Analysis and modelling of the structures of β-cyclodextrin complexes

Myles, Arthur; Barlow, D. J.; Lawrence, M.J.

doi:10.1016/0304-4165(94)90092-2

Cited by 30 publications

(15 citation statements)

References 36 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The 4)/~U-values and r.m.s. fluctuations averaged over all residues are: 4)= 111.6 ° (_+12.5 °) and tP=-ll4.1 ° (_+13.9°), values which are in good agreement with those found for related disaccharides (4)/q'= 116.1°/-118.0 °) (Takusagawa and Jacobson 1978) or MD studies of ]3 CD (Myles et al 1994). Upon hydration, 4)/tPare slightly altered averaging now to: 4)= 108.6 ° (+8.8 °) and hu=-i 13.1 ° (_+13.0°).…”

Section: Conformation Of a CDsupporting

confidence: 77%

“…Two sides of a CD can be distinguished: the "mOH"-side bearing the primary hydroxyl groups C(6)H(61, 62)0(6)H(63), and the "OH"-side (secondary hydroxyl groups O(2)H(21) and O(3)H(31) ). In the cyclodextrin ring, a total of 3 hydroxyl groups per glucose residue provide donors for hydrogen-bonding based stabilisation of the macrocycle and the possibility of a flexible bonding scheme with other organic compounds in contact with czCD (Myles et al 1994). …”

Section: Molecular Modelmentioning

confidence: 99%

See 1 more Smart Citation

Molecular dynamics study of an ?-cyclodextrin-phosphatidylinositol inclusion complex

1996

View full text Add to dashboard Cite

Cyclodextrins are cyclic oligosaccharides known for their ability to include substrate molecules in their hydrophobic cavity. Moreover, cyclodextrins show a hemolytic activity when mM concentrations are added to blood. This hemolysis is commonly interpreted as a massive dissociation of phospholipids from the cell membrane due to the formation of complexes with the cyclodextrins. In the literature, a complexation between alpha-cyclodextrin (alpha CD) and phosphatidylinositol (PI) specific to the inositol headgroup has been proposed. But the need for the detailed interaction mechanism between the two molecules motivated the present work based on molecular dynamics simulations. Investigation of long range electrostatic interactions shows that a mutual approach of the molecules is only possible when the primary hydroxyl side of alpha CD faces the inositol headgroup of PI. This orientation is also the most favourable from adiabatic-and free-energy profiles calculated along a reaction coordinate that leads to an inclusion of PI into alpha CD. For free energy simulations, partial hydration of the model has been used. A study of glycosidic bond dihedral angles in alpha CD shows an increase in dihedral fluctuations before complexation and a dihedral "freezing" once the complex is formed.

show abstract

Section: Conformation Of a CDsupporting

confidence: 77%

Section: Molecular Modelmentioning

confidence: 99%

Molecular dynamics study of an ?-cyclodextrin-phosphatidylinositol inclusion complex

1996

View full text Add to dashboard Cite

show abstract

“…Association constants have been determined using a number of chemical and physical methods, such as spectroscopy, potentiometry, kinetics, and solubility techniques 10. These methods are mostly based on a typical complexation between G and CD to form a single inclusion type with a 1:1 stoichiometry and a few of the multiple‐stepwise models with 1:1 and 1:2 stoichiometries 11–14. However, very little is known concerning multiple types of inclusion complexes with 1:1 stoichiometry.…”

Section: Introductionmentioning

confidence: 99%

Multimodal Inclusion Complexes Between Barbiturates and 2‐Hydroxypropyl‐β‐Cyclodextrin in Aqueous Solution: Isothermal Titration Microcalorimetry, 13C NMR Spectrometry, and Molecular Dynamics Simulation

