197
Food Sci Nutr 56(12):1981–2004. https://
doi.org/10.1080/10408398.2013.809513
3. Irie T, Uekama K (1997) Pharmaceutical
applications of cyclodextrins. III. Toxicological
issues and safety evaluation. J Pharm Sci
86(2):147–162. https://doi.org/10.1021/
js960213f
4. Gidwani B, Vyas A (2015) A comprehensive
review on cyclodextrin-based carriers for delivery of chemotherapeutic cytotoxic anticancer
drugs. Biomed Res Int 2015:198268. https://
doi.org/10.1155/2015/198268
5. Jacob S, Nair AB (2018) Cyclodextrin complexes: perspective from drug delivery and
formulation. Drug Dev Res 79(5):201–217.
https://doi.org/10.1002/ddr.21452
6. Brewster ME, Loftsson T (2007) Cyclodextrins
as pharmaceutical solubilizers. Adv Drug
Deliv Rev 59(7):645–666. https://doi.
org/10.1016/j.addr.2007.05.012
7. Loftsson
T,
Brewster
ME
(2010)
Pharmaceutical applications of cyclodextrins:
basic science and product development. J Pharm
Pharmacol 62(11):1607–1621. https://doi.
org/10.1111/j.2042-7158.2010.01030.x
8. Velasco J, Carmona C, Muñoz MA et al
(1999) Influence of the cyclodextrin size
cavity in the complexation of tetrahydroharmane. J Incl Phenom Macrocycl Chem
35(4):637–648.
https://doi.org/10.102
3/A:1008090723172
9. Charumanee S, Okonogi S, Sirithunyalug J
et al (2016) Effect of cyclodextrin types and
co-solvent on solubility of a poorly water soluble drug. Sci Pharm 84(4):694–704. https://
doi.org/10.3390/scipharm84040694
10. Rozou S, Voulgari A, Antoniadou-Vyza E
(2004) The effect of pH dependent molecular conformation and dimerization phenomena
of piroxicam on the drug: cyclodextrin complex stoichiometry and its chromatographic
behaviour. A new specific HPLC method for
piroxicam:cyclodextrin formulations. Eur
J Pharm Sci 21(5):661–669. https://doi.
org/10.1016/j.ejps.2004.01.007
11. Aki H, Ikeda H, Yukawa M et al (2009)
Effect of pH on the formation of inclusion complexes between β-lactam antibiotics and 2-hydroxypropyl-β-cyclodextrin in
aqueous solution. J Therm Anal Calorim
95(2):421–426. https://doi.org/10.1007/
s10973-008-9251-4
12. Zheng Y, Dong LN, Liu M et al (2014) Effect
of pH on the complexation of kaempferol4′-glucoside with three beta-cyclodextrin
derivatives: isothermal titration calorimetry
and spectroscopy study. J Agric Food Chem
62(1):244–250. https://doi.org/10.1021/
jf404320w
13. Qi X, Virden R (1990) Extent of accumulation of an acylenzyme during beta-lactamase
catalysis. Biochem Soc Trans 18(5):924–925.
https://doi.org/10.1042/bst0180924
14. Kellici TF, Ntountaniotis D, Leonis G et al
(2015) Investigation of the interactions of silibinin with 2-hydroxypropyl-beta-cyclodextrin
through biophysical techniques and computational methods. Mol Pharm 12(3):954–965.
https://doi.org/10.1021/mp5008053
15. Kellici
TF,
Chatziathanasiadou
MV,
Diamantis D et al (2016) Mapping the
interactions and bioactivity of quercetin(2-hydroxypropyl)-beta-cyclodextrin complex.
Int J Pharm 511(1):303–311. https://doi.
org/10.1016/j.ijpharm.2016.07.008
16. Ntountaniotis D, Andreadelis I, Kellici TF et al
(2019) Host-guest interactions between candesartan and its prodrug candesartan cilexetil
in complex with 2- hydroxypropyl-beta- cyclo
dextrin: on the biological potency for angiotensin II antagonism. Mol Pharm 16(3):1255–
1271.
https://doi.org/10.1021/acs.
molpharmaceut.8b01212
17. Diamantis DA, Ramesova S, Chatzigiannis
CM et al (2018) Exploring the oxidation
and iron binding profile of a cyclodextrin
encapsulated quercetin complex unveiled a
controlled complex dissociation through a
chemical stimulus. Biochim Biophys Acta
Gen Subj 1862(9):1913–1924. https://doi.
org/10.1016/j.bbagen.2018.06.006
18. Liossi AS, Ntountaniotis D, Kellici TF et al
(2017) Exploring the interactions of irbesartan
and
irbesartan-2-hydroxypropylbeta-cyclodextrin complex with model
membranes.
Biochim
Biophys
Acta
Biomembr 1859(6):1089–1098. https://doi.
org/10.1016/j.bbamem.2017.03.003
19. Escuder-Gilabert L, Martin-Biosca Y, MedinaHernandez MJ et al (2014) Cyclodextrins
in capillary electrophoresis: recent developments and new trends. J Chromatogr A
1357:2–23.
https://doi.org/10.1016/j.
chroma.2014.05.074
20. Matencio A, Hernandez-Garcia S, GarciaCarmona F et al (2017) An integral study
of cyclodextrins as solubility enhancers of
alpha-methylstilbene, a resveratrol analogue.
