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Journal articles on the topic 'Host-Guest inclusion complex'

Author: Grafiati

Published: 18 May 2024

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1

Tanaka, Koichi, Naoki Daikawa, and Shigeru Ohba. "Novel Bisurea Host Compounds." Journal of Chemical Research 2002, no. 11 (November 2002): 579–81. http://dx.doi.org/10.3184/030823402103170853.

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New host molecules, 4,4′-bis(dimethylamino-urea)diphenylmethane (1) and its derivatives (2 and 3), are reported. These hosts are shown to give inclusion complex crystals with a wide variety of organic guest molecules with high selectivity. The crystal structure of 1:2 inclusion complex of 1 with THF has been determined from X-ray crystal structure analysis. The cyclic N–H...O intermolecular hydrogen bonds between host molecules were found to form columns for accommodation of the guest molecules.

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2

Li, Chun-Rong, Hua-Ming Feng, Jin-Yi Zhao, Zhu Li, Bing Bian, Tie-Hong Meng, Xian-Yun Hu, Heng Wang, and Xin Xiao. "Supramolecular Interaction Between Cucurbit[8]uril and the Quinolone Antibiotic Ofloxacin." Australian Journal of Chemistry 72, no. 12 (2019): 983. http://dx.doi.org/10.1071/ch19341.

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The host–guest inclusion complex of cucurbit[8]uril (Q[8]) and ofloxacin (OFLX) has been prepared and characterised by means of 1H NMR spectroscopy, MALDI-TOF mass spectrometry, isothermal titration calorimetry (ITC), fluorescence spectroscopy, and UV-vis absorption spectroscopy. The findings demonstrated that a host–guest inclusion complex could be formed through an encapsulation of the methylmorpholine and piperazine rings in OFLX. ITC results indicated that the formation of this inclusion complex (1:1 molar ratio) was primarily dependent on enthalpy and entropy changes. In addition, the release of OFLX from the inclusion complex was increased under acidic conditions.

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3

Wagner, Brian D., Shannon J. Fitzpatrick, Monica A. Gill, Andrew I. MacRae, and Natasa Stojanovic. "A fluorescent host-guest complex of cucurbituril in solution: a molecular Jack O'Lantern." Canadian Journal of Chemistry 79, no. 7 (July 1, 2001): 1101–4. http://dx.doi.org/10.1139/v01-094.

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Fluorescence enhancement of a probe molecule in solution by the container molecule cucurbituril (CB) is reported for the first time. The fluorescence of the probe 2-anilinonaphthalene-6-sulfonate (2,6-ANS) in aqueous Na2SO4 solution is found to increase by a maximum factor of 5.0 upon addition of cucurbituril. This fluorescence enhancement is the result of the formation of a hostguest inclusion complex, in which the guest 2,6-ANS is incorporated inside the cavity of the host, cucurbituril. Measurement of the enhancement as a function of cucurbituril concentration yielded a value of the equilibrium constant (K) of 52 ± 10 M1. It is proposed that the mode of inclusion involves the phenyl group of the 2,6-ANS, because of the relatively small size of the cucurbituril cavity. It is further proposed that the observed enhancement is a result of loss of rotational mobility of the phenyl ring relative to the naphthyl fluorophore of 2,6-ANS upon inclusion of the phenyl ring. Since the name cucurbituril is derived from the Latin word for "pumpkin," this fluorescent host-guest complex is referred to as a "molecular Jack O'Lantern," with the 2,6-ANS serving as the candle.Key words: hostguest chemistry, fluorescence, cucurbituril, inclusion compounds.

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4

Tahir, M. Nazir, Yihong Cao, Abdelkrim Azzouz, and René Roy. "Host-guest chemistry of the sulfasalazine-β-cyclodextrin inclusion complex." Tetrahedron 85 (April 2021): 132052. http://dx.doi.org/10.1016/j.tet.2021.132052.

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5

D’Aria, Federica, Carla Serri, Marcella Niccoli, Laura Mayol, Vincenzo Quagliariello, Rosario Vincenzo Iaffaioli, Marco Biondi, and Concetta Giancola. "Host–guest inclusion complex of quercetin and hydroxypropyl-β-cyclodextrin." Journal of Thermal Analysis and Calorimetry 130, no. 1 (February 16, 2017): 451–56. http://dx.doi.org/10.1007/s10973-017-6135-5.