Aki

Niiya

Iwase

et al. 2001

Journal of Pharmaceutical Sciences

View full text Add to dashboard Cite

“…[11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28] Some of these studies have aided the interpretation of nuclear magnetic resonance (NMR) and other experimental techniques in the context of CD complexes. [23][24][25][26][27][28] However, conformational analyses of energetically stable conformations of the CDs [12][13][14] and their complexes [15][16][17][18][19][20][21][22] have been the main targeted subjects. Molecular dynamics (MD) simulations are more timeconsuming but provide a better connection between atomistic constitution and macroscopic properties when compared to pure geometry optimizations methods.…”

Section: Introductionmentioning

confidence: 99%

Revisiting the internal conformational dynamics and solvation properties of cyclodextrins

Pereira¹,

Moura²,

Freitas³

et al. 2007

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

Simulações de dinâmica molecular são utilizadas para investigar a dinâmica conformacional interna e propriedades de solvatação das três ciclodextrinas naturais, α-, β-e γ-ciclodextrina em água e temperatura ambiente. Estes oligossacarídeos derivados da glicose apresentam uma estrutura molecular peculiar que lhes confere a habilidade de formar complexos de inclusão e modificar as propriedades físico-químicas das moléculas complexadas. As características estruturais das ciclodextrinas em solução são determinantes para a complexação. As análises das trajetórias obtidas mostram que ligações de hidrogênio secundárias entre resíduos de glicose adjacentes estão presentes em solução e apresentam um caráter altamente dinâmico, onde ligações de hidrogênio alternativas podem ser formadas com moléculas de água. Apesar do baixo caráter hidrofílico, as cavidades apresentam-se solvatadas e o número de moléculas de água dentro da cavidade é aproximadamente duplicada por unidade de glicose adicionada ao macrociclo. Os tempos de residência para as moléculas de água dentro das cavidades são inversamente proporcionais ao seu respectivo tamanho.Molecular dynamics simulations were used to investigate the internal conformational dynamics and solvation properties of the three natural cyclodextrins, α-, β-and γ-cyclodextrin in aqueous solution at room temperature. These glucose-derived oligosacharides present a molecular structure that confers them the ability to complex guest molecules and change their physicochemical properties. The structural behavior of cyclodextrins in solution is crucial for their complexation abilities. Analyses of the obtained trajectories show that inter-glucose hydrogen bonds between the secondary hydroxyl groups are present in solution, but show a very dynamical character where alternative hydrogen bonds to water molecules can be formed. Despite the lower hydrophilicity of the cyclodextrins inner-cavities, they were found to be solvated and the number of water molecules inside the cavity roughly doubles per glucose unit added to the ring. The residence times for water molecules inside the cavities are inversely proportional to the cavity size. Keywords: cyclodextrins, molecular dynamics, solvation, flexibility IntroductionCyclodextrins (CDs) have been extensively studied since their discovery in the late nineteenth century.1 Their peculiar properties and behavior have interested scientists in many different fields.2 These cyclic oligosaccharides, obtained from starch by glucanotransferase degradation, are formed by a certain number of α-D-glucopyranose units linked by α(1→4) glycosidic bonds. This arrangement produces a truncated cone shape with a central cavity relatively hydrophobic and an external surface relatively hydrophilic.1-3 Naturally occurring CDs, known as α-, β-and γ-CD, present six, seven and eight glucose units, respectively.1-3 The structural features of these saccharides allow them to form inclusion complexes with a great variety of compounds.3 Due to their ability to form host-guest complexe...

show abstract

Analysis and modelling of the structures of β-cyclodextrin complexes

Cited by 30 publications

References 36 publications

Molecular dynamics study of an ?-cyclodextrin-phosphatidylinositol inclusion complex

Molecular dynamics study of an ?-cyclodextrin-phosphatidylinositol inclusion complex

Multimodal Inclusion Complexes Between Barbiturates and 2‐Hydroxypropyl‐β‐Cyclodextrin in Aqueous Solution: Isothermal Titration Microcalorimetry, 13C NMR Spectrometry, and Molecular Dynamics Simulation

Revisiting the internal conformational dynamics and solvation properties of cyclodextrins

Contact Info

Product

Resources

About