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Molecules (Basel, Switzerland) Nov 2022Despite the immense therapeutic advances in the field of health sciences, cancer is still to be found among the global leading causes of morbidity and mortality.... (Review)
Review
Despite the immense therapeutic advances in the field of health sciences, cancer is still to be found among the global leading causes of morbidity and mortality. Ethnomedicinally, natural bioactive compounds isolated from various plant sources have been used for the treatment of several cancer types and have gained notable attention. Ferulic acid, a natural compound derived from various seeds, nuts, leaves, and fruits, exhibits a variety of pharmacological effects in cancer, including its proapoptotic, cell-cycle-arresting, anti-metastatic, and anti-inflammatory activities. This review study presents a thorough overview of the molecular targets and cellular signaling pathways modulated by ferulic acid in diverse malignancies, showing high potential for this phenolic acid to be developed as a candidate agent for novel anticancer therapeutics. In addition, current investigations to develop promising synergistic formulations are also discussed.
Topics: Humans; Phenol; Coumaric Acids; Signal Transduction; Neoplasms; Carcinogenesis
PubMed: 36364478
DOI: 10.3390/molecules27217653 -
Journal of Colloid and Interface Science Dec 2022Hydrophobicity and the presence or absence of charge in phenol derivatives are relevant on the rheology and phase behavior when they are assembled with a cationic...
HYPOTHESIS
Hydrophobicity and the presence or absence of charge in phenol derivatives are relevant on the rheology and phase behavior when they are assembled with a cationic surfactant, forming wormlike micelles. The incorporation of phenols with a greater number of rings into the micellar palisade is entropically favored, but a solubilization limit or coacervation are two paths followed by the solutions, depending on the electrical nature of the aromatic co-solutes.
EXPERIMENTS
The investigations were carried out with systems formed by a fixed concentration of hexadecyltrimethylammonium bromide (CTAB) and increasing concentrations of neutral phenols (1-naphthol, 2-naphthol, 2,3-dihydroxynaphthalene and R and S-binol) and with their corresponding phenolate derivatives. The monophasic limits of the systems were established, as well as their linear and non-linear rheology. The structural investigation of the coacervates formed with the phenolates were done using SAXS and Cryo-TEM.
FINDINGS
The zero-shear viscosity of the solutions reaches maxima values close to the solubility limit of the aromatics, which depends on the numbers of rings and hydroxyl groups (position and number). However, when the correspondent ionized phenols were investigated, beyond the maxima values for the zero-shear viscosity, liquid-liquid biphasic systems are formed, in which the upper phase contains a coacervate, associated with branched wormlike micelles. However, when the ratio between phenolate and CTAB is around 3:1 the coacervate evolves to a lamellar structure.
Topics: Cetrimonium; Hydrophobic and Hydrophilic Interactions; Micelles; Phenol; Phenols; Scattering, Small Angle; Surface-Active Agents; X-Ray Diffraction
PubMed: 35863194
DOI: 10.1016/j.jcis.2022.07.044 -
Sudebno-meditsinskaia Ekspertiza 2023The aim of this study is to research the stability of 2.6-di(propan-2-yl)phenol in biomaterial. GC-MS (column DB-5MS EVIDEX (25 m×0.2 mm); stationary liquid phase of...
The aim of this study is to research the stability of 2.6-di(propan-2-yl)phenol in biomaterial. GC-MS (column DB-5MS EVIDEX (25 m×0.2 mm); stationary liquid phase of 5%-phenyl-95% dimethylpolysiloxane), TLC (Sorbfil plates, mobile phase of hexane-diethyl ether (9:1) and spectrophotometry (solvent medium - 95% ethanol) were used as methods of analysis. 2.6-di(propan-2-yl)phenol was isolated from the biomatrix (liver tissue) by infusion with a mixture of ethyl acetate-acetone (7:3). The analyte was purified by combining extraction (water-ethyl acetate system) and semi-preparative chromatography on a column of silica gel L 40/100 µm, eluent - hexane-acetone (7:3). It was found that at -22 °C, 0 °C, 12 °C, 20 °C and 30 °C 2.6-di(propan-2-yl)phenol can be present in the liver tissue for 119, 98, 70, 56 and 42 days, respectively. The possibility of mathematical description of analyte decomposition dynamics in biomaterial (liver tissue) at the considered temperatures on the basis of hyperbola equation has been studied. The experimentally calculated coefficients in the hyperbola equation (k) for temperatures -22 °C, 0 °C, 12 °C, 20 °C and 30 °C are equal to 1823, 1130, 697, 510, and 255, respectively. The dependence k on the conserving temperature (t) was educed. The equation for the description of dependence is offered: k=30.61∙(50-t)-402.39. It is shown that this equation can be the basis for prediction of 2.6-di(propan-2-yl)phenol stability in biomaterial (liver tissue) in the temperature range from -22 °C to 30 °C.