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6

Aramoto, Hikaru, Motofumi Osaki, Subaru Konishi, Chiharu Ueda, Yuichiro Kobayashi, Yoshinori Takashima, Akira Harada, and Hiroyasu Yamaguchi. "Redox-responsive supramolecular polymeric networks having double-threaded inclusion complexes." Chemical Science 11, no. 17 (2020): 4322–31. http://dx.doi.org/10.1039/c9sc05589d.

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7

Alrawashdeh, Lubna, Khaleel I. Assaf, Walhan Alshaer, Fadwa Odeh, and Suhair A. Bani-Atta. "Preparation, characterization, and biological activity study of thymoquinone-cucurbit[7]uril inclusion complex." RSC Advances 12, no. 4 (2022): 1982–88. http://dx.doi.org/10.1039/d1ra08460g.

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8

Wilson, Lee D., and Ronald E. Verrall. "A 1H NMR study of cyclodextrin - hydrocarbon surfactant inclusion complexes in aqueous solutions." Canadian Journal of Chemistry 76, no. 1 (January 1, 1998): 25–34. http://dx.doi.org/10.1139/v97-208.

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A 1H NMR chemical shift ( delta ) study of a homologous series of hydrocarbon (hc) (CxH2x + 1CO2Na, x = 5, 7, 9, 11, 13) surfactants (S) has been carried out in water and in binary solvent (D2O + cyclodextrin (CD)) systems at 22°C. Complementary 1H NMR chemical shift ( delta ) data of the cyclodextrins in binary (D2O + S) systems containing hc surfactants have also been obtained. Complex induced shift (CIS) values for selected host or guest protons were found to increase as the alkyl chain (Cx) length of the surfactant increased. The CIS values are found to depend on the following factors: (i) the magnitude of the binding constant (Ki, i = 1:1, 2:1), (ii) the chain length of the surfactant, (iii) the mole ratio of the host to guest species, (iv) the host-guest stoichiometry, and (v) the host-guest inclusion geometry. The CIS values of the CD-S systems have been analyzed using equilibrium models in which 1:1 complexes, 1:1 plus 2:1 complexes, and uncomplexed species are present. Differences in the binding affinity, stoichiometry, and inclusion geometry of the complexes formed between a given hc surfactant and the various cyclodextrins were observed.Key words: cyclodextrin, surfactant, NMR, chemical shift, complex, binding constant.

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9

Zhou, Jiong, Bin Hua, Li Shao, Hao Feng, and Guocan Yu. "Host–guest interaction enhanced aggregation-induced emission and its application in cell imaging." Chemical Communications 52, no. 33 (2016): 5749–52. http://dx.doi.org/10.1039/c6cc01860b.

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A host–guest inclusion complex based on a monofunctionalized pillar[5]arene and a tetraphenylethene derivative was prepared, resulting in an enhanced emission from the tetraphenylethene-based guest, which was applied in cell imaging.

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10

Rahaman, Habibur, Niloy Roy, Aditi Roy, Samapika Ray, and Mahendra Nath Roy. "Exploring Existence of Host-Guest Inclusion Complex of β-Cyclodextrin of a Biologically Active Compound with the Manifestation of Diverse Interactions." Emerging Science Journal 2, no. 5 (November 4, 2018): 251. http://dx.doi.org/10.28991/esj-2018-01149.

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The host–guest interaction of p-nitro benzaldehyde as guest β-Cyclodextrins have been investigated which have significant applications in the field of medicine such as controlled drug delivery. The 1H NMR study confirms the formation of inclusion complex while surface tension and conductivity studies support the formation inclusion complex with 1:1 stoichiometry. The stoichiometry of the inclusion complex was also supported with Job’s plot method by UV-Visible spectroscopy. FT-IR spectra and SEM study also support the inclusion process. Association constants of the inclusion complexes have been calculated using the Benesi–Hildebrand method, while the thermodynamic parameters have been estimated with the help of van’t Hoff equation.

