Synthesis and biological evaluation of isomeric derivatives of naturally occurring spatozoate.

An isomer of the natural phthalate ester spatozoate (1), n-butyl 2-benzoyloxymethylbenzoate (2a) and a series of its new derivatives 2b-2s were synthesized and exposed to selected biological screening, as phthalates were reported to possess different biological activities. Compound 2g was found to be the most potent cytotoxic agent with a LD50 = 8.98 microg/ml. In a bactericidal assay the compounds showed a broad spectrum of activities. Compound 2a has a very promising fungicidal activity against Microsporum canis.

Efficient synthesis of isobenzofuran-1(3H)-ones (phthalides) and selected biological evaluations.

The studies presented here deal with the convenient and efficient one-step conversion of o-alkylbenzoic acids into their corresponding isobenzofuran-1 (3H)-ones (phthalides) using NaBrO3/NaHSO3 in a two-phase system. A range of o-alkylbenzoic acids was used with the object of getting a variety of phthalide derivatives as multipurpose biologically active compounds. Seventeen phthalides have been synthesized and tested for cytotoxicity, antibacterial and antifungal activities. Some of these compounds showed promising cytotoxic effects against Artemia salina. Compounds 4j-4p were highly active against Gram-negative and Gram-positive bacteria among all tested compounds. In the fungicidal assay, the compounds showed a broad spectrum of activity against six fungi. All compounds were characterized via elemental analysis, UV, IR, mass and-NMR spectroscopy.

Splitless on-line coupling of capillary high-performance liquid chromatography, capillary electrochromatography and pressurized capillary electrochromatography with nuclear magnetic resonance spectroscopy.

A mixture of unsaturated fatty acid methyl esters was separated with a new splitless capillary set-up. With the employed apparatus configuration different capillary separation techniques such as capillary high-performance liquid chromatography (cHPLC), capillary electrochromatography (CEC) and pressurized capillary electrochromatography (pCEC) could be applied. The detection and identification of the sample compounds were accomplished by hyphenating these capillary separation techniques with nuclear magnetic resonance (NMR) spectroscopy using a novel configuration of the detection capillary set-up. Using modified electrokinetically driven separation techniques, the electric field was applied solely across the separation column. With this improved interface for capillary liquid chromatography-NMR on-line coupling, the stereochemical assignment of the cis and trans configuration of unsaturated fatty acids could be easily accomplished. Finally, the results of cHPLC-NMR, CEC-NMR and pCEC-NMR coupling experiments were compared.

Performance of capillary gel electrophoretic analysis of oligonucleotides coupled on-line with electrospray mass spectrometry.

Synthetic oligonucleotides (ODNs) are routinely analyzed using capillary gel electrophoresis (CGE) for size-sieving based separations as well as electrospray mass spectrometry (ESI-MS) for identification. On-line coupling of these methods is therefore desired in order to combine the analytical capabilities provided by both methods. Performance of on-line CGE-ESI-MS systems is influenced by various parameters, and choice of optimal conditions is crucial for successful coupling experiments. In this study, we explore characteristics of the on-line coupled CGE-ESI-MS system for ODN analysis. Effects of CGE buffer concentration, capillary length, separation and orifice voltage on CGE separation and MS detection of a phosphodiester ODN mixture were examined. Attention was paid to the influence of the interface, such as geometry of capillary alignment, sheath liquid flow-rate and sheath liquid composition on performance of the system.

Comparison of different setups for one- and two-dimensional capillary high-performance liquid chromatography and pressurized capillary electrochromatography coupled on-line with mass spectrometry.

A comparison of different separation methods (high-performance liquid chromatography (HPLC), capillary HPLC (CHPLC) and pressurized capillary electrochromatography (pCEC)) coupled on-line with mass spectrometry (MS) is undertaken using the separation of a crude extract of ergot fungus (secalis cornuti) as an example. New and simple setups for a two-dimensional CHPLC coupled on-line with electrospray ionization (ESI)-MS (2D-CHPLC-MS) as well as for capillary size-exclusion chromatography performed under pCEC conditions and coupled on-line with ESI-MS (CSEC-pCEC-MS) are shown. In addition, an improved method for column packing is presented.

On-line coupling of packed capillary electrochromatography with coordination ion spray-mass spectrometry for the separation of enantiomers.

Pressure-supported packed capillary electrochromatography (CEC) and packed capillary high-performance liquid chromatography (pHPLC) have been coupled on-line to electrospray ionization-mass spectrometry (ESI-MS) and coordination ion spray-mass spectrometry (CIS-MS). Separation of enantiomers of barbiturates and chlorinated alkyl phenoxypropanoates were performed on a permethylated beta-cyclodextrin stationary phase by pressure-supported CEC. For on-line detection with ESI- and CIS-MS, a modified sheath-liquid interface was used. CIS-MS is a universal, novel ionization technique which improves the selectivity as well as the sensitivity. Charged complexes were formed through the addition of central complexing ions such as silver(I), cobalt(II), copper(II), and lithium(I) to the sheath flow. Advantages of CIS-MS detection compared to the ESI-MS mode are discussed. In the CIS-MS mode, increased sensitivity and high selectivity was attained through different possibilities of complexation. The superiority of pressure-supported CEC compared to pHPLC in the hyphenation with CIS-MS is demonstrated.

Coordination-Ionspray-MS (CIS-MS), a Universal Detection and Characterization Method for Direct Coupling with Separation Techniques.

By on-line addition of a central atom (for example, AgI , BIII , PdII , LiI ) positively or negatively charged complexes of analytes can be formed for CIS-MS. This technique is applicable to both polar and nonpolar compounds-for example, for alcohols, ethers, and a large number of olefins, polyolefins, and arenes as well as steroids, vitamins of the D and E families, carotinoids, polystyrols, terpenes, and unsaturated fatty acids-and can be readily coupled with separation techniques.