Topics: Phenol; Hexanes; Acetone; Biocompatible Materials; Phenols
PubMed: 37192459
DOI: 10.17116/sudmed20236603146 -
The Journal of Organic Chemistry Jul 2022The ubiquity of benzoxazoles in natural products, drugs, and functional materials has stimulated numerous efforts toward their synthesis; however, the developed methods...
The ubiquity of benzoxazoles in natural products, drugs, and functional materials has stimulated numerous efforts toward their synthesis; however, the developed methods rely on prefunctionalized substrates and lack generality. Under metal-free conditions, a highly general synthesis of benzoxazoles direct from abundant and easily available phenols and amines is developed via a modular phenol functionalization controlled by TEMPO. In the reaction, various phenols and primary amines with a broad range of functional groups are compatible, producing structurally and functionally diverse benzoxazoles (64 examples) without or with trace observation of the byproducts of phenol transformation with amines. The practical synthesis, especially for drug tafamidis, demonstrates decisive advantages in generality, selectivity, efficiency, and atom- and step-economies over traditional methods, even in the cases of low yields. Mechanistically, the radical adducts of TEMPO with -cyclohexa-2,4-dien-1-one radicals rather than the well-recognized cyclohexa-3,5-diene-1,2-diones may serve as intermediates.
Topics: Amines; Benzoxazoles; Catalysis; Metals; Oxidative Stress; Phenol; Phenols
PubMed: 35786919
DOI: 10.1021/acs.joc.2c00790 -
Food & Function Nov 2023(Poly)phenol (PP)-rich blackcurrant (BC) extracts reduce postprandial glucose concentrations. Combinations with other fruit (poly)phenols and fruit fibre may enhance the...
Acute effects of drinks containing blackcurrant and citrus (poly)phenols and dietary fibre on postprandial glycaemia, gut hormones, cognitive function and appetite in healthy adults: two randomised controlled trials.
(Poly)phenol (PP)-rich blackcurrant (BC) extracts reduce postprandial glucose concentrations. Combinations with other fruit (poly)phenols and fruit fibre may enhance the effect. This study investigated the acute effects of combinations of BC extracts, high (H-BC) and low (L-BC) (poly)phenol concentrations, sweet orange extracts (SO) and fibre-rich orange pulp (F) in reducing postprandial glycaemia. In two randomised, double-blind, crossover design studies, healthy participants consumed seven types of 200 mL beverages: in the GLU-FX trial, H-BC (1600 mg PP); L-BC (800 mg PP); SO (800 mg PP); BC + SO (1600 mg PP) or CON (placebo); in the GLU-MIX trial, BC + F (800 mg PP), F (1.5 g fibre), or CON2 (placebo), immediately followed by consumption of 75 g available carbohydrate (starch and sugars). Blood was sampled at baseline and postprandially to measure changes in glucose, insulin, and gut hormones; appetite changes were assessed by visual analogue scales and, in GLU-MIX, food intake and cognitive function were assessed. Twenty-nine and thirty-seven adults completed GLU-FX and GLU-MIX, respectively. L-BC reduced early postprandial glycaemia (0-30 min) with no differences in glucose incremental or total glycaemic response. No significant effect was observed following other drinks relative to CON. L-BC and H-BC drinks inhibited insulin secretion up to 30 min and GIP up to 120 min. In GLU-MIX, BC + F improved some indicators of cognitive function but not all. Measures of appetite were unaffected. The impact of (poly)phenol-rich BC extracts on total postprandial glycaemia in healthy participants was minimal and not enhanced when administered in combination with an orange (poly)phenol extract or orange pulp. Clinical Trials registered at https://www.clinicaltrials.gov: NCT03184064 (GLU-FX) and NCT03572296 (GLU-MIX).