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11

Eteer, Shahrazad Ali. "UV-Vis Spectroscopic Characterization of β-Cyclodextrin-Vanillin Inclusion Complex." Mediterranean Journal of Chemistry 12, no. 2 (October 11, 2022): 175. http://dx.doi.org/10.13171/mjc02210111645eteer.

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<p>Cyclodextrin molecules can form inclusion complexes with various compounds of appropriate shape and size. The complexation can enhance the solubility and stability of the inclusion guest compound. The stoichiometry and stability constant of the host-guest complex are highly important for physical, chemical, biological, and environmental studies. A simple and rapid spectroscopic method investigated the inclusion of vanillin and β-cyclodextrin (β-CD). The continuous variation technique was used to estimate the stoichiometry of the inclusion complex. The association constant of vanillin with β-CD was determined by using Benesi- Hildebrand and Scott's methods which were calculated to be 179 and 187 M<sup>-1,</sup> respectively, with the stoichiometry ratio, was 1:1 for the inclusion complex of β-CD with vanillin.</p>

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12

Suwinska, Kinga. "Intermolecular interactions in inclusion complexes." Acta Crystallographica Section A Foundations and Advances 70, a1 (August 5, 2014): C673. http://dx.doi.org/10.1107/s2053273314093267.

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The whole range of interactions can be found between host and guest in supramolecular assemblies from ion-ion interactions, ion-dipole interactions, dipol-dipol interactions through hydrogen bonding, cation-π interactions, π-π stacking to van der Waals forces. Additionally, the same interactions exist between the supramolecular complex and its surrounding, i.e. solvent molecules, neighboring complexes, gases, etc. Recently the interest of scientists in the field of supramolecular chemistry is focused on design and synthesis of water-soluble synthetic macrocyclic ligands which are good receptors for biologically important guest molecules and can mimic the models of biological systems. Studying such complexes may provide new insight into the mechanisms of the formation of similar natural systems and as a consequence will help in better understanding the processes which occur in biological systems and in developing new materials with specific properties and functions. In this presentation the interactions which are stabilizing inclusion complexes of calix[n]arenes and cyclodextrins (host molecules) with guest molecules of biological interest, especially drug molecules will be discussed. This research was partly financed by the European Union within the European Regional Development Fund (POIG.01.01.02-14-102/09)

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13

Rui, Leilei, Yudong Xue, Yong Wang, Yun Gao, and Weian Zhang. "A mitochondria-targeting supramolecular photosensitizer based on pillar[5]arene for photodynamic therapy." Chemical Communications 53, no. 21 (2017): 3126–29. http://dx.doi.org/10.1039/c7cc00950j.

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14

Hirahara, Masanari, Shota Furutani, Hiroki Goto, Keiichi Fujimori, and Takayo Moriuchi-Kawakami. "A visible-light and temperature responsive host–guest system: the photoisomerization and inclusion complex formation of a ruthenium complex with cyclodextrins." Dalton Transactions 51, no. 11 (2022): 4477–83. http://dx.doi.org/10.1039/d1dt04003k.

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15

Liu, Chun Yuan, Wei In Lin, and Jenshi B. Wang. "Polymer Blend through Inclusion Complexation." Advanced Materials Research 936 (June 2014): 8–11. http://dx.doi.org/10.4028/www.scientific.net/amr.936.8.

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A new method is proposed to improve blend compatability through inclusion complexation. The host polymer and the guest polymer are synthesized respectively and blended to form a film. The transparency of blend film increases and, at some composition, a third Tg is obsereved, indicating the inclusion complex between these two polymers

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16

Lin, Chang-Gen, Gizaw D. Fura, Yong Long, Weimin Xuan, and Yu-Fei Song. "Polyoxometalate-based supramolecular hydrogels constructed through host–guest interactions." Inorganic Chemistry Frontiers 4, no. 5 (2017): 789–94. http://dx.doi.org/10.1039/c7qi00030h.

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17

Archana Sumohan Pillai, Sivaraj Ramasamy, Varnitha Manikandan, Aleyamma Alexander, and Israel V.M.V. Enoch. "Anticancer Activity of the Host-Guest Complex of Camptothecin with β-Cyclodextrin-Folate Conjugate. Encapsulation and Efficacy." International Journal of Research in Pharmaceutical Sciences 11, SPL4 (December 21, 2020): 1286–91. http://dx.doi.org/10.26452/ijrps.v11ispl4.4294.

