Structural aspects of crystalline derivatized cyclodextrins and their inclusion complexes

Current Organic Chemistry

Volumn 15, Issue 6, 2011, Pages 815-830

  Caira, Mino R ^a  

^a UNIVERSITY OF CAPE TOWN   (South Africa)

Author keywords

Crystal packing; Derivatized cyclodextrins; Host conformation; Host design; Isostructurality; Powder X ray diffraction; Single crystal X ray diffraction; Supramolecular structures

Indexed keywords

CYCLODEXTRINS; X RAY DIFFRACTION ANALYSIS;

CRYSTAL PACKINGS; DERIVATIZED CYCLODEXTRIN; HOST CONFORMATION; HOST DESIGN; INCLUSION COMPLEX; ISOSTRUCTURALITY; SINGLE CRYSTAL X-RAY DIFFRACTION; STRUCTURAL ASPECTS; SUPRAMOLECULAR STRUCTURE; X- RAY DIFFRACTIONS;

SINGLE CRYSTALS;

EID: 80051813596     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527211794518862     Document Type: Review

References (52)

1. Steiner, T; Saenger, W. Closure of the cavity in permethylated cyclodextrinsthrough glucose inversion, flipping and kinking. Angew. Chem. Int. Ed.,1998, 37, 3404-3407.
2. 4conformation of a methylglucose residue in crystalline permethyl-β-cyclodextrin monohydrate. J. Chem. Soc., Perkin Trans., 1994, 2071-2072.
3. Frömming, K.H.; Szejtli, J. Cyclodextrins in Pharmacy, Kluwer: Dordrecht, 1994.
4. Harata, K. In: Cyclodextrins and Their Complexes; Dodziuk, H., Ed.; Wiley-VCH Verlag GmBH & Co. KgaA: Weinheim, 2006, pp. 147-198.
5. Hattori, K.; Ikeda, H. In: Cyclodextrins and Their Complexes; Dodziuk, H., Ed.; Wiley-VCH Verlag GmBH & Co. KgaA: Weinheim, 2006, pp. 31-64.
6. Rissanen, K. In: Analytical Methods in Supramolecular Chemistry, Schalley, C.S., Ed.; Wiley-VCH Verlag GmBH & Co. KgaA: Weinheim, 2007, pp.305-336.
7. Caira, M.R. On the isostructurality of cyclodextrin inclusion complexes andits practical utility. Rev. Roum. Chim., 2001, 46, 371-386.
8. Cambridge Structural Database and Cambridge Structural Database System, ConQuest Version 1.11, Cambridge Crystallographic Data Centre, University Chemical Laboratory: Cambridge, England, 2009.
9. Grandeury, A.; Renou, L.; Dufour, F.; Petit, S.; Gouhier, G.; Coquerel, G. Chiral resolution by crystallization of host-guest supramolecular complexes. J. Therm. Anal. Calorim., 2004, 77, 377-390.
10. Caira, M.R.; Mhlongo, W.T.; Li, J. Structural elucidation of chemically modified cyclodextrins and their inclusion complexes for medicine applications.J. Optoelect. Adv. Mater., 2008, 10, 2255-2260.
11. Cruickshank, D.; Rougier, N.M.; Vico, R.V.; de Rossi, R.H.; Buján, E.I.; Bourne, S.A.; Caira, M.R. Solid-state structures and thermal properties of inclusion complexes of the organophosphate insecticide fenitrothion with permethylatedcyclodextrins. Carbohydr.Res., 2010, 345, 141-147.
12. Takashima, Y.; Sakamoto, K.; Oizumi, Y.; Yamaguchi, H.; Kamitori, S.; Harada, A. Complex formation of cyclodextrins with various thiophenes andtheir polymerization in water: preparation of poly-pseudo-rotaxanes containingpoly(thiophene)s. J. Incl. Phenom. Macrocycl. Chem., 2006, 56, 45-53.
13. Pereira, C.L.L.; Diogo, C.V.; Burgeiro, A.; Oliveira, P.J.; Marques, M.P.M.; Braga, S.S.; Almeida Paz, F.A.; Pillinger, M.; Gonçalves, I.S. Complex formationbetween heptakis(2,6-di-O-methyl)-β-cyclodextrin and cyclopentadienylmolybdenum(II) dicarbonyl complexes: structural studies and cytotoxicityevaluations. Organometallics, 2008, 27, 4948-4956.
14. Caira, M.R.; Bourne, S.A.; Dean, P.M.; Mhlongo, W.T. New crystallineforms of permethylated β-cyclodextrin. Chem. Commun.,2004, 2216-2217.
15. Shi, J; Guo, D.S.; Ding, F; Liu, Y. Unique regioselective binding of permethylated β-cyclodextrin with azobenzene derivatives. Eur. J. Org. Chem.2009, 923-931.
