Research Projects
A. Cyclodextrin Inclusion
Complexes:
crystalline state and solution structures and properties
Figure 1.
Schematic view of the
βCD
(pink) dimer formation upon inclusion of a guest molecule (blue).
Organisation of the dimers into 2-D layers. Packing of the layers into
four distinct modes: (a) Channel
(CH), the guest in the cavity is shielded from the aqueous environment.
(b) Chessboard (CB), the
guest end-groups emerging from the primary sides of the dimer are
exposed to the aqueous environment. (c)
Intermediate
(IN)
a case in-between the CH and CB modes, adjacent layers are parallel, but
the dimer’s 7-fold axis forms an angle of about 20o with the
stacking axis. Consequently, dimers are far from exactly aligned, thus a
breaking of the channel is observed that leaves parts of the guests free
to interact with hydroxy groups of adjacent hosts, as well as with water
molecules. (d) Screw Channel (SC), where although the lateral
displacement between two consecutive
βCD
dimers along the channel is only 2.7Å,
as in the CH mode, the dimer’s 7-fold axis forms an approximately angle
of 10o with the stacking axis but the 2-D layers are related
by a 2-fold screw axis and they are not parallel therefore, the guests
interact with water molecules and hydroxy groups of adjacent hosts
channels.
References
1.
“The
Crystal Structure of the 4-tert-Butylbenzyl Alkohol
β
-Cyclodextrin Complex.
Common Features in the
Geometry of the
β-cyclodextrin
Dimeric Complexes”
D. Mentzafos, I. M. Mavridis,
G. Le Bas and G.Tsoucaris,
Acta Crystallogr.
1991,
B47,
746-757.
2.
“The
Crystal Structure of the Inclusion Complex of Cyclomaltoheptaose (β
-cyclodextrin) with 3,3-Dimethylbutylamine”
I.
M. Mavridis,
3.
“The Crystal
Structure of the Inclusion Complex of Cyclomaltoheptaose (β
-cyclodextrin) with 4-tert-Butyltoluene”
I. M. Mavridis,
4.
“The
Crystal Structure of the Inclusion Complex of Cyclomaltoheptaose with
4-tert-Butylbenzoic acid”
A.
Rontoyanni, I. M. Mavridis,
5.
“Organization of Long
Aliphatic Monocarboxylic Acids in
β-Cyclodextrin
Channels.
Crystal
Structures of the Inclusion Complexes of Tridecanoic Acid and (Z)-tetradecenoic
Acid in
β-Cyclodextrin”,
S. Makedonopoulou,
I. M. Mavridis, K.
Yannakopoulou, J. Papaioannou,
J. Chem. Soc.
Chem. Commun.
1998, 2133-2134.
6.
“The Dimeric
Complex of
β-cyclodextrin
with 1,13-tridecanedioic acid” S. Makedonopoulou, A. Tulinsky,
7.
“Dimeric
Complex of Alpha-cyclodextrin with 1,12-Diaminododecane. Comparison with
other Alpha Cyclodextrin Dimeric Complexes”
Α.
Rontoyianni,
8.
“Structure of the Inclusion Complex of
β-Cyclodextrin
with 1,12-Dodecanodioic Acid using Synchrotron Radiation Data.
A Detailed
dimeric
β-Cyclodextrin
Structure”
S. Makedonopoulou, I. M.
Mavridis,
Acta Crystallogr.
2000, B56, 322-331.
9.
“Crystal
Structure of the Inclusion Complex of
β-Cyclodextrin
with the Aliphatic monoacids Tridecanoic Acid and (Z)-Tetradecenoic
Acid.
Formation of [3]Pseudorotaxanes”
S. Makedonopoulou, J. Papaioannou, I. Argyroglou,
10.
“The dimeric complex of beta
cyclodextrin with 1,14-tetradecanedioic acid.
Comparison with related
complexes”
S. Makedonopoulou, I. M.
Mavridis,
Carbohydr. Res.
2001, 335, 213-220.
11.
“Influence of the Guest on
the Packing of Dimeric
β-Cyclodextrin
Complexes”, I. M. Mavridis
in Current
Challenges on Large Supramolecular Assemblies,
Ed. G.Tsoucaris, , NATO A
12.
“Molecular structures of
the inclusion complexes
β-Cyclodextrin/1,2-bis(4-aminophenyl)ethane
and
β-Cyclodextrin/4,4΄-diaminobiphenyl.
Packing of dimeric
β-Cyclodextrin
inclusion complexes”
13.
“β-Cyclodextrin
trimers enclosing an unusual organization of guest:
The inclusion complex
β-Cyclodextrin/4-pyridinealdazine”
S. D. Chatziefthimiou, K. Yannakopoulou, I. M. Mavridis,
Cryst.
14.
“NMR
Detection of Simultaneous Formation of [2]- and [3]Pseudorotaxanes in
Aqueous Solution between
α-Cyclodextrin
and Linear Aliphatic
α,ω-Aminoacids,
an
α,ω-Diamine
and an
α,ω-Diacid
of Similar Length, and Comparison with The Solid State Structures”
Κ.
Eliadou, K.
Yannakopoulou, A. Rontoyianni,
I. M. Mavridis, J. Org. Chem.
1999, 64, 6217-6226.
15.
“Partial Thermal Dethreading of
[3]pseudorotaxanes of
α-Cyclodextrin
with Linear Aliphatic
α,ω-Aminoacids
in Aqueous Solution” A. Tsortos, K. Yannakopoulou, K. Eliadou,
I.M. Mavridis and G.
Nounesis, J. Phys. Chem.
2001, B105, 2664-2667.
16.
“Rotaxanation of Congo Red into
γ-Cyclodextrin.
