83 research outputs found
8,8-Diethyl-1,4,5,8-tetrahydronaphthalene-1,4,5-trione
The title molecule, C14H14O3, contains two fused six-membered carbon rings with keto groups at positions 1, 4 and 5 and a gem-diethyl group at position 8. The molecule is close to planar (maximum deviation = 0.044 Å), with one ethyl group at each side of the molecular plane, with exception of the keto group at position 1 which is slightly deviated from the plane and disordered over two positions one on each side of it (occupancies 0.80/0.20). The packing of the molecule shows weak bonded chains along a through C—H⋯O contacts and two intramolecular C—H⋯O interactions are also present
On the reduction of 4-oxo-4h-benzopyran-3-carbaldehydes : global and local electrophilicity patterns
The theoretical global and local electrophilicity patterns of substituted and chelated
4-oxo-4H-benzopyran-3-carbaldehydes (formylchromones) have been evaluated using the electrophilicity
index proposed by Parr et al [J. Am. Chem. Soc. 1999, 121, 1922]. The complexation of formylchromones
with aluminum predicts a strong electrophilic character of these compounds against nucleophiles.
Local response at the active sites may also be assessed in terms of a global contribution described by
the global electrophilicity, and a local contribution described by the variations in electrophilic
Fukui function at those sites. The highest local electrophilicity is found at the formyl group of
the chelated formylchromones, in spite of that, the highest positive charge is located on the pyrone
carbonyl group. This result is consistent with the experimental observed reactivity displayed by
4-oxo-4H-benzopyran-3-carbaldehydes in the presence of 2-propanol and alumina
4-Acetyl-3,3-diethyl-5-hydroxy-2-morpholino-2,3-dihydro-1-benzofuran
In the title compound, C18H25NO4, the benzofuran ring is almost planar and the morpholino ring displays a chair conformation. The packing of compound has a one-dimensional structure constructed through intermolecular O—H⋯O hydrogen bonds. The conformation is stabilized by intramolecular C—H⋯N and C—H⋯O interactions
9,10-Dihydroxy-4,4-dimethyl-5,8-dihydroanthracen-1(4H)-one
In the title molecule, C16H16O3, the ring system is planar and an intramolecular hydrogen bond is present. The molecular packing is dominated by an intermolecular hydrogen bond and by π-stacking interactions [interplanar separation 3.8012 Å]
Composition effect on the aggregate/solution interface of a nematic lyotropic liquid crystal
Lyotropic nematic liquid crystals (lnlc) have attracted attention due to their resemblance to natural
membranes and several technological applications. The effect of tetradecyltrimethyl ammonium chloride
(TTAC) in the viscosity of a new lnlc containing also decanol, NaCl and natural lipids, was studied. In this
article we study how the concentration of phospholipids, decanol and NaCl affects the bilayer and the
liquid crystal/solution interface structures. 2
H-NMR quadrupole splittings and longitudinal relaxation
times of several deuterated species were measured. Polarized light microscopy, transmission electron
microscopy and kinematic viscosity measurements were also obtained. The structure of the bilayer is
dominated by the surface charge density of TTAC. Water rotation, translation and ion solvation depend
on the charge and distance from the interface. With increasing TTAC, MD predicts hydrocarbon chain
inter-digitation and lipid rafts formation. This was rationalized using energy arguments.The authors are pleased to acknowledge financial support from Fondecyt-Chile
(Grant No. 1150138). ARRF acknowledges a fellowship from Conicyt. Authors
also acknowledge the Staff of the Computing Center at the Polytechnic University
of Cartagena for their support and facilities. JJLC and FGDB acklowledge the financial support from Fundación Séneca (Grants No 19353/PI/14 and 19499/PI/14,
respetively). JJGC acknowledges the Ministry of Economy and Competitiveness
for a Ramon y Cajal contract (#RyC-2014-14956)
Pictolysin-III, a Hemorrhagic Type-III Metalloproteinase Isolated from Bothrops pictus (Serpentes: Viperidae) Venom, Reduces Mitochondrial Respiration and Induces Cytokine Secretion in Epithelial and Stromal Cell Lines
From the venom of the Bothrops pictus snake, an endemic species from Peru, we recently have described toxins that inhibited platelet aggregation and cancer cell migration. In this work, we characterize a novel P-III class snake venom metalloproteinase, called pictolysin-III (Pic-III). It is a 62 kDa proteinase that hydrolyzes dimethyl casein, azocasein, gelatin, fibrinogen, and fibrin. The cations Mg2+ and Ca2+ enhanced its enzymatic activity, whereas Zn2+ inhibited it. In addition, EDTA and marimastat were also effective inhibitors. The amino acid sequence deduced from cDNA shows a multidomain structure that includes a proprotein, metalloproteinase, disintegrin-like, and cysteine-rich domains. Additionally, Pic-III reduces the convulxin- and thrombin-stimulated platelet aggregation and in vivo, it has hemorrhagic activity (DHM = 0.3 µg). In epithelial cell lines (MDA-MB-231 and Caco-2) and RMF-621 fibroblast, it triggers morphological changes that are accompanied by a decrease in mitochondrial respiration, glycolysis, and ATP levels, and an increase in NAD(P)H, mitochondrial ROS, and cytokine secretion. Moreover, Pic-III sensitizes to the cytotoxic BH3 mimetic drug ABT-199 (Venetoclax) in MDA-MB-231 cells. To our knowledge, Pic-III is the first SVMP reported with action on mitochondrial bioenergetics and may offer novel opportunities for promising lead compounds that inhibit platelet aggregation or ECM–cancer-cell interactions.</p
Ethyl (1R*,10S*,12R*,15S*)-4-Hydroxy-2-oxo-15- (2-oxo-1-pyrrolidinyl)-9-oxatetracyclo[10.2.2.01,10.03,8]hexadeca-3,5,7,13-tetraene-13-carboxylate
N-Vinylpirrolidinone reacts with (E)-ethyl 5-hydroxy-3-(4-oxo-4H-chromen-3-yl) acrylate (1) through a domino reaction similar to that reported reaction for ethyl vinyl ether. Inverse electron demand Diels–Alder (IEDDA)–elimination-IEDDA generates isomeric tetracycles 5 and 6. The assignment of the relative stereochemistry of the products was made by comparing the proton couplings with those obtained by reaction with ethyl vinyl ether
Targeting Metastasis with Snake Toxins: Molecular Mechanisms
Metastasis involves the migration of cancer cells from a primary tumor to invade and establish secondary tumors in distant organs, and it is the main cause for cancer-related deaths. Currently, the conventional cytostatic drugs target the proliferation of malignant cells, being ineffective in metastatic disease. This highlights the need to find new anti-metastatic drugs. Toxins isolated from snake venoms are a natural source of potentially useful molecular scaffolds to obtain agents with anti-migratory and anti-invasive effects in cancer cells. While there is greater evidence concerning the mechanisms of cell death induction of several snake toxin classes on cancer cells; only a reduced number of toxin classes have been reported on (i.e., disintegrins/disintegrin-like proteins, C-type lectin-like proteins, C-type lectins, serinproteases, cardiotoxins, snake venom cystatins) as inhibitors of adhesion, migration, and invasion of cancer cells. Here, we discuss the anti-metastatic mechanisms of snake toxins, distinguishing three targets, which involve (1) inhibition of extracellular matrix components-dependent adhesion and migration, (2) inhibition of epithelial-mesenchymal transition, and (3) inhibition of migration by alterations in the actin/cytoskeleton network
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