16. Mieusset, J.L.; Krois, D.; Pacar, M.; Brecker, L.; Giester, G.; Brinker, U.H. Supramolecular recognition and structural elucidation of inclusion complexesof an achiral carbene precursor in β-and permethylated β-cyclodextrin. Org. Lett., 2004, 6, 1967-1970.
17. 2Cl. Organometallics, 2007,26, 6857-6863.
18. Pereira, C.L.L.; Nolasco, M.; Braga, S.S.; Almeida Paz, F.A.; Ribeiro-Claro, P.; Pillinger, M.; Gonçalves, I.S. A combined theoretical-experimental studyof the inclusion of niobocene dichloride in native and permethylated β-cyclodextrins. Organometallics, 2007, 26, 4220-4228.
19. Hunter, R.; Kaschula, C.H.; Parker, I.Q.; Caira, M.R.; Richards, P.; Travis, S.; Taute, F.; Qwebani, T. Substituted ajoenes as novel anti-cancer agents. Bioorg. Med. Chem. Lett., 2008, 18, 5277-5279.
20. Caira, M.R.; Hunter, R.; Bourne, S.A.; Smith, V.J. Preparation, thermal behaviour, and solid-state structures of inclusion compounds of permethylated β-cyclodextrin with the garlic-derived antithrombotics (E)- and (Z)-Ajoene. Supramol. Chem., 2004, 16, 395-403.
21. Stellenboom, N.; Hunter, R.; Caira, M.R.; Bourne, S.A.; Cele, K.; Qwebani, T.; le Roex, T. Synthesis and inclusion of S-aryl alkylthiosulfinates as stableAllicin mimics. ARKIVOC, 2007, (ix), 53-63.
22. Caira, M.R.; Bourne, S.A.; Vilakazi, S.L; Reddy, L. Inclusion of anestheticsin cyclodextrins: structural investigation of solid inclusion complexes of butamben.Supramol. Chem., 2004, 16, 279-285.
23. Caira, M.R.; Giordano, F.; Vilakazi, S.L. X-ray structure and thermal propertiesof a 1:1 inclusion complex between permethylated β-cyclodextrin and Psoralen. Supramol. Chem., 2004, 16, 389-393.
24. Dean, P.M. Structural and thermal characterization of cyclodextrin-suprofen Complexes. Austr. J. Chem., 2007, 60, 133-138.
25. Marques, J.; Santos, T.M.; Marques, M.P.; Braga, S.S. A glycine rutheniumtrithiacyclononane complex and its molecular encapsulation using cyclodextrins.Dalton Trans., 2009, 9812-9819.
26. Morillo, E. In: Cyclodextrins and Their Complexes; Dodziuk, H., Ed.; Wiley-VCH Verlag GmBH & Co. KgaA: Weinheim, 2006, pp. 459-466.
27. Tsorteki, F.; Bethanis, K.; Mentzafos, D. Structure of the inclusion complexesof heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin with indole-3-butyricacid and 2,4-dichlorophenoxyacetic acid. Carbohydr. Res., 2004, 339, 233-240.
28. Tsorteki, F.; Bethanis, K.; Pinotsis, N.; Giastas, P.; Mentzafos, D. Inclusioncompounds of plant growth regulators in cyclodextrins. V. 4-chlorophenoxyacetic acid encapsulated in β-cyclodextrin and heptakis(2,3,6-tri-O-methyl)- β-cyclodextrin. Acta Crystallogr.Section B: Structural Science.,2005, 61, 207-217.
29. Ferron, L.; Guillen, F.; Coste, S.; Coquerel, G.; Plaquevent, J.C. Is the opticalrotation sign/absolute configuration relationship still a problem? Examplestaken from unnatural quaternary aminoacids. CHIRALITY. 2006, 18,662-666.
30. Grandeury, A.; Petit, S.; Coste, S; Coquerel, G.; Perrio, C; Gouhier, G. Newsynthesis of (Z,E)-2,7-bis(4-cyanobenzylidene)cycloheptan-1-one understereospecific constraints induced by host-guest interactions. Chem. Commun.,2005, 4007-4009.
31. Caira, M.R.; Cruickshank, D. Effect of perethylation on the conformation of γ-cyclodextrin. Supramol. Chem., 2009, 21, 473-478.
32. Anibarro, M.; Gessler, K.; Uson, I.; Sheldrick, G.M.; Harata, K.; Uekama, K.; Hirayama, F.; Abe, Y.; Saenger, W. Effect of peracylation of β-cyclodextrin on the molecular structure and on the formation of inclusioncomplexes: an x-ray study. J. Am. Chem. Soc., 2001, 123, 11854-11862.