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Cyclodextrins are cyclic oligosachcharides that act as molecular hosts and accommodate drug molecules forming host: guest complexes. They aid in the sustained release of the encapsulated drugs through diffusion in solution and protect their unstable forms. In this paper, we report the synthesis of a β-cyclodextrin-folate by a simple coupling reaction. The compound is characterized using IR, NMR, and mass spectroscopic techniques. The amide carbonyl band is observed at 1680 cm-1. The mass spectrum shows the molecular ion peak of the β-cycloxetrin-folate conjugate at an m/z value of 1615.35. An inclusion complex of the anticancer drug, camptothecin, with the β-cycloxetrin-folate is formed on the stepwise addition of the β-cycloxetrin-folate to the guest molecule. The complex formation is studied using UV-visible and fluorescence spectroscopy. The formation of host: guest complexes is known to enable the sustained release of the encapsulated drug molecule. Herein, we examined the in vitro anticancer activity of the host: guest complex against cervical cancer (HeLa) cells. The host: guest complex formation results in enhanced efficacy of the drug. Dose-dependent cytotoxicity is observed for the β-cyclodextrin-folate: camptothecin complex. The cytotoxicity is more for the complex than for the free drug in solution.

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18

Qi, Miao, Pei Zi Tan, Fei Xue, Haripal Singh Malhi, Zhong-Xing Zhang, David J. Young, and T. S. Andy Hor. "A supramolecular recyclable catalyst for aqueous Suzuki–Miyaura coupling." RSC Advances 5, no. 5 (2015): 3590–96. http://dx.doi.org/10.1039/c4ra13953d.

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19

Heinrich, Lothar A., Betina Pajaziti, and Rakhimdzhan Roziev. "Drug Delivery System of a Radio-Protective Inclusion Complex." Advanced Materials Research 872 (December 2013): 231–36. http://dx.doi.org/10.4028/www.scientific.net/amr.872.231.

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The novel radio-protective drug 9-phenyl symm octahydro selenoxanthene is insoluble in water. The complexation with hydroxypropyl beta-cyclodextrin increases the water solubility improving the bioavailability. The stoichiometry of the supramolecular host-guest complex was studied by displacement experiments using fluorescence spectroscopy. With respect to the application in the radiologic brachy therapy the inclusion complex was encapsulated by spray drying with both, poly D,L-lactic-co-glycolic acid and gelatin. The in-vitro irradiation tests of the final ointment formulation show the inhibition of neoplasm development, and an efficient protection effect against radiation.

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20

Wu, Xuan, Yan Li, Chen Lin, Xiao-Yu Hu, and Leyong Wang. "GSH- and pH-responsive drug delivery system constructed by water-soluble pillar[5]arene and lysine derivative for controllable drug release." Chemical Communications 51, no. 31 (2015): 6832–35. http://dx.doi.org/10.1039/c5cc01393c.

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21

Haiahem, Sakina, Leila Nouar, Imen Djilani, Abdelazize Bouhadiba, Fatiha Madi, and Djamel Eddine Khatmi. "Host-guest inclusion complex between β-cyclodextrin and paeonol: A theoretical approach." Comptes Rendus Chimie 16, no. 4 (April 2013): 372–79. http://dx.doi.org/10.1016/j.crci.2012.11.008.

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22

Peng, Lei, Musong Lin, Sheng Zhang, Li Li, Qiang Fu, and Junbo Hou. "A Self-Healing Coating with UV-Shielding Property." Coatings 9, no. 7 (July 1, 2019): 421. http://dx.doi.org/10.3390/coatings9070421.

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A self-healing coating with UV-shielding property was prepared in this paper. The self-healing property was based on the inclusion between a host (β-CD-TiO2) and a guest HEMA-Ad). After inclusion of the host and guest, the host–guest complex (HEMA-Ad/β-CD-TiO2) was polymerized with other reactive monomers (HEMA and BA) to obtain the final coating. The coating had good hydrophobicity (water contact angle >90°, moisture absorption rate <2%) and excellent UV-shielding performance (ultra-violet protect factor >90%), and could be firmly bonded to a soft substrate. In addition, the coating had good self-healing property, which means that cracks in the material can recover many times after being damaged and that the UV-shielding ability can be fully restored with the self-healing process.

