Cyclodextrins inclusion chemistry

Bakkour Y, Vermeersch G, Morcellet M, Boschin F, Martel B, Azaroual N. 2006. Formation of cyclodextrin inclusion complexes with doxycyclin-hyclate NMR investigation of their characterisation and stability. Journal of Inclusion Phenomena and Macrocyclic Chemistry 54(1-2) 109-114. 

Furuta T, Yoshii H, Miyamoto A, Yasunishi A, Hirano H. 1993. Effects of water of inclusion complexes of D-limonene and cyclodextrins. Supramolecular Chemistry 1 321-325. 

The gas-phase chemistry of cyclodextrin inclusion complexes 01ACR653. 

Recently marked progress was made in cyclodextrin chemistry. In this review we dealt with only the materials relevant to the use of cyclodextrins as enzyme models since it is beyond the scope of this review to cover all the papers in this field. During this decade, many X-ray analyses of cyclodextrin inclusion complexes were made, giving much important information. Readers who are interested in them are recommended to refer to the book on cyclodextrin chemistry [1]. 

Individual reaction in living organisms is strictly controlled by reactant-substrate specificity, as exemplified in enzymatic reactions, even though the total mode of action is systematically controlled by correlation with other reactions. Host-guest interaction in inclusion chemistry using cyclodextrin [3] is a typical example of specific reactions in an artificial field. On the other hand, nonspecific catalysts that are tolerant to various functional... 

The chemistry of inclusion compounds also looks back on a lively history There are many events of significance in the area of inclusion chemistry till the middle of the twentieth century including the discovery of new inclusion compounds and hosts (Fig. 1), among them the graphite intercalates, the P-quinol and cyclodextrin inclusion compounds, the Hofmann-type clathrates as well as the inclusion compounds of tri-o-thymotide, Dianin s compound, the choleic acids, of phenols, of urea and others specified in comprehensive monographs... 

Yuan, C and ZY Jin (2008). Preparation and stabihty of the inclusion complex of astaxanthin with hydroxypropyl-beta-cyclodextrin. Pood Chemistry, 109(2), 264-268. 

Liu, L, KS Song, XS Li, and QX Guo (2001). Charge-transfer interaction A driving force for cyclodextrin. Inclusion complexation. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 40, 35-39. 

Warmuth R (2012) Carcerands and hemicarcerands. In Gale PA, Steed JW (eds) Supramolecular chemistry from molecules to nanomaterials, vol 3. Wiley, New York, pp 917-954 Li J (2009) Cyclodextrin inclusion polymers forming hydrogels. In Wenz G (ed) Inclusion polymers, vol 222. Springer, Berlin, pp 175-203 Chen G, Jiang M (2011) Chem Soc Rev 40 2254-2266 Harada A, Takashima Y, Yamaguchi H (2009) Chem Soc Rev 38 875-882 Chen Y, Liu Y (2010) Chem Soc Rev 39 495-505... 

R208 A. Moreira da SUva, Food Antioxidants Cyclodextrin Inclusion Compounds Molecular Spectroscopic Studies and Molecular ModeUing , in Macrocyclic Chemistry, eds. D. W. Fitzpatrich and H. J. Ulrich, Nova Science Pubhshers, Inc. Hauppauge, N. Y., 2010, p. 447. 

The Joint Meeting comprising the 3rd International Symposium on Clathrate Compounds and Molecular Inclusion Phenomena and the 2nd International Symposium on Cyclodextrins was held on 23-27 July, 1984, in Tokyo, Japan. It was organized by the Japan Association for Inclusion Chemistry together with the International Organization Committee, with the auspices of sixteen societies and associations in Japan. This event was the first joint meeting with the hope of unifying the above two symposia. 

For inclusion of cyclodextrins, interested readers may see Bender, M. L. Komiyama, M. Cyclodextrin Chemistry, Springer-Verlag, Berlin, 1978. 

