection of labile analytes through activity based fluorogenic sensing is meaningful but remains a challenge because of nonrapid reaction kinetic. Herein, we present a signaling reporter engineering strategy to accelerate azoreduction reaction by positively charged fluorophore promoted unstable anion recognition for rapidly sensing sodium dithionite (Na2S2O4), a kind of widespread used but harmful inorganic reducing agent. Its quick decomposition often impedes application reliability of traditional fluorogenic probes in real samples because of their slow responses. In this work, four azo-based probes with different charged fluorophores (positive, zwitterionic, neutral, and negative) were synthesized and compared. Among of them, with sequestration effect of positively charged anthocyanin fluorophore for dithionite anion via electrostatic attraction, the cationic probe Azo-Pos displayed ultrafast fluorogenic response (∼2 s) with the fastest response kinetic (kpos' = 0.373 s-1) that is better than other charged ones (kzwi' = 0.031 s-1, kneu' = 0.013 s-1, kneg' = 0.003 s-1). Azo-Pos was demonstrated to be capable to directly detect labile Na2S2O4 in food samples and visualize the presence of Na2S2O4 in living systems in a timely fashion. This new probe has potential as a robust tool to fluorescently monitor excessive food additives and biological invasion of harmful Na2S2O4. Moreover, our proposed accelerating strategy would be versatile to develop more activity-based sensing probes for quickly detecting other unstable analytes of interest.


Fluorescent Dyes , Fluorescent Dyes/chemistry , Humans , Dithionite/chemistry , Azo Compounds/chemistry , Kinetics
4.
Molecules ; 29(9)2024 Apr 24.
Article En | MEDLINE | ID: mdl-38731445

Reducing high concentrations of pollutants such as heavy metals, pesticides, drugs, and dyes from water is an emerging necessity. We evaluated the use of Luffa cylindrica (Lc) as a natural non-conventional adsorbent to remove azo dye mixture (ADM) from water. The capacity of Lc at three different doses (2.5, 5.0, and 10.0 g/L) was evaluated using three concentrations of azo dyes (0.125, 0.250, and 0.500 g/L). The removal percent (R%), maximum adsorption capacity (Qm), isotherm and kinetics adsorption models, and pH influence were evaluated, and Fourier-transform infrared spectroscopy and scanning electron microscopy were performed. The maximum R% was 70.8% for 10.0 g L-1Lc and 0.125 g L-1 ADM. The Qm of Lc was 161.29 mg g-1. Adsorption by Lc obeys a Langmuir isotherm and occurs through the pseudo-second-order kinetic model. Statistical analysis showed that the adsorbent dose, the azo dye concentration, and contact time significantly influenced R% and the adsorption capacity. These findings indicate that Lc could be used as a natural non-conventional adsorbent to reduce ADM in water, and it has a potential application in the pretreatment of wastewaters.


Azo Compounds , Coloring Agents , Luffa , Water Pollutants, Chemical , Water Purification , Luffa/chemistry , Azo Compounds/chemistry , Azo Compounds/isolation & purification , Adsorption , Water Pollutants, Chemical/chemistry , Water Pollutants, Chemical/isolation & purification , Water Purification/methods , Kinetics , Coloring Agents/chemistry , Hydrogen-Ion Concentration , Spectroscopy, Fourier Transform Infrared , Water/chemistry
5.
Medicine (Baltimore) ; 103(16): e37846, 2024 Apr 19.
Article En | MEDLINE | ID: mdl-38640324

The current study aimed to investigate the potential role of astragaloside IV (AS-IV) in improving cellular lipid deposition and its underlying mechanism. A fatty liver cell model was established by treating hepatoma cells with palmitic acid. AS-IV and SC79 were used for treatment. Oil Red O staining was applied to detect intracellular lipid deposition, and transmission electron microscopy was utilized to assess autophagosome formation. Immunofluorescence double staining was applied to determine microtubule-associated proteins 1A/1B light chain 3 (LC3) expression. Western blot analysis was performed to detect the expression of LC3, prostacyclin, Beclin-1, V-akt murine thymoma viral oncogene homolog (Akt), phosphorylated Akt, mTOR, and phosphorylated mTOR. Oil Red O staining revealed that AS-IV reduced intracellular lipid accumulation. Further, it increased autophagosome synthesis and the expression of autophagy proteins LC3 and Beclin-1 in the cells. It also reduced the phosphorylation levels of Akt and mTOR and the levels of prostacyclin. However, the effects of AS-IV decreased with SC79 treatment. In addition, LC3B + BODIPY493/503 fluorescence double staining showed that AS-IV reduced intracellular lipid deposition levels by enhancing autophagy. AS-IV can reduce lipid aggregation in fatty liver cells, which can be related to enhanced hepatocyte autophagy by inhibiting the Akt/mTOR signaling pathway.


