Potential of the octanol–water partition coefficient (logP) to predict the dermal penetration behaviour of amphiphilic compounds in aqueous solutions

Korinth, Gintautas; Wellner, Tanja; Schaller, K. H.; Drexler, Hans

doi:10.1016/j.toxlet.2012.09.013

Cited by 42 publications

(19 citation statements)

References 15 publications

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“…Dendrimers offering log P values close to neutral ( 14a , 15a, and 16a ) should migrate faster through membranes than other highly hydrophilic PPDs at the expense of solubility in the aqueous media. For comparison, efficient dermal penetration of amphiphilic compounds was predicted for amphiphiles with log P values from −0.31 up to 1.17 . These values are within the log P range, which we can adapt precisely with our amphiphilic dendrimers ( 13a–18 ).…”

Section: Resultsmentioning

confidence: 56%

Tuning Polarity of Polyphenylene Dendrimers by Patched Surface Amphiphilicity—Precise Control over Size, Shape, and Polarity

Stangenberg

Saeed

Kuan

et al. 2013

Macromol. Rapid Commun.

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In the ideal case, a precise synthesis yields molecules with a constitutional as well as a conformational perfectness. Such a case of precision is demonstrated by the synthesis of semi-rigid amphiphilic polyphenylene dendrimers (PPDs). Polar sulfonate groups are precisely placed on their periphery in such a manner that patches of polar and non-polar regions are created. Key structural features are the semi-rigid framework and shape-persistent nature of PPDs since the limited flexibility introduces a nano-phase-separated amphiphilic rim of the dendrimer. This results in both attractive and repulsive interactions with a given solvent. Frustrated solvent structures then lead to a remarkable solubility in solvents of different polarity such as toluene, methanol, and water or their mixtures. Water solubility combined with defined surface structuring and variable hydrophobicity of PPDs that resemble the delicate surface textures of proteins are important prerequisites for their biological and medical applications based upon cellular internalization.

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Section: Resultsmentioning

confidence: 56%

Tuning Polarity of Polyphenylene Dendrimers by Patched Surface Amphiphilicity—Precise Control over Size, Shape, and Polarity

Stangenberg

Saeed

Kuan

et al. 2013

Macromol. Rapid Commun.

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“…The logarithm of the partition coefficient of a drug molecule between octanol and water (log P), is considered to be an important parameter (hydrophobic parameter) which can be related to the activity of the drug 10 . It has been applied to correlate various phenomena including skin penetration of drugs.…”

Section: Measurement Of Log P Valuesmentioning

confidence: 99%

A Study of Some Anthraquinones of Rubia Cordifolia L. Incorporated Into Pinda Oil: An Ayurvedic Medicinal Oil Used for Topical Application in Dermatological and Inflammatory Conditions

Mahendra¹,

Bandara²,

Chandanie³

et al. 2014

Int. J. Res. Ayurveda Pharm.

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'Pinda oil' is an Ayurvedic medicinal oil use in dermatological and inflammatory conditions, prepared from Rubia cordifolia, Glycyrrhiza glabra and Cryptolepis buchnani. Qualitative and quantitative analysis of plant secondary metabolites incorporated in the oil is important in the standardization of the oil. The oil has a deep wine red color due to the incorporation of anthraquinones from Rubia cordifolia. The major anthraquinones present in 'Pinda oil' were identified to be alizarin, xanthopurpurin, purpurin and rubiadin. A method was developed to quantitatively extract the anthraquinones by a solid phase extraction method using polyamide and to quantify them by HPLC. The precision of the method for alizarin, xanthopurpurin, purpurin and rubiadin are 6.5, 4.5, 4.0 and 4.8 % CV (n = 7) respectively. Analysis of market samples of the oil showed a wide variation in the values obtained indicating the need to standardize the manufacturing procedure. The Log P values of these compounds were determined by the HPLC method and gave values in the range 2.8-4.3. These are reported here for the first time.

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“…The chemical properties and bioactivities of polycyclic aromatics are of considerable interest due to their extensive uses in the petroleum industry, chemical manufacturing, and pharmaceutical industries . Additionally, certain properties of polycyclic aromatic compounds such as dermal penetrations and toxicity appear to be firmly correlated with multiple TIs of polycyclic benzenoid aromatic compounds . Carbon nanocones or graphene‐based nanomaterials, functionalized by various methodologies, have attracted incredible consideration for energy storage because of their substantial explicit surface area, high conductivity, and mechanical properties .…”

Section: Introductionmentioning

confidence: 99%

Mostar indices of carbon nanostructures and circumscribed donut benzenoid systems

Arockiaraj¹,

Clement

Tratnik

2019

Int J of Quantum Chemistry

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On the great success of bond‐additive topological indices such as Szeged, Padmakar‐Ivan, Zagreb, and irregularity measures, yet another index, the Mostar index, has been introduced recently as a quantitative refinement of the distance nonbalancedness and also a peripherality measure in molecular graphs and networks. In this direction, we introduce other variants of bond‐additive indices, such as edge‐Mostar and total‐Mostar indices. The present article explores a computational technique for Mostar, edge‐Mostar, and total‐Mostar indices with respect to the strength‐weighted parameters. As an application, these techniques are applied to compute the three indices for the family of coronoid and carbon nanocone structures.

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Potential of the octanol–water partition coefficient (logP) to predict the dermal penetration behaviour of amphiphilic compounds in aqueous solutions

Cited by 42 publications

References 15 publications

Tuning Polarity of Polyphenylene Dendrimers by Patched Surface Amphiphilicity—Precise Control over Size, Shape, and Polarity

Tuning Polarity of Polyphenylene Dendrimers by Patched Surface Amphiphilicity—Precise Control over Size, Shape, and Polarity

A Study of Some Anthraquinones of Rubia Cordifolia L. Incorporated Into Pinda Oil: An Ayurvedic Medicinal Oil Used for Topical Application in Dermatological and Inflammatory Conditions

Mostar indices of carbon nanostructures and circumscribed donut benzenoid systems

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