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Biomedical subjects

J Bojarski

Publications and source records attributed to J Bojarski.

At least 19 recordsLinked to original sources
PubMed2001

Enantioseparation of chiral thiobarbiturates using cyclodextrin-modified capillary electrophoresis.

The racemates of several chiral thiobarbiturates were separated by using different cyclodextrins in capillary electrophoresis (CE). Six neutral and negatively charged cyclodextrins 1 (CDs) were employed as chiral separators whereof five led to successful separation of enantiomeric thiobarbiturate pairs. The CDs used were the native alpha-CD, beta-CD, gamma-CD, and heptakis-(2,6-di-O-methyl)-beta-cyclodextrin (HDM) as well as heptakis-(2,3-di-O-methyl-6-sulfato)-beta-cyclodextrin (HDMS) and heptakis-(2,3-di-O-acetyl-6-sulfato)-beta-CD (HDAS). Five of the six chiral thiobarbiturates studied could be resolved at a basic pH value of 9.4 and a phosphate buffer concentration of 100 mM in a fused-silica capillary. Structurally related substances showed a similar behavior in separation: 1 and 2 bearing the center of chirality in the side chain at C5 can be best separated using gamma-CD, the N-alkyl-substituted compounds 3 and 4 as well as the N/S-dialkyl-substituted compound 5 could be resolved with HDM. Using the neutral CDs, the migration times were relatively small (< 11 min). 3 and 4 could be also resolved by means of the negatively charged HDMS. In the latter case, the migration time is twice as long as with HDM.

Cyclodextrins↗
PubMed2000

The impact of chirality of the fluorinated volatile inhalation anaesthetics on their clinical applications.

This review discusses the various chromatographic enantioseparation methods on an analytical and preparative scale for fluorinated inhalation anaesthetics used clinically, namely halothane, enflurane, desflurane and isoflurane. The differences in the pharmacodynamics and pharmacokinetics between the enantiomers of those anaesthetics are presented. It can be concluded that using a single enantiomer for these fluorinated anaesthetics is advantageous over using the racemic mixture. The racemic switch to a single enantiomer for these fluorinated volatile anaesthetics offers a more effective and safe general anaesthetic.

Anesthetics, Inhalation↗
PubMed2000

Retention of barbituric acid derivatives on immobilized artificial membrane stationary phase and its correlation with biological activity.

A series of 30 barbituric acid derivatives were subjected to high-performance liquid chromatography (HPLC) on the 'immobilized artificial membrane' (IAM) column with acetonitrile buffer mobile phase. The retention parameter log k(IAM) was related to the logarithms of partition coefficients determined in octanol-water partition system, log P, to a thin-layer chromatographic (TLC) parameter from partition TLC, R(m0), to an adsorption HPLC retention parameter, log k(0), and to a solubility parameter, delta. It was demonstrated that log k(IAM) correlated significantly to the other parameters of barbiturates determined in partition systems but not to delta. However, log k(IAM) appeared to be a distinctive descriptor of hydrophobicity of barbiturates as compared to the standard log P parameters. The parameter log k(IAM) was shown to correlate with bioactivity data of the agents studied.

Barbiturates↗
PubMed1999

Enantioselective high performance liquid chromatographic assay of acebutolol and its active metabolite diacetolol in human serum.

A stereoselective direct liquid chromatographic method for assay of the enantiomers of the beta-adrenergic blocker acebutolol (AC) and its active metabolite, diacetolol (DC), in human serum was developed. The assay is based on extraction with ethyl acetate and separation of enantiomers on an amylose tris-(3,5-dimethylphenylcarbamate) chiral stationary phase (Chiralpak AD) column. The method was validated and proved useful for the determination of the enantiomers in serum samples of patients suffering from hypertension and chronically treated with racemic AC. The results were compared and found similar with an indirect assay based on derivatization of the enantiomers with (+)-(S)-1-(1-naphthyl)ethyl isocyanate (NEIC).

Acebutolol↗
PubMed1994

[Atypical overgrowth of the left suprarenal gland imitating pheochromocytoma].

In the work a case of an excessive functional activity of core of hyper suprarenal gland is presented. It is caused by atypical overgrowth of the left suprarenal gland. The cyst observed on the left kidney covering pathologically the changed suprarenal gland was an additional diagnostic difficulty.

Adrenal Gland Diseases↗
PubMed1993

Enantioselective lipase-catalyzed ester hydrolysis: effects on rates and enantioselectivity from a variation of the ester structure.

