Assessment of Bioavailability Parameters of Mono- and Bistriazole Derivatives of Propynoylbetulin
Bioavailability describes the properties that determine the passage of a compound through biological barriers. In many cases, bioavailability depends on the lipophilicity of the compound. In this study, the lipophilicity as well as other bioavailability properties of the mono- and bistriazole deriva...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2024-02-01
|
| Series: | Applied Sciences |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2076-3417/14/5/1695 |
| _version_ | 1797264821948776448 |
|---|---|
| author | Monika Kadela-Tomanek Arkadiusz Sokal Klaudia Stocerz Ewa Bębenek Elwira Chrobak Paweł Olczyk |
| author_facet | Monika Kadela-Tomanek Arkadiusz Sokal Klaudia Stocerz Ewa Bębenek Elwira Chrobak Paweł Olczyk |
| author_sort | Monika Kadela-Tomanek |
| collection | DOAJ |
| description | Bioavailability describes the properties that determine the passage of a compound through biological barriers. In many cases, bioavailability depends on the lipophilicity of the compound. In this study, the lipophilicity as well as other bioavailability properties of the mono- and bistriazole derivatives of betulin are presented. The lipophilicity was determined using RP-TLC and theoretical methods. The experimental lipophilicity of mono- and bistriazole derivatives is in the range from 4.39 to 7.85 and from 3.75 to 8.83, respectively. The lipophilicity of mono- and bistriazoles is similar, and the logP<sub>TLC</sub> depends on the type of substituent at the triazole ring. The introduction of a substituent with oxygen and nitrogen atoms decreases lipophilicity. Comparing the experimental and theoretical lipophilicity shows that the milogP and XLOGP3 programs best reproduce the experimental values. The in silico-determined pharmacokinetic parameters show that monotriazole derivatives could be used as oral drugs while bistriazoles show low availability after oral administration. Triazoles could be used as transdermal drugs. The analysis of in silico bioavailability parameters shows that the type of substituent at the triazole ring influences the pharmacokinetic properties, while the number of triazole rings slightly affects the bioavailability properties of the compound. |
| first_indexed | 2024-04-25T00:35:00Z |
| format | Article |
| id | doaj.art-068a7ad564e04a23bbf19467b9dcffdb |
| institution | Directory Open Access Journal |
| issn | 2076-3417 |
| language | English |
| last_indexed | 2024-04-25T00:35:00Z |
| publishDate | 2024-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Applied Sciences |
| spelling | doaj.art-068a7ad564e04a23bbf19467b9dcffdb2024-03-12T16:38:31ZengMDPI AGApplied Sciences2076-34172024-02-01145169510.3390/app14051695Assessment of Bioavailability Parameters of Mono- and Bistriazole Derivatives of PropynoylbetulinMonika Kadela-Tomanek0Arkadiusz Sokal1Klaudia Stocerz2Ewa Bębenek3Elwira Chrobak4Paweł Olczyk5Department of Organic Chemistry, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia, Katowice, 4 Jagiellońska Str., 41-200 Sosnowiec, PolandStudents Scientific Group of Department of Organic Chemistry, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia, Katowice, 4 Jagiellońska Str., 41-200 Sosnowiec, PolandStudents Research Club at the Department of Community Pharmacy, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia, Katowice, 3 Kasztanowa Str., 41-200 Sosnowiec, PolandDepartment of Organic Chemistry, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia, Katowice, 4 Jagiellońska Str., 41-200 Sosnowiec, PolandDepartment of Organic Chemistry, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia, Katowice, 4 Jagiellońska Str., 41-200 Sosnowiec, PolandDepartment of Community Pharmacy, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia, Katowice, 3 Kasztanowa Str., 41-200 Sosnowiec, PolandBioavailability describes the properties that determine the passage of a compound through biological barriers. In many cases, bioavailability depends on the lipophilicity of the compound. In this study, the lipophilicity as well as other bioavailability properties of the mono- and bistriazole derivatives of betulin are presented. The lipophilicity was determined using RP-TLC and theoretical methods. The experimental lipophilicity of mono- and bistriazole derivatives is in the range from 4.39 to 7.85 and from 3.75 to 8.83, respectively. The lipophilicity of mono- and bistriazoles is similar, and the logP<sub>TLC</sub> depends on the type of substituent at the triazole ring. The introduction of a substituent with oxygen and nitrogen atoms decreases lipophilicity. Comparing the experimental and theoretical lipophilicity shows that the milogP and XLOGP3 programs best reproduce the experimental values. The in silico-determined pharmacokinetic parameters show that monotriazole derivatives could be used as oral drugs while bistriazoles show low availability after oral administration. Triazoles could be used as transdermal drugs. The analysis of in silico bioavailability parameters shows that the type of substituent at the triazole ring influences the pharmacokinetic properties, while the number of triazole rings slightly affects the bioavailability properties of the compound.https://www.mdpi.com/2076-3417/14/5/1695betulintriazolelipophilicity |
| spellingShingle | Monika Kadela-Tomanek Arkadiusz Sokal Klaudia Stocerz Ewa Bębenek Elwira Chrobak Paweł Olczyk Assessment of Bioavailability Parameters of Mono- and Bistriazole Derivatives of Propynoylbetulin Applied Sciences betulin triazole lipophilicity |
| title | Assessment of Bioavailability Parameters of Mono- and Bistriazole Derivatives of Propynoylbetulin |
| title_full | Assessment of Bioavailability Parameters of Mono- and Bistriazole Derivatives of Propynoylbetulin |
| title_fullStr | Assessment of Bioavailability Parameters of Mono- and Bistriazole Derivatives of Propynoylbetulin |
| title_full_unstemmed | Assessment of Bioavailability Parameters of Mono- and Bistriazole Derivatives of Propynoylbetulin |
| title_short | Assessment of Bioavailability Parameters of Mono- and Bistriazole Derivatives of Propynoylbetulin |
| title_sort | assessment of bioavailability parameters of mono and bistriazole derivatives of propynoylbetulin |
| topic | betulin triazole lipophilicity |
| url | https://www.mdpi.com/2076-3417/14/5/1695 |
| work_keys_str_mv | AT monikakadelatomanek assessmentofbioavailabilityparametersofmonoandbistriazolederivativesofpropynoylbetulin AT arkadiuszsokal assessmentofbioavailabilityparametersofmonoandbistriazolederivativesofpropynoylbetulin AT klaudiastocerz assessmentofbioavailabilityparametersofmonoandbistriazolederivativesofpropynoylbetulin AT ewabebenek assessmentofbioavailabilityparametersofmonoandbistriazolederivativesofpropynoylbetulin AT elwirachrobak assessmentofbioavailabilityparametersofmonoandbistriazolederivativesofpropynoylbetulin AT pawełolczyk assessmentofbioavailabilityparametersofmonoandbistriazolederivativesofpropynoylbetulin |