Chirality 2010-05-05

Supramolecular dynamics of thalidomide and its derivatives in water-sediment system.

Imran Ali, Vinod K Gupta, Hassan Y Aboul-Enein

Index: Chirality 22(4) , 416-24, (2010)

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Abstract

The contamination of drug residues, including chiral ones, is not acceptable in earth's ecosystem. The dynamicity of enantiomers of thalidomide and its derivatives (3-methyl thalidomide, 3-ethyl thalidomide, and 3-butyl thalidomide) was ascertained at supramolecular level in water-sediment system using solid phase extraction (SPE) and stereoselective HPLC. Enantiomeric separation of these drugs was carried out on Ceramosphere RU-2 (25 cm x 0.46 cm, particle size 50 microm) chiral column using pure ethanol (1.0 ml/min) as eluent at 230 nm detection. Retention times, capacity, separation, and resolution factors of the enantiomers of these drugs were in the range of 20.0-36.0, 2.08-3.93, 1.35-1.57, and 1.0-2.0 min, respectively. Percentage recoveries of the enantiomers in SPE were in the range of 90.0 to 95.0 in water-sediment system. Langmuir and Freundlich model were best fitted for dynamic equilibrium concentrations at different experimental parameters. Thalidomide and its derivatives follow first-order kinetics at dynamic equilibrium. The rate constants of chiral interconversions were 0.390 and 0.385 days(-1) for S- and R-enantiomers, respectively. The uptake of thalidomide by sediment is quite good and of endothermic nature indicating good self-purification capacity of the nature for such toxic species.2009 Wiley-Liss, Inc.