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1.
Int J Mol Sci ; 22(13)2021 Jun 22.
Article in English | MEDLINE | ID: mdl-34206572

ABSTRACT

Lipophilicity of 15 derivatives of sodium cholate, defined by the octan-1-ol/water partition coefficient (log P), has been theoretically determined by the Virtual log P method. These derivatives bear highly hydrophobic or highly hydrophilic substituents at the C3 position of the steroid nucleus, being linked to it through an amide bond. The difference between the maximum value of log P and the minimum one is enlarged to 3.5. The partition coefficient and the critical micelle concentration (cmc) are tightly related by a double-logarithm relationship (VirtuallogP=-(1.00±0.09)log(cmcmM)+(2.79±0.09)), meaning that the Gibbs free energies for the transfer of a bile anion from water to either a micelle or to octan-1-ol differ by a constant. The equation also means that cmc can be used as a measurement of lipophilicity. The demicellization of the aggregates formed by three derivatives of sodium cholate bearing bulky hydrophobic substituents has been studied by surface tension and isothermal titration calorimetry. Aggregation numbers, enthalpies, free energies, entropies, and heat capacities, ΔCP,demic, were obtained. ΔCP,demic, being positive, means that the interior of the aggregates is hydrophobic.


Subject(s)
Bile Acids and Salts/chemistry , Hydrophobic and Hydrophilic Interactions , Algorithms , Calorimetry , Chemical Phenomena , Micelles , Models, Theoretical , Molecular Structure , Thermodynamics
2.
Molecules ; 27(1)2021 Dec 27.
Article in English | MEDLINE | ID: mdl-35011370

ABSTRACT

The yellow-legged Asian hornet (Vespa velutina Lepeletier 1836 (Hymenoptera: Vespidae)) is naturally distributed in China, Southeast Asia, and India; however, recently it has been detected outside of its native area, confirmed as being established in South Korea, Europe, and Japan. Health risks and deaths caused by the invasive Vespa velutina stings have become a public health concern, being the most common cause of anaphylaxis due to hymenopterans in some European regions. This in turn has led to increased demand from medical practitioners and researchers for Vespa velutina venom for diagnostic and therapeutic purposes. In this study, a straightforward, quick, and inexpensive method for obtaining Vespa velutina venom by electric stimulation is described. The venom extracts were analyzed by nuclear magnetic resonance spectroscopy (1H-NMR). The availability of Vespa velutina venom will lead to improved diagnostic and therapeutic methods, mainly by venom immunotherapy (VIT), in patients allergic to this invasive species.


Subject(s)
Wasp Venoms/isolation & purification , Animals , Electric Stimulation/methods , Female , Wasp Venoms/chemistry , Wasps/chemistry , Wasps/physiology
3.
Molecules ; 25(2)2020 Jan 17.
Article in English | MEDLINE | ID: mdl-31963436

ABSTRACT

Fifteen years ago, at least one multimated female yellow-legged Asian hornet (Vespa velutina Lepeletier 1836) arrived in France, which gave rise to a pan-European invasion. In this study, the isolation and characterization of chitin (CHI) that was obtained from Vespa velutina (CHIVV) is described. In addition, an easy procedure is carried out to capture the raw insect, selectively and with high rates of success. The chitin contents of dry VV was observed to be 11.7%. Fourier transform infrared spectroscopy (FTIR), solid-state NMR (ssNMR), elemental analysis (EA), scanning electron microscopy (SEM), and thermogravimetric analysis (TG) characterized the physicochemical properties of CHIVV. The obtained CHIVV is close to pure (43.47% C, 6.94% H, and 6.85% N), and full acetylated with a value of 95.44%. Additionally, lifetime and kinetic parameters such as activation E and the frequency factor A using model-free and model-fitting methods, were determined. For CHIVV the solid state mechanism that follows the thermodegradation is of type F2 (random nucleation around two nuclei). The invasive Asian hornet is a promising alternative source of CHI, based on certain factors, such as the current and probable continued abundance of the quantity and quality of the product obtained.


Subject(s)
Chitin/chemistry , Chitin/isolation & purification , Wasps/chemistry , Acetylation , Animals , Female , Finite Element Analysis , Introduced Species , Magnetic Resonance Spectroscopy , Microscopy, Electron, Scanning , Spectroscopy, Fourier Transform Infrared , Thermogravimetry
4.
Adv Colloid Interface Sci ; 254: 94-98, 2018 Apr.
Article in English | MEDLINE | ID: mdl-29580548

ABSTRACT

The actual significance of the so-called compensation temperature Tc for micellization of surfactants is reviewed. It is demonstrated that it is possible to obtain as many Tc values as the number of temperature intervals in which the dependencies of enthalpy and entropy changes with temperature are analyzed. The value of each Tc will be the central value To of each temperature interval. These two facts suggest that Tc is simply such experimental To. Thus any physical interpretation derived from Tc is unfounded.

