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Sphingosine kinases (SK) catalyze the phosphorylation of proapoptotic sphingosine to the prosurvival factor sphingosine 1-phosphate (S1P), thereby promoting oncogenic processes. Breast (MDA-MB-231), lung (NCI-H358), and colon (HCT 116) carcinoma cells were transduced with shRNA to downregulate SK-1 expression or treated with a pharmacologic SK-1 inhibitor. The effects of SK-1 targeting were investigated by measuring the level of intracellular sphingosine, the activity of protein kinase C (PKC) and cell cycle regulators, and the mitotic index. Functional assays included measurement of cell proliferation, colony formation, apoptosis, and cell cycle analysis. Downregulation of SK-1 or its pharmacologic inhibition increased intracellular sphingosine and decreased PKC activity as shown by reduced phosphorylation of PKC substrates. In MDA-MB-231 cells this effect was most pronounced and reduced cell proliferation and colony formation, which could be mimicked using exogenous sphingosine or the PKC inhibitor RO 31-8220. SK-1 downregulation in MDA-MB-231 cells increased the number of cells with 4N and 8N DNA content, and similar effects were observed upon treatment with sphingosine or inhibitors of SK-1 or PKC. Examination of cell cycle regulators unveiled decreased cdc2 activity and expression of Chk1, which may compromise spindle checkpoint function and cytokinesis. Indeed, SK-1 kd cells entered mitosis but failed to divide, and in the presence of taxol also failed to sustain mitotic arrest, resulting in further increased endoreduplication and apoptosis. Our findings delineate an intriguing link between SK-1, PKC and components of the cell cycle machinery, which underlines the significance of SK-1 as a target for cancer therapy.
The fused five- and six-membered rings in the title compound, C14H12N2O, are essentially planar, the largest deviation from the mean plane being 0.023 (2) Å. The dihedral angle between the benzimidazole mean plane and the phenyl ring is 68.50 (6)°. In the crystal, each molecule is linked to its symmetry equivalent created by a crystallographic inversion center by pairs of N—H[cdots, three dots, centered]O hydrogen bonds, forming inversion dimers.
In the mol-ecule of the title compound, C(12)H(12)BrN(3)O, the fused-ring system is essentially planar, the largest deviation from the mean plane being 0.0148 (3) Å. The two allyl groups are nearly perpendicular to the imidazo[4,5-b]pyridine plane [C-C-N-C torsion angles of 81.6 (4) and -77.2 (4)°] and point in the same direction. The planes through the atoms forming each allyl group are nearly perpendicular to the imidazo[4,5-b]pyridin-2-one system, as indicated by the dihedral angles between them of 80.8 (5) and 73.6 (5)°.
The two fused five- and six-membered rings building the molecule of the title compound, C13H10BrN3, are approximately planar, the largest deviation from the mean plane being 0.004 (2) Å. The dihedral angle between the imidazo[4,5-b]pyridine mean plane and that of the phenyl ring is 41.84 (11)°. The structure is held together by slipped π–π stacking between symmetry-related molecules, with an interplanar distance of 3.583 (1) Å and a centroid–centroid vector of 3.670 (2) Å.
The structure of the title compound, (C15H15N2O4)[AgI2], consists of an organic 4-[3-(isonicotinoyloxy)propoxycarbonyl]pyridinium cation which has a gauche–gauche (O/C/C/C—O/C/C/C or GG’) conformation and lies on a twofold rotation axis, which passes through the central C atom of the aliphatic chain, and an inorganic [AgI2]− anion. In the complex anion, the Ag+ cation is bound to two I− anions in a linear geometry. The anion was modelled assuming disorder around a crystallographic inversion centre near the location of the Ag+ cation. The crystal packing is stabilized by a strong intermolecular N—H[cdots, three dots, centered]N hydrogen bond, which links the cations into zigzag chains with graph-set notation C(16) running along the face diagonal of the ac plane. The N-bound H atom is disordered over two equally occupied symmetry-equivalent sites, so that the molecule has a pyridinium ring at one end and a pyridine ring at the other.
In the molecular structure of the title compound, C21H18N2O, the fused-ring system is essentially planar, the largest deviation from the mean plane being 0.0121 (9) Å. The O atom and adjacent C atom are located in Wyckoff position 4e on a twofold axis (0, y, 1/4). The two benzyl groups are almost perpendicular to the benzimidazole plane, but point in opposite directions. The dihedral angle between the benzimidazole mean plane and the phenyl ring is 81.95 (5)°, whereas that between the two benzyl groups is 60.96 (7)°.
The asymmetric unit of the title compound, C16H23ClN2O, comtains two independent molecules in which the fused-ring systems are essentially planar, the largest deviation from the mean plane of each molecule being 0.011 (2) Å and 0.016 (2) Å. The benzimidazole rings of the two molecules make a dihedral angle of 66.65 (7)°. The nonyl substituents are almost perpendicular to the benzimidazole planes [C—N—C—C tosrsion angles = 96.0 (3) and 81.0 (2)°]. In the crystal, each independent molecule forms an inversion dimer via a pair of N—H[cdots, three dots, centered]O hydrogen bonds. In one of the independent molecules, the terminal –CH2–CH3 group of the alkyl chain is disordered over two sets of sites with a refined occupancy ratio of 0.746 (7):0.254 (7).
The title compound, [Li4O4(C12H8BO)4(C4H10O)4], features a Li4O4 cube. Each Li atom in the cube is additionally coordinated by a diethyl ether molecule and each O atom in the cube carries a 9-oxa-10-boraanthracene residue. The crystal studied was a non-merohedral twin [twin law (-1 0 0 / 0 0 1 / 0 1 0); the contribution of the major twin component refined to 0.553 (3)] emulating apparent tetragonal symmetry, whereas the actual crystal system is just orthorhombic.