Topics: Humans; Adult; Appetite; Blood Glucose; Phenols; Citrus; Phenol; Glucose; Dietary Fiber; Gastrointestinal Hormones; Insulin; Cognition; Postprandial Period; Cross-Over Studies; Randomized Controlled Trials as Topic
PubMed: 37902089
DOI: 10.1039/d3fo03085g -
Revista Da Associacao Medica Brasileira... 2023We investigated the effectiveness of combining laser treatment with phenol in the management of pilonidal sinus.
OBJECTIVE
We investigated the effectiveness of combining laser treatment with phenol in the management of pilonidal sinus.
METHODS
We present here a retrospective analysis of patients with pilonidal sinus disease who were treated in the general surgery clinic of the Balikesir University Hospital between October 2019 and February 2022.
RESULTS
Recurrence was observed in three patients (13.6%) in the laser treatment group and one patient (4.8%) in the laser-phenol treatment group after the fourth month. Notably, 22 (91.7%) patients in the laser treatment group and 21 (95.5%) patients in the laser-phenol treatment group had complete healing.
CONCLUSION
Although not statistically significant, the laser-phenol treatment group exhibited a lower recurrence rate and a higher complete healing rate.
Topics: Humans; Phenol; Retrospective Studies; Pilonidal Sinus; Treatment Outcome; Neoplasm Recurrence, Local; Phenols; Lasers; Skin Diseases; Recurrence
PubMed: 37971129
DOI: 10.1590/1806-9282.20230740 -
Proceedings of the Japan Academy.... 2022Biaryl synthesis continues to occupy a central role in chemical synthesis. From blockbuster drug molecules to organic electronics, biaryls present numerous possibilities...
Biaryl synthesis continues to occupy a central role in chemical synthesis. From blockbuster drug molecules to organic electronics, biaryls present numerous possibilities and new applications continue to emerge. Transition-metal-catalyzed coupling reactions represent the gold standard for biaryl synthesis and the mechanistic steps, such as reductive elimination, are well established. Developing routes that exploit alternative mechanistic scenarios could give unprecedented biaryl structures and expand the portfolio of biaryl applications. We have developed metal-free C-H/C-H couplings of aryl sulfoxides with phenols to afford 2-hydroxy-2'-sulfanylbiaryls. This cascade strategy consists of an interrupted Pummerer reaction and [3,3] sigmatropic rearrangement. Our method enables the synthesis of intriguing aromatic molecules, including oligoarenes, enantioenriched dihetero[8]helicenes, and polyfluorobiaryls. From our successes in aryl sulfoxide/phenol couplings and a deeper understanding of sigmatropic rearrangements for biaryl synthesis, we have established related methods, such as aryl sulfoxide/aniline and aryl iodane/phenol couplings. Overall, our fundamental interests in underexplored reaction mechanisms have led to various methods for accessing important biaryl architectures.
Topics: Metals; Phenol; Sulfoxides
PubMed: 35400695
DOI: 10.2183/pjab.98.012 -
Chemistry (Weinheim An Der Bergstrasse,... Jul 2023Multiple triggered-release strategies are widely utilized to control the release of caged target molecules. Among them, photocages with conditional triggers provide...
Multiple triggered-release strategies are widely utilized to control the release of caged target molecules. Among them, photocages with conditional triggers provide extra layers of control in photorelease. In this work, a series of pH-responsive photocages was designed that could be triggered under irradiation and specific intracellular pH values. pH-sensitive phenolic groups were conjugated with o-nitrobenzyl (oNB) to form azo-phenolic NPX photocages with tunable pKa. These azo-phenol-based oNB photocages showed differentiable photoreleasing profiles at pH 5.0, 7.2 and 9.0. By attaching fluorogenic cargos, it was shown that one of the photocages, NPdiCl, could be used to differentiate between acidic pH 5.0 and neutral pH 7.2 in cells under artificial pH conditions. Finally, NPdiCl was identified as a promising pH-responsive photocage for photoreleasing cargo inside acidic tumor cells.
