Synthesis and α-Glucosidase Inhibitory Mechanisms of Bis(2,3-dibromo-4,5-dihydroxybenzyl) Ether, a Potential Marine Bromophenol α-Glucosidase Inhibitor
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis of BDDE
2.2. BDDE Binding Quenched the Intrinsic Fluorescence of α-Glucosidase
2.3. BDDE Binding Reduced the Hydrophobicity of α-Glucosidase
2.4. BDDE Binding Influenced the Secondary Structures of α-Glucosidase
2.5. Protein 3D Structure Generation and Molecular Docking
3. Experimental Section
3.1. Materials
3.2. Synthesis of BDDE
3-Bromo-4-hydroxy-5-methoxybenzaldehyde (2)
3-Bromo-4,5-dimethoxybenzaldehyde (3)
2,3-Dibromo-4,5-dimethoxybenzaldehyde (4)
(2,3-Dibromo-4,5-dimethoxyphenyl)methanol (5)
5,5′-Oxybis(methylene)bis(3,4-dibromo-1,2-dimethoxybenzene) (6)
Bis(2,3-dibromo-4,5-dihydroxybenzyl) ether (7)
3.3. Intrinsic Fluorescence Measurements
3.4. Hydrophobic Analysis of α-Glucosidase Using Bis-ANS
3.5. Circular Dichroism Spectroscopy
3.6. Molecular Modeling and Docking
4. Conclusions
Acknowledgments
- Samples Availability: Available from the authors.
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Marine bromophenol | (μM) | Inhibition mode | Reference |
---|---|---|---|
Bis(2,3,6-tribromo-4,5-dihydroxybenzyl) ether | 0.03 | Unknown | [13] |
Bis(2,3-dibromo-4,5-dihydroxybenzyl) ether | 0.098 | Competitive | [12,13,15] |
2,3,6-Tribromo-4,5-dihydroxybenzyl alcohol | 11 | Mixed | [15] |
4-Bromo-2,3-dihydroxy-6-hydroxymethylphenyl-2,5-dibromo-6-hydroxy-3-hydroxymethylphenyl ether | 25 | Unknown | [12] |
2,4,6-Tribromophenol | 60.3 | Mixed | [14] |
2,3-Dibromo-4,5-dihydroxybenzyl alcohol | 89 | Mixed | [12] |
3-Bromo-4,5-dihydroxybenzyl alcohol | 100 | Mixed | [13] |
2,4-Dibromophenol | 110.4 | Mixed | [14] |
BDDE (μM) | α-Helix (%) | β-Sheet (%) | β-Turn (%) | Random (%) |
---|---|---|---|---|
0 | 27.5 | 39.4 | 7.1 | 26 |
25 | 30.3 | 33.8 | 5.6 | 30.3 |
50 | 28.9 | 34.7 | 8.3 | 28.2 |
100 | 31.2 | 31.6 | 7.1 | 30.2 |
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Liu, M.; Zhang, W.; Wei, J.; Lin, X. Synthesis and α-Glucosidase Inhibitory Mechanisms of Bis(2,3-dibromo-4,5-dihydroxybenzyl) Ether, a Potential Marine Bromophenol α-Glucosidase Inhibitor. Mar. Drugs 2011, 9, 1554-1565. https://doi.org/10.3390/md9091554
Liu M, Zhang W, Wei J, Lin X. Synthesis and α-Glucosidase Inhibitory Mechanisms of Bis(2,3-dibromo-4,5-dihydroxybenzyl) Ether, a Potential Marine Bromophenol α-Glucosidase Inhibitor. Marine Drugs. 2011; 9(9):1554-1565. https://doi.org/10.3390/md9091554
Chicago/Turabian StyleLiu, Ming, Wei Zhang, Jianteng Wei, and Xiukun Lin. 2011. "Synthesis and α-Glucosidase Inhibitory Mechanisms of Bis(2,3-dibromo-4,5-dihydroxybenzyl) Ether, a Potential Marine Bromophenol α-Glucosidase Inhibitor" Marine Drugs 9, no. 9: 1554-1565. https://doi.org/10.3390/md9091554