5.
Molecules ; 22(6)2017 Jun 15.
Article in English | MEDLINE | ID: mdl-28617341

ABSTRACT

In the present work, 12 novel Schiff's bases containing a thiadiazole scaffold and benzamide groups coupled through appropriate pharmacophore were synthesized. These moieties are associated with important biological properties. A facile, solvent-free synthesis of a series of novel 7(a-l) N-((5-(substituted methylene amino)-1,3,4-thiadiazol-2-yl)methyl) benzamide was carried out under microwave irradiation. Structures of the synthesized compounds were confirmed by IR, NMR, mass spectral study and elemental analysis. All the synthesized hybrids were evaluated for their in vitro anticancer activity against a panel of four human cancer cell lines, viz. SK-MEL-2 (melanoma), HL-60 (leukemia), HeLa (cervical cancer), MCF-7 (breast cancer) and normal breast epithelial cell (MCF-10A) using 3-(4,5-dimethythiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay method. Most of the synthesized compounds exhibited promising anticancer activity, showed comparable GI50 values comparable to that of the standard drug Adriamycin. The compounds 7k, 7l, 7b, and 7a were found to be the most promising anticancer agents in this study. A molecular docking study was performed to predict the probable mechanism of action and computational study of the synthesized compounds 7(a-l) was performed to predict absorption, distribution, metabolism, excretion and toxicity (ADMET) properties, by using QikProp v3.5 (Schrödinger LLC). The results showed the good oral drug-like behavior of the synthesized compounds 7(a-l).


Subject(s)
Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/pharmacology , Benzamides/chemistry , Microwaves , Molecular Docking Simulation/methods , Antineoplastic Agents/chemistry , Cell Line, Tumor , Cell Proliferation/drug effects , Doxorubicin/pharmacology , Drug Screening Assays, Antitumor/methods , HeLa Cells , Humans , Molecular Structure , Structure-Activity Relationship
6.
Molecules ; 21(8)2016 Jul 29.
Article in English | MEDLINE | ID: mdl-27483213

ABSTRACT

Herein, we report an environmentally friendly, rapid, and convenient one-pot ultrasound-promoted synthesis of 5-amino-2-(4-chlorophenyl)-7-substituted phenyl-8,8a-dihydro-7H-(1,3,4)thiadiazolo(3,2-α)pyrimidine-6-carbonitrile derivatives. The in-vitro anticancer activities of these compounds were evaluated against four human tumor cell lines. Among all the synthesized derivatives, compound 4i, which has substituent 3-hydroxy-4-methoxyphenyl is found to have the highest GI50 value of 32.7 µM, 55.3 µM, 34.3 µM, 28.9 µM for MCF-7, K562, HeLa and PC-3 cancer cell lines respectively. A docking study of the newly synthesized compounds were performed, and the results showed good binding mode in the active site of thymidylate synthase enzyme. ADME properties of synthesized compounds were also studied and showed good drug like properties.


Subject(s)
Molecular Docking Simulation , Neoplasm Proteins/antagonists & inhibitors , Nitriles , Thymidylate Synthase/antagonists & inhibitors , Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Drug Screening Assays, Antitumor , Enzyme Inhibitors/chemical synthesis , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/pharmacology , HeLa Cells , Humans , K562 Cells , MCF-7 Cells , Nitriles/chemical synthesis , Nitriles/chemistry , Nitriles/pharmacology , Ultrasonic Waves
7.
Int J Mol Sci ; 15(2): 3287-98, 2014 Feb 21.
Article in English | MEDLINE | ID: mdl-24566150

ABSTRACT

Ammonium trichloro[1,2-ethanediolato-O,O']-tellurate (AS101) is the most important synthetic Te compound from the standpoint of its biological activity. It is a potent immunomodulator with a variety of potential therapeutic applications and antitumoral action in several preclinical and clinical studies. An experimental design has been used to develop and optimize a novel microwave-assisted synthesis (MAOS) of the AS101. In comparison to the results observed in the literature, refluxing Te(IV) chloride and ethylene glycol in acetonitrile (Method A), or by refluxing Te(IV) chloride and ammonium chloride in ethylene glycol (Method B), it was found that the developed methods in the present work are an effective alternative, because although performance slightly decreases compared to conventional procedures (75% vs. 79% by Method A, and 45% vs. 51% by Method B), reaction times decreased from 4 h to 30 min and from 4 h to 10 min, by Methods A and B respectively. MAOS is proving to be of value in the rapid synthesis of compounds with new and improved biological activities, specially based on the benefit of its shorter reaction times.


