Synthesis, optical properties, DNA, β-cyclodextrin interactions, and antioxidant evaluation of novel isoxazolidine derivative (ISoXD2): A multispectral and computational analysis
Ibrahim A. Alhagri,
Raghad Alsowayan,
Siwar Ghannay,
Sadeq M. Al-Hazmy,
Iqrar Ahmad,
Harun Patel,
Adel Kadri,
Kaiss Aouadi
Affiliations
Ibrahim A. Alhagri
Department of Chemistry, College of Science, Qassim University, Buraidah, 51452, Saudi Arabia; Department of Chemistry, Faculty of Sciences, Ibb University, Ibb, Yemen
Raghad Alsowayan
Department of Chemistry, College of Science, Qassim University, Buraidah, 51452, Saudi Arabia
Siwar Ghannay
Department of Chemistry, College of Science, Qassim University, Buraidah, 51452, Saudi Arabia
Sadeq M. Al-Hazmy
Department of Chemistry, College of Science, Qassim University, Buraidah, 51452, Saudi Arabia; Department of Chemistry, College of Science, Sana'a University, Sana'a, P.O. Box 1247, Yemen
Iqrar Ahmad
Division of Computer Aided Drug Design, Department of Pharmaceutical Chemistry, R. C. Patel Institute of Pharmaceutical Education and Research, Shirpur, 425405, Maharashtra, India
Harun Patel
Division of Computer Aided Drug Design, Department of Pharmaceutical Chemistry, R. C. Patel Institute of Pharmaceutical Education and Research, Shirpur, 425405, Maharashtra, India
Adel Kadri
Faculty of Science and Arts in Baljurashi, Al-Baha University, P.O. Box (1988), Al-Baha, 65527, Saudi Arabia; Faculty of Science of Sfax, Department of Chemistry, University of Sfax, B.P. 1171, 3000, Sfax, Tunisia
Kaiss Aouadi
Department of Chemistry, College of Science, Qassim University, Buraidah, 51452, Saudi Arabia; Department of Chemistry, Laboratory of Heterocyclic Chemistry Natural Product and Reactivity/CHPNR, Faculty of Science of Monastir, University of Monastir, Avenue of the Environment, Monastir, 5019, Tunisia; Corresponding author. Department of Chemistry, College of Science, Qassim University, Buraidah, 51452, Saudi Arabia.
ISoXD2 are well explored among versatile and outstanding class of pharmacophores for the preparation and discovery of drugs. Herein, the electronic absorption and emission spectra of ISoXD2 were investigated in three different solvents. The observed transition was attributed to π-π* with charge transfer character. Changes in the excited state and shift of the absorption and emission peaks to longer wavelengths are observed as a result of increasing solvent polarity, due to the interactions between the ISoXD2 molecule and the solvent molecules surrounding it. Changing the solvent confirms its solvatochromic effect. UV–vis and fluorescence analysis revealed that ISoXD2 binds to deoxyribonucleic acid (DNA) by intercalation mode, with a stoichiometric ratio of 1:1.5. Moreover, the fluorescence intensity of DNA bound to ethidium bromide (EB) in the presence of ISoXD2 was investigated. From this analysis, the Stern-Volmer quenching constant (Ksv), quenching rate constant (kq), binding constant (Kb) and binding sites number (n) were found to be 5.654 × 103 M−1, 2.827 × 1011 M−1 s−1, 3.81 × 104 M−1 and 1.225, respectively. The interaction between ISoXD2 and β-CD was investigated through absorption spectra analysis. Kb for this interaction was determined to be 4.9 × 104 M−1. The free radical-scavenging ability of the prepared ISoXD2, examined by DPPH and ABTS assays have shown a good antioxidant activity. Furthermore, modeling study was conducted to explore their plausible binding mechanism with ISoXD2 and to support the experimental results.
