Modeling and prediction (correction) of partition coefficients of bile acids and their derivatives by multivariate regression methods

Sârbu, Costel; Onişor, Cristina; Poša, Mihalj; Kevrešan, Slavko; Kuhajda, Ksenija

doi:10.1016/j.talanta.2007.11.061

Cited by 30 publications

(24 citation statements)

References 21 publications

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“…Some of papers, about application of QSPR techniques in the development of a new and simplified approach to prediction of compounds properties were published. [25][26][27][28][29] Experimental determination of K o/w is often complex and time-consuming and can be done only for already synthesized compounds. For this reason, a number of computational methods for the prediction of this parameter have been proposed.…”

Section: Introductionmentioning

confidence: 99%

QSPR study of partition coefficient (Ko/w) of some organic compounds using radial basic function-partial least square (RBF-PLS)

Goudarzi¹,

Goodarzi²

2010

J. Braz. Chem. Soc.

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Neste trabalho, nós introduzimos um novo método da função de base radial por regressão de mínimos quadrados (RBF-PLS) com elevada exatidão e precisão nos estudos quantitativos da relação entre a estrutura-propriedade de compostos orgânicos (QSPR). Três métodos QSPR foram comparados para a predição dos coeficientes de partição no sistema n-octanol-água (K o/w ) (de alguns compostos orgânicos). A regressão linear múltipla (MLR), a regressão parcial dos mínimos quadrados (PLS) e a regressão base radial com funções pelo método de mínimos quadrados (RBF-PLS) foram empregadas para construir os modelos lineares e não-lineares e predizer o valor de K o/w . Os descritores teóricos foram calculados por Dragon e por Gaussian 98 e foram explorados pelas regressões parciais, codificando diferentes aspectos topológicos, geométricos e eletrônicos das estruturas moleculares. A raiz quadrada dos erros médios previstos (RMSEP) para as etapas de testes e da previsão teórica por modelos de MLR, de PLS e de RBF-PLS foram 0,4022; 0,4128; 0,3050; 0,3564; 0,0364 e 0,0533 respectivamente. Também, o erro padrão relativo previsto (RSEP) para os testes e de previsão teórica por MLR, PLS e RBF-PLS foram de 13,24; 13,60; 10,04; 11,74; 1,197 e 1,757 respectivamente. Os dados mostram que o RBF-PLS produziu resultados melhores do que PLS e MLR.In this work, we introduce a new method ability radial basic function-partial least square (RBF-PLS) with high accuracy and precision in QSPR studies. Three quantitative structure-propertty relationship (QSPR) methods have been compared for the prediction of n-octanol-water partition coefficients (K o/w ) of some organic compounds. The multiple linear regressions (MLR), partial least square (PLS) and radial basis function-partial least squares (RBF-PLS) models were employed to construct linear and nonlinear models to predict of K o/w . The theoretical descriptors that calculated by Dragon and Gaussian 98 were explored by stepwise regressions, encoding different aspects of the topological, geometrical and electronic molecular structures. The root means square error of prediction (RMSEP) for training and prediction sets by MLR, PLS and RBF-PLS models were 0.4022, 0.4128, 0.3050, 0.3564, 0.0364 and 0.0533, respectively. Also, the relative standard error of prediction (RSEP) for training and prediction sets by MLR, PLS and RBF-PLS models were 13. 24, 13.60, 10.04, 11.74, 1.197 and 1.757 respectively. The resultant data explained that RBF-PLS produced better results than PLS and MLR.

