Investigation of Solvolysis Kinetics of New Synthesized Fluocinolone Acetonide C-21 Esters-An In Vitro Model for Prodrug Activation

2011
Autori
Marković, Bojan
Dobričić, Vladimir

Vladimirov, Sote
Čudina, Olivera

Savić, Vladimir

Karljiković-Rajić, Katarina

Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
In this study the solvolysis of newly synthesized fluocinolone acetonide C-21 esters was analysed in comparison with fluocinonide during a 24-hour period of time. The solvolysis was performed in an ethanol-water (90:10 v/v) mixture using the excess of NaHCO(3). The solvolytic mixtures of each investigated ester have been assayed by a RP-HPLC method using isocratic elution with methanol-water (75:25 v/v); flow rate 1 mL/min; detection at 238 nm; temperature 25 degrees C. Solvolytic rate constants were calculated from the obtained data. Geometry optimizations and charges calculations were carried out by Gaussian W03 software. A good correlation (R = 0.9924) was obtained between solvolytic rate constants and the polarity of the C-O2 bond of those esters. The established relation between solvolytic rate constant (K) and lipophilicity (cLogP) with experimental anti-inflammatory activity could be indicative for topical corticosteroid prodrug activation.
Ključne reči:
prodrug / fluocinolone acetonide esters / solvolysis / descriptor / in vitro modelIzvor:
Molecules, 2011, 16, 3, 2658-2671Izdavač:
- MDPI, Basel
Finansiranje / projekti:
DOI: 10.3390/molecules16032658
ISSN: 1420-3049
PubMed: 21441868
WoS: 000288853400053
Scopus: 2-s2.0-79953090073
Institucija/grupa
PharmacyTY - JOUR AU - Marković, Bojan AU - Dobričić, Vladimir AU - Vladimirov, Sote AU - Čudina, Olivera AU - Savić, Vladimir AU - Karljiković-Rajić, Katarina PY - 2011 UR - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1524 AB - In this study the solvolysis of newly synthesized fluocinolone acetonide C-21 esters was analysed in comparison with fluocinonide during a 24-hour period of time. The solvolysis was performed in an ethanol-water (90:10 v/v) mixture using the excess of NaHCO(3). The solvolytic mixtures of each investigated ester have been assayed by a RP-HPLC method using isocratic elution with methanol-water (75:25 v/v); flow rate 1 mL/min; detection at 238 nm; temperature 25 degrees C. Solvolytic rate constants were calculated from the obtained data. Geometry optimizations and charges calculations were carried out by Gaussian W03 software. A good correlation (R = 0.9924) was obtained between solvolytic rate constants and the polarity of the C-O2 bond of those esters. The established relation between solvolytic rate constant (K) and lipophilicity (cLogP) with experimental anti-inflammatory activity could be indicative for topical corticosteroid prodrug activation. PB - MDPI, Basel T2 - Molecules T1 - Investigation of Solvolysis Kinetics of New Synthesized Fluocinolone Acetonide C-21 Esters-An In Vitro Model for Prodrug Activation VL - 16 IS - 3 SP - 2658 EP - 2671 DO - 10.3390/molecules16032658 ER -
@article{ author = "Marković, Bojan and Dobričić, Vladimir and Vladimirov, Sote and Čudina, Olivera and Savić, Vladimir and Karljiković-Rajić, Katarina", year = "2011", abstract = "In this study the solvolysis of newly synthesized fluocinolone acetonide C-21 esters was analysed in comparison with fluocinonide during a 24-hour period of time. The solvolysis was performed in an ethanol-water (90:10 v/v) mixture using the excess of NaHCO(3). The solvolytic mixtures of each investigated ester have been assayed by a RP-HPLC method using isocratic elution with methanol-water (75:25 v/v); flow rate 1 mL/min; detection at 238 nm; temperature 25 degrees C. Solvolytic rate constants were calculated from the obtained data. Geometry optimizations and charges calculations were carried out by Gaussian W03 software. A good correlation (R = 0.9924) was obtained between solvolytic rate constants and the polarity of the C-O2 bond of those esters. The established relation between solvolytic rate constant (K) and lipophilicity (cLogP) with experimental anti-inflammatory activity could be indicative for topical corticosteroid prodrug activation.", publisher = "MDPI, Basel", journal = "Molecules", title = "Investigation of Solvolysis Kinetics of New Synthesized Fluocinolone Acetonide C-21 Esters-An In Vitro Model for Prodrug Activation", volume = "16", number = "3", pages = "2658-2671", doi = "10.3390/molecules16032658" }
Marković, B., Dobričić, V., Vladimirov, S., Čudina, O., Savić, V.,& Karljiković-Rajić, K.. (2011). Investigation of Solvolysis Kinetics of New Synthesized Fluocinolone Acetonide C-21 Esters-An In Vitro Model for Prodrug Activation. in Molecules MDPI, Basel., 16(3), 2658-2671. https://doi.org/10.3390/molecules16032658
Marković B, Dobričić V, Vladimirov S, Čudina O, Savić V, Karljiković-Rajić K. Investigation of Solvolysis Kinetics of New Synthesized Fluocinolone Acetonide C-21 Esters-An In Vitro Model for Prodrug Activation. in Molecules. 2011;16(3):2658-2671. doi:10.3390/molecules16032658 .
Marković, Bojan, Dobričić, Vladimir, Vladimirov, Sote, Čudina, Olivera, Savić, Vladimir, Karljiković-Rajić, Katarina, "Investigation of Solvolysis Kinetics of New Synthesized Fluocinolone Acetonide C-21 Esters-An In Vitro Model for Prodrug Activation" in Molecules, 16, no. 3 (2011):2658-2671, https://doi.org/10.3390/molecules16032658 . .