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首页> 外文期刊>Chemistry: A European journal >Structural features and hydrogen-bond properties of galanthamine and codeine: An experimental and theoretical study
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Structural features and hydrogen-bond properties of galanthamine and codeine: An experimental and theoretical study

机译：Galthamine和ComeIte的结构特征和氢键特性：实验与理论研究

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摘要

Structural features of galanthamine and codeine, two allosteric potentiating ligands of nicotinic acetylcholine receptors (nAChRs), have been investigated through experimental studies in solution by FTIR and NMR spectroscopy and by quantum chemical calculations in the isolated state. The infrared spectra accumulated in solvents of various polarities show that the intramolecular OH?O hydrogen bond in galanthamine is stronger than the corresponding interaction in codeine. Molecular electrostatic potential calculations allow rationalisation of the experimental trends. NOE measurements on the two ligands in the same solvent range show significant differences. In apolar solvents, the NMR spectroscopic data indicate the occurrence of CH?O hydrogen-bond interactions, whereas in the more polar solvents, a trans orientation of the methoxy group with respect to the furanyl oxygen atom is favoured. A natural bond orbital (NBO) analysis provides evidence that these stabilising interactions originate in the hyperconjugation between the lone pairs of the furanyl oxygen atoms, n(O), and the methoxy antibonding σ*(C-H) orbitals within the two molecules. Despite the strong structural similarities between the two allosteric modulators, FTIR equilibrium constants measurements of hydrogen-bond complexation combined with quantum chemistry calculations point out the significant increase of hydrogen-bond accepting strength of galanthamine relative to codeine. This increase is mainly assignable to the stronger hydrogen-bond basicity of the hydroxyl group, and to a lesser extent to the higher hydrogen-bond accepting strength of the amino nitrogen of galanthamine in comparison with the corresponding groups of codeine. An analysis of the interactions that occur between the two ligands and acetylcholine esterase (AChE) suggests significant differences with Trp84, a key component of the AChE catalytic active site. In contrast, both ligands appear to interact similarly with acetylcholine binding protein (AChBP).
机译：通过FTIR和NMR光谱法的溶液中的实验研究以及隔离状态的量子化学计算，研究了Galthamine和Comeince，两种变构乙酰胆碱受体（NACHRS）的构胞增强配体，并通过溶液中的量子化学计算来研究烟酰乙酰胆碱受体（NACHRS）。在各种极性的溶剂中累积的红外光谱表明，在Galanthamine中的分子内OH·o氢键比可待因的相应相互作用更强。分子静电势计算允许合理化实验趋势。在相同溶剂范围内的两个配体上的NOE测量显示出显着的差异。在恶性溶剂中，NMR光谱数据表明氢键相互作用的氢键相对，而在更极性的溶剂中，甲氧基相对于呋喃基原子的反式取向是有利的。天然键（NBO）分析提供了证据表明，这些稳定相互作用起源于两种分子内呋喃基氧原子，N（O）和甲氧基抗体σα（C-H）轨道之间的溶液对的血管间隙。尽管两种颠覆调节剂之间具有强大的结构相似性，但FTIR平衡常数与量子化学计算结合的氢键络合的测量结果指出，接受Galanthamine的氢键相对于可待因的显着增加。这种增加主要是可分配到羟基的氢键碱度较强的氢粘合性，并且在与相应的可醌的相应组相比，较高的氢键接受加蒽氨基氮的强度。对两种配体和乙酰胆碱酯酶（ACHE）之间发生的相互作用的分析表明与TRP84的显着差异，ACHE催化活性位点的关键组分。相反，两个配体似乎与乙酰胆碱结合蛋白（ACHBP）类似地相互作用。

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  • 来源
    《Chemistry: A European journal》 |2011年第41期|共13页
  • 作者

    Atkinson A.P.; Baguet E.; Galland N.; Le Questel J.-Y.; Planchat A.; Graton J.;

  • 作者单位

    Laboratoire CEISAM UMR 6230 CNRS Faculté des Sciences et des Techniques de Nantes 2 rue de la Houssinière 44322 Nantes Cedex 3 France;

    Laboratoire CEISAM UMR 6230 CNRS Faculté des Sciences et des Techniques de Nantes 2 rue de la Houssinière 44322 Nantes Cedex 3 France;

    Laboratoire CEISAM UMR 6230 CNRS Faculté des Sciences et des Techniques de Nantes 2 rue de la Houssinière 44322 Nantes Cedex 3 France;

    Laboratoire CEISAM UMR 6230 CNRS Faculté des Sciences et des Techniques de Nantes 2 rue de la Houssinière 44322 Nantes Cedex 3 France;

    Laboratoire CEISAM UMR 6230 CNRS Faculté des Sciences et des Techniques de Nantes 2 rue de la Houssinière 44322 Nantes Cedex 3 France;

    Laboratoire CEISAM UMR 6230 CNRS Faculté des Sciences et des Techniques de Nantes 2 rue de la Houssinière 44322 Nantes Cedex 3 France;

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 应用化学;
  • 关键词

    codeine; FTIR spectroscopy; galanthamine; hydrogen bonds; NMR spectroscopy; quantum chemistry;

    机译：可待因;FTIR光谱;Galthamine;氢键;NMR光谱;量子化学;

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