Inclusion complexation of chloroquine with α and β-cyclodextrin: Theoretical insights from the new B97-3c composite method

Oral tissue regeneration has received growing attention for improving the quality of life of patients. Regeneration of oral tissues such as alveolar bone and widely defected bone has been extensively investigated, including regenerative treatment of oral tissues using therapeutic cells and growth factors. Additionally, small-molecule drugs that promote bone formation have been identified and tested as new regenerative treatment. However, treatments need to progress to realize successful regeneration of oral functions. In this review, we describe recent progress in development of regenerative treatment of oral tissues. In particular, we focus on cyclodextrin (CD)-based pharmaceutics and polyelectrolyte complexation of growth factors to enhance their solubility, stability, and bioactivity. CDs can encapsulate hydrophobic small-molecule drugs into their cavities, resulting in inclusion complexes. The inclusion complexation of osteoinductive small-molecule drugs improves solubility of the drugs in aqueous solutions and increases in vitro osteogenic differentiation efficiency. Additionally, various anionic polymers such as heparin and its mimetic polymers have been developed to improve stability and bioactivity of growth factors. These polymers protect growth factors from deactivation and degradation by complex formation through electrostatic interaction, leading to potentiation of bone formation ability. These approaches using an inclusion complex and polyelectrolyte complexes have great potential in the regeneration of oral tissues.

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ß-Cyclodextrin Inclusion Complexes with Catechol-Containing Antioxidants Protocatechuic Aldehyde and Protocatechuic Acid—An Atomistic Perspective on Structural and Thermodynamic Stabilities

Molecules ◽

10.3390/molecules26123574 ◽

2021 ◽

Vol 26 (12) ◽

pp. 3574

Author(s):

Thammarat Aree

Keyword(s):

Inclusion Complexes ◽

Protocatechuic Acid ◽

Inclusion Complexation ◽

Geometry Optimization ◽

Therapeutic Effects ◽

Full Geometry Optimization ◽

Oh Groups ◽

X Ray ◽

Protocatechuic Aldehyde ◽

Crystal Contacts

Protocatechuic aldehyde (PCAL) and protocatechuic acid (PCAC) are catechol derivatives and have broad therapeutic effects associated with their antiradical activity. Their pharmacological and physicochemical properties have been improved via the cyclodextrin (CD) encapsulation. Because the characteristics of b-CD inclusion complexes with PCAL (1) and PCAC (2) are still equivocal, we get to the bottom of the inclusion complexation by an integrated study of single-crystal X-ray diffraction and DFT full-geometry optimization. X-ray analysis unveiled that PCAL and PCAC are nearly totally shielded in the b-CD wall. Their aromatic rings are vertically aligned in the b-CD cavity such that the functional groups on the opposite side of the ring (3,4-di(OH) and 1-CHO/1-COOH groups) are placed nearby the O6–H and O2–H/O3–H rims, respectively. The preferred inclusion modes in 1 and 2 help to establish crystal contacts of OH×××O H-bonds with the adjacent b-CD OH groups and water molecules. By contrast, the DFT-optimized structures of both complexes in the gas phase are thermodynamically stable via the four newly formed host–guest OH⋯O H-bonds. The intermolecular OH×××O H-bonds between PCAL/PCAC 3,4-di(OH) and b-CD O6–H groups, and the shielding of OH groups in the b-CD wall help to stabilize these antioxidants in the b-CD cavity, as observed in our earlier studies. Moreover, PCAL and PCAC in distinct lattice environments are compared for insights into their structural flexibility.

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NMR studies of inclusion complexation of the pyrrolizidine alkaloid retronecine and p-sulfonic acid calix[6]arene

Journal of Inclusion Phenomena and Macrocyclic Chemistry ◽

10.1007/s10847-010-9825-1 ◽

2010 ◽

Vol 69 (1-2) ◽

pp. 149-155 ◽

Cited By ~ 17

Author(s):

Daniel Leite Silva ◽

Eder Couto Tavares ◽

Leila Souza Conegero ◽

Ângelo Fátima ◽

Ronaldo Aloise Pilli ◽

...

Keyword(s):

Sulfonic Acid ◽

Pyrrolizidine Alkaloid ◽

Inclusion Complexation ◽

Nmr Studies

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Spectral and photophysical studies on the inclusion complexation between Triton X-100 and β-cyclodextrin: A competitive method using a substituted 3H-indole probe

Journal of Photochemistry and Photobiology A Chemistry ◽

10.1016/j.jphotochem.2007.06.023 ◽

2008 ◽

Vol 193 (2-3) ◽

pp. 178-186 ◽

Cited By ~ 16

Author(s):

Yifeng He ◽

Xinghai Shen ◽

Hongcheng Gao ◽

Yongke He

Keyword(s):

Inclusion Complexation ◽

Photophysical Studies ◽

Triton X

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Studies on the inclusion complexation between intramolecular charge transfer probe trans-ethyl p-(dimethylamino) cinamate and β-cyclodextrin in presence of ionic and nonionic surfactants

Journal of Luminescence ◽

10.1016/j.jlumin.2013.04.016 ◽

2013 ◽

Vol 143 ◽

pp. 120-127 ◽

Cited By ~ 5

Author(s):

T. Sanjoy Singh ◽

Sivaprasad Mitra

Keyword(s):

Charge Transfer ◽

Nonionic Surfactants ◽

Intramolecular Charge Transfer ◽

Inclusion Complexation

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Enhanced photocatalytic activity of CeO2 using β-cyclodextrin on visible light assisted decoloration of methylene blue

Water Science & Technology ◽

10.2166/wst.2013.553 ◽

2013 ◽

Vol 69 (1) ◽

pp. 113-119 ◽

Cited By ~ 5

Author(s):

Sakthivel Pitchaimuthu ◽

Ponnusamy Velusamy

Keyword(s):

Methylene Blue ◽

Photocatalytic Activity ◽

Visible Light ◽

Inclusion Complexation ◽

Processing Parameters ◽

Operational Parameters ◽

Illumination Time ◽

Operational Conditions ◽

Electron Microscopy Analysis ◽

Initial Ph

An attempt has been made to enhance the photocatalytic activity of CeO2 for visible light assisted decoloration of methylene blue (MB) dye in aqueous solutions by β-cyclodextrin (β-CD). The inclusion complexation patterns between host and guest (i.e., β-CD and MB) have been confirmed with UV–visible spectral data. The interaction between CeO2 and β-CD has also been characterized by field emission scanning electron microscopy analysis. The photocatalytic activity of the catalyst under visible light was investigated by measuring the photodegradation of MB in aqueous solution. The effects of key operational parameters such as initial dye concentration, initial pH, CeO2 concentration as well as illumination time on the decolorization extents were investigated. Among the processing parameters, the pH of the reaction solution played an important role in tuning the photocatalytic activity of CeO2. The maximum photodecoloration rate was achieved at basic pH (pH 11). Under the optimum operational conditions, approximately 99.6% dye removal was achieved within 120 min. The observed results indicate that the decolorization of the MB followed a pseudo-first order kinetics.

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