Preparation and characterization of hydroxypropyl-β-cyclodextrin inclusion complex of eugenol: differential pulse voltammetry and (1)H-NMR

The objective of present investigation was to improve the solubility of Eugenol by preparing the inclusion complex of Eugenol with hydroxypropyl-β-cyclodextrin (Hp-β-CD) and characterize the prepared complex by using NMR and differential pulse voltammetry (DPV). Phase solubility curve was plotted using Hp-β-CD in ranging from 0-40 mM of Hp-β-CD and found to be linear. Therefore, inclusion complex was prepared in equimolar ratio of Eugenol and Hp-β-CD by lyophilization method. Fourier transform infrared spectroscopy (FT-IR), (1)H-NMR and DPV were performed for Eugenol, Hp-β-CD and prepared inclusion complex of Eugenol. 2D (two dimensional) NMR was also performed for prepared inclusion complex. The proton of phenol moiety of Eugenol experienced a pronounced chemical shift variation in (1)H-NMR. The positive sign of the variation for proton in (1)H-NMR indicated that the proton was located near to an oxygen atom in the Hp-β-CD cavity and its magnitude showed a strong interaction between -OH proton of Eugenol and Hp-β-CD. 2D NMR confirms the interaction between phenolic group and hydrogen atoms of Hp-β-CD. A well defined anodic peak current corresponding to oxidation of Eugenol in non-encapsulated and Hp-β-CD-Eugenol inclusion complex in phosphate buffer (pH 6.8) was obtained at about 0.35 V and 0.40 V, respectively. The positive shift in oxidation potential indicated the formation of complex via hydrophobic interactions. The oxidant power of Eugenol was retained in complex form as indicated by DPV results. Thus, its oxidation dependent pharmacological property such as antimicrobial activity is not affected after complexation with Hp-β-CD. Thus, (1)H-NMR, 2D-NMR and DPV techniques can be used as valuable tools to determine the mechanism of complexation and state of electrochemical active drug in inclusion complex.     

Determination of oxytocin in milk of cows administered oxytocin

To address people's concerns of exogenous oxytocin (OT) administration to lactating bovines, a study was undertaken to (a) establish an enzyme immunoassay (EIA) for OT determination in milk, (b) quantify OT in milk of cows administered OT, and (c) study influence of pasteurization on OT stability in milk. A sensitive EIA validated according to the criteria of European Union—Decision 2002/657/EC was developed for OT in skim milk in an analytical range of 10-250 pg mL⁻¹ with a decision limit (CCα) of 30 pg mL⁻¹ and detection capability (CCβ) of 41.5 pg mL⁻¹. Milk samples collected from cows (n = 38) administered either 25 or 50 IU OT prior to milking were investigated for the presence of OT. There was no significant difference among both groups with the mean concentrations of OT being 15.8 and 14.9 pg mL⁻¹ for cows subjected to 25 and 50 IU OT administration, respectively. The OT levels in skim milk of control cows (n = 30; untreated) were basal (around 10 pg mL⁻¹). All the analyzed milk samples were below the CCα value of 30 pg mL⁻¹. Pasteurization of OT spiked milk samples at different temperature and sample holding conditions reduced the immunological activity of OT to 43% at 110 °C. However, no further decline occurred in the immunological activity with increased pasteurization temperature and time. It was concluded that the milk OT concentrations after OT administrations were minimal and below the assay decision limit. However, OT was quite stable to pasteurization in OT spiked milk.     

ChemInform Abstract: Calculational Study of Fluoroammonium and Related Cations and Dications.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.     

13C NMR/DFT/GIAO studies of phenylene bis(1,3-dioxolanium) dications and 2,4,6-triphenylene tris(1,3-dioxolanium) trication

The o-, m-, and p-phenylene bis(1,3-dioxolanium) dications (4-6) and 2,4,6-triphenylene tris(1,3-dioxolanium) trication (7) have been prepared by the ionization of the corresponding 2-methoxyethyl benzoates in FSO(3)H or CF(3)SO(3)H at 40 and 60 degrees C, respectively. The charge delocalization in these carbocations was probed by (13)C NMR chemical shifts and substantiated by GIAO/DFT calculations. Relatively less charge is delocalized into the aromatic ring of the carbotrication 7. The rotational barrier around the C(+)-Ar bond for carbodications 4 and 5 was also estimated to be 8-10 kcal/mol.     

Effect of Bridging Units on Photophysical and DNA Binding Properties of a Few Cyclophanes

A few novel anthracene-based cyclophanes CP-1 , CP-2 and CP-3 were synthesized and their interactions with DNA were investigated employing photophysical and biophysical techniques. In methanol and acetonitrile, these systems exhibited optical properties characteristic of the anthracene chromophore. However, in the aqueous medium, the symmetric cyclophane CP-1 showed a dual emission having λ_max at 430 and 550 nm, due to the monomer and excimer, respectively. In contrast, the cyclophanes CP-2 and CP-3 in the aqueous medium showed structured anthracene absorption and emission spectra similar to those obtained in methanol and acetonitrile. DNA binding studies indicate that CP-1 undergoes efficient nonclassical partial intercalative interactions with DNA resulting in the exclusive formation of a sandwich-type excimer having enhanced emission intensity and lifetimes. The cyclophane CP-2 having one anthracene moiety exhibited nonclassical intercalative binding with DNA, albeit with less efficiency compared with CP-1 . In contrast, CP-3 , having sterically bulky viologen bridging group showed DNA electrostatic as well as groove binding interactions. These results demonstrate that the nature of the bridging unit plays an important role in the binding mode of the cyclophanes with DNA and in the formation of the novel sandwich-type excimer.     

Synthesis and electrochemical studies of charge-transfer complexes of thiazolidine-2,4-dione with σ and π acceptors

In the present work, we report the synthesis and characterization of novel charge-transfer complexes of thiazolidine-2,4-dione (TZD) with sigma acceptor (iodine) and pi acceptors (chloranil, dichlorodicyanoquinone, picric acid and duraquinone). We also evaluated their thermal and electrochemical properties and we conclude that these complexes are frequency dependent. Charge-transfer complex between thiazolidine-2,4-dione and iodine give best conductivity. In conclusion, complex with sigma acceptors are more conducting than with pi acceptors.     

Electronic Properties-Morphology Correlation of a Rod-Rod Semiconducting Liquid Crystalline Block Copolymer Containing Poly(3-hexylthiophene)

The influence of the solvent and annealing temperature on the field-effect mobilities and morphologies of poly(3-hexylthiophene)-b-poly(γ-benzyl-l-glutamate) (P3HT-b-PBLG) rod-rod diblock copolymer has been investigated. Thin film X-ray diffraction studies show peaks originating from both P3HT and PBLG indicating that the crystalline nature of both the blocks is conserved after the formation of the block copolymer. It has been observed that the field-effect mobilities of the diblock copolymer are independent of the annealing temperatures for thin films deposited from both 1,2,4-trichlorobenzene and chloroform solvents. The correlation between the field-effect mobility and morphology indicates that the P3HT block self-assembles at the surface SiO(2) dielectric.     

Recent Developments in the Synthesis of Five‐ and Six‐Membered Heterocycles Using Molecular Iodine

Heterocyclic scaffolds represent the key structural subunits of many biologically active compounds. Over the last few years iodine‐mediated reactions have been extensively studied due to their low cost and eco‐friendliness. This Review covers advances in the field of iodine‐mediated synthesis of heterocyclic compounds since 2006, especially with an emphasis on mechanisms of ring formation. In this article, syntheses of different heterocycles are classified based on the manipulation of functional groups.