Solution Structures and Thermodynamic Parameters of 1:1 and 2:2 Adducts,
as Obtained from NMR Spectroscopy and Microcalorimetry”
17.
“Threading of
long end-functionalised organic molecules into cyclodextrins: Structural
analysis in aqueous solution by NMR spectroscopy and in the solid state
by X-ray crystallography” K. Yannakopoulou and
I. M. Mavridis,
Current Org. Chem. 2004,
8, 25-34.
18.
“Rotaxane
and Catenane Structures Involving Cyclodextrins”
K. Yannakopoulou, and
19.
“NMR Differentiation of Enantiomeric (+)- and (-)-α-Pinene via
Complexation with Cyclodextrins in Water" A. Botsi, K. Yannakopoulou, E.
Hadjoudis and B. Perly, J. Chem.
Soc. Chem. Commun. 1993,
1085.
20.
“Inclusion Complexes of Cyclomaltoheptaose
and its Methylated Derivatives with the Main Components of the
Pheromone of the Olive Fruit Fly", A. Botsi, K. Yannakopoulou, E.
Hadjoudis, Carbohydr. Res.
1993,
241, 37.
21.
"Crystal Structure of the
Heptakis (2,3,6-tri-O-methyl)-β-cyclodextrin
Complex with Ethyldodecanoate Ester"
I. M. Mavridis, D. Mentzafos and H. Schenk, Carbohydr. Res.
1994,
253,
39-50.
22.
“Positive or Adverse Effects of Methylation on the Inclusion Behaviour
of Cyclodextrins. A Comparative
NMR Study Using Pheromone Constituents of the Olive Fruit Fly",
A. Botsi, K. Yannakopoulou, B. Perly and E. Hadjoudis,
J. Org. Chem.,
1995,
60, 4017.
23.
“Structural Aspects of Permethylated Cyclodextrins and Comparison to
their Parent Oligosaccharides, as Derived from Unequivocally Assigned
1H
and
13C NMR Spectra in Aqueous Solutions" A. Botsi, K. Yannakopoulou,
B. Perly and
24.
“AM1 Calculations on Inclusion Complexes of Cyclomaltoheptaose with
1,7-Dioxaspiro[5.5]undecane and Nonanal, and Comparison with
Experimental Results." A. Botsi, K. Yannakopoulou, E. Hadjoudis, and J.
Waite, Carbohydr. Res.,
1996,
283, 1-16.
25.
“Controlled
Release of the Prays Oleae Pheromone, as a Consequence of Supramolecular
Structure: Study of the Z-7-Tetradecenal/β-Cyclodextrin
Complex in the Solid state and in Solution.”
K. Yannakopoulou, J. A.
Ripmeester,
26.
“β
-Cyclodextrin (Z)-9-Dodecen-1-ol 2:1 Complex” D. Mentzafos,
I. M. Mavridis, Acta
Crystallogr. 1996,
C52, 1220-1223.
27.
“β
-Cyclodextrin (Z)-9-Dodecen-1-ol 2:1 Complex” D. Mentzafos,
I. M. Mavridis, Acta
Crystallogr. 1996,
C52, 1220-1223.
28.
“Inclusion Compounds of Plant Growth Regulators in Cyclodextrins. Part
II. Structure of the Complex of
β-Cyclodextrin
with
β-Naphthyloxyacetic
acid in solid state and in aqueous solution” A. Kokkinou,
K. Yannakopoulou, I.M.
Mavridis, D. Mentzafos, Carbohydr.Res.
2001,
332, 85-94.
29.
Eur. Patent No 92 401
709.8, 1992;
30.
“Chiral Recognition of (R)-(_)-1,7-Dioxaspiro[5.5]undecane
by Hexakis(2,3,6-tri-O-methyl)-α-Cyclodextrin”
K. Yannakopoulou, D. Mentzafos, I. M. Mavridis and K. Dandika,
Angew. Chem. Int. Ed. Engl.
1996
35,
2480-2482.
31.
“Non-covalent interactions
in the crystallization of enantiomers of 1,7-dioxaspiro[5.5]undecane
(olive fly sex pheromone) by enantiospecific cyclodextrin hosts, hexakis(2,3,6-tri-O-methyl)-α-cyclodextrin
and heptakis(2,36-tri-O-methyl)-β-cyclodextrin”.
S. Makedonopoulou, K. Yannakopoulou, D. Mentzafos, V. Lamzin,
A. Popov, and I. M. Mavridis,
Acta Crystallogr.
2001,
B57, 399-409.
32.
The Self-Association of the Drug Acemetacin and its Intermolecular
Interactions and Stability with
β-Cyclodextrin
in Aqueous Solution. An NMR and HPLC Study»
D. Zouvelekis, K.
Yannakopoulou, A.
Antoniadou-Vyza, I.M. Mavridis, Carbohydr.
Res.,
2002,
337, 1387-1395.
33.
“Positive Effect of Natural and
Negatively Charged Cyclodextrins on the Stabilization of Penicillins
towards
β-Lactamase
Degradation due to Inclusion and External Guest-Host Association. An NMR
and MS Study” D.
Maffeo, L. Leondiadis,
34.
“Crystal structure of the
inclusion complex of the antibacterial agent triclosan in
β-cyclodextrin
and NMR study of its molecular encapsulation in positively and
negatively charged cyclodextrins” A. Paulidou, D. Maffeo, K.
Yannakopoulou, I M. Mavridis Carbohydr.
Res.
2008,
343, 2634-2640.
35.
“Similar
modes of inclusion in complexes of
β-cyclodextrin
with sulfonylurea hypoglycemic drugs”
A. Paulidou, D. Maffeo, K. Yannakopoulou, I.M. Mavridis,
Cryst.