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Molecular recognition between 4aS/R-galanthamine diastereoisomers and α-cyclodextrin

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Abstract

Molecular recognition between 4aS/R-galanthamine diastereoisomers (1: 4aS-galanthamine; 2: 4aR-galanthamine) and α-cyclodextrin (α-CD) were studied by use of docking and molecular dynamics (MD) simulation approaches. The binding energy of constructed 2···α-CD complexes is ~17 kcal mol−1 lower than that of 1···α-CD, implying a stronger binding ability of 2 with α-CD than that of 1. The theoretical modeling result is consistent with our previous CZE result, which demonstrated that α-CD is an efficient chiral additive for separating 1 and 2. The modeling result also indicates that both hydrophobic interaction and H-bond force may work as major factors for molecular recognition between the galanthamine diastereoisomers and α-CD.

Figure Chemical structures of 4aS-galanthamine (left) and 4aR-galanthamine (right)

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Abbreviations

Galanthamine:

4aS,6R,8aS-4a,5,9,10,11,12-Hexahydroxy-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-e,f]benzazepin-6-ol

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Acknowledgements

This work was supported by the Chinese National Natural Science Foundation (No. 20132020 and No. 20175026), The Ministry of Science and Technology, The Chinese Ministry of Education and Tsinghua University, and The Tianjin Science Foundation (No. 023606511).

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Authors and Affiliations

  1. The Key Laboratory of Bioorganic Phosphorus Chemistry, Ministry of Education, China; Department of Chemistry, School of Life Science and Engineering, Tsinghua University, 100084, Beijing, China

    Ming Sun, Xiaohong Liu, Liushui Yan, Guoan Luo & Yufen Zhao

  2. School of Chemistry and Life Science, Tianjin Normal University, 300074, Tianjin, China

    Ming Sun

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  1. Ming Sun
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  2. Xiaohong Liu
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  3. Liushui Yan
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  4. Guoan Luo
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  5. Yufen Zhao
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Correspondence to Yufen Zhao.

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Sun, M., Liu, X., Yan, L. et al. Molecular recognition between 4aS/R-galanthamine diastereoisomers and α-cyclodextrin. J Mol Model 9, 419–422 (2003). https://doi.org/10.1007/s00894-003-0162-9

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  • DOI: https://doi.org/10.1007/s00894-003-0162-9

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