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Supramolecular dynamics of thalidomide and its derivatives in water‐sediment system
Author(s) -
Ali Imran,
Gupta Vinod K.,
AboulEnein Hassan Y.
Publication year - 2009
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20757
Subject(s) - chemistry , enantiomer , chromatography , chirality (physics) , stereochemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
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 × 0.46 cm, particle size 50 μm) 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. Chirality, 2010. © 2009 Wiley‐Liss, Inc.