The chromatographic behavior of a series of coxibs and oxicams, drugs from a group of non-steroidal anti-inflammatory drugs, was studied by reversed-phase thin-layer chromatography with binary mobile phases containing water and the organic modifiers: methanol, acetone, 1,4-dioxane, acetonitrile and 2-propanol. Linear relationships were obtained between the retention RM values of the compounds and the concentration of organic modifier in the mobile phase. Values of RM0, represent the theoretical RM values at 0% organic solvent in the mobile phase were calculated by extrapolation. These experimental lipophilicity values were correlated with lipophilicity (logP) from databases. The obtained results show that reversed-phase chromatography (experimental parameters) may be a good instrument for analytics in describing the lipophilic nature of investigated compounds as well as the activity.
Abstract Lipophilicity properties have long been considered a vital component of drug discovery and development, providing insight into the role of molecular properties in the biological activity of known and new compounds. An extensive survey of the literature published in analytical and pharmaceutical chemistry journals has been conducted. Separation, optical, electrochemical and calculation methods which were developed and used for determination of lipophilicity non-steroidal anti-inflammator...
#1Yi Bo Liou(TMU: Taipei Medical University)H-Index: 5
#2Hsiu O. Ho(TMU: Taipei Medical University)H-Index: 31
Last. Ming Thau Sheu(TMU: Taipei Medical University)H-Index: 34
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Abstract In this study, an empirical model of the quantitative structure-permeability relationship (QSPR) of the transdermal delivery of non-steroidal anti-inflammatory drugs (NSAIDs) was constructed in an attempt to predict the permeability coefficients ( k P ). Thirteen model NSAIDs were selected, and their in vitro permeation through the full skin of nude mice was examined. The biological parameters of transepidermal water loss (TEWL), hydration content (HD), lipid content (SB), resonance run...
Selective inhibition of cyclooxygenase-2 inhibitors is an important strategy in designing of potent anti-inflammatory compounds with significantly reduced side effects. The present quantitative structure–activity relationship study, attempts to explore the structural and physicochemical requirements of 2-sulfonyl–phenyl–indol derivatives (n = 30) for COX-2 inhibitory activity using chemical, topological, geometrical, and quantum descriptors. Some statistical techniques like stepwise regression, ...
#1Hirak Chakraborty(SINP: Saha Institute of Nuclear Physics)H-Index: 16
#2Sutapa Mondal(SINP: Saha Institute of Nuclear Physics)H-Index: 2
Last. Munna Sarkar(SINP: Saha Institute of Nuclear Physics)H-Index: 20
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Abstract Membrane fusion is an important event in many biological processes and is characterized by several intermediate steps of which content mixing between the two fusing vesicles signals the completion of the process. Fusion induced solely by small drug molecules is not a common event. Non Steroidal Anti-Inflammatory Drugs (NSAIDs), that control pain and inflammation, are also capable of exhibiting diverse functions. In this study we present a new function of NSAIDs belonging to the oxicam g...
The role of n-octanol as mobile phase additive for the lipophilicity assessment of 45 structurally diverse acidic drugs both at neutral (pH 2.5) and ionized form (pH 7.4) was investigated. Extrapolated retention factors log kw were determined on a BDS C18 column using methanol as organic modifier and different amounts of n-octanol as mobile phase additive. For more polar compounds, the effect of n-octanol in retention was found to decrease as their lipophilicity increased. In the case of carboxy...
High-performance methods of testing of drug candidates for properties of pharmacokinetics and pharmacodynamics importance, in particular lipophilicity and acidity, are necessary to overcome innovation stagnation in the pharmaceutical industry. Reversed-phase high-performance liquid chromatography (RP HPLC) might be a unique tool for the determination of both pKa and the apparent (pH-dependent) partition coefficient, applicable in high-throughput analysis of multicomponent mixtures, e.g., samples...
#1Hirak Chakraborty(SINP: Saha Institute of Nuclear Physics)H-Index: 16
#2Sujata Roy(SINP: Saha Institute of Nuclear Physics)H-Index: 2
Last. Munna Sarkar(SINP: Saha Institute of Nuclear Physics)H-Index: 20
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Small unilamellar vesicles (SUVs) formed by the dimyristoylphosphatidylcholine (DMPC), a phospholipid; serve as a membrane mimetic system that can be used to study the effect of absence of net surface charges on drug–membrane interaction. The targets of non-steroidal anti-inflammatory drugs (NSAIDs) are cyclooxygenases, which are membrane active enzymes. Hence, to approach their targets NSAIDs have to pass different bio-membranes. Different membrane parameters are expected to guide the first lev...
Sorting out new chemical entities (NCE) with inappropriate absorption, distribution, metabolism, excretion (ADME) behaviour at an early stage of drug discovery and development is a major challenge in pharmaceutical profiling. An accepted strategy to predict absorption is the measurement of the permeability of a drug candidate. One step earlier the lipophilicity of a compound is determined, which is directly related to permeability and fraction absorbed. Here, we compare today's state of the art ...
Selective COX-2 inhibitors have attracted much attention in recent times in the design of non-steroidal anti-inflammatory agents (NSAID), which are devoid of the common side effects of classical NSAIDs. QSAR studies have been performed on a series of diaryl furanones that acts as selective COX-2 inhibitor using Molecular Operating Environment (MOE). The studies were carried out on 43 analogs. These studies produced good predictive models and give statistically significant correlations of selecti...