Food Funct 8(1):270–277. https://doi.
org/10.1039/c6fo01677d
21. Shao-Jun D, Dong-Bo Z (1988) Study of
inclusion complexes of cyclodextrin by cyclic
voltammetry. Acta Chim Sinica Engl Ed
6(2):116–122.
https://doi.org/10.1002/
cjoc.19880060205
Unveiling the Thermodynamic Aspects of Drug-Cyclodextrin Interactions…
Food Sci Nutr 56(12):1981–2004. https://
doi.org/10.1080/10408398.2013.809513
3. Irie T, Uekama K (1997) Pharmaceutical
applications of cyclodextrins. III. Toxicological
issues and safety evaluation. J Pharm Sci
86(2):147–162. https://doi.org/10.1021/
js960213f
4. Gidwani B, Vyas A (2015) A comprehensive
review on cyclodextrin-based carriers for delivery of chemotherapeutic cytotoxic anticancer
drugs. Biomed Res Int 2015:198268. https://
doi.org/10.1155/2015/198268
5. Jacob S, Nair AB (2018) Cyclodextrin complexes: perspective from drug delivery and
formulation. Drug Dev Res 79(5):201–217.
https://doi.org/10.1002/ddr.21452
6. Brewster ME, Loftsson T (2007) Cyclodextrins
as pharmaceutical solubilizers. Adv Drug
Deliv Rev 59(7):645–666. https://doi.
org/10.1016/j.addr.2007.05.012
7. Loftsson
T,
Brewster
ME
(2010)
Pharmaceutical applications of cyclodextrins:
basic science and product development. J Pharm
Pharmacol 62(11):1607–1621. https://doi.
org/10.1111/j.2042-7158.2010.01030.x
8. Velasco J, Carmona C, Muñoz MA et al
(1999) Influence of the cyclodextrin size
cavity in the complexation of tetrahydroharmane. J Incl Phenom Macrocycl Chem
35(4):637–648.
https://doi.org/10.102
3/A:1008090723172
9. Charumanee S, Okonogi S, Sirithunyalug J
et al (2016) Effect of cyclodextrin types and
co-solvent on solubility of a poorly water soluble drug. Sci Pharm 84(4):694–704. https://
doi.org/10.3390/scipharm84040694
10. Rozou S, Voulgari A, Antoniadou-Vyza E
(2004) The effect of pH dependent molecular conformation and dimerization phenomena
of piroxicam on the drug: cyclodextrin complex stoichiometry and its chromatographic
behaviour. A new specific HPLC method for
piroxicam:cyclodextrin formulations. Eur
J Pharm Sci 21(5):661–669. https://doi.
org/10.1016/j.ejps.2004.01.007
11. Aki H, Ikeda H, Yukawa M et al (2009)
Effect of pH on the formation of inclusion complexes between β-lactam antibiotics and 2-hydroxypropyl-β-cyclodextrin in
aqueous solution. J Therm Anal Calorim
95(2):421–426. https://doi.org/10.1007/
s10973-008-9251-4
12. Zheng Y, Dong LN, Liu M et al (2014) Effect
of pH on the complexation of kaempferol4′-glucoside with three beta-cyclodextrin
derivatives: isothermal titration calorimetry
and spectroscopy study. J Agric Food Chem
62(1):244–250. https://doi.org/10.1021/
jf404320w
13. Qi X, Virden R (1990) Extent of accumulation of an acylenzyme during beta-lactamase
catalysis. Biochem Soc Trans 18(5):924–925.
https://doi.org/10.1042/bst0180924
14. Kellici TF, Ntountaniotis D, Leonis G et al
(2015) Investigation of the interactions of silibinin with 2-hydroxypropyl-beta-cyclodextrin
through biophysical techniques and computational methods. Mol Pharm 12(3):954–965.
https://doi.org/10.1021/mp5008053
15. Kellici
TF,
Chatziathanasiadou
MV,
Diamantis D et al (2016) Mapping the
interactions and bioactivity of quercetin(2-hydroxypropyl)-beta-cyclodextrin complex.
Int J Pharm 511(1):303–311. https://doi.
org/10.1016/j.ijpharm.2016.07.008
16. Ntountaniotis D, Andreadelis I, Kellici TF et al
(2019) Host-guest interactions between candesartan and its prodrug candesartan cilexetil
in complex with 2- hydroxypropyl-beta- cyclo
dextrin: on the biological potency for angiotensin II antagonism. Mol Pharm 16(3):1255–
1271.
https://doi.org/10.1021/acs.
molpharmaceut.8b01212
17. Diamantis DA, Ramesova S, Chatzigiannis
CM et al (2018) Exploring the oxidation
and iron binding profile of a cyclodextrin
encapsulated quercetin complex unveiled a
controlled complex dissociation through a
chemical stimulus. Biochim Biophys Acta
Gen Subj 1862(9):1913–1924. https://doi.
org/10.1016/j.bbagen.2018.06.006
18. Liossi AS, Ntountaniotis D, Kellici TF et al
(2017) Exploring the interactions of irbesartan
and
irbesartan-2-hydroxypropylbeta-cyclodextrin complex with model
membranes.
Biochim
Biophys
Acta
Biomembr 1859(6):1089–1098. https://doi.
org/10.1016/j.bbamem.2017.03.003
19. Escuder-Gilabert L, Martin-Biosca Y, MedinaHernandez MJ et al (2014) Cyclodextrins
in capillary electrophoresis: recent developments and new trends. J Chromatogr A
1357:2–23.
https://doi.org/10.1016/j.
chroma.2014.05.074
20. Matencio A, Hernandez-Garcia S, GarciaCarmona F et al (2017) An integral study
of cyclodextrins as solubility enhancers of
alpha-methylstilbene, a resveratrol analogue.
Food Funct 8(1):270–277. https://doi.
org/10.1039/c6fo01677d
21. Shao-Jun D, Dong-Bo Z (1988) Study of
inclusion complexes of cyclodextrin by cyclic
voltammetry. Acta Chim Sinica Engl Ed
6(2):116–122.
https://doi.org/10.1002/
cjoc.19880060205
Unveiling the Thermodynamic Aspects of Drug-Cyclodextrin Interactions…