Comprehensive multispectral and computational study of isoxazolidine derivative ‘ISoXD3’: Synthesis, spectral characteristics, DNA binding, and comparative effects of allyl and propargyl groups on optical properties
In this article, we have synthesized and examined the spectral properties of the isoxazolidine derivative ISoXD3, particularly its UV–Visible and fluorescence spectra. ISoXD3 shows a strong absorbance peak at 228 nm (S₀ → S₂ transition) and another at 290 nm (S₀ → S₁ transition). The absorption spec...
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Elsevier
2025-03-01
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| Series: | Results in Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2211715625000633 |
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| author | Ibrahim A. Alhagri Siwar Ghannay Norah A. Al-Suwailem Rania Hussien Al-Ashwal Sadeq M. AlHazmy Sabri Messaoudi Kaiss Aouadi |
| author_facet | Ibrahim A. Alhagri Siwar Ghannay Norah A. Al-Suwailem Rania Hussien Al-Ashwal Sadeq M. AlHazmy Sabri Messaoudi Kaiss Aouadi |
| author_sort | Ibrahim A. Alhagri |
| collection | DOAJ |
| description | In this article, we have synthesized and examined the spectral properties of the isoxazolidine derivative ISoXD3, particularly its UV–Visible and fluorescence spectra. ISoXD3 shows a strong absorbance peak at 228 nm (S₀ → S₂ transition) and another at 290 nm (S₀ → S₁ transition). The absorption spectra are stable in n-hexane and methanol but shift bathochromically in water due to hydrogen bonding. A notable Stokes shift of about 129 nm is observed in ethanol, indicating vibrational relaxation. The emission spectrum exhibits a 34 nm red shift related to the solvatochromic effect, highlighting solvent interactions. Increased solvent polarity decreases fluorescence intensity and quantum yield, suggesting significant solvation effects. Additionally, substituting the propargyl group with an allyl group in ISoXD3 in ethanol decreases excited-state stabilization but increases fluorescence intensity due to reduced steric hindrance and enhanced electronic transitions. Transitions were studied using DFT. This study investigates the interaction between the synthesized compound ISoXD3 and DNA using UV–Vis and fluorescence spectra. The UV–Vis spectral analysis revealed a red shift and hyperchromic effect, suggesting intercalative binding between ISoXD3 and DNA. EB displacement experiments further supported the intercalation hypothesis, showing a 50.6 % reduction in EB-DNA fluorescence. Docking studies have shown a favorable interaction of the molecule with DNA. Quenching analysis revealed static quenching behavior with a Stern-Volmer constant Ksv = 4.91 × 103 M−1, a quenching rate constant kq = 2.45 × 1011 M−1 s−1 and binding constant Kb = 1.44 × 104 M. |
| format | Article |
| id | doaj-art-6dad71638a9a4f23bef11f4ba5fced0b |
| institution | Kabale University |
| issn | 2211-7156 |
| language | English |
| publishDate | 2025-03-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Results in Chemistry |
| spelling | doaj-art-6dad71638a9a4f23bef11f4ba5fced0b2025-02-02T05:27:07ZengElsevierResults in Chemistry2211-71562025-03-0114102080Comprehensive multispectral and computational study of isoxazolidine derivative ‘ISoXD3’: Synthesis, spectral characteristics, DNA binding, and comparative effects of allyl and propargyl groups on optical propertiesIbrahim A. Alhagri0Siwar Ghannay1Norah A. Al-Suwailem2Rania Hussien Al-Ashwal3Sadeq M. AlHazmy4Sabri Messaoudi5Kaiss Aouadi6Department of Chemistry, College of Science, Qassim University, Buraidah 51452, Saudi ArabiaDepartment of Chemistry, College of Science, Qassim University, Buraidah 51452, Saudi ArabiaDepartment of Chemistry, College of Science, Qassim University, Buraidah 51452, Saudi ArabiaAdvanced Diagnostic and Progressive Human Care Research Group, University Technology Malaysia, 81310 Johor Bahru, Johor, Malaysia; Department of Biomedical Engineering and Health Sciences, Faculty of Electrical Engineering, University Technology Malaysia, 81310 Johor Bahru, Johor, Malaysia.Department of Chemistry, College