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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 collection 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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