Autophagy , Fatty Liver , Lipid Metabolism , Saponins , Triterpenes , Animals , Humans , Mice , Autophagy/drug effects , Azo Compounds , Beclin-1/metabolism , Fatty Liver/drug therapy , Lipids , Prostaglandins I , Proto-Oncogene Proteins c-akt/drug effects , Proto-Oncogene Proteins c-akt/metabolism , Saponins/pharmacology , TOR Serine-Threonine Kinases/drug effects , TOR Serine-Threonine Kinases/metabolism , Triterpenes/pharmacology , Lipid Metabolism/drug effects
6.
Zhongguo Zhong Yao Za Zhi ; 49(3): 763-769, 2024 Feb.
Article Zh | MEDLINE | ID: mdl-38621880

This study aims to investigate the effect of Erchen Decoction(ECD) on liver mitochondrial function in mice with a high-fat diet and its possible mechanism. A total of sixty C57BL/6J mice were randomly divided into a normal group, high-fat group, ECD group, mTORC1 activator(MHY) group, ECD+MHY group, and polyene phosphatidyl choline(PPC) group, with 10 rats in each group. The normal group was given a normal diet, and the other groups were fed a high-fat diet for 20 weeks. At the 17th week, the ECD group and ECD+MHY group were given ECD(8.7 g·kg~(-1)) daily, and the PPC group was given PPC(0.18 g·kg~(-1)) daily, while the remaining groups were given normal saline(0.01 mL·g~(-1)) daily for four weeks. In the 19th week, the MHY group and ECD+MHY group were injected intraperitoneally with MHY(5 mg·kg~(-1)) every other day for two weeks. During the experiment, the general conditions of the mice were observed. The contents of triglyceride(TG) and total cholesterol(TC) in serum were measured. Morphological changes in liver tissue were examined through HE and oil red O staining. The content of adenosine triphosphate(ATP) was determined using chemiluminescence, and mitochondrial membrane potential was assessed using a fluorescence probe(JC-1). Western blot was performed to detect the expression of rapamycin target protein complex 1(mTOR1), ribosomal protein S6 kinase B1(S6K), sterol regulatory element binding protein 1(SREBP1), and caveolin 1(CAV1). RESULTS:: revealed that compared with the normal group, the mice in the high-fat group exhibited significant increases in body weight and abdominal circumference(P<0.01). Additionally, there were significant increases in TG and TC levels(P<0.01). HE and oil red O staining showed that the boundaries of hepatic lobules were unclear; hepatocytes were enlarged, round, and irregularly arranged, with obvious lipid droplet deposition and inflammatory cell infiltration. The liver ATP content and mitochondrial membrane potential decreased significantly(P<0.01). The expression of p-mTOR, p-S6K, and n-SREBP1 increased significantly(P<0.01), while the expression of CAV1 decreased significantly(P<0.01). Compared with the high-fat group, the body weight and TG content of mice in the ECD group and PPC group decreased significantly(P<0.05). Improvements were observed in hepatocyte morphology, lipid deposition, and inflammatory cell infiltration. Furthermore, there were significant increases in ATP content and mitochondrial membrane potential(P<0.05 or P<0.01). The expression of p-mTOR, p-S6K, and n-SREBP1 decreased significantly in the ECD group(P<0.01), while CAV1 expression increased significantly(P<0.01). However, the indices mentioned above did not show improvement in the MHY group. When the ECD+MHY group was compared with the MHY group, there were significant reductions in body weight and TG contents(P<0.05). The morphological changes of hepatocytes, lipid deposition, and inflammatory cell infiltration were recovered. Moreover, there were significant increases in liver ATP content and mitochondrial membrane potential(P<0.05 or P<0.05). The expression of p-mTOR, p-S6K, and n-SREBP1 decreased significantly(P<0.01), while CAV1 expression increased significantly(P<0.01). In conclusion, ECD can improve mitochondrial function by regulating the mTORC1/SREBP1/CAV1 pathway. This mechanism may be involved in the resolution of phlegm syndrome and the regulation of lipid metabolism.


