Human Intestinal Absorption—Neutral Molecules and Ionic Species

Abraham, Michael H.

doi:10.1002/jps.24024

Cited by 25 publications

(11 citation statements)

References 74 publications

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“…NaPB-sodium phosphate buffer, pH 6.8. It should be mentioned that Willauer et al in the study [41] of partitioning of a set of 29 organic compounds in PEG-2000-K 3 PO 4 ATPS described partition behavior of compounds by the so-called linear free energy relationship (LFER) model by Abraham [42][43][44][45]. It was concluded [41] that partitioning of organic compounds in PEGsalt ATPS is governed by the solute size, basicity, and aromaticity or halogenicity.…”

Section: Tablementioning

confidence: 99%

Analysis of partitioning of organic compounds and proteins in aqueous polyethylene glycol-sodium sulfate aqueous two-phase systems in terms of solute–solvent interactions

Silva

Ferreira

Madeira

et al. 2015

Journal of Chromatography A

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Partition behavior of nine small organic compounds and six proteins was examined in poly(ethylene glycol)-8000-sodium sulfate aqueous two-phase systems containing 0.5M osmolyte (sorbitol, sucrose, trehalose, TMAO) and poly(ethylene glycol)-10000-sodium sulfate system, all in 0.01M sodium phosphate buffer, pH 6.8. The differences between the solvent properties of the coexisting phases (solvent dipolarity/polarizability, hydrogen bond donor acidity, and hydrogen bond acceptor basicity) were characterized with solvatochromic dyes using the solvatochromic comparison method. Differences between the electrostatic properties of the phases were determined by analysis of partitioning of sodium salts of dinitrophenylated (DNP-) amino acids with aliphatic alkyl side-chain. It was found out that the partition coefficient of all compounds examined (including proteins) may be described in terms of solute-solvent interactions. The results obtained in the study show that solute-solvent interactions of nonionic organic compounds and proteins in polyethylene glycol-sodium sulfate aqueous two-phase system differ from those in polyethylene glycol-dextran system.

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Section: Tablementioning

confidence: 99%

Analysis of partitioning of organic compounds and proteins in aqueous polyethylene glycol-sodium sulfate aqueous two-phase systems in terms of solute–solvent interactions

Silva

Ferreira

Madeira

et al. 2015

Journal of Chromatography A

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“…In conjunction with this data base, we have assembled a complementary set of equations for physicochemical and biological properties of solutes, so that a combination of solute descriptors and equation coefficients can be used to predict various physicochemical and biological properties, as set out in a number of reviews. − This work − dealt only with neutral species, but was extended to cover charged solutes, specifically ions such as K + and Cl – and ionic species, defined as protonated base cations and deprotonated acid anions, − as recently reviewed . The total method, for neutral and ionic species, has already been applied to a number of systems. − Although we had descriptors for a large number of charged species, we have not investigated the α-aminoacids that are electrically neutral but with an internal charge separation, that is, zwitterions. Our study on betaine, Me 3 N + CH 2 CO 2 – , showed that it could not be treated as a “neutral” molecule, but that it was essential to include ionic descriptors.…”

Section: Methodsmentioning

confidence: 99%

Solvation Descriptors for Zwitterionic α-Aminoacids; Estimation of Water–Solvent Partition Coefficients, Solubilities, and Hydrogen-Bond Acidity and Hydrogen-Bond Basicity