In principle, mass spectrometry is not suitable to differentiate enantiomers. However, mass spectrometry is able to distinguish between diastereomers and has been applied to stereochemical problems in different areas of chemistry. In the field of chiral cluster chemistry, mass spectrometry, sometimes in combination with chiral chromatography, has been extensively applied to studies of proton- and metal-bound clusters, self-recognition processes, cyclodextrin and crown ethers inclusion complexes, carbohydrate complexes, and others. Several excellent reviews on this topic are nowadays available. A survey of the most relevant examples will be given in this section. Most of the studies was based on ion abundance analysis, often coupled with MIKE and CID ion fragmentation on MS " and FT-ICR mass spectrometric instruments, using Cl, MALDI, FAB, and ESI, and atmospheric pressure ionization (API) methods. 

Miertus, S., Nair, A. C., Frecer, V., Chiellini, E., Chiellini, R, Solaro, R. and Tomasi, J. Modelling of 3-cyclodextrin with L-a-aminoacids residnes. J. of Inclusion Phenomena and Marcrocyclic Chemistry, 1999, 34, 69-84. 

It should be stressed that there is not alwaysjustice in reseach evaluation. The selective formation of inclusion complexes by cyclodextrins (such as 11) was established by Cramer [6] at least 15 years earlier than that by crown ethers. However, cyclodextrin studies forming an independent branch of host-guest chemistry seem underestimated in spite of their considerably greater practical importance at present than that of other host macrocycles (crown ethers 17, calixarenes 18, etc.). Sometimes they are even totally neglected by discussing inclusion phenomena [7]. 

Let us compare the methods applied by Pedersen for establishing the complex formation with a modern approach. Today tedious solubility studies are carried out almost exclusively with practical applications in mind, but they are not performed to prove the complex formation. For instance, one ofthe main reasons for the use of cyclodextrin complexes in the pharmaceutical industry is their solubilizing effect on drugs [8]. There, and almost only there, solubility studies are a must. As concerns spectroscopic methods, at present the NMR technique is one ofthe main tools enabling one to prove the formation of inclusion complex, carry out structural studies (for instance, making use of the NOE effect [9a]), determine the complex stability [9b, c] and mobility of its constituent parts [9d]. However, at the time when Pedersen performed his work, the NMR method was in the early stage of development, and thus inaccurate, and its results proved inconclusive. UV spectra retained their significance in supramolecular chemistry, whilst at present the IR method is used to prove the complex formation only in very special cases. 

Reviews, 1998, 98, (5) covers several aspects of CDs chemistry while the books listed below mainly present their applications (b) Comprehensive Supramolecular Chemistry, v. 3, J. Szejtli, Ed., Kluwer Academic Publishers, Elsevier, Oxford, 1996 J. Szejtli, Cyclodextrin Technology, Kluwer, Dordrecht, 1988 (c) Cyclodextrins and Their Industrial Uses, D. Duchene, Ed., Edition du Sante, Paris, France, 1987 New Trends in Cyclodextrins and Derivatives, D. Duchene, Ed., Edition du Sante, Paris, France. 1991 (d) W. Saenger, Angew. Chem. Int. Ed. Engl., 1980, 19, 344 W. Saenger, in Inclusion Compounds, J. T. Atwood. J. E. D. Davies, D. D. MacNicol, Eds., v. 2, Academic Press. London, 1984, p. 231 K. Harata, ibid., v. 5, 1991, p. 311. 

Electrostatic self-assembly was combined with supramolecular chemistry to obtain inclusion complexes of a polymeric nonlinear optical (NLO) active dye and modified [3-cyclodextrin with induced chromophore orientation [37], The polyanion is a N,N-diallyl-aniline and sodium-2-acrylamido-2-methylpropanesulfonate copolymer functionalized with pendant azo group. The modified /i-cyclodextrin oligo-cation was obtained by treatment of hcptakis(6-dco y-6-iodo-/i-cyclodcxtrin) with excess pyridine. A linear polyamine, chitosan, was also combined with the polyanion, for comparison. Films were deposited on glass slides by dipping them alternatively in aqueous solutions of the cation and the polyanion. UV-visible spectra indicate dye aggregation and suggest the formation of an inclusion complex of the dye with the cyclodextrin, thus isolating the chromophores. 

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