Azo Compounds , Diet, High-Fat , Non-alcoholic Fatty Liver Disease , Mice , Rats , Animals , Diet, High-Fat/adverse effects , Mechanistic Target of Rapamycin Complex 1/metabolism , Mechanistic Target of Rapamycin Complex 1/pharmacology , Caveolin 1/metabolism , Caveolin 1/pharmacology , Mice, Inbred C57BL , Liver , Non-alcoholic Fatty Liver Disease/metabolism , TOR Serine-Threonine Kinases/metabolism , Triglycerides/metabolism , Body Weight , Adenosine Triphosphate/pharmacology
7.
Int J Biol Macromol ; 267(Pt 2): 131478, 2024 May.
Article En | MEDLINE | ID: mdl-38604434

In this study, an environmentally friendly, effective, easily synthesizable and recoverable nano-sized catalyst system (Ag@NaAlg-keratin) was designed by decorating Ag nanoparticles on microbeads containing sodium alginate (NaAlg) and keratin obtained from goose feathers. The structure, morphology and crystallinity of the Ag@NaAlg-keratin nanocatalyst were evaluated by XRD, FT-IR, FE-SEM, EDS/EDS mapping and TEM analyses. Catalytic ability of designed Ag@NaAlg-keratin nanocatalyst was then investigated against 4-nitrophenol (4-NP) and methyl orange (MO) reductions. Ag@NaAlg-keratin nanocatalyst effectively reduced 4-NP in 6 min and MO in 5 min, with rate constants of 0.17 min-1 and 0.16 min-1, respectively. Additionally, activation energies (Ea) were found as 39.8 kJ/mol for 4-NP and 37.9 kJ/mol for MO. Performed recyclability tests showed that the Ag@NaAlg-keratin nanocatalyst was easily recovered due to its microbead form and successfully reused five times, maintaining both its activity and structure. Furthermore, antioxidant activity of Ag@NaAlg-keratin nanocatalyst was the highest (73.16 %).


Alginates , Antioxidants , Keratins , Metal Nanoparticles , Microspheres , Silver , Alginates/chemistry , Metal Nanoparticles/chemistry , Silver/chemistry , Keratins/chemistry , Catalysis , Antioxidants/chemistry , Antioxidants/pharmacology , Animals , Nitrophenols/chemistry , Feathers/chemistry , Azo Compounds/chemistry
8.
Int J Biol Macromol ; 267(Pt 2): 131533, 2024 May.
Article En | MEDLINE | ID: mdl-38608988

As a renewable aromatic compound with enormous production potential, lignin has various potential high-value utilization pathways, but the success achieved in the field of photocatalysis is limited. Herein, this work prepares a new type of photocatalyst by modifying Graphitic Carbon Nitride Nanotubes (CNT) with self-assembled lignin nanospheres for the photocatalytic production of H2O2 and the degradation of azo dyes. Under light conditions, lignin enhances the production of H2O2 through oxygen reduction and collaborates with carbon nitride tubes to generate O2- and 1O2. Furthermore, carbon nitride tubes form electron-rich regions with lignin, promoting the transfer of electrons from adsorbed aromatic pollutants to this region, thereby facilitating their degradation. The experimental results indicate that the addition of 5 % lignin significantly enhances the photocatalytic degradation efficiency of azo dyes, with a degradation rate 1.87 times higher than that of the original carbon nitride tubes. Furthermore, CNL also have excellent degradation ability to pollutants in actual wastewater. This study provides new insights and prospects for the high-value utilization of lignin, enabling it to be used as a photocatalytic co-catalyst to participate in the photocatalytic degradation of environmental pollutants.