In order to make a preliminary study of substituent effects on the rate and enantioselectivity obtained in esterolytic reactions catalyzed by a lipase from Candida rugosa, a series of racemic esters, derived from some alpha-alkyl and alpha-halo phenylacetic acids, were prepared. The reactions were studied at pH 6.0 and 50 degrees C under which conditions uncatalyzed hydrolysis was relatively slow. Reaction samples were studied at different points of time by means of analytical chiral reversed-phase liquid chromatography, which permitted the simultaneous determination of product enantiomeric excess and of the degree of total ester hydrolysis. These data were then used to calculate initial rates as well as enantioselectivity. An increase of the steric bulk of the alpha-substituent was found to highly decrease the rate of the reaction. On the other hand, rates were higher for the p-nitrophenyl esters than for the corresponding 2-chloroethyl esters. Consistently, the enantioselectivity was found to be higher for the latter type of ester. The esters of the alpha-halo (bromo and chloro) phenylacetic acids gave mandelic acid as the final product. This was caused by a rapid solvolysis of the alpha-halo phenylacetic acid initially formed.

Candida↗
PubMed1990

Photochemical reactions of quindoxin, olaquindox, carbadox and cyadox with protein, indicating photoallergic properties.

Quindoxin (quinoxaline-1,4-dioxide), a former 'growth promoter' used in animal husbandry, has been taken from the market because of its photoallergic properties. Nowadays its derivatives olaquindox, carbadox and cyadox are frequently applied for the same purpose. Recent reports show that olaquindox too, can induce photoallergic skin reactions in stockmen. From the present investigation it appeared that all compounds mentioned, form a reactive oxaziridine upon exposure to light, just like many other imino-N-oxides. Photoreactivity with protein, which is considered as an important condition for a compound to be a potential photoallergen, was also studied. Quindoxin and olaquindox proved to meet this condition, as was expected. But carbadox and cyadox also react and were shown to be even more reactive towards human serum albumin.

Animals↗
PubMed1988

Resolution of chiral barbiturates into enantiomers by reversed-phase high-performance liquid chromatography using methylated beta-cyclodextrins.

The correlation between the capacity factors of enantiomers of chiral barbiturates and the concentrations of beta-cyclodextrin, heptakis(2,6-di-O-methyl)-beta-cyclodextrin and heptakis(2,3,6-tri-O-methyl)-beta-cyclodextrin dissolved in the mobile phase was studied using LiChrosorb RP-18 as the stationary phase. Owing to the very strong adsorption of permethylated beta-cyclodextrin on the ODS surface a chiral stationary phase is generated dynamically and forms complexes with the solutes; this mechanism has been found to be the only factor responsible for the chiral recognition of the investigated compounds at all applied concentrations. The inclusion of barbiturates in the cavities of permethylated beta-cyclodextrin involves a distinct and entirely new kind of enantioselectivity compared with that observed for beta-cyclodextrin and its dimethyl derivative. Using permethylated beta-cyclodextrin baseline resolutions have been obtained with barbiturates containing a chiral centre in the heterocyclic ring or in the aliphatic side-chain.

Barbiturates↗
PubMed1988

(R)-(-)-10-methyl-11-hydroxyaporphine: a highly selective serotonergic agonist.

Prior work in these laboratories identified (+/-)-5-hydroxy-6-methyl-2- (di-n-propylamino)tetralin as a dopaminergic agonist prodrug. The ortho methyl hydroxy aromatic substitution pattern in this molecule has now been incorporated into the aporphine ring system to give a congener of the dopaminergic agonist apomorphine in which the position 10 OH group has been replaced by methyl. Preparation of the target compound involved acid-catalyzed rearrangement of the 3-(1-phenyltetrazolyl) ether of morphine and subsequent molecular modification of the product, the 10-(1-phenyltetrazolyl) ether of (R)-(-)-apomorphine. Surprisingly, the target compound elicited no responses in any assays for effects at dopamine receptors, but rather it displayed pharmacological properties consistent with its being a serotonergic agonist with a high degree of selectivity for 5-HT1A receptors similar to the serotonergic agonist 8-hydroxy-2-(di-n-propylamino)tetralin.

Animals↗
PubMed1988

Photochemical degradation of barbituric acid derivatives. Part 8: Photolysis of sodium salts of barbiturates in solid state.

After the UV irradiation of suspensions of barbiturate sodium salts in paraffin oil the IR spectra revealed two IR absorption bands at ca. 2170 and 2250 cm-1. The effects of different conditions of the photochemical process and the addition of nucleophilic reagents after irradiation on the intensity of these bands were studied. The origin of 2170 cm-1 band was interpreted in terms of the isocyanate intermediate which is formed after the pyrimidine ring opening.

Barbiturates↗