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A PAMPA Assay as Fast Predictive Model of Passive Human Skin Permeability of New Synthesized Corticosteroid C-21 Esters

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2012
1720.pdf (322.6Kb)
Authors
Marković, Bojan
Vladimirov, Sote
Čudina, Olivera
Odović, Jadranka
Karljiković-Rajić, Katarina
Article (Published version)
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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 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.

Keywords:
corticosteroid C-21 esters / prodrug / PAMPA / membrane retention / permeation parameter
Source:
Molecules, 2012, 17, 1, 480-491
Publisher:
  • MDPI, Basel
Funding / projects:
  • Development of molecules with antiinflammatory and cardioprotective activity: structural modifications, modelling, physicochemical characterization and formulation investigations (RS-172041)

DOI: 10.3390/molecules17010480

ISSN: 1420-3049

PubMed: 22222907

WoS: 000299535700032

Scopus: 2-s2.0-84856199554
[ Google Scholar ]
23
16
URI
https://farfar.pharmacy.bg.ac.rs/handle/123456789/1722
Collections
  • Radovi istraživača / Researchers’ publications
Institution/Community
Pharmacy
TY  - 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 . .

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