5,8,9,10,14-Pentaacetoxy-3-benzoyloxy-15-hydroxypepluane

Determination of the stereoisomers in aqueous medium and serum and validation studies of racemic aminoalkanol derivatives of 1,7-dimethyl-8,9-diphenyl-4-azatricyclo[5.2.1.0(2,6) ]dec-8-ene-3,5,10-trione, potential new anticancer drugs, by capillary electrophoresis.[Pubmed:27421088]

J Sep Sci. 2016 Aug;39(16):3246-53.

A new method for the determination of the stereoisomers, in aqueous medium and serum, of the racemic aminoalkanol derivatives I and II of 1,7-dimethyl-8,9-diphenyl-4-azatricyclo[5.2.1.0(2,6) ]dec-8-ene-3,5,10-trione, which were found in earlier studies to be potential anticancer drugs, was developed and validated. The optimized conditions included 25 mM phosphate buffer adjusted to pH 2.5, containing gamma-cyclodextrin at a concentration of 5% m/v, as background electrolyte, an applied voltage of +10 kV, and a temperature of 25 degrees C. Separations were carried out using a fused-silica capillary. The developed method of determining the enantiomers of compounds I(S), I(R) and II(S), II(R) was characterized by the following parameters: a detection time within 10.8 min, a detection limit in the range of 141.2-141.7 ng/mL using the UV absorption detection at 200 nm. Good linearity (R(2) = 0.9989-0.9998) was achieved within the range of concentrations studied. A very good extraction yield of 95.4-99.7% was achieved, and recoveries were carried out from both aqueous solutions and matrix serum. The repeatability of the method for peak areas with an accuracy of the determined concentrations of the analytes in the range of 1.43-1.89%, and limits of quantitation in the range of 432.4-436.3 ng/mL were achieved.

Crystal structure of (acetato-kappaO)(ethanol-kappaO)[(9S,17S,21S,29S)-9,17,21,29-tetra-hydroxy-18,30- dioxa-octa-cyclo-[18.10.0.0(2,7).0(8,19).0(9,17).0(11,16).0(21,29).0(23,28)]triac onta-1,3,5,7,11(16),12,14,19,23(28),24,26-undeca-ene-10,22-dione-kappa(3) O (18),O (21),O (22)]caesium ethanol monosolvate.[Pubmed:27555923]

Acta Crystallogr E Crystallogr Commun. 2016 Jun 3;72(Pt 7):884-7.

The title compound, [Cs(CH3COO)(C28H16O8)(C2H5OH)].C2H5OH, is the product of the complexation between one vasarene analogue [1], bis ninhydrin naphthalene-1,3-diol and CsF, where the F(-) ion has reacted with residual acetic acid (AcOH), to form a [1].CsOAc complex. The inter-molecular inter-actions with the multiple oxygen-containing functional groups of the ligand, as well as O-Hcdots, three dots, centeredO hydrogen bonds involving the ethanol solvent mol-ecules, stabilize the complex, forming a chain along [100]. Additional parallel-displaced pi-pi stacking, with an inter-planar distance of 3.669 (1) A, connect several unit cells in a three-dimensional supra-molecular structure, though, the larger size of AcO(-) (1.60 A) compared to F(-) (1.33 A) prevents the tight packing that was once achieved with other vasarene complexes of CsF.

Spectral investigation of the effect of anion on the stability of non covalent assemblies of 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecine (benzo-15-crown-5) with sodium halides.[Pubmed:27591702]

Spectrochim Acta A Mol Biomol Spectrosc. 2017 Jan 15;171:507-514.

A series of complexes of 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecine (benzo-15-crown-5) with sodium halides was synthesized in acetonitrile. The effect of anion on the stability and spectral properties of complexes of benzo-15-crown-5 with sodium halides was investigated. The synthesis of complexes of sodium fluoride and sodium chloride are reported for the first time. Chloroform was used as solvent to study the assembly in solution state by (1)H and (13)C NMR techniques. Single crystal diffraction studies on the easily crystallizable bromide complex confirmed 1:1 stoichiometry of the complex. IR and Raman studies provided valuable evidence for a water molecule shared between the crown encapsulated cation and the counter ion to give a solvent shared ion pair (SSIP). The fluorescence spectra of the complexes were obtained in chloroform by excitation at 270nm to study the effect of complexation on the fluorescent properties of benzo-15-crown-5.

Hybrid gels by conjugation of hyaluronic acid with poly(itaconic anhydride-co-3,9-divinyl-2,4,8,10-tetraoxaspiro (5.5)undecane) copolymers.[Pubmed:28153463]

Int J Biol Macromol. 2017 May;98:407-418.

The approach of covalent conjugation for coupling synthetic polymers with biomolecules represents an appealing strategy to produce new compounds with distinctive properties for biomedical applications. In the present study we generated hybrid gels with tunable characteristics by using hyaluronic acid (HA) and four variants of poly(itaconic anhydride-co-3,9-divinyl-2,4,8,10-tetraoxaspiro[5.5] undecane) (PITAU) copolymers, differing through the molar ratios between comonomers. The new bioconjugate compounds were realized by using a ''grafting to'' strategy, for further ensuring new ways for coupling of various bioactive compounds, taking into account that the grafted copolymers are dual sensitive to pH and temperature. The procedure of chemical crosslinking, by opening the anhydride cycle of the copolymer with the hydroxyl groups of hyaluronic acid, was used to prepare the bioconjugates. The chemical conjugation between HA and PITAU copolymers, as well as the structure of the new compounds, was confirmed by FTIR and NMR techniques. The physical properties of the new gels as thermal stability, swelling capacity, and rheological properties were investigated. The bioconjugate networks were also investigated as drug delivery carriers by using indomethacin as a model drug. In vitro and in vivo tests attested the homogeneity of the bioactive compounds as well as a good biochemical response, showing good biocompatibility for the new structures.