Last. S.C. Chaturvedi(Devi Ahilya Vishwavidyalaya)H-Index: 4
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Selective COX-2 inhibitors have attracted much attention in recent times in the design of non-steroidal anti-inflammatory agents (NSAID), which are devoid of the common side effects of classical NSAIDs. QSAR studies have been performed on a series of diaryl furanones that acts as selective COX-2 inhibitor using Molecular Operating Environment (MOE). The studies were carried out on 43 analogs. These studies produced good predictive models and give statistically significant correlations of selecti...
Lipophilicity study of selected NSAIDs, the group of the bioactive compounds usually used in humans and animals medicine, with the use of experimental and calculation methods was evaluated. LogP values are proposed and compared as descriptors of the lipophilicity of eleven compounds (from oxicams and coxibs). Obtained data were designated by thin-layer chromatography (TLC) in various chromatographic conditions, with stationary phases with different properties. The mobile phase systems were prepa...
Abstract Numerous structurally different amides and imides including succinimide derivatives exhibit diverse bioactive potential. The development of new compounds requires rationalization in the design in order to provide structural changes that guarantee favorable physico-chemical properties, pharmacological activity and safety. In the present research, a comprehensive study with comparison of the chromatographic lipophilicity and other physico-chemical properties of five groups of 1-arylsuccin...
Last. Zorica Vujić(University of Belgrade)H-Index: 8
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Retention behaviour of twenty-one chalcones synthesized in our laboratory was tested in three thin-layer chromatography (RP-TLC) systems (acetonitrile–water, ethanol–water and acetone–water) and chromatography parameters $ {R}_M^0 , S and C0 were calculated. The most suitable RP-TLC system (acetonitrile–water) and chromatography parameter (C0) for lipophilicity prediction of tested compounds were selected on the basis of the highest correlations with calculated logP values. In selected system...
A class of drugs called coxibs (COX-2 inhibitors) were created to help relieve pain and inflammation of osteoarthritis and rheumatoid arthritis with the lowest amount of side effects possible. The presented paper describes a new developed, optimized and validated thin layer chromatographic (TLC)-densitometric procedure for the simultaneous assay of five coxibs: celecoxib, etoricoxib, firecoxib, rofecoxib and cimicoxib. Chromatographic separation was conducted on HPTLC F254 silica gel chromatogra...
Last. Klára Valkó(The Hertz Corporation)H-Index: 28
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Abstract Thin-layer chromatography (TLC) will continue to play a basic role in determining the separation possibilities of chromatographic methods for the routine analysis of large numbers of samples or to analyze samples in cases where high-performance liquid chromatography has difficulties. TLC has the advantage that it does not require sophisticated and expensive analytical instrumentation. Several samples can be analyzed simultaneously and it provides the possibility of a wide variety of det...
Lipophilicity is a vital physicochemical parameter of a molecule, which affects several biological processes such as absorption, tissue distribution, and pharmacokinetic properties. In this study, evaluation of lipophilicities of a series of novel fluoroquinolone-Safirinium dye hybrids using chromatographic and computational methods is presented. Fluoroquinolone-Safirinium dye hybrids have been synthesized as new dual-acting hydrophilic antibacterial agents. Reversed phase thin-layer chromatogra...
Last. Momir Mikov(University of Novi Sad)H-Index: 29
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Abstract Increased antimicrobial resistance together with the lack of new antimicrobial drugs suggest on an urgent need for new therapeutics in this field. Vanilidene derivatives of Meldrum’s acid present one of the possible approaches. In this work lipophilicity of 13 vanilidene derivatives of Meldrum’s acid as well as their predicted antimicrobial activity towards several characteristic species has been evaluated. 10 vanilidene derivatives have been previously synthesized and 3 new compounds a...
ABSTRACTThe methods of correlating molecular structure of substances expressed as descriptors, to their biological activity are commonly denoted as Quantitative Structure-Activity Relationships (QSARs). This concept, typically applied in drug discovery processes, is also widely used for correlation of molecular structure and physicochemical properties of solutes in so-called quantitative structure-property relationship (QSPR) studies, as well as for explanation of chromatographic behavior, i.e.,...
Octanol–water partition coefficients (log Po/w) of fifteen previously synthesized 17β-carboxamide glucocorticoid derivatives and prednisolone were determined using shake-flask method. The retention behavior of selected compounds was tested in five reversed-phased thin-layer chromatography (RP-TLC) systems, consisting of water and organic solvent (acetonitrile, acetone, ethanol 96%, methanol, or tetrahydrofuran), and chromatography parameters (RM0, S, and C0) were calculated. Simple linear regres...
: The chromatographic behavior of a series of thiazolyl-1,3,4-oxadiazoles with antifungal activity was studied by reverse-phase thin-layer chromatography (RP-TLC). The lipophilicity parameters derived from RP-TLC were correlated with the data derived from liquid-chromatography mass-spectrometry. Good linear relationships were observed between the chromatographic lipophilicity parameters and the theoretical lipophilicity descriptors (logP) generated by various computer software and internet modul...