Graphite , Hydrogen Peroxide , Lignin , Lignin/chemistry , Graphite/chemistry , Catalysis , Hydrogen Peroxide/chemistry , Nanotubes/chemistry , Nitriles/chemistry , Azo Compounds/chemistry , Boron Compounds/chemistry , Water Pollutants, Chemical/chemistry , Photochemical Processes , Nanotubes, Carbon/chemistry , Nitrogen Compounds
9.
Chemosphere ; 355: 141879, 2024 May.
Article En | MEDLINE | ID: mdl-38570050

The use of emerging composite materials has been booming to remove environmental pollutants. The aim of this research is to develop a new composite based on Cs3Bi2Cl9 perovskite and graphitic carbon nitride (g-C3N4) to investigate the photocatalytic performance under visible light irradiation. To achieve this, we produce the Cs3Bi2Cl9/g-C3N4 heterojunctions through a simple self-assembly synthesis. The as-synthesized composites are characterized using XRD, FTIR, FESEM, TEM, BET and EDX techniques. The photocatalytic performance of Cs3Bi2Cl9/g-C3N4 is examined in the degradation of various water contaminants, including 4-nitrophenol (4-NP), tetracycline antibiotic (TC), methylene blue (MB) and methyl orange (MO). The experimental results indicate the superior photocatalytic performance of the composites in the degradation of pollutants compared to pure Cs3Bi2Cl9 and g-C3N4. The 10% Cs3Bi2Cl9/g-C3N4 composite achieves the optimal degradation efficiency of 100, 92, 98.7, and 85.1% of 4-NP, TC, MB, and MO, respectively. This superior photocatalytic activity attributes to improved optical and electrochemical properties, including enhanced absorption ability, narrowing band gap, promoted separation efficiency of photogenerated carriers, and a high redox potential, which is confirmed by UV-vis DRS, PL, EIS, and CV analyses. The 10% Cs3Bi2Cl9/g-C3N4 composite also demonstrates high photocatalytic stability after four consecutive cycles. Radical trapping tests show that superoxide radicals (•O2-), holes (h+), and hydroxyl radicals (•OH) contribute to the photocatalytic process. Based on the obtained data, a direct Z-scheme heterojunction mechanism is proposed. Overall, this research offers a new stable photocatalyst with excellent prospect for photocatalytic applications.


Azo Compounds , Environmental Pollutants , Water , Kinetics , Physics , Methylene Blue
10.
BMC Oral Health ; 24(1): 407, 2024 Mar 31.
Article En | MEDLINE | ID: mdl-38556862

BACKGROUND: Dental pulp stem cells (DPSCs) are a kind of undifferentiated dental mesenchymal stem cells with strong self-renewal ability and multi-differentiation potential. This study aimed to investigate the regulatory functions of succinylation modification in DPSCs. METHODS: DPSCs were isolated from the dental pulp collected from healthy subjects, and then stem cell surface markers were identified using flow cytometry. The osteogenic differentiation ability of DPSCs was verified by alkaline phosphatase (ALP) and alizarin red staining methods, while adipogenic differentiation was detected by oil red O staining. Meanwhile, the mRNA of two desuccinylases (SIRT5 and SIRT7) and three succinylases (KAT2A, KAT3B, and CPT1A) in DPSCs before and after mineralization induction were detected using quantitative real-time PCR. The cell cycle was measured by flow cytometry, and the expression of bone-specific genes, including COL1a1 and Runx2 were evaluated by western blotting and were combined for the proliferation and differentiation of DPSCs. Co-immunoprecipitation (co-IP) and immunofluorescence were combined to verify the binding relationship between proteins. RESULTS: The specific markers of mesenchymal stem cells were highly expressed in DPSCs, while the osteogenic differentiation ability of isolated DPSCs was confirmed via ALP and alizarin red staining. Similarly, the oil red O staining also verified the adipogenic differentiation ability of DPSCs. The levels of KAT2A were found to be significantly upregulated in mineralization induction, which significantly decreased the ratio of G0/G1 phase and increased S phase cells; converse results regarding cell cycle distribution were obtained when KAT2A was inhibited. Moreover, overexpression of KAT2A promoted the differentiation of DPSCs, while its inhibition exerted the opposite effect. The elevated KAT2A was found to activate the Notch1 signaling pathway, which succinylated Notch1 at the K2177 site to increase their corresponding protein levels in DPSCs. The co-IP results showed that KAT2A and Notch1 were endogenously bound to each other, while inhibition of Notch1 reversed the effects of KAT2A overexpression on the DPSCs proliferation and differentiation. CONCLUSION: KAT2A interacted directly with Notch1, succinylating the Notch1 at the K2177 site to increase their corresponding protein levels in DPSCs. Similarly, KAT2A-mediated succinylation modification of Notch1 promotes the DPSCs proliferation and differentiation, suggesting that targeting KAT2A and Notch1 may contribute to tooth regeneration.