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Section: Introductionmentioning

confidence: 99%

QSPR study of partition coefficient (Ko/w) of some organic compounds using radial basic function-partial least square (RBF-PLS)

Goudarzi¹,

Goodarzi²

2010

J. Braz. Chem. Soc.

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“…Kitakaro and Sato are carried out the oxidation of chenodeoxycholic acid (6) using CrO 3 in glacial acetic acid. In this way, they got a 3.7-diketo-5β-cholanic acid (9). Further reduction of this compound with sodium in the secondary butanol was obtained a ursodeoxycholic acid (8) Scheme 10 6 .…”

Section: Scheme 9: the Synthesis Of Ursodeoxycholic Acid From 3-hydrmentioning

confidence: 99%

“…Between the water molecules, formed the same number of hydrogen bonds. The change in enthalpy for each subsystem, during the formation of hydration shell, is zero 9,10 . Molecules of water with a hydrophilic side of bile acids (amphiphilic molecules) are stabilized, while the molecules with the hydrophobic side of bile acids unstabilized.…”

Section: Physico-chemical Properties Of Bile Acidsmentioning

confidence: 99%

“…The ratio of hydrophilic and hydrophobic surface bile acids determines the overall change in Gibbs free energy of formation of hydration cage (G). At molecules of bile acids, hydrophobicity is expressed through the logP value 9,10 . It can be examined by using chromatographic parameters and over the partition coefficient.…”

Section: Physico-chemical Properties Of Bile Acidsmentioning

confidence: 99%

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Untitled

2018

IJPSR

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ABSTRACT:The main roles of bile acids as amphiphilic molecules are the micellar solubilization of the lipids, in the course of the welding process and the regulation of cholesterol homeostasis, which is essential as a precursor for the synthesis of bile acids. From the hydrophobic and hydrophilic surfaces of bile acids directly depends the level of their attachment to the receptors, ion channels and their effectiveness in the solubilization of lipid (hydrophobic drugs). The toxicity of membrane of bile acids is mainly determined by their hydrophobicity. We have synthesized the methyl ester of 7α-hydroxy-3-oxo-5β-cholanoic acid. We have reviewed and discussed the effects of the structure of bile acids to their hydrophobicity, which is expressed by the retention parameters by reverse phase chromatography, and hydrophobic properties, which is represented by partition coefficient 1-octanol / water. It also discusses the role of the lipophilicity of bile acids in their interactions with biological systems.

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“…This coexistence of non-polar and polar surfaces influences their physico-chemical properties [1][2][3][4] such as formation of self-association micelles that have significant role in the physiology of the metabolism of fats, absorption of liposoluble vitamins and hydrophobic drugs. Beside their physiological role, micellar solutions of bile acids can solubilizate poorly soluble organic substances [5].…”

Section: Introductionmentioning

confidence: 99%

Influence of Bile Salts as Excipients in Ranitidine, Aminophylline and Phenobarbital Tablets on Dissolution Rate

Pocuca¹,

Cvejić²,

Vukmirović³

et al. 2017

Clin Pharmacol Biopharm

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Aim: The aim of this study is to investigate the influence of bile salts, sodium cholate, sodium 12-ketocholate and sodium dehydrocholate, as excipients in ranitidine, aminophylline and phenobarbital tablets on dissolution rate.Methods: Four groups of tablets (control without bile salts and three investigational groups containing different bile salts) were prepared for three different drug substances: ranitidine, aminophylline and phenobarbital. Dissolution rate was measured.Results: Dissolution rate is increased significantly in all investigational groups comparing to the control group in all three drug substances. Discussion:Presented results are very favourable and encouraging in case of dissolution enhancing and should be further investigated, especially in drug substances that are classified in class II and IV as per Biopharmaceutical Classification System (BCS) classification. Conclusion:Bile acid salts are very promising excipients, proven to act as surfactants and as lubricants. Running title: Bile salts as excipients in ranitidine, aminophylline and phenobarbital tablets.

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Modeling and prediction (correction) of partition coefficients of bile acids and their derivatives by multivariate regression methods

Cited by 30 publications

References 21 publications

QSPR study of partition coefficient (Ko/w) of some organic compounds using radial basic function-partial least square (RBF-PLS)

QSPR study of partition coefficient (Ko/w) of some organic compounds using radial basic function-partial least square (RBF-PLS)

Untitled

Influence of Bile Salts as Excipients in Ranitidine, Aminophylline and Phenobarbital Tablets on Dissolution Rate

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