Abstract
Quercetin (QCT), a flavonoid derived from many fruits and vegetables, is endowed with manifold biological properties, such as the ability to elicit a strong inhibitory effect on the growth of several tumor cell lines. Unfortunately, the pharmacological application of QCT is severely restricted by its inherent hydrophobicity and consequent low in vivo bioavailability. The therapeutic potential of QCT can be unraveled by enhancing its solubility through the formation of a host–guest complex with hydroxypropyl-β-cyclodextrin (HPβCD). In this study, HPβCD·QCT complex has been obtained in liquid phase, at 37 °C and under a prolonged mixing (72 h), and using two buffers at pH = 3.6 and pH = 8.0. Phase solubility and differential scanning calorimetry (DSC) studies revealed that, at pH = 8.0, the complex was obtained with a 1:1 stoichiometric ratio and a strong enhancement of QCT solubility, while in acidic buffer complex formation was significantly thwarted. The affinity constant was calculated by isothermal calorimetry at pH = 8 and was found to be 489 ± 38 M−1, in good agreement with the value indirectly obtained from phase solubility tests 394 ± 101 M−1. The results confirmed the formation of the inclusion complex between QCT and HPβCD and highlight the importance of the choice of the appropriate solvent, pH, temperature and mixing time on the formation of host guest inclusion complex with active ingredient(s) and HPβCD.
| Original language | English |
|---|---|
| Pages (from-to) | 1-6 |
| Number of pages | 6 |
| Journal | Journal of Thermal Analysis and Calorimetry |
| DOIs | |
| Publication status | Published - Oct 2017 |
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Keywords
- DSC
- Hydroxypropyl-β-cyclodextrin
- Inclusion complex
- Isothermal Calorimetry
- Phase solubility
- Quercetin
ASJC Scopus subject areas
- Condensed Matter Physics
- Physical and Theoretical Chemistry
Cite this
Host–guest inclusion complex of quercetin and hydroxypropyl-β-cyclodextrin : A calorimetric study. / D’Aria, Federica; Serri, Carla; Niccoli, Marcella; Mayol, Laura; Quagliariello, Vincenzo; Iaffaioli, Rosario Vincenzo; Biondi, Marco; Giancola, Concetta.
In: Journal of Thermal Analysis and Calorimetry, 10.2017, p. 1-6.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Host–guest inclusion complex of quercetin and hydroxypropyl-β-cyclodextrin
T2 - A calorimetric study
AU - D’Aria, Federica
AU - Serri, Carla
AU - Niccoli, Marcella
AU - Mayol, Laura
AU - Quagliariello, Vincenzo
AU - Iaffaioli, Rosario Vincenzo
AU - Biondi, Marco
AU - Giancola, Concetta
PY - 2017/10
Y1 - 2017/10
N2 - Quercetin (QCT), a flavonoid derived from many fruits and vegetables, is endowed with manifold biological properties, such as the ability to elicit a strong inhibitory effect on the growth of several tumor cell lines. Unfortunately, the pharmacological application of QCT is severely restricted by its inherent hydrophobicity and consequent low in vivo bioavailability. The therapeutic potential of QCT can be unraveled by enhancing its solubility through the formation of a host–guest complex with hydroxypropyl-β-cyclodextrin (HPβCD). In this study, HPβCD·QCT complex has been obtained in liquid phase, at 37 °C and under a prolonged mixing (72 h), and using two buffers at pH = 3.6 and pH = 8.0. Phase solubility and differential scanning calorimetry (DSC) studies revealed that, at pH = 8.0, the complex was obtained with a 1:1 stoichiometric ratio and a strong enhancement of QCT solubility, while in acidic buffer complex formation was significantly thwarted. The affinity constant was calculated by isothermal calorimetry at pH = 8 and was found to be 489 ± 38 M−1, in good agreement with the value indirectly obtained from phase solubility tests 394 ± 101 M−1. The results confirmed the formation of the inclusion complex between QCT and HPβCD and highlight the importance of the choice of the appropriate solvent, pH, temperature and mixing time on the formation of host guest inclusion complex with active ingredient(s) and HPβCD.
AB - Quercetin (QCT), a flavonoid derived from many fruits and vegetables, is endowed with manifold biological properties, such as the ability to elicit a strong inhibitory effect on the growth of several tumor cell lines. Unfortunately, the pharmacological application of QCT is severely restricted by its inherent hydrophobicity and consequent low in vivo bioavailability. The therapeutic potential of QCT can be unraveled by enhancing its solubility through the formation of a host–guest complex with hydroxypropyl-β-cyclodextrin (HPβCD). In this study, HPβCD·QCT complex has been obtained in liquid phase, at 37 °C and under a prolonged mixing (72 h), and using two buffers at pH = 3.6 and pH = 8.0. Phase solubility and differential scanning calorimetry (DSC) studies revealed that, at pH = 8.0, the complex was obtained with a 1:1 stoichiometric ratio and a strong enhancement of QCT solubility, while in acidic buffer complex formation was significantly thwarted. The affinity constant was calculated by isothermal calorimetry at pH = 8 and was found to be 489 ± 38 M−1, in good agreement with the value indirectly obtained from phase solubility tests 394 ± 101 M−1. The results confirmed the formation of the inclusion complex between QCT and HPβCD and highlight the importance of the choice of the appropriate solvent, pH, temperature and mixing time on the formation of host guest inclusion complex with active ingredient(s) and HPβCD.
KW - DSC
KW - Hydroxypropyl-β-cyclodextrin
KW - Inclusion complex
KW - Isothermal Calorimetry
KW - Phase solubility
KW - Quercetin
UR - http://www.scopus.com/inward/record.url?scp=85013077549&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85013077549&partnerID=8YFLogxK
U2 - 10.1007/s10973-017-6135-5
DO - 10.1007/s10973-017-6135-5
M3 - Article
SP - 1
EP - 6
JO - Journal of Thermal Analysis and Calorimetry
JF - Journal of Thermal Analysis and Calorimetry
SN - 1388-6150
ER -