Conglomerate and racemate formation of 2,3-bisfluoren-9-ylidenesuccinic acid by inclusion complexation with achiral guest molecules

2004 ◽  
Vol 28 (3) ◽  
pp. 329 ◽  
Author(s):  
Koichi Tanaka ◽  
Toshimasa Iwamoto ◽  
Mino R. Caira
Keyword(s):  
Inclusion Complexation ◽  
Guest Molecules

Inclusion complexation involving sugar-containing species: β-cyclodextrin and sugar surfactants

2004 ◽  
Vol 82 (1) ◽  
pp. 45-49 ◽  
Author(s):  
Vincent C Reinsborough ◽  
Vanessa C Stephenson
Keyword(s):  
Surface Tension ◽  
Critical Micelle Concentration ◽  
Inclusion Complex ◽  
Computer Modeling ◽  
Inclusion Complexation ◽  
Binding Constants ◽  
Guest Molecules ◽  
Sugar Moiety ◽  
G 12 ◽  
Concentration Surface

Surface tension, proton NMR, and computer modeling studies were undertaken in nonionic alkylpolyglycoside (APG) solutions containing β-cyclodextrin (β-CD) with a view to characterize the inclusion complexes formed and to determine if the sugar entities of the host and guest molecules played a significant role in the process. The APGs investigated were four glucopyranosides (octyl G8, decyl G10, dodecyl G12, tetradecyl G14) and two maltosides (decyl M10, dodecyl M12). Critical micelle concentrations (CMC) were obtained in the surfactant–β-CD systems, which in all cases increased with increasing β-CD concentration. The 1:1 APG–β-CD inclusion complex was principally formed with binding constants of 425 (mol L–1)–1 for the G12 complex, 340 (mol L–1)–1 for the G10 complex, and 125 (mol L–1)–1 for the M12 complex. The preferred configuration of the G-12–β-CD complex has the surfactant tail coiled in the CD cavity with the surfactant sugar moiety sealing off the narrower opening of the CD torus.Key words: alkylpolyglycoside, β-cyclodextrin, NMR, critical micelle concentration, surface tension.

scholarly journals Inclusion complexes of 2-methoxyestradiol with dimethylated and permethylated β-cyclodextrins: models for cyclodextrin–steroid interaction

2015 ◽  
Vol 11 ◽  
pp. 2616-2630 ◽  
Author(s):  
Mino R Caira ◽  
Susan A Bourne ◽  
Halima Samsodien ◽  
Vincent J Smith
Keyword(s):  
Inclusion Complexes ◽  
Anticancer Agent ◽  
Inclusion Complexation ◽  
Aqueous Solubility ◽  
X Ray Diffraction ◽  
Guest Molecules ◽  
X Ray ◽  
Rapid Dissolution ◽  
First Time ◽  
Secondary Side

The interaction between the potent anticancer agent 2-methoxyestradiol (2ME) and a series of cyclodextrins (CDs) was investigated in the solid state using thermal analysis and X-ray diffraction, while the possibility of enhancing its poor aqueous solubility with CDs was probed by means of equilibrium solubility and dissolution rate measurements. Single crystal X-ray diffraction studies of the inclusion complexes between 2ME and the derivatised cyclodextrins heptakis(2,6-di-O-methyl)-β-CD (DIMEB) and heptakis(2,3,6-tri-O-methyl)-β-CD (TRIMEB) revealed for the first time the nature of the encapsulation of a bioactive steroid by representative CD host molecules. Inclusion complexation invariably involves insertion of the D-ring of 2ME from the secondary side of each CD molecule, with the 17-OH group generally hydrogen bonding to a host glycosidic oxygen atom within the CD cavity, while the A-ring and part of the B-ring of 2ME protrude from the secondary side. In the case of the TRIMEB·2ME complex, there is evidence that complexation proceeds with mutual conformational adaptation of host and guest molecules. The aqueous solubility of 2ME was significantly enhanced by CDs, with DIMEB, TRIMEB, randomly methylated β-CD and hydroxypropyl-β-CD being the most effective hosts. The 2:1 host–guest β-CD inclusion complex, prepared by two methods, yielded very rapid dissolution in water at 37 °C relative to untreated 2ME, attaining complete dissolution within 15 minutes (co-precipitated complex) and 45 minutes (complex from kneading).