Anthraquinones , Azo Compounds , Osteogenesis , Stem Cells , Humans , Osteogenesis/physiology , Stem Cells/metabolism , Dental Pulp , Cell Proliferation , Cell Differentiation , Cells, Cultured , Histone Acetyltransferases/metabolism
11.
Medicina (Kaunas) ; 60(4)2024 Mar 30.
Article En | MEDLINE | ID: mdl-38674213

Background and Objectives: There are many surgical techniques for oroantral communication treatment, one of which is the buccal fat pad. Of particular interest is the high reparative potential of the buccal fat pad, which may be contributed to by the presence of mesenchymal stem cells. The purpose of this work is to evaluate the reparative potential of BFP cells using morphological and immunohistochemical examination. Materials and Methods: 30 BFP samples were provided by the Clinic of Maxillofacial and Plastic Surgery of the Russian University of Medicine (Moscow, Russia) from 28 patients. Morphological examination of 30 BFP samples was performed at the Institute of Clinical Morphology and Digital Pathology of Sechenov University. Hematoxylin-eosin, Masson trichrome staining and immunohistochemical examination were performed to detect MSCs using primary antibodies CD133, CD44 and CD10. Results: During staining with hematoxylin-eosin and Masson's trichrome, we detected adipocytes of white adipose tissue united into lobules separated by connective tissue layers, a large number of vessels of different calibers, as well as the general capsule of BFP. The thin connective tissue layers contained neurovascular bundles. Statistical processing of the results of the IHC examination of the samples using the Mann-Whitney criterion revealed that the total number of samples in which the expression of CD44, CD10 and CD133 antigens was confirmed was statistically significantly higher than the number of samples where the expression was not detected (p < 0.05). Conclusions: During the morphological study of the BFP samples, we revealed statistically significant signs of MSCs presence (p < 0.05), including in the brown fat tissue, which proves the high reparative potential of this type of tissue and can make the BFP a choice option among other autogenous donor materials when eliminating OAC and other surgical interventions in the maxillofacial region.


Adipose Tissue , Azo Compounds , Cheek , Immunohistochemistry , Humans , Immunohistochemistry/methods , Female , Male , AC133 Antigen/analysis , Hyaluronan Receptors/analysis , Neprilysin/analysis , Mesenchymal Stem Cells , Adult , Eosine Yellowish-(YS) , Hematoxylin , Methyl Green
12.
ACS Nano ; 18(17): 11042-11057, 2024 Apr 30.
Article En | MEDLINE | ID: mdl-38627898

PD-1 blockade is a first-line treatment for recurrent/metastatic cervical cancer but benefits only a small number of patients due to low preexisting tumor immunogenicity. Using immunogenic cell death (ICD) inducers is a promising strategy for improving immunotherapy, but these compounds are limited by the hypoxic environment of solid tumors. To overcome this issue, the nanosensitizer AIBA@MSNs were designed based on sonodynamic therapy (SDT), which induces tumor cell death under hypoxic conditions through azo free radicals in a method of nonoxygen radicals. Mechanistically, the azo free radicals disrupt both the structure and function of tumor mitochondria by reversing the mitochondrial membrane potential and facilitating the collapse of electron transport chain complexes. More importantly, the AIBA@MSN-based SDT serves as an effective ICD inducer and improves the antitumor immune capacity. The combination of an AIBA@MSN-based SDT with a PD-1 blockade has the potential to improve response rates and provide protection against relapse. This study provides insights into the use of azo free radicals as a promising SDT strategy for cancer treatment and establishes a basic foundation for nonoxygen-dependent SDT-triggered immunotherapy in cervical cancer treatment.