33. Bettinetti, G.; Sorrenti, M.; Catenacci, L.; Ferrari, F.; Rossi, S. Polymorphism,pseudopolymorphism, and amorphism of peracetylated α-, β-, and γ-cyclodextrins. J. Pharm.Biomed. Anal., 2006, 41, 1205-1211.
34. Caira, M.R.; Bettinetti, G.; Sorrenti, M.; Catenacci, L.; Cruickshank, D.; Davies, K. Effect of peracetylation on the conformation of γ-cyclodextrin.Chem. Commun., 2007, 1221-1223.
35. Bettinetti, G.P; Mura, P.; Faucci, M.T.; Sorrenti, M.; Setti, M. Interaction ofnaproxen with noncrystalline acetyl β- and acetyl γ-cyclodextrins in the solidand liquid state. Eur. J. Pharm. Sci. 2002, 15,21-29.
36. I-O-(3-nitrophenyl)cyclomaltoheptaose. Carbohydr.Res., 2005, 340, 513-517.
37. Zhao, Y.; Liu, Y. Self-assembly behavior of phenyl modified β-cyclodextrins. Science in China, Series B: Chemistry, 2006, 49, 230-237.
38. Tellini, V.H.S.; Jover, A.; Galantini, L; Meijide, F.; Tato, J.V. Crystal structureof the supramolecular linear polymer formed by the self-assembly ofmono-6-deoxy-6-adamantylamide- β-cyclodextrin. Acta Crystallogr., SectionB: Structural Science, 2004, 60, 204-210.
39. Armspach, D.; Poorters, L.; Matt, D.; Benmerad, B.; Balegroune, F.; Toupet, L. A new approach to A, B-di-functionalization of cyclodextrins using bulky1,3-bis [bis(aryl)chloromethyl]benzene as capping reagents. Org. Biomol.Chem., 2005, 3, 2588-2592.
40. Poorters, L.; Armspach, D.; Matt, D.; Toupet, L.; Choua, S.; Turek, P. Synthesis and properties of TRANSDIP, a rigid chelator built upon a cyclodextrincavity: Is TRANSDIP an authentic trans-spanning ligand? Chem. Eur. J.2007, 13, 9448-9461.
41. 3-ion. AngewandteChemie., Int. Ed., 2007, 46, 2663-2665.
42. Benmerad, B.; Claire, P.; Armspach, D.; Matt, D.; Balegroune, F.; Toupet, L. Sulfur-capped cyclodextrins: a new class of cavitands with extroverted aswell as Introverted donor functionalities. Chem. Commun., 2006, 2678-2680.
43. Armspach, D.; Poorters, L.; Matt, D.; Benmerad, B.; Jones, P.; Dix, I.; Toupet, L. Cyclodextrin-based thiacavitands as building blocks for the constructionof metallo-nanotubes. J. Incl. Phenom. Macrocycl. Chem., 2007, 57,243-250.
44. Poorters, L.; Armspach, D.; Matt, D.; Toupet, L. α-TEPHOS: a cyclodextrinderivedtetraphosphine for multiple metal binding. Dalton Trans., 2007, 29,3195-3202.
45. 2O. Z. Kristallogr. NCS, 2009, 224, 265-268.
46. Bonnet, C.; Gadelle, A.; Pecaut, J.; Fries, P. H.; Delangle, P. Inclusion complexesof trivalent lutetium cations with an acidic derivative of per(3,6-anhydro)-α-cyclodextrin. Chem. Commun., 2005, 625-627.
47. Baudin, C.; Camara, M.; Navaza, A. Supramolecular crystal structures ofper(3,6-anhydro)- α-cyclodextrin grown from KCl or NaI solutions. J. Mol.Struct., 2007, 839, 58-63.
48. Geisselmann, A.; Kluefers, P.; Kropfgans, C.; Mayer, P.; Piotrowski, H. Carbohydrate-metal interactions shaped by supramolecular assembling. AngewandteChemie., Int. Ed., 2005, 44, 924-927.
49. Cooper, A.; Nutley, M.; MacLean, E.J.; Cameron, K.; Fielding, L.; Mestres, J.; Palin, R. Mutual induced fit in cyclodextrin-rocuronium complexes. Org.Biol. Chem., 2005, 3, 1863-1871.
50. Kraus, T.; Budesinsky, M.; Cisarova, I.; Zavada, J. A homologous series ofpersubstituted cyclodextrin amino acids: the quest for tubular self-assembly.Eur. J. Org. Chem., 2004, 4060-4069.
51. Giastas, P.; Eliadou, K.; Plyta, Z.F.; Yannakopoulo, K.; Mavridis, I.M. X-ray crystallography and solution NMR spectroscopy characterization of heptakis(2,3-di-O-acetyl-6-bromo-6-deoxy)cyclomaltoheptaose. Carbohydr.Res., 2004, 339, 1189-1194.
52. Paulidou, A.; Giastas, P.; Moutzis, N.; Yannakopolou, K.; Mavridis, I.M. Crystal and molecular structure of octakis(6-bromo-6-deoxy)-γ-cyclodextrin.A novel stacking of a distorted macrocycle. Carbohydr. Res., 2007, 342,1519-1524.