Synthesis of betulin derivatives and the determination of their relative lipophilicities using reversed‐phase thin‐layer chromatography

Achrem-Achremowicz, Jacek; Kępczyńska, Elżbieta; Zylewski, Marek; Janeczko, Zbigniew

doi:10.1002/bmc.1282

Cited by 14 publications

(10 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Table 1 presents the partition coefficient values calculated in the MestReNova program. The lipophilicity of each compound is represented as the decimal logarithm of the partition coefficient ( log P) [ 34 ].…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Enhancement of the Antioxidant and Skin Permeation Properties of Betulin and Its Derivatives

et al. 2021

View full text Add to dashboard Cite

This study investigated the antioxidant activity DPPH, ABTS, and Folin–Ciocalteu methods of betulin (compound 1) and its derivatives (compounds 2–11). Skin permeability and accumulation associated with compounds 1 and 8 were also examined. Identification of the obtained products (compound 2–11) and betulin isolated from plant material was based on the analysis of 1H- NMR and 13C-NMR spectra. The partition coefficient was calculated to determine the lipophilicity of all compounds. In the next stage, the penetration through pig skin and its accumulation in the skin were evaluated of ethanol vehicles containing compound 8 (at a concentration of 0.226 mmol/dm3), which was characterized by the highest antioxidant activity. For comparison, penetration studies of betulin itself were also carried out. Poor solubility and the bioavailability of pure compounds are major constraints in combination therapy. However, we observed that the ethanol vehicle was an enhancer of skin permeation for both the initial betulin and compound 8. The betulin 8 derivative showed increased permeability through biological membranes compared to the parent betulin. The paper presents the transformation of polycyclic compounds to produce novel derivatives with marked antioxidant activities and as valuable intermediates for the pharmaceutical industry. Moreover, the compounds contained in the vehicles, due to their mechanism of action, can have a beneficial effect on the balance between oxidants and antioxidants in the body, minimizing the effects of oxidative stress. The results of this work may contribute to knowledge regarding vehicles with antioxidant potential. The use of vehicles for this type of research is therefore justified.

show abstract

Section: Resultsmentioning

confidence: 99%

“…The high lipophilicity ( log P 4.777–9.684) of the obtained compounds 1 – 11 , favors their excessive accumulation in lipid membranes. This way, the diffusion of active substances administered epidermally, will be hindered through the living layers of the epidermis [ 34 , 35 ].…”

Section: Resultsmentioning

confidence: 99%

Enhancement of the Antioxidant and Skin Permeation Properties of Betulin and Its Derivatives

et al. 2021

View full text Add to dashboard Cite

show abstract

“…The shake-flask method causes problems in the case of polar or highly lipophilic substance. It also requires the high purity of the substance analyzed and the solute [13]. There are also some chromatographic methods, very useful and popular for lipophilicity determination.…”

Section: Introductionmentioning

confidence: 99%

Application of TLC for Evaluation of the Lipophilicity of Newly Synthetized Esters: Betulin Derivatives

Bober

Bębenek

Boryczka

2019

Journal of Analytical Methods in Chemistry

View full text Add to dashboard Cite

The problem of designing a new drug is nowadays very important for researches representing many branches of science. This work considers the usefulness of the analytical method such as thin-layer chromatography for the lipophilicity of newly synthesized compounds, betulin derivatives, which could be potential drugs with anticancer activity. The two mobile phases were used for the purpose of experimental determination of lipophilicity for mono- and diesters investigated. The first mobile phase consists of acetate and Tris buffer, whilst the second consists of 1,4-dioxane and acetate buffer. The value of the retardation factor was recalculation into the RM value, and then RM0 values were obtained by extrapolating acetone or 1,4-dioxane concentration to zero. The chromatographic data of lipophilicity were correlated with theoretically obtained values of ALOGPS, AClogP, miLogP, ALOGP, MLOGP, XLOGP2, and XLOGP3. The particular correlation equations were obtained. The cluster analysis was also used to find similarity between the esters investigated on the basis of the experimental or theoretical value of lipophilicity obtained. The good correlation between experimentally and theoretically calculated lipophilicity gives the possibility of prediction of this value on the basis of the correlation equation. On the basis of similarity analysis was stated strong connections between the structure and the value of lipophilicity, for both experimental and theoretical values.

show abstract

“…There have been dozens of papers published since the first part of our study. To mention only several examples, in reversed phase, methanol is used mainly as a modifier [3][4][5][6][7]; however, there are also studies done with acetone [8][9][10], acetonitrile and tetrahydrofurane [11][12][13] or dioxane [14]. Several new papers report use of micellar TLC [15][16] or even reversed phase thin-layer chromatography (RP-TLC) done on silica plates impregnated with oils or fats [17][18][19][20].…”

Section: Introductionmentioning

confidence: 99%

Revisiting thin-layer chromatography as a lipophilicity determination tool. Part IV — A closer look on extrapolation and averaging

Komsta

Gowin

2014

Acta Chromatographica

View full text Add to dashboard Cite

Summary. The paper compares linear, quadratic, and cubical regression together with several weighted and robust approaches in the context of lipophilicity determination. The comparison is done on 35 model compounds on data from different modifiers used on RP18, CN, and silica plates. It can be concluded that the use of weighted and moderately robust regression technique increases correlation between extrapolated retention and real lipophilicity, whereas polynomial and very robust techniques give visibly worse results due to their excessive flexibility and higher extrapolation uncertainty. Additionally, we have compared averaging retention from different modifiers by R F , k, and R M values. The results are similar; however, surprisingly, R F averaging performs slightly better to the other approaches.

show abstract

Synthesis of betulin derivatives and the determination of their relative lipophilicities using reversed‐phase thin‐layer chromatography

Cited by 14 publications

References 38 publications

Enhancement of the Antioxidant and Skin Permeation Properties of Betulin and Its Derivatives

Enhancement of the Antioxidant and Skin Permeation Properties of Betulin and Its Derivatives

Application of TLC for Evaluation of the Lipophilicity of Newly Synthetized Esters: Betulin Derivatives

Revisiting thin-layer chromatography as a lipophilicity determination tool. Part IV — A closer look on extrapolation and averaging

Contact Info

Product

Resources

About