Immunotherapy , Uterine Cervical Neoplasms , Uterine Cervical Neoplasms/therapy , Uterine Cervical Neoplasms/pathology , Uterine Cervical Neoplasms/immunology , Female , Free Radicals/chemistry , Humans , Mice , Animals , Azo Compounds/chemistry , Azo Compounds/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Mice, Inbred BALB C , Drug Screening Assays, Antitumor , Cell Proliferation/drug effects , Membrane Potential, Mitochondrial/drug effects
13.
Molecules ; 29(7)2024 Mar 24.
Article En | MEDLINE | ID: mdl-38611732

The use of privileged scaffolds as a starting point for the construction of libraries of bioactive compounds is a widely used strategy in drug discovery and development. Scaffold decoration, morphing and hopping are additional techniques that enable the modification of the chosen privileged framework and better explore the chemical space around it. In this study, two series of highly functionalized pyrimidine and pyridine derivatives were synthesized using a scaffold morphing approach consisting of triazine compounds obtained previously as antiviral agents. Newly synthesized azines were evaluated against lymphoma, hepatocarcinoma, and colon epithelial carcinoma cells, showing in five cases acceptable to good anticancer activity associated with low cytotoxicity on healthy fibroblasts. Finally, ADME in vitro studies were conducted on the best derivatives of the two series showing good passive permeability and resistance to metabolic degradation.


Antineoplastic Agents , Carcinoma, Hepatocellular , Liver Neoplasms , Humans , Antineoplastic Agents/pharmacology , Antiviral Agents/pharmacology , Azo Compounds
15.
Environ Pollut ; 349: 123902, 2024 May 15.
Article En | MEDLINE | ID: mdl-38580061

The textile industry contributes substantially to water pollution. To investigate bioremediation of dye-containing wastewater, the decolorization and biotransformation of three textile azo dyes, Red HE8B, Reactive Green 27, and Acid Blue 29, were considered using an integrated remediation approach involving the microalga Chlamydomonas mexicana and activated sludge (ACS). At a 5 mg L-1 dye concentration, using C. mexicana and ACS alone, decolorization percentages of 39%-64% and 52%-54%, respectively, were obtained. In comparison, decolorization percentages of 75%-79% were obtained using a consortium of C. mexicana and ACS. The same trend was observed for the decolorization of dyes at higher concentrations, but the potential for decolorization was low. The toxic azo dyes adversely affect the growth of microalgae and at high concentration 50 mg L-1 the growth rate inhibited to 50-60% as compared to the control. The natural textile wastewater was also treated with the same pattern and got promising results of decolorization (90%). Moreover, the removal of BOD (82%), COD (72%), TN (64%), and TP (63%) was observed with the consortium. The HPLC and GC-MS confirm dye biotransformation, revealing the emergence of new peaks and the generation of multiple metabolites with more superficial structures, such as N-hydroxy-aniline, naphthalene-1-ol, and sodium hydroxy naphthalene. This analysis demonstrates the potential of the C. mexicana and ACS consortium for efficient, eco-friendly bioremediation of textile azo dyes.


Biodegradation, Environmental , Coloring Agents , Microalgae , Sewage , Textile Industry , Waste Disposal, Fluid , Water Pollutants, Chemical , Coloring Agents/metabolism , Coloring Agents/chemistry , Sewage/chemistry , Water Pollutants, Chemical/metabolism , Microalgae/metabolism , Waste Disposal, Fluid/methods , Wastewater/chemistry , Textiles , Azo Compounds/metabolism
16.
Langmuir ; 40(18): 9761-9774, 2024 May 07.
Article En | MEDLINE | ID: mdl-38663878

Stimuli-responsive behaviors and controlled release in liposomes are pivotal in nanomedicine. To this end, we present an approach using a photoresponsive azobenzene nanocluster (AzDmpNC), prepared from azobenzene compounds through melting and aggregation. When integrated with liposomes, they form photoresponsive vesicles. The morphology and association with liposomes were investigated by using transmission electron microscopy. Liposomes loaded with calcein exhibited a 9.58% increased release after UV exposure. To gain insights into the underlying processes and elucidate the mechanisms involved. The molecular dynamic simulations based on the reactive force field and all-atom force field were employed to analyze the aggregation of isomers into nanoclusters and their impacts on phospholipid membranes, respectively. The results indicate that the nanoclusters primarily aggregate through π-π and T-stacking forces. The force density inside the cis-isomer of AzDmpNC formed after photoisomerization is lower, leading to its easier dispersion, rapid diffusion, and penetration into the membrane, disrupting the densification.


