Investigation of new acyloxy derivatives of cholic acid and their esters as drug absorption modifiers

Mrózek, Lech; Dvořáková, Lenka; Mandelová, Zuzana; Rárová, Lucie; Rezácová, A; Plaček, Lukáš; Opatřilová, Radka; Dohnal, Jiří; Paleta, O.; Král, Vladimı́r; Drašar, Pavel; Jampílek, Josef

doi:10.1016/j.steroids.2011.04.014

Cited by 29 publications

(7 citation statements)

References 46 publications

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“…Under these reaction conditions the tosylate 6 was obtained in a 70 % yield, after chromatographic purification: it is to note that all the attempts to obtain selectively the corresponding mesylate failed, the product possessing two mesylate groups at 3 and 24 positions being obtained. The esterification of the two secondary hydroxyl groups of 6 with decanoyl chloride was carried out according to a protocol used to derivatize the methyldeoxycholanoate, [53] which was modified for the reaction temperature. The control of the reaction temperature was crucial: in fact at room temperature only the hydroxyl group at the position 3, which is equatorial, reacted, whereas in refluxing toluene, as in the original protocol, both the hydroxyl groups were derivatized but, at the same time, the displacement of the tosylate group by the chloride ion, present in the reaction mixture, was obtained.…”

Section: Resultsmentioning

confidence: 99%

Chiral Biobased Ionic Liquids with Cations or Anions including Bile Acid Building Blocks as Chiral Selectors in Voltammetry

et al. 2021

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Chiral ionic liquids (CILs), or ionic liquids (ILs) with chiral additives, are very attractive chiral media for enantioselective electroanalysis, on account of their high chiral structural order at the electrochemical interphase. A family of molecular salts with CIL properties is now introduced, based on the chiral steroid building block of deoxycholic acid implemented either in the anion or cation. Testing them as chiral additives in a commercial achiral IL, they enable voltammetric discrimination of the enantiomers of a model chiral probe on disposable screen-printed electrodes in terms of peak potential differences, which is the most desirable transduction mode of the enantiorecognition event. The probe enantiomer sequence is the same for all selectors, consistent with their sharing the same chiral building block configuration. This proof-of-concept widens the application fields of bile acid derivatives as chiral selectors, while also enriching the still very few CIL families so far explored for applications in chiral electroanalysis.

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Section: Resultsmentioning

confidence: 99%

Chiral Biobased Ionic Liquids with Cations or Anions including Bile Acid Building Blocks as Chiral Selectors in Voltammetry

et al. 2021

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“…In addition, bile acid derivatives have shown potential as drug absorption modifiers. 21,22 Gels play increasingly important roles in modern life since they appear in myriad of applications ranging from optoelectronics 23,24 and biomedicine [23][24][25] to environmental clean-up. 26,27 Universally a gel is defined as a viscoelastic solid like material which consists of flexible cross-linked network and solvent.…”

Section: Introductionmentioning

confidence: 99%

Biocompatible hydrogelators based on bile acid ethyl amides

et al. 2016

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Four novel bile acid ethyl amides were synthetized using a well-known method. All the four compounds were characterized by IR, SEM, and X-ray crystal analyses. In addition, the cytotoxicity of the compounds was tested. Two of the prepared compounds formed organogels. Lithocholic acid derivative 1 formed hydrogels as 1% and 2% (w/v) in four different aqueous solutions. This is very intriguing regarding possible uses in biomedicine.

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“…Since the publication of these review chapters, a number of advances in skin penetration enhancer research have been made. They include those from our studies (e.g., [ 30 , 31 ]) and studies from other groups [ 32 , 33 , 34 , 35 ] on the structure-enhancement activity relationship of penetration enhancers in transdermal transport. A complete review on penetration enhancers will not be provided here due to the extensive literature on this topic.…”

Section: Introductionmentioning

confidence: 99%

Structure Enhancement Relationship of Chemical Penetration Enhancers in Drug Transport across the Stratum Corneum

Chantasart

2012

Pharmaceutics

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The stratum corneum is a major barrier of drug penetration across the skin in transdermal delivery. For effective transdermal drug delivery, skin penetration enhancers are used to overcome this barrier. In the past decades, a number of research studies were conducted to understand the mechanisms of skin penetration enhancers and to develop a structure enhancement relationship. Such understanding allows effective prediction of the effects of skin penetration enhancers, assists topical and transdermal formulation development, and avoids extensive enhancer screening in the transdermal delivery industry. In the past two decades, several hypotheses on chemical enhancer-induced penetration enhancement for transport across the skin lipoidal pathway have been examined based on a systematic approach. Particularly, a hypothesis that skin penetration enhancement is directly related to the concentration of the enhancers in the stratum corneum lipid domain was examined. A direct relationship between skin penetration enhancer potency (based on enhancer aqueous concentration in the diffusion cell chamber) and enhancer n-octanol-water partition coefficient was also established. The nature of the microenvironment of the enhancer site of action in the stratum corneum lipid domain was found to be mimicked by n-octanol. The present paper reviews the work related to these hypotheses and the relationships between skin penetration enhancement and enhancer concentration in the drug delivery media and stratum corneum lipids.

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Investigation of new acyloxy derivatives of cholic acid and their esters as drug absorption modifiers

Cited by 29 publications

References 46 publications

Chiral Biobased Ionic Liquids with Cations or Anions including Bile Acid Building Blocks as Chiral Selectors in Voltammetry

Chiral Biobased Ionic Liquids with Cations or Anions including Bile Acid Building Blocks as Chiral Selectors in Voltammetry

Biocompatible hydrogelators based on bile acid ethyl amides

Structure Enhancement Relationship of Chemical Penetration Enhancers in Drug Transport across the Stratum Corneum

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