Topics: Hydrogen-Ion Concentration; Phenol; Phenols; Azo Compounds
PubMed: 37154791
DOI: 10.1002/chem.202300884 -
Medicine Dec 2022There are 2 mainstays of sacrococcygeal pilonidal disease (SPD) treatment: non-operative and surgical. None of them was superior, and it was associated with some degree...
There are 2 mainstays of sacrococcygeal pilonidal disease (SPD) treatment: non-operative and surgical. None of them was superior, and it was associated with some degree of recurrence. Crystallized phenol treatment is a non-operative procedure performed in outpatient settings. This retrospective study aimed to asses crystallized phenol treatment in patients with primary and recurrent SPD and the factors that influence disease recurrence. A total of 92 patients were included and followed up. Crystallized phenol was administered in an outpatient setting under local anesthesia. All demographic, patient, sinus features, procedure and outcome data were recorded and analyzed for treatment success and factors for recurrence were identified. Between January 2019 and December 2021, 92 patients (77 male and 15 female) with a mean age of 28.4 were treated with 1, 2, or 3 doses of crystallized phenol. Recurrence rate after the procedure was 20.7%. Univariate regression analysis showed that the grade of hirsutism, initial presence of abscess, pit number and number of showers per week had statistically significant effect on recurrence. Multivariate logistic regression analysis pointed on the hirsutism grade (P = .008) and the number of pit openings (P = .003) as a statistically significant factors for recurrence. Crystallized phenol application for primary and recurrent SPD is safe, inexpensive and efficient non-operative method with few minor complications, even when is repeated. Factors responsible for the recurrence of the procedure are grade of hirsutism and sinus pit number.
Topics: Humans; Male; Female; Adult; Phenol; Retrospective Studies; Pilonidal Sinus; Hirsutism; Neoplasm Recurrence, Local; Phenols; Treatment Outcome; Recurrence; Sacrococcygeal Region
PubMed: 36550830
DOI: 10.1097/MD.0000000000031934 -
Journal of Food Biochemistry Jan 2021The study aims to evaluate the relation between peroxidases of day-6 garden cress sprouts and phenolic compounds. Three cationic, three anionic, and two unbounded...
The study aims to evaluate the relation between peroxidases of day-6 garden cress sprouts and phenolic compounds. Three cationic, three anionic, and two unbounded peroxidases were separated from day-6 garden cress sprouts. Cationic (GCP1) and anionic (GCP2) peroxidases were purified with molecular masses of 25 and 40 kDa, respectively. The K values of GCP1 toward H O and guaiacol were lower than GCP2. The anionic GCP2 exhibited high affinity toward some lignin monomers, sinapyl alcohol, coniferyl alcohol, cinnamic and ferulic acids. Therefore, GCP2 is considered as a lignin peroxidase and contributed in lignin synthesis. The activity of GCP1 and GCP2 was stable at a wide pH range 5.5-8.0 and 6.0-7.5, respectively. Both peroxidases showed the same thermal stability range 20-50°C. GCP2 was more resistant against the effect of metal ions than GCP1. GCP2 showed high ability to remove of phenol and p-chlorophenol from effluent compared to GCP1. PRACTICAL APPLICATIONS: Generally, garden cress is used as a test plant to conduct biomonitoring of pollution in urban soil on a wide scale because of its simplicity, sensitivity, and cost-effectiveness. Peroxidase is an important antioxidant enzyme, which elevated when plant subjected to pollution. Recently, we reported that the increase of peroxidase activity was strongly correlated with high phenolic content and antioxidant activity during the germination of garden cress. In the present study, anionic peroxidase GCP2 may play an important role in lignification process and removal of phenol and p-chlorophenol from polluted soil/wastewater as well as resisted the harmful effect of heavy metals. Cationic peroxidase GCP1, as a natural scavenger, had high affinity toward H O coupled to oxidation of some plant phenolic compounds suggesting its role in consuming of excess H O .
Topics: Chlorophenols; Lepidium sativum; Peroxidases; Phenol; Phenols
PubMed: 33140461
DOI: 10.1111/jfbc.13526