Azo Compounds , Liposomes , Molecular Dynamics Simulation , Azo Compounds/chemistry , Azo Compounds/radiation effects , Liposomes/chemistry , Nanoparticles/chemistry , Ultraviolet Rays , Fluoresceins/chemistry , Photochemical Processes
18.
Bioresour Technol ; 400: 130698, 2024 May.
Article En | MEDLINE | ID: mdl-38615967

The growing textile industry produces large volumes of hazardous wastewater containing dyes, which stresses the need for cheap, efficient adsorbing technologies. This study investigates a novel preprocessing method for producing activated carbons from abundantly available softwood bark. The preprocessing involved a continuous steam explosion preconditioning step, chemical activation with ZnCl2, pyrolysis at 600 and 800 °C, and washing. The activated carbons were subsequently characterized by SEM, XPS, Raman and FTIR prior to evaluation for their effectiveness in adsorbing reactive orange 16 and two synthetic dyehouse effluents. Results showed that the steam-exploded carbon, pyrolyzed at 600 °C, obtained the highest BET specific surface area (1308 m2/g), the best Langmuir maximum adsorption of reactive orange 16 (218 mg g-1) and synthetic dyehouse effluents (>70 % removal) of the tested carbons. Finally, steam explosion preconditioning could open up new and potentially more sustainable process routes for producing functionalized active carbons.


Azo Compounds , Charcoal , Plant Bark , Steam , Adsorption , Plant Bark/chemistry , Azo Compounds/chemistry , Charcoal/chemistry , Coloring Agents/chemistry , Carbon/chemistry , Spectroscopy, Fourier Transform Infrared , Water Purification/methods , Water Pollutants, Chemical , Wastewater/chemistry , Spectrum Analysis, Raman
19.
Food Chem ; 449: 139206, 2024 Aug 15.
Article En | MEDLINE | ID: mdl-38579658

Novel aqueous biphasic systems (ABSs) developed with benzyl-based quaternary ammonium salts-deep eutectic solvents (DESs) and polypropylene glycol (PPG) were herein proposed. The liquid-liquid equilibrium and the partitioning behavior of pigments in the systems were addressed. The results suggested that the shorter the carbon chain length of the DES, the easier to form two phases. The analysis of mixed samples showed that the selective separation was achieved in the ABSs, including 99.47% of tartrazine in the DES-rich phase and 98.47% of sudan III in the PPG-rich phase. Additionally, the systems were successfully applied to the extraction of pigments from the actual beverage samples with recoveries ranging from 93.43% to 102.15%. Furthermore, the study on the separation mechanism indicated that the hydrogen bonding played a significant role in the separation process. All the above results highlight the proposed DES/polymer-based ABSs have great advantages in selective and high-performance separation of pigments from beverages.


Azo Compounds , Beverages , Deep Eutectic Solvents , Polymers , Beverages/analysis , Polymers/chemistry , Deep Eutectic Solvents/chemistry , Propylene Glycols/chemistry , Propylene Glycols/isolation & purification , Coloring Agents/chemistry , Coloring Agents/isolation & purification , Solvents/chemistry , Quaternary Ammonium Compounds/chemistry
20.
Food Chem Toxicol ; 188: 114653, 2024 Jun.
Article En | MEDLINE | ID: mdl-38599274

Sunset Yellow (SY), an azo synthetic food dye, is widely used in the food industry. Although there are different opinions on its effect on people, its use is regulated in the European Union. If the Acceptable Daily Intake of 2.5 mg/kg/bw is exceeded, it may have pathological and biochemical effects on organs. There are not enough studies on the effects of SY on growth and development in mammals. This study was conducted to determine the effect of SY on the morphological parameters of mice at different ages (four, eight, and ten weeks old). The treatment and control groups were created with Swiss Albino mice (n: 6). SY was administered orally for 28 days (30 mg/kg/bw/week). On the last day of the study, the mice were weighed, and tail, temporal region, femur, and crown-rubmp-length values were measured using a digital caliper. A statistical difference in average body weight was observed in the SY groups (p < 0.05). SY administration during childhood caused retardation in growth and development parameters. Therefore, SY may cause weight gain and affect morphological parameters. Additional studies are required to investigate the effects of SY at different doses and durations.


Azo Compounds , Animals , Mice , Male , Body Weight/drug effects , Food Coloring Agents
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