The crystal structure of the title compound, hexa-μ2-bromido-μ4-oxido-tetrakis[(diethyl ether)magnesium], [Mg4Br6O(C4H10O)4], determined from data measured at 173 K, differs from the previously known structure of diethyl ether magnesium oxybromide, which was determined from room-temperature data [Stucky & Rundle (1964 [triangle]). J. Am. Chem. Soc. 86, 4821–4825]. The title compound crystallizes in the tetragonal space group I An external file that holds a picture, illustration, etc. Object name is e-67-m1614-efi7.jpg, whereas the previously known structure crystallizes in a different tetragonal space group, namely P An external file that holds a picture, illustration, etc. Object name is e-67-m1614-efi7.jpg21 c. Both molecules have crystallographic An external file that holds a picture, illustration, etc. Object name is e-67-m1614-efi7.jpg symmetry and show almost identical geometric parameters for the Mg, Br and O atoms. The crystal of the title compound turned out to be a merohedral twin emulating a structure with apparent Laue symmetry 4/mmm, whereas the correct Laue group is just 4/m. The fractional contribution of the minor twin component converged to 0.462 (1).
The title compound, C26H18BrNO4, features a functionalized chromene. The cyclohexene ring adopts a sofa conformation and has the nitro group and the bromophenyl ring in an axial position. The ten atoms of the chromene moiety lie close to a common plane (r.m.s. deviation = 0.066 Å). The attached phenyl ring is twisted by 32.89 (10)° from the chromene plane. The crystal packing is stabilized by C—H[cdots, three dots, centered]O interactions.
The title molecule, C17H25N3O3, is built up from fused six- and five-membered rings linked to a –C10H21 chain. The fused-ring system is essentially planar, the largest deviation from the mean plane being 0.009 (2) Å. The chain is roughly perpendicular to this plane, making a dihedral angle of 79.5 (2)°. In the crystal, N—H[cdots, three dots, centered]O hydrogen bonds build infinite chains along [010]. There are channels in the structure containing disordered hexane. The contribution of this solvent to the scattering power was suppressed using the SQUEEZE option in PLATON [Spek (2009 [triangle]). Acta Cryst. D65, 148–155].
The title compound, C(19)H(14)ClNO(3)·0.2H(2)O, crystallizes with five mol-ecules and a disordered water mol-ecule in the asymmetric unit. Four of the five mol-ecules form hydrogen-bonded dimers via N-H⋯O hydrogen bonds towards another symmetry-independent mol-ecule, whereas the fifth mol-ecule forms a hydrogen-bonded dimer with its symmetry equivalent, also via N-H⋯O hydrogen bonds. The dihedral angle between the planes of the fused benzene ring and the five-membered ring to which it is attached is 79.45 (13), 49.00 (15), 72.49 (16), 81.91 (18) and 76.38 (16)° for the five mol-ecules in the asymmetric unit.
The structure of the title compound, C14H12N2O2 {systematic name: 2,2′-[hydrazinediylidenebis(methanylylidene)]diphenol}, has already been determined in the triclinic space group P An external file that holds a picture, illustration, etc. Object name is e-68-0o255-efi1.jpg with Z = 4 [El-Medani, Aboaly, Abdalla & Ramadan (2004 [triangle]). Spectrosc. Lett. 37, 619–632]. However, the correct space group should be P21/c with Z = 4. This structure is a new polymorph of the already known monoclinic polymorph of salicyladehyde azine, which crystallizes in space group P21/n with Z = 2. The benzene rings form a dihedral angle of 46.12 (9)°. Two intramolucular O—H[cdots, three dots, centered]N hydrogen bonds occur.
In the title compound, C15H14N2O4, (I), the molecule lies on a twofold rotation axis which passes through the central C atom of the aliphatic chain, giving one half-molecule per asymmetric unit. The structure is a monoclinic polymorph of the triclinic structure previously reported [Brito, Vallejos, Bolte & López-Rodríguez (2010). Acta Cryst. E66, o792], (II). The most obvious difference between them is the O/C/C/C—O/C/C/C torsion angle [58.2 (7)° in (I) and 173.4 (3)/70.2 (3)° in (II) for GG and TG conformations, respectively]. Another important difference is observed in the dihedral angle between the planes of the aromatic rings [86.49 (7)° for (I) and 76.4 (3)° for (II)]. The crystal structure features a weak π–π interaction [centroid–centroid distance = 4.1397 (10)Å]; this latter kind of interaction is not evident in the triclinic polymorph.
In the title compound, [Ag(BF4)(C14H12N2O4)]n, the coordination of the Ag+ ion is trigonal–bipyramidal with the N atoms of two ethane-1,2-diyl bis(pyridine-3-carboxylate) ligands in the apical positions and three F atoms belonging to different tetrafluoridoborate anions in the equatorial plane. The material consists of infinite chains of [Ag(C14H12N2O4)] units running along [001], held together by BF4 − bridging anions.
Prostate cancer is one of the most common tumor diseases worldwide. Often being non-aggressive, prostate tumors in these cases do not need immediate treatment. However, about 20% of diagnosed prostate cancers tend to metastasize and require treatment. Existing diagnostic methods may fail to accurately recognize the transition of a dormant, non-aggressive tumor into highly malignant prostate cancer. Therefore, new diagnostic tools are needed to improve diagnosis and therapy of prostate carcinoma. This review evaluates existing methods to diagnose prostate carcinoma, such as the biochemical marker prostate-specific antigen (PSA), but also discusses the possibility to use the altered expression of integrins and laminin-332 in prostate carcinomas as diagnostic tools and therapeutic targets of prostate cancer.