Abraham

Acree

2019

ACS Omega

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The literature data on solubilities and water–solvent partition coefficients have been used to obtain properties or “Absolv descriptors” for zwitterionic α-aminoacids: glycine, α-alanine (α-aminopropanoic acid), α-aminobutanoic acid, norvaline (α-aminopentanoic acid), norleucine (α-aminohexanoic acid), valine (α-amino-3-methylbutanoic acid), leucine (α-amino-4-methylpentanoic acid), and α-phenylalanine. Together with equations that we have previously constructed, these descriptors can be used to estimate further solubilities and partition coefficients in a variety of organic solvents and in water–methanol and water–ethanol mixtures. It is shown that equations for neutral solutes are inadequate for the description of solubilities and partition coefficients for these α-aminoacids, and our equations developed for use with both neutral and ionic solutes must be used. The Absolv descriptors include those for hydrogen-bond acidity, A , and hydrogen-bond basicity, B . We find that both of these descriptors are far smaller in value than those for compounds that contain the corresponding ionic groups. Thus, A for α-alanine is 0.28, but A for the ethylammonium cation is 1.31; B for α-alanine is 0.83, and yet B for the acetate anion is no less than 2.93. The additional descriptors that we developed for equations that involve ions, J + and J – , are very significant for the α-aminoacids, although numerically smaller than for ionic species such as EtNH 3 + and CH 3 CO 2 – .

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“…1 (E, S, A, B, V, J + and J − ) are properties or descriptors of the solutes and the coefficients (c, e, s, a, b, v, j + and j − ) are the complementary properties of the solvent system. Solute and solvent properties have been described in detail in earlier publications [13][14][15][16][17][18][19][20][21], there are several reviews on our method [22][23][24], and a number of applications [25][26][27] and so only an outline will be given here. E is the solute excess molar refraction in cm 3 ·mol −1 /10, S is a measure of the solute polarity/polarizability, A and B refer to the hydrogen bond acidity and hydrogen bond basicity of the solute, and V is McGowan's characteristic molecular volume of the solute in cm 3 ·mol −1 /100 [28].…”

Section: Methodsmentioning

confidence: 99%

Limiting Diffusion Coefficients for Ions and Nonelectrolytes in Solvents Water, Methanol, Ethanol, Propan-1-ol, Butan-1-ol, Octan-1-ol, Propanone and Acetonitrile at 298 K, Analyzed Using Abraham Descriptors

Abraham

Acree

2019

J Solution Chem

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We have used literature data on the conductivity of single ions to obtain limiting diffusion coefficients (D o ) of ions in water, alcohols, propanone and acetonitrile. We then used literature data on limiting diffusion coefficients of nonelectrolytes in order to set up linear free energy relationships that combine data for ions and nonelectrolytes, as log 10 (D o ) in the same equation, all values being at 298 K. These equations are for solvents water (N = 377, SD = 0.0474), methanol (N = 96, SD = 0.0332), ethanol (N = 96, SD = 0.0666), propan-1-ol (N = 71, SD = 0.0487), butan-1-ol (N = 53, SD = 0.0600), octan-1-ol (N = 61, SD = 0.0684), propanone (N = 86, SD = 0.0366) and acetonitrile (N = 74, SD = 0.0438) where N is the number of data points, that is ions plus nonelectrolytes, and SD is the standard deviation in log 10 (D o ). It is shown that solute hydrogen bond acidity, solute hydrogen bond basicity and solute volume all lower the diffusion constants of ions and nonelectrolytes in the various solvents studied.

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Human Intestinal Absorption—Neutral Molecules and Ionic Species

Cited by 25 publications

References 74 publications

Analysis of partitioning of organic compounds and proteins in aqueous polyethylene glycol-sodium sulfate aqueous two-phase systems in terms of solute–solvent interactions

Analysis of partitioning of organic compounds and proteins in aqueous polyethylene glycol-sodium sulfate aqueous two-phase systems in terms of solute–solvent interactions

Solvation Descriptors for Zwitterionic α-Aminoacids; Estimation of Water–Solvent Partition Coefficients, Solubilities, and Hydrogen-Bond Acidity and Hydrogen-Bond Basicity

Limiting Diffusion Coefficients for Ions and Nonelectrolytes in Solvents Water, Methanol, Ethanol, Propan-1-ol, Butan-1-ol, Octan-1-ol, Propanone and Acetonitrile at 298 K, Analyzed Using Abraham Descriptors

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