Crystalline inclusion complexes as media of molecular recognitions and selective reactions

2001 ◽  
Vol 73 (7) ◽  
pp. 1137-1145 ◽  
Author(s):  
Fumio Toda
Keyword(s):  
Inclusion Complexes ◽  
Chemical Reaction ◽  
Active Compound ◽  
Inclusion Complexation ◽  
Photochemical Reactions ◽  
Optically Active ◽  
Crystalline Inclusion ◽  
Guest Molecules ◽  
Water Suspension ◽  
Enantioselective Reactions

Hexaol host compounds which include guest molecules maximum in 1:6 ratio were prepared. Aromatic hexaol host, hexahydroxytriphenylene, was found to form chiral inclusion crystal by complexation with achiral guest molecules. Some interesting and important optical resolutions of rac-guests by inclusion complexation with a chiral host were described. When chemical reaction and the inclusion complexation procedures in a water suspension medium are combined, new economical and ecological method of the preparation of optically active compound can be established. When photochemical reactions are carried out in an inclusion crystal with a chiral host, enantioselective reactions occur, and optically active product can be obtained. Several successful reactions are described.

scholarly journals Computational Insights Into the Influence of Substitution Groups on the Inclusion Complexation of β-Cyclodextrin

2021 ◽  
Vol 9 ◽  
Author(s):  
Xianghua Yan ◽  
Yue Wang ◽  
Tong Meng ◽  
Hui Yan
Keyword(s):  
Aromatic Hydrocarbons ◽  
Inclusion Complexation ◽  
Md Simulations ◽  
Ring Structure ◽  
Water Soluble ◽  
The Other ◽  
Guest Molecules ◽  
Hydrophobic Cavity ◽  
Polycyclic Aromatic ◽  
The Stability

Cyclodextrins (CDs) and their derivatives have good prospects in soil remediation application due to their ability to enhance the stability and solubility of low water-soluble compounds by inclusion performance. To investigate the effect of different structural properties of cyclodextrin and its derivatives on the inclusion complexation, molecular dynamic (MD) simulations were performed on the inclusion complexes formed by three kinds of CDs with polycyclic aromatic hydrocarbons (PAHs). Based on neutral β-CD, the other two CDs were modified by introducing substitutional groups, including 2-hydroxypropyl and sulfonated butyl (SBE) functional groups in the ring structure, called HP-CD and SBE-CD. MD results show that PAH can merely enter into the cavity of SBE–β-CD from its wide rim. The substitutional groups significantly affect the structure of CDs, which may also cause the flipping of the glucose units. However, the substitutional groups can also enlarge the volume of the hydrophobic cavity, resulting in a tight combination with the guest molecules.

scholarly journals Inclusion Complexation of Benzanilide and Fast Violet B with β-cyclodextrin-A Theoretical Approach

2020 ◽  
pp. 23-28
Author(s):  
A. Antony Muthu Prabhu
Keyword(s):  
Gas Phase ◽  
Aromatic Ring ◽  
Inclusion Complexes ◽  
Theoretical Investigation ◽  
Theoretical Approach ◽  
Inclusion Complexation ◽  
The Other ◽  
Guest Molecules ◽  
Och3 Group ◽  
Structural Assignment

The theoretical investigation of inclusion complexation of amide-imidol tautomer of two guest molecules benzanilide (BA) and fast violet B (FVB) with β-cyclodextrin (β-CD) using DFT B3LYP 3-21G  method in the gas phase. Benzanilide has no substitution in the basic skeleton and the other selected compound substituted with three groups such as –NH2, -CH3 and –OCH3 group in the same aromatic ring. The tautomer  of two selected compounds was formed the stable inclusion complexes with the β-CD supramolecule. The theoretically calculated complexation energy was observed the negative value for all the inclusion complexes. This method was applicable to determine the structural assignment of the inclusion complexes between BA, FVB and β-CD.

