Micellar Distribution Equilibria: Ultracentrifugal Study of Apparent Partition Coefficients

Park, Jung Youl; Rippie, Edward G.

doi:10.1002/jps.2600660631

Cited by 10 publications

(4 citation statements)

References 16 publications

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“…Despite being used for isotropic lipophilicity determination, nano-absorbent-based methods acquire particular relevance for the determination of anisotropic lipophilicity. Nano-sized artificial membranes, like liposomes [50] or micelles [51], act as absorbents enabling the direct determination of the lipophilicity in these biomimetic nonaqueous phase. The partitioning occurs just by mixing the artificial membranes with an aqueous solution of the compound to be tested.…”

Section: Nano-absorbent Based Methodsmentioning

confidence: 99%

“…While n-octanol and water are two immiscible solvents, liposomes and micelles form a colloidal suspension in water. The most used techniques for phase separation are ultrafiltration [50] and ultracentrifugation [51]. The partition coefficient is determined by quantifying the compound present in the filtrate or in the supernatant.…”

Section: Nano-absorbent Based Methodsmentioning

confidence: 99%

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Liquid Chromatography on the Different Methods for the Determination of Lipophilicity: An Essential Analytical Tool in Medicinal Chemistry

et al. 2022

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Lipophilicity is one of many parameters involved in the biological activity of drugs, as it affects their pharmacokinetic and pharmacodynamic behavior. Generally, lipophilicity is assessed by the partition coefficient of a compound between a nonpolar phase (n-octanol) and an aqueous phase (water), expressed as P (partition coefficient) or as its decimal logarithm (Log P). The gold standard method for the experimental determination of Log P is the shake-flask method. In this context, chromatographic methods enable the direct and simple quantification of the partitioned compound between the two phases. This review discusses the use of liquid chromatography (LC) for direct and indirect determination of lipophilicity. Beyond the classical isotropic log P determination, methods for assessing anisotropic lipophilicity are also reviewed. Several examples are discussed that highlight the versatility of LC technique and current trends. The last section of this review focuses on a case study describing an experience of our group and emphasizing the dual role of LC in determining Log P.

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Section: Nano-absorbent Based Methodsmentioning

confidence: 99%

Section: Nano-absorbent Based Methodsmentioning

confidence: 99%

Liquid Chromatography on the Different Methods for the Determination of Lipophilicity: An Essential Analytical Tool in Medicinal Chemistry

et al. 2022

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“…Partition theory (Park & Ripple 1977) was used to design a vehicle that would retain drugs until resident in the small intestine. Simply stated, the theory implies that a drug dissolved in an enzyme-sensitive vehicle, remains in that vehicle until the vehicle is degraded by the appropriate enzyme.…”

Section: Abstract-liquidmentioning

confidence: 99%

Use of Enzymatic Activity for Design of Orally Administered Enteric Dosing Forms

Nishihata¹,

Yamamoto²,

Ishizaka³

1993

Journal of Pharmacy and Pharmacology

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Liquid and semi-solid enteric dosage forms were prepared by entrapping drug with an appropriate partition coefficient in a lipid base vehicle which would then be released by the action of intestinal enzymes. Lipid ester derivatives such as glyceryl monocaprylate and polysorbate 80 were used as vehicles. These vehicles readily dissolved the poorly water-soluble compounds used in the study, itazigrel, indomethacin and the dye, sudan II, and were digested by lipase and esterase, releasing the test drugs with time profiles similar to those observed in dissolution studies. The vehicles released little or only a small amount of the drugs into aqueous medium in the absence of an appropriate enzyme. The enzyme-sensitive enteric vehicles when containing sudan II did not release the dye in the stomach of rats after oral administration, but released significant amounts of the dye in the small intestine.

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“…Smith et al [9] developed a membrane diffusion method and derived the diffusion coefficient for BKC with C12 and C14 in water. Ultrafiltration or ultracentrifugation methods have been adopted to determine the partition coefficient of BKC and the free BKC surfactant concentration 2 of 13 in micellar solutions [10,11]. In the biological and chemical fields, both solubilization and stabilization play important roles in their specific applications.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Analysis of Aqueous Benzalkonium Chloride Micellar Solution and Its Mediated Electrocatalytic De-Chlorination Application

2019

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The physicochemical properties of biologically important benzalkonium chlorides (BKCs) and the effects of its structure on the de-chlorination of allyl chloride was studied by electrogenerated [Co(I)(bipyridine)3]+ (Co(I)) using an electrochemical technique. The results of [Co(II)(bipyridine)3]2+ (Co(II)) cyclic voltammetry in the presence of BKC demonstrates Co(II)/Co(III) redox couple for physicochemical analysis of BKC and Co(II)/Co(I) redox couple for catalytic application. Cyclic voltammetry over a range of scan rates and BKC concentrations revealed the BKC-bound Co(II)/Co(III) micelles showed that the identification of cmc and association of the probe Co(II) species, associated more in the hydrophobic region. In addition, change in diffusion coefficient value of Co(II)/Co(III) with BKC concentration demonstrates the association of Co(II) in micellar hydrophobic region. The beneficial effects of BKC could be accounted for by considering the benzyl headgroup-Co (II) precatalyst-volatile organic compounds (VOCs) (allyl chloride here) substrate interaction. Chromatography/mass spectroscopy (GC/MS) revealed 100% complete de-chlorination of allyl chloride accompanied by three non-chloro products. This is the first report of benzyl headgroup-induced micellar enhancement by an electrochemical method, showing that it is possible to use hydrophobic benzyl headgroup-substitution to tune the properties of micelles for various applications.

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Micellar Distribution Equilibria: Ultracentrifugal Study of Apparent Partition Coefficients

Cited by 10 publications

References 16 publications

Liquid Chromatography on the Different Methods for the Determination of Lipophilicity: An Essential Analytical Tool in Medicinal Chemistry

Liquid Chromatography on the Different Methods for the Determination of Lipophilicity: An Essential Analytical Tool in Medicinal Chemistry

Use of Enzymatic Activity for Design of Orally Administered Enteric Dosing Forms

Electrochemical Analysis of Aqueous Benzalkonium Chloride Micellar Solution and Its Mediated Electrocatalytic De-Chlorination Application

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