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Molecules 2011, 16(3), 2658-2671; doi:10.3390/molecules16032658
Article

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

1,* , 1, 1, 1, 2 and 3
1 Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, 11221 Belgrade, Serbia 2 Department of Organic Chemistry, Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, 11221 Belgrade, Serbia 3 Department of Analytical Chemistry, Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, 11221 Belgrade, Serbia
* Author to whom correspondence should be addressed.
Received: 18 January 2011 / Revised: 16 March 2011 / Accepted: 21 March 2011 / Published: 23 March 2011
(This article belongs to the Special Issue Prodrugs)
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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 NaHCO3. 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 °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.
Keywords: prodrug; fluocinolone acetonide esters; solvolysis; descriptor; in vitro model prodrug; fluocinolone acetonide esters; solvolysis; descriptor; in vitro model
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Markovic, B.D.; Dobricic, V.D.; Vladimirov, S.M.; Cudina, O.A.; Savic, V.M.; Karljikovic-Rajic, K.D. Investigation of Solvolysis Kinetics of New Synthesized Fluocinolone Acetonide C-21 Esters—An In Vitro Model for Prodrug Activation. Molecules 2011, 16, 2658-2671.

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