Synthesis of Amylosic Supramolecular Materials by Glucan Phosphorylase-Catalyzed Enzymatic Polymerization According to the Vine-Twining Approach

Synlett ◽  
2020 ◽  
Vol 31 (07) ◽  
pp. 648-656 ◽  
Author(s):  
Jun-ichi Kadokawa
Keyword(s):  
Inclusion Complexes ◽  
Inclusion Complexation ◽  
Soft Materials ◽  
Enzymatic Polymerization ◽  
Hierarchical Architecture ◽  
Supramolecular Network ◽  
Guest Molecules ◽  
Supramolecular Materials ◽  
Glucan Phosphorylase ◽  
Supramolecular Networks

This article overviews the synthesis of amylosic supramolecular materials through inclusion complexation in glucan phosphorylase (GP)-catalyzed enzymatic polymerization. Amylose is a polysaccharide that is known to form inclusion complexes with a number of hydrophobic small guest molecules. A pure amylose can be synthesized by the enzymatic polymerization of α-d-glucose 1-phosphate monomer with a maltooligosaccharide primer catalyzed by GP. The author has reported that the propagating amylosic chain in the enzymatic polymerization twines around hydrophobic polymers present in aqueous reaction media to form supramolecular inclusion complexes. As it is similar to the way that vines of a plant grow around a rod, this polymerization is termed ‘vine-twining polymerization’. Amylosic supramolecular network materials have been obtained through the vine-twining polymerization by using copolymers, where hydrophobic guest polymers are covalently grafted on hydrophilic main-chain polymers. The enzymatically produced amylosic chains form complexes with the guest polymers among graft copolymers, which act as cross-linking points to form supramolecular networks, resulting in the formation of soft materials, such as gels and films. Vine-twining polymerization using appropriately designed guest polymers has also been performed, which leads to supramolecular products that exhibit new functionality.1 Introduction2 Vine-Twining Polymerization to Form Supramolecular Inclusion Complexes3 Selective Complexation of Amylose toward Guest Polymers in Vine-Twining Polymerization4 Hierarchical Architecture of Amylosic Supramolecular Network Materials by Vine-Twining Polymerization Approach5 Hierarchical Fabrication of Amylosic Supramolecular Materials by Vine-Twining Polymerization Using Designed Guest Polymers6 Conclusions

scholarly journals Cyclodextrins and ternary complexes: technology to improve solubility of poorly soluble drugs

2011 ◽  
Vol 47 (4) ◽  
pp. 665-681 ◽  
Author(s):  
Janisse Crestani de Miranda ◽  
Tércio Elyan Azevedo Martins ◽  
Francisco Veiga ◽  
Humberto Gomes Ferraz
Keyword(s):  
Inclusion Complexation ◽  
Main Property ◽  
High Volume ◽  
Water Soluble ◽  
Guest Molecules ◽  
Water Soluble Polymers ◽  
Soluble Polymers ◽  
Host Molecules ◽  
Poorly Soluble ◽  
Low Soluble Drugs

Cyclodextrins (CDs) are cyclic oligosaccharides composed of D-glucopyranoside units linked by glycosidic bonds. Their main property is the ability to modify the physicochemical and biological characteristics of low-soluble drugs through the formation of drug:CD inclusion complexes. Inclusion complexation requires that host molecules fit completely or partially within the CD cavity. This adjustment is directly related to the physicochemical properties of the guest and host molecules, easy accommodation of guest molecules within the CD cavity, stoichiometry, therapeutic dose, and toxicity. However, dosage forms may achieve a high volume, depending on the amount of CD required. Thus, it is necessary to increase solubilization efficiency in order to use smaller amounts of CD. This can be achieved by adding small amounts of water-soluble polymers to the system. This review addresses aspects related to drug complexation with CDs using water-soluble polymers to optimize the amount of CD used in the formulation in order to increase drug solubility and reduce dosage form volume.

Tuning the configuration of the flexible metal–alkene-framework affords pure cycloisomers in solid state photodimerization

2021 ◽  
Author(s):  
Yong Wang ◽  
Meng-Fan Wang ◽  
David James Young ◽  
Hua Zhu ◽  
Fei-Long Hu ◽  
...  
Keyword(s):  
Solid State ◽  
Cycloaddition Reaction ◽  
Guest Molecules ◽  
Flexible Metal

The bulkiness of the guest molecules influences the conformations of the ligand and the final outcomes of the cycloaddition reaction.

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