Lipophilicity: Chemical Nature and Biological Relevance

Caron, Giulia; Ermondi, Giuseppe

doi:10.1002/9783527621286.ch12

Cited by 8 publications

(8 citation statements)

References 16 publications

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“…The lipophilicity of a drug is a key feature directly related to its ability to passively cross cellular membranes [49,50]. Generally, the shake-flask log P o/w , in which n-octanol is taken as a model of the lipid bilayer of a cell membrane and water mimics the extracellular environment, is used to represent the lipophilicity of a molecule.…”

Section: Lipophilicity and Cellular Accumulation Of 1-4 Complexes On mentioning

confidence: 99%

Cellular trafficking, accumulation and DNA platination of a series of cisplatin-based dicarboxylato Pt(IV) prodrugs

Ravera

Gabano

Zanellato

et al. 2015

Journal of Inorganic Biochemistry

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Section: Lipophilicity and Cellular Accumulation Of 1-4 Complexes On mentioning

confidence: 99%

Cellular trafficking, accumulation and DNA platination of a series of cisplatin-based dicarboxylato Pt(IV) prodrugs

Ravera

Gabano

Zanellato

et al. 2015

Journal of Inorganic Biochemistry

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“…20 lipophilicity) required for the early prediction of ADME profile [2][3][4][5][6] . As a result, there is a new interest in overcoming limitations in the determination and interpretation of lipophilicity data.…”

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confidence: 99%

The Block Relevance (BR) analysis to aid medicinal chemists to determine and interpret lipophilicity

2013

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A major issue related to chromatographic determination of lipophilicity is about the conversion to log P. 5The interconversion of lipophilicity indexes can be made only if two systems express the same balance of intermolecular solute/system forces. The deconvolution of intermolecular interactions is generally obtained by solvation parameter models. Block Relevance (BR) analysis is a new tool specifically designed for medicinal chemists to interpret partitioning/retention phenomena in a very practical way. This paper describes the application of BR analysis to literature data (ElogP) and experimentally 10 determined chromatographic indexes on a Supelcosil TM LC-ABZ column for a series of 36 drugs. Results indicate that BR analysis is a solid and reliable tool that captures the main information encoded in any lipophilicity descriptor.

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“…Lipophilicity (logP), or logarithm of partition coefficient, is one of the most important molecular features that affect biological behavior of compounds (9). LogP descriptor takes into account only neutral forms of a molecule, while the distribution coefficient UDC: 547.92: 616-006.04-084]:66.011 DOI: https://doi.org/10.2298/APT1950123K BIBLID: 1450-7188 (2019) 50, 123-133…”

Section: Introductionmentioning

confidence: 99%

Computational modeling of distribution coefficients and their correlations with pharmacokinetic properties of 17α-picolyl and 17(E)-picolinylidene androstane derivatives

et al. 2019

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The present study describes the computational modeling of distribution coefficient (logD) of 17α-picolyl and 17(E)-picolinylidene androstane derivatives, as a group of compounds with significant anticancer activities. The determination of logD is practically important for estimation and prediction of pharmacokinetic and pharmacodynamic behavior of compounds in a living organism and it is related to blood-brain barrier permeability, skin permeability, gastrointestinal absorption, binding to plasma proteins, etc. These features are crucial for the determination of potential drug candidates as well. The results presented in this study include determination of pH versus logD profiles, pH versus molecular charge profiles and determination of isoelectric point of eleven 17αpicolyl androstane derivatives and thirteen 17(E)-picolinylidene androstane derivatives. Since the pH of the organism differs depending on the organ (for example, the pH of the blood is significantly different from the pH of the stomach), these profiles are significant because they indicate in what form the molecule will exist and how it will be distributed between different phases at certain pH value. The influence of tautomerization and resonance was taken into account during the modeling of logD parameters. Eventually, the correlations between logD values and specific absorption, distribution, metabolism, and excretion (ADME) properties, such as human intestinal absorption (HIA) and permeability of heterogeneous human epithelial colorectal adenocarcinoma cells (Caco-2), were determined.

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Lipophilicity: Chemical Nature and Biological Relevance

Cited by 8 publications

References 16 publications

Cellular trafficking, accumulation and DNA platination of a series of cisplatin-based dicarboxylato Pt(IV) prodrugs

Cellular trafficking, accumulation and DNA platination of a series of cisplatin-based dicarboxylato Pt(IV) prodrugs

The Block Relevance (BR) analysis to aid medicinal chemists to determine and interpret lipophilicity

Computational modeling of distribution coefficients and their correlations with pharmacokinetic properties of 17α-picolyl and 17(E)-picolinylidene androstane derivatives

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