A PAMPA Assay as Fast Predictive Model of Passive Human Skin Permeability of New Synthesized Corticosteroid C-21 Esters
2012
Autori
Marković, BojanVladimirov, Sote
Čudina, Olivera
Odović, Jadranka
Karljiković-Rajić, Katarina
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
The permeation properties of twenty newly synthesized alpha-alkoxyalkanoyl and alpha-aryloxyalkanoyl C-21 esters of standard corticosteroids: Fluocinolone acetonide, dexamethasone, triamcinolone acetonide and hydrocortisone were established using a PAMPA assay (70% silicone oil and 30% isopropyl myristate). The data were compared with parent corticosteroids with addition of mometasone furoate and hydrocortisone acetate. All newly synthesized corticosteroid C-21 esters have effective permeability coefficients higher then -6, mostly followed with high values of retention factors and low permeation. The examined compounds were grouped through relationship between obtained retention factors and permeation parameters (groups I-III). The classification confirmed group I (membrane retentions as well as permeation lower then 30%) for all corticosteroid standards except mometasone furoate, a potent topical corticosteroid which, with high membrane retention (81%) and low permeation (7.7%) fits i...nto group III. The largest number of new synthesized corticosteroids C-21 esters, among them all fluocinolone acetonide C-21 esters, have high membrane retentions (32.4%-86.5%) and low permeations (1.3%-27.1%), fitting in group III. The classification was related to previously obtained anti-inflammatory activity data for the fluocinolone acetonide C-21 esters series. According to the PAMPA results the new synthesized esters could be considered as potential new prodrugs with useful benefit/risk ratio.
Ključne reči:
corticosteroid C-21 esters / prodrug / PAMPA / membrane retention / permeation parameterIzvor:
Molecules, 2012, 17, 1, 480-491Izdavač:
- MDPI, Basel
Finansiranje / projekti:
- Razvoj molekula sa antiinflamatornim i kardioproaktivnim dejstvom: strukturne modifikacije, modelovanje, fizičkohemijska karakterizacija i formulaciona ispitivanja (RS-MESTD-Basic Research (BR or ON)-172041)
DOI: 10.3390/molecules17010480
ISSN: 1420-3049
PubMed: 22222907
WoS: 000299535700032
Scopus: 2-s2.0-84856199554
Institucija/grupa
PharmacyTY - JOUR AU - Marković, Bojan AU - Vladimirov, Sote AU - Čudina, Olivera AU - Odović, Jadranka AU - Karljiković-Rajić, Katarina PY - 2012 UR - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1722 AB - The permeation properties of twenty newly synthesized alpha-alkoxyalkanoyl and alpha-aryloxyalkanoyl C-21 esters of standard corticosteroids: Fluocinolone acetonide, dexamethasone, triamcinolone acetonide and hydrocortisone were established using a PAMPA assay (70% silicone oil and 30% isopropyl myristate). The data were compared with parent corticosteroids with addition of mometasone furoate and hydrocortisone acetate. All newly synthesized corticosteroid C-21 esters have effective permeability coefficients higher then -6, mostly followed with high values of retention factors and low permeation. The examined compounds were grouped through relationship between obtained retention factors and permeation parameters (groups I-III). The classification confirmed group I (membrane retentions as well as permeation lower then 30%) for all corticosteroid standards except mometasone furoate, a potent topical corticosteroid which, with high membrane retention (81%) and low permeation (7.7%) fits into group III. The largest number of new synthesized corticosteroids C-21 esters, among them all fluocinolone acetonide C-21 esters, have high membrane retentions (32.4%-86.5%) and low permeations (1.3%-27.1%), fitting in group III. The classification was related to previously obtained anti-inflammatory activity data for the fluocinolone acetonide C-21 esters series. According to the PAMPA results the new synthesized esters could be considered as potential new prodrugs with useful benefit/risk ratio. PB - MDPI, Basel T2 - Molecules T1 - A PAMPA Assay as Fast Predictive Model of Passive Human Skin Permeability of New Synthesized Corticosteroid C-21 Esters VL - 17 IS - 1 SP - 480 EP - 491 DO - 10.3390/molecules17010480 ER -
@article{ author = "Marković, Bojan and Vladimirov, Sote and Čudina, Olivera and Odović, Jadranka and Karljiković-Rajić, Katarina", year = "2012", abstract = "The permeation properties of twenty newly synthesized alpha-alkoxyalkanoyl and alpha-aryloxyalkanoyl C-21 esters of standard corticosteroids: Fluocinolone acetonide, dexamethasone, triamcinolone acetonide and hydrocortisone were established using a PAMPA assay (70% silicone oil and 30% isopropyl myristate). The data were compared with parent corticosteroids with addition of mometasone furoate and hydrocortisone acetate. All newly synthesized corticosteroid C-21 esters have effective permeability coefficients higher then -6, mostly followed with high values of retention factors and low permeation. The examined compounds were grouped through relationship between obtained retention factors and permeation parameters (groups I-III). The classification confirmed group I (membrane retentions as well as permeation lower then 30%) for all corticosteroid standards except mometasone furoate, a potent topical corticosteroid which, with high membrane retention (81%) and low permeation (7.7%) fits into group III. The largest number of new synthesized corticosteroids C-21 esters, among them all fluocinolone acetonide C-21 esters, have high membrane retentions (32.4%-86.5%) and low permeations (1.3%-27.1%), fitting in group III. The classification was related to previously obtained anti-inflammatory activity data for the fluocinolone acetonide C-21 esters series. According to the PAMPA results the new synthesized esters could be considered as potential new prodrugs with useful benefit/risk ratio.", publisher = "MDPI, Basel", journal = "Molecules", title = "A PAMPA Assay as Fast Predictive Model of Passive Human Skin Permeability of New Synthesized Corticosteroid C-21 Esters", volume = "17", number = "1", pages = "480-491", doi = "10.3390/molecules17010480" }
Marković, B., Vladimirov, S., Čudina, O., Odović, J.,& Karljiković-Rajić, K.. (2012). A PAMPA Assay as Fast Predictive Model of Passive Human Skin Permeability of New Synthesized Corticosteroid C-21 Esters. in Molecules MDPI, Basel., 17(1), 480-491. https://doi.org/10.3390/molecules17010480
Marković B, Vladimirov S, Čudina O, Odović J, Karljiković-Rajić K. A PAMPA Assay as Fast Predictive Model of Passive Human Skin Permeability of New Synthesized Corticosteroid C-21 Esters. in Molecules. 2012;17(1):480-491. doi:10.3390/molecules17010480 .
Marković, Bojan, Vladimirov, Sote, Čudina, Olivera, Odović, Jadranka, Karljiković-Rajić, Katarina, "A PAMPA Assay as Fast Predictive Model of Passive Human Skin Permeability of New Synthesized Corticosteroid C-21 Esters" in Molecules, 17, no. 1 (2012):480-491, https://doi.org/10.3390/molecules17010480 . .