Comparison of the DNA-binding interactions of 5-hydroxymethylfurfural and its synthesized derivative, 5, 5’[oxy-bis(methylene)]bis-2-furfural: experimental, DFT and docking studies
In this study, the in vitro DNA-binding interactions of the food/drug additive, 5-hydroxymethylfurfural (HMF) and its major degradant, 5, 5'[oxy-bis(methylene)]bis-2-furfural (OBMF) were investigated. OBMF was synthesized and characterized using IR, NMR and mass spectrometry. Photometric titrat...
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| Format: | Article |
| Language: | English |
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Taylor & Francis Group
2023-12-01
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| Series: | Journal of Taibah University for Science |
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| Online Access: | https://www.tandfonline.com/doi/10.1080/16583655.2023.2183705 |
| _version_ | 1797215143358103552 |
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| author | Olusegun Emmanuel Thomas Rashidat Temitope Oduwole Akintayo Akin-Taylor |
| author_facet | Olusegun Emmanuel Thomas Rashidat Temitope Oduwole Akintayo Akin-Taylor |
| author_sort | Olusegun Emmanuel Thomas |
| collection | DOAJ |
| description | In this study, the in vitro DNA-binding interactions of the food/drug additive, 5-hydroxymethylfurfural (HMF) and its major degradant, 5, 5'[oxy-bis(methylene)]bis-2-furfural (OBMF) were investigated. OBMF was synthesized and characterized using IR, NMR and mass spectrometry. Photometric titrations revealed OBMF induced more extensive perturbations in the 258 nm band of DNA and exhibited binding constants that were 5–12-folds higher than those of HMF. The greatest net changes in viscosity of DNA induced by HMF and OBMF were 10.5 and 8.9%, respectively which confirmed both compounds as minor groove binders. Docking revealed that OBMF and HMF bound to the guanine–cytosine regions of minor groove of DNA with global binding energies of −36.36 and −26.12 kcal/mol, respectively. DFT calculations revealed the higher electrophilicity of OBMF contributed to its increased interaction with the negatively charged DNA backbone. There is a need for stricter control of permissible levels of OBMF in food and drug products. |
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| format | Article |
| id | doaj.art-38418b2485fc4d0083e75c93221d59a8 |
| institution | Directory Open Access Journal |
| issn | 1658-3655 |
| language | English |
| last_indexed | 2024-04-24T11:25:23Z |
| publishDate | 2023-12-01 |
| publisher | Taylor & Francis Group |
| record_format | Article |
| series | Journal of Taibah University for Science |
| spelling | doaj.art-38418b2485fc4d0083e75c93221d59a82024-04-10T20:17:48ZengTaylor & Francis GroupJournal of Taibah University for Science1658-36552023-12-0117110.1080/16583655.2023.2183705Comparison of the DNA-binding interactions of 5-hydroxymethylfurfural and its synthesized derivative, 5, 5’[oxy-bis(methylene)]bis-2-furfural: experimental, DFT and docking studiesOlusegun Emmanuel Thomas0Rashidat Temitope Oduwole1Akintayo Akin-Taylor2Department of Pharmaceutical Chemistry, University of Ibadan, Orita UI, NigeriaDepartment of Pharmaceutical Chemistry, University of Ibadan, Orita UI, NigeriaDepartment of Pharmaceutical Chemistry, University of Ibadan, Orita UI, NigeriaIn this study, the in vitro DNA-binding interactions of the food/drug additive, 5-hydroxymethylfurfural (HMF) and its major degradant, 5, 5'[oxy-bis(methylene)]bis-2-furfural (OBMF) were investigated. OBMF was synthesized and characterized using IR, NMR and mass spectrometry. Photometric titrations revealed OBMF induced more extensive perturbations in the 258 nm band of DNA and exhibited binding constants that were 5–12-folds higher than those of HMF. The greatest net changes in viscosity of DNA induced by HMF and OBMF were 10.5 and 8.9%, respectively which confirmed both compounds as minor groove binders. Docking revealed that OBMF and HMF bound to the guanine–cytosine regions of minor groove of DNA with global binding energies of −36.36 and −26.12 kcal/mol, respectively. DFT calculations revealed the higher electrophilicity of OBMF contributed to its increased interaction with the negatively charged DNA backbone. There is a need for stricter control of permissible levels of OBMF in food and drug products.https://www.tandfonline.com/doi/10.1080/16583655.2023.2183705HydroxymethylfurfuralDNA viscosity studydensity functional theorymolecular modellingstructure-activity relationships |
| spellingShingle | Olusegun Emmanuel Thomas Rashidat Temitope Oduwole Akintayo Akin-Taylor Comparison of the DNA-binding interactions of 5-hydroxymethylfurfural and its synthesized derivative, 5, 5’[oxy-bis(methylene)]bis-2-furfural: experimental, DFT and docking studies Journal of Taibah University for Science Hydroxymethylfurfural DNA viscosity study density functional theory molecular modelling structure-activity relationships |
| title | Comparison of the DNA-binding interactions of 5-hydroxymethylfurfural and its synthesized derivative, 5, 5’[oxy-bis(methylene)]bis-2-furfural: experimental, DFT and docking studies |
| title_full | Comparison of the DNA-binding interactions of 5-hydroxymethylfurfural and its synthesized derivative, 5, 5’[oxy-bis(methylene)]bis-2-furfural: experimental, DFT and docking studies |
| title_fullStr | Comparison of the DNA-binding interactions of 5-hydroxymethylfurfural and its synthesized derivative, 5, 5’[oxy-bis(methylene)]bis-2-furfural: experimental, DFT and docking studies |
| title_full_unstemmed | Comparison of the DNA-binding interactions of 5-hydroxymethylfurfural and its synthesized derivative, 5, 5’[oxy-bis(methylene)]bis-2-furfural: experimental, DFT and docking studies |
| title_short | Comparison of the DNA-binding interactions of 5-hydroxymethylfurfural and its synthesized derivative, 5, 5’[oxy-bis(methylene)]bis-2-furfural: experimental, DFT and docking studies |
| title_sort | comparison of the dna binding interactions of 5 hydroxymethylfurfural and its synthesized derivative 5 5 oxy bis methylene bis 2 furfural experimental dft and docking studies |
| topic | Hydroxymethylfurfural DNA viscosity study density functional theory molecular modelling structure-activity relationships |
| url | https://www.tandfonline.com/doi/10.1080/16583655.2023.2183705 |
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