ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Stereoselective analysis and enantioseparation of isoproterenol in spiked human plasma

Vinod Kumar Vashistha, Renu Bala, Ankit Mittal, Rajasekhar V. S. R. Pullabhotla, Suman Yadav, and Nishant Verma

Department of Chemistry, GLA University, Mathura, India

E-mail: vinod.vashistha@gla.ac.in

Received: 22 June 2023  Accepted: 26 October 2023

Abstract:

The present work deals with the synthesis of a novel chiral derivatizing reagent (CDR), namely, N-(4-chloro-6-piperidinyl-[1,3,5]-triazine-2-yl)-D-phenylglycine and its use for stereoselective separation of (RS)-isoproterenol (ISP) in spiked human plasma. The synthesized CDR was utilized for the derivatization of ISP enantiomers, and the diastereomers obtained were resolved using a LiChrospher C₁₈ column. The mobile phase consists of acetonitrile and 0.15% aq. TFA (added as an organic modifier) in the following ratio: 75:25% (by v/v) was used in an isocratic elution mode. The coefficient of determination was observed to be greater than 0.982, and the RSD value was less than 4.28%. The detection and quantitation limits were reported to be 3.6 ng mL⁻¹ and 10.8 ng mL⁻¹, respectively, for diastereomeric derivatives. The mechanism of chiral recognition and elution order was supported by optimizing the minimum energy structures of diastereomers obtained by employing a density functional theory program.

Keywords: Isoproterenol; Chiral derivatizing reagent; D-phenylglycine; HPLC; Density functional theory; 1,3,5-Trichloro triazine; Active pharmaceutical ingredient

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-023-03185-5

Chemical Papers 78 (1) 613–622 (2024)