Premium
Determination of enantio‐separation, absolute configuration and chiral recognition mechanism of ofloxacin and flumequine by HPLC and modeling studies
Author(s) -
Ali Imran,
Sekkoum Khaled,
Belboukhari Nasser,
Rebizi Mohamed N,
Zaid Mohammed El Amin,
Yusuf Kareem,
Alothman Asma A,
AlJumah Bayan A,
Ouladsmane Mohamed
Publication year - 2021
Publication title -
journal of chemical technology and biotechnology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.64
H-Index - 117
eISSN - 1097-4660
pISSN - 0268-2575
DOI - 10.1002/jctb.6843
Subject(s) - flumequine , enantiomer , ofloxacin , high performance liquid chromatography , chemistry , chromatography , resolution (logic) , stereochemistry , ciprofloxacin , biochemistry , enrofloxacin , artificial intelligence , computer science , antibiotics
BACKGROUND The determination of enantio‐separation, absolute configuration and chiral recognition mechanism of ofloxacin and flumequine was carried out by high‐performance liquid chromatography (HPLC) and modeling studies. The column used was a Chiralcel OD‐H with normal and polar organic mobile phase modes. The exhaustive chiral separation was optimized through various HPLC parameters. RESULTS The selectivity, separation factors and resolution factors for ofloxacin were 8.2 and 9.4, 1.15 and 2.43 in the normal mobile phase, while these values were 10.5 and 12.0, 1.14 and 2.40 for flumequine in polar organic mobile phase mode, respectively. The thermodynamic parameters were Δ H (−0.137 J mol −1 ), Δ S (7.35 × 10 −4 J mol −1 ) and Δ G (−0.360 J mol −1 K −1 ) for ofloxacin, and Δ H (−0.035 J.mol −1 ), Δ S (21.3 × 10 −4 J mol −1 ) and Δ G (−0.105 J mol −1 K −1 ) for flumequine, confirming spontaneous chiral separation at all temperatures. The chiral recognition mechanism was established by HPLC and modeling results. The modeling binding affinity were −2.5 kcal mol –1 ( R ‐enantiomer) and −2.6 kcal mol –1 ( S ‐enantiomer) for ofloxacin, and −2.30 kcal mol –1 ( R ‐enantiomer) and −2.40 kcal mol –1 ( S ‐enantiomer) for flumequine enantiomers. The chiral resolution is controlled by hydrogen bonding, π–π interactions and other forces. CONCLUSION These methods were applied to monitor ofloxacin and flumequine quinolones in urine samples. Briefly, the developed chiral HPLC methods are effective and may be used to analyze the reported enantiomers in any biological sample. © 2021 Society of Chemical Industry (SCI).