Quantitative retention—structure and retention—activity relationship studies of ionic and non-ionic catecholamines by micellar liquid chromatography

Mallols, J. M. Sanchis; Camañas, R. M. Villanueva; Sagrado, S.; Medina-Hernández, M.J.

doi:10.1007/bf02490520

Cited by 41 publications

(15 citation statements)

References 17 publications

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“…The chromatographic data and the logP values for the series of compounds listed in Table I were collected from the literature in the case of monosubstituted benzenes, aromatic compounds, barbiturates and catecholamines [18,[20][21][22]. Also, a series ofphenylureas and a set formed of seven compounds (named calibration set) was chromatographed under the conditions given in Table I.…”

Section: Datamentioning

confidence: 99%

The chromatographic quantification of hydrophobicity using micellar mobile phases

et al. 1999

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SummaryIn micellar liquid chromatography (MLC), the hydrophobicity of a compound is the predominant factor in its retention and interaction with micelles. A non-linear empirical model can describe the dependence between the retention factor (logk) in MLC and the logarithm of partition coefficients octanol-water (logP). An algorithm based on such a model has been used to make logP predictions. Retention data for series of neutral compounds eluted with different mobile phases and alkylbonded stationary phases have been used to test the predictive ability of the algorithm. The results of this approach are compared with those obtained from automatic computational software packages. compound in RPLC is governed by hydrophobic interactions, linear relationships between the logarithm of retention factor (logk) and logP could be expected according to linear free energy relationships. Although this method has received a great deal of attention, some problems have been reported [6][7]. For instance, hydrophobicity estimations depend on the mobile phase composition and the nature of the stationary phase, and for alkyl-bonded stationary phases, different relationships are observed for different groups of congeneric compounds, because of the presence of free silanol groups and impurities in the stationary phase. The use ofmicellar mobile phases in RPLC instead the traditional aqueous-organic mobile phases to quantifying hydrophobicity has several advantages: i) the retention behaviour of compounds (apolar, polar or ionic) chromatographed with anionic, cationic and non-ionic surfactants is accurately modelled [8][9]. In fact, the retention of a non-ionizable compound as a function of micellar concentrations can be deduced by:

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Section: Datamentioning

confidence: 99%

The chromatographic quantification of hydrophobicity using micellar mobile phases

et al. 1999

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“…Our research group has demonstrated that the use of retention data obtained in a chromatographic system constituted by polioxyethylene 23 lauryl ether Brij35 micellar mobile phases and C 18 reversed stationary phase in adequate experimental conditions is helpful in describing the biological behaviour of different kinds of drugs (Escuder-Gilabert et al, 1998aCuencaBenito et al, 1998;Sanchis-Mallols et al, 1997;MoleroMonfort et al, 1999MoleroMonfort et al, , 2000Quiñones-Torrelo et al, 1999;Martín-Biosca et al, 1999;Martínez-Pla et al, submitted). We have called this drug biopartitioning simulation chromatographic system biopartitioning micellar chromatography (BMC).…”

Section: Introductionmentioning

confidence: 93%

Development of predictive retention–activity models of butyrophenones by biopartitioning micellar chromatography

Martı́n-Biosca

Molero-Monfort

Sagrado

et al. 2001

Biomedical Chromatography

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The predictive and interpretative capability of quantitative chromatographic retention-biological activity models is supported by the fact that in adequate experimental conditions the solute partitioning into the chromatographic system can emulate the solute partitioning into lipid bilayers of biological membranes, which is the basis of drug and metabolite uptake, passive transport across membranes and bioaccumulation. The use of retention data obtained in biopartitioning micellar chromatography (BMC) has been demonstrated to be helpful in describing the biological behaviour of different kinds of drugs. In this chromatographic system, polioxyethylene 23 lauryl ether Brij35 micellar mobile phases and C 18 reversed stationary phase in adequate experimental conditions are used. The RP-HPLC capacity factors of butyrophenones were determined using different Brij35 concentrations as micellar mobile phases. Relationships between seven biological activities of butyrophenones reported in bibliography and retention data were established and their predictive and interpretative ability evaluated. These relationships were significant between preclinical pharmacology and therapeutic efficacy parameters and the retention factors of butyrophenones (0.89 < R 2 < 0.98). The results indicate that the retention of compounds in BMC is capable of describing and predicting in vitro the biological activities of butyrophenones. This approach can be very useful in the development of new neuroleptic drugs, avoiding the use of experimental animals.

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“…Successful applications of MLC to quantitative retention-activity relationships have been reported to describe substituted phenol bioactivity (Breyer et al,1991), the anesthetic potency of local anesthetics (Escuder-Gilabert et al, 1998a, b), the hypnotic activity of barbiturates (Cuenca-Benito et al, 1998), and the a-and b-adrenergic activity of catecholamines (Sanchis-Mallols et al, 1997). In this paper we have focused our attention on benzodiazepines.…”

Section: Introductionmentioning

confidence: 97%

Retention-activity relationship studies of benzodiazepines by micellar liquid chromatography

Molero-Monfort

Sagrado

Villanueva-Camañas

et al. 1999

Biomed. Chromatogr.

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Quantitative retention—structure and retention—activity relationship studies of ionic and non-ionic catecholamines by micellar liquid chromatography

Cited by 41 publications

References 17 publications

The chromatographic quantification of hydrophobicity using micellar mobile phases

The chromatographic quantification of hydrophobicity using micellar mobile phases

Development of predictive retention–activity models of butyrophenones by biopartitioning micellar chromatography

Retention-activity relationship studies of benzodiazepines by micellar liquid chromatography

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