of Science, Qassim University, Buraidah 51452, Saudi ArabiaDepartment of Chemistry, College of Science, Qassim University, Buraidah 51452, Saudi ArabiaDepartment of Chemistry, College of Science, Qassim University, Buraidah 51452, Saudi Arabia; Corresponding author.In this article, we have synthesized and examined the spectral properties of the isoxazolidine derivative ISoXD3, particularly its UV–Visible and fluorescence spectra. ISoXD3 shows a strong absorbance peak at 228 nm (S₀ → S₂ transition) and another at 290 nm (S₀ → S₁ transition). The absorption spectra are stable in n-hexane and methanol but shift bathochromically in water due to hydrogen bonding. A notable Stokes shift of about 129 nm is observed in ethanol, indicating vibrational relaxation. The emission spectrum exhibits a 34 nm red shift related to the solvatochromic effect, highlighting solvent interactions. Increased solvent polarity decreases fluorescence intensity and quantum yield, suggesting significant solvation effects. Additionally, substituting the propargyl group with an allyl group in ISoXD3 in ethanol decreases excited-state stabilization but increases fluorescence intensity due to reduced steric hindrance and enhanced electronic transitions. Transitions were studied using DFT. This study investigates the interaction between the synthesized compound ISoXD3 and DNA using UV–Vis and fluorescence spectra. The UV–Vis spectral analysis revealed a red shift and hyperchromic effect, suggesting intercalative binding between ISoXD3 and DNA. EB displacement experiments further supported the intercalation hypothesis, showing a 50.6 % reduction in EB-DNA fluorescence. Docking studies have shown a favorable interaction of the molecule with DNA. Quenching analysis revealed static quenching behavior with a Stern-Volmer constant Ksv = 4.91 × 103 M−1, a quenching rate constant kq = 2.45 × 1011 M−1 s−1 and binding constant Kb = 1.44 × 104 M.http://www.sciencedirect.com/science/article/pii/S2211715625000633Molecular docking simulationDNAOptical propertiesDFTIsoxazolidine |
| spellingShingle | Ibrahim A. Alhagri Siwar Ghannay Norah A. Al-Suwailem Rania Hussien Al-Ashwal Sadeq M. AlHazmy Sabri Messaoudi Kaiss Aouadi Comprehensive multispectral and computational study of isoxazolidine derivative ‘ISoXD3’: Synthesis, spectral characteristics, DNA binding, and comparative effects of allyl and propargyl groups on optical properties Results in Chemistry Molecular docking simulation DNA Optical properties DFT Isoxazolidine |
| title | Comprehensive multispectral and computational study of isoxazolidine derivative ‘ISoXD3’: Synthesis, spectral characteristics, DNA binding, and comparative effects of allyl and propargyl groups on optical properties |
| title_full | Comprehensive multispectral and computational study of isoxazolidine derivative ‘ISoXD3’: Synthesis, spectral characteristics, DNA binding, and comparative effects of allyl and propargyl groups on optical properties |
| title_fullStr | Comprehensive multispectral and computational study of isoxazolidine derivative ‘ISoXD3’: Synthesis, spectral characteristics, DNA binding, and comparative effects of allyl and propargyl groups on optical properties |
| title_full_unstemmed | Comprehensive multispectral and computational study of isoxazolidine derivative ‘ISoXD3’: Synthesis, spectral characteristics, DNA binding, and comparative effects of allyl and propargyl groups on optical properties |
| title_short | Comprehensive multispectral and computational study of isoxazolidine derivative ‘ISoXD3’: Synthesis, spectral characteristics, DNA binding, and comparative effects of allyl and propargyl groups on optical properties |
| title_sort | comprehensive multispectral and computational study of isoxazolidine derivative isoxd3 synthesis spectral characteristics dna binding and comparative effects of allyl and propargyl groups on optical properties |
| topic | Molecular docking simulation DNA Optical properties DFT Isoxazolidine |
| url | http://www.sciencedirect.com/science/article/pii/S2211715625000633 |
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