Subject(s)
Ethylenes/chemical synthesis , Immunologic Factors/chemical synthesis , Microwaves , Drug Design , Ethylenes/chemistry , Immunologic Factors/chemistry
8.
Molecules ; 17(7): 8561-77, 2012 Jul 17.
Article in English | MEDLINE | ID: mdl-22805507

ABSTRACT

In this study the characterization of a total of 60 honey samples with Protected Denomination of Origin (PDO) collected over three harvests (2009-2011, inclusive), from the Northeast of Portugal was carried out based on the presence of pollen, physicochemical and microbiological characteristics. All samples were found to meet the European Legislation, but some didn't meet the requirements of the PDO specifications. Concerning the floral origin of honey, our results showed the prevalence of rosemary (Lavandula pedunculata) pollen. The microbiological quality of all the analyzed samples was satisfactory, since fecal coliforms, sulfite-reducing clostridia and Salmonella were absent, and molds and yeasts were detected in low counts. Significant differences between the results were studied using one-way analysis of variance (ANOVA), followed by Tukey's HSD test. The samples were submitted to discriminant function analysis, in order to determine which variables differentiate between two or more naturally occurring groups (Forward Stepwise Analysis). The variables selected were in this order: diastase activity, pH, reducing sugars, free acidity and HMF. The pollen spectrum has perfect discriminatory power. This is the first study in which a honey with PDO was tested, in order to assess its compliance with the PDO book of specifications.


Subject(s)
Honey , Rosmarinus , Amylases/analysis , Animals , Fungi/isolation & purification , Honey/microbiology , Honey/standards , Humans , Hydrogen-Ion Concentration , Pollen/chemistry , Pollen/physiology , Portugal , Rosmarinus/chemistry , Rosmarinus/physiology
9.
Molecules ; 17(7): 8359-77, 2012 Jul 11.
Article in English | MEDLINE | ID: mdl-22785265

ABSTRACT

Organic bee pollen (BP, n = 22) harvested from the Douro International Natural Park (DINP, Portugal) was studied. Nine botanical families were found in the mixture of the samples. The water activity and pH ranged 0.21-0.37 and 4.3-5.2, respectively. The BP analyses averaged 67.7% carbohydrates, 21.8% crude protein, 5.2% crude fat and 2.9% ash. The energy ranged from 396.4 to 411.1 kcal/100 g. The principal fatty acid found was linolenic, followed by linoleic acid, palmitic acid and oleic acid. The phenolic and flavonoid contents varied from 12.9 to 19.8 mg of gallic acid equivalents/g of extract and from 4.5 to 7.1 mg of catechin equivalents/g of extract, respectively. The scavenger activity and ß-carotene bleaching assays values (EC50) were 3.0 ± 0.7 mg/mL and 4.6 mg/mL ± 0.9 mg/mL, respectively. E. coli, sulphite-reducing Clostridia, Salmonella and S. aureus were not found. Since there are studies indicating appreciable differences among BPs from different regions, the full characterization of BP from diverse origins still appears to be a sound research priority in order to obtain reliable data about this beehive product.


Subject(s)
Antioxidants/analysis , Bees/chemistry , Organic Chemicals/analysis , Plants/chemistry , Pollen/chemistry , Pollen/microbiology , Animals , Fatty Acids/analysis , Flavonoids/analysis , Hydrogen-Ion Concentration , Nutritive Value , Phenols/analysis , Water
10.
Molecules ; 17(6): 6716-27, 2012 Jun 04.
Article in English | MEDLINE | ID: mdl-22664463

ABSTRACT

Camellia japonica (CJ) has oil-rich seeds, but the study of these oils has received little attention and has mainly focused only on their health properties. In the present work the relative composition of the fatty acid (FA) components of the triglycerides in cold-pressed oil from CJ is studied by ¹H-NMR. The results obtained were: 75.75%, 6.0%, 0.17% and 18.67%, for oleic, linoleic, linolenic and saturated FA respectively. Levels of C18 unsaturated FA found in CJ oil were similar to those reported for olive oils. We also checked the possibility of using ¹³C-NMR spectroscopy; however, the results confirmed the drawback of ¹³C over ¹H-NMR for the study of FA components of CJ triglycerides due to its low gyromagnetic ratio and its very low natural abundance.


Subject(s)
Camellia/chemistry , Plant Oils/chemistry , Triglycerides/chemistry , Fatty Acids/chemistry , Fatty Acids, Unsaturated/chemistry , Nuclear Magnetic Resonance, Biomolecular
11.
Magn Reson Chem ; 47(1): 84-6, 2009 Jan.
Article in English | MEDLINE | ID: mdl-18802969

ABSTRACT

A series of 21 substituted pyrazolo[3,4-d]pyrimidines-4-amines were studied by (1)H and (13)C NMR. The application of two-dimensional techniques, HMQC and HMBC, allowed the complete assignment of the spectra for all the compounds.


Subject(s)
Magnetic Resonance Spectroscopy/methods , Pyrazoles/chemistry , Pyrimidines/chemistry , Carbon Isotopes , Protons
12.
J Org Chem ; 70(7): 2855-8, 2005 Apr 01.
Article in English | MEDLINE | ID: mdl-15787587

ABSTRACT

[reaction: see text] Eco-friendly direct solvent-free synthesis of flavones is achieved by microwave irradiation of phloroglucinol and beta-ketoesters. Heating with microwaves versus under classical conditions was shown to be higher yielding, cleaner, and faster. The reaction goes through a cycloaddition of an alpha-oxo ketene intermediate followed by an uncatalyzed thermal Fries rearrangement.


Subject(s)
Flavones/chemical synthesis , Microwaves , Solvents/chemistry , Flavones/chemistry
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