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23

Hettiarachchi, D. Saroja N., and Donal H. Macartney. "Cucurbit[7]uril host-guest complexes with cationic bis(4,5-dihydro-1H-imidazol-2-yl) guests in aqueous solution." Canadian Journal of Chemistry 84, no. 6 (June 1, 2006): 905–14. http://dx.doi.org/10.1139/v06-099.

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The host–guest interactions between cucurbit[7]uril and a series of novel cationic bis(4,5-dihydro-1H-imidazol-2-yl)arene and 1-(4,5-dihydro-1H-imidazol-2-yl)- and 1,3-bis(4,5-dihydro-1H-imidazol-2-yl)-adamantane guests have been investigated in aqueous solution using UV–vis and NMR spectroscopy, and electrospray mass spectrometry. With the exception of the 1,3-bis(4,5-dihydro-1H-imidazol-2-yl)adamantane (which binds externally to the CB[7]), these guests form very stable inclusion complexes with slow exchange on the 1H NMR timescale. The direction and magnitude of the complexation-induced shifts (CIS) in the proton resonances of the guests are indicative of the residence of the hydrophobic core of the guest within the CB[7] cavity and the charged 4,5-dihydro-1H-imidazol-2-yl units outside the cavity adjacent to the carbonyl-lined portals of the host. The CIS values and the inclusion stability constants have been correlated with the nature of the guest core and with the distance between the charges on the terminal 4,5-dihydro-1H-imidazol-2-yl rings.Key words: cucurbit[7]uril, host–guest complex, dihydroimidazolyl, inclusion stability constants.

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24

Kobrina, Larisa, Valentina Boyko, Halyna Hliieva, Sergii Riabov, Sergiy Rogalsky, and Karolina Yanova. "PECULIARITIES OF COMPLEX FORMATION IN THE SULFOBUTYL ETHER-β-CYCLODEXTRIN - IONIC LIQUID SYSTEM." Ukrainian Chemistry Journal 88, no. 1 (February 16, 2022): 49–66. http://dx.doi.org/10.33609/2708-129x.88.01.2022.49-66.

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The inclusion complexation of sulfobutyl ether-β-cyclodextrin sodium salt (SBECD) - ionic liquid (IL) has been investigated by a series of appropriate methods. The stability constant of the complex of SBECD-IL (K = 72.4 m-1) was determined by the method of Higuchi and Connors. An increase in the surface tension of solutions with different SBECD’s content was recorded by using the method of Wilhelm's plate, which could serve as an additional evidence of the formation of inclusion complex between SBECD and IL. Analysis of the TGA results provided for the initial IL and SBECD, their mechanical mixture and the complex elaborated allows us to conclude that the "guest-host" type complexation is emerged. Differential scanning calorimetry (DSC) data also confirmed the formation of inclusion complex between SBECD and IL. While the guest molecule is incorporated into cyclodextrin cavity, its thermal properties are changed. So, the loss of physically bonded water in the complex is equal to 5% by weight, indicating the IL’s molecule being located in the SBECD’s hydrophobic cavity. The thermogram of inclusion complex demonstrates just one endothermic peak at 74 oC. The complex is formed by entering the long alkyl chain of ionic liquid into the hydrophobic cavity of SBECD. Since the bonds of sulfo groups and β-СD’s glucopyran cycles become weaker, this may testify an additional interactions between SBECD and IL. With thermograviometric analysis (TGA) of the original IR and SB-β-CD, their mechanical mixture and the test compound fixed the formation of not a classical complex, but an associated complex of inclusion type "guest-host", which is formed by entering a long alkyl chain IR in the hydrophobic cavity SB-β-CD.

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25

Caira, Mino, Susan Bourne, and Buntubonke Mzondo. "Cyclodextrin inclusion complexes of the antioxidant α-lipoic acid." Acta Crystallographica Section A Foundations and Advances 70, a1 (August 5, 2014): C992. http://dx.doi.org/10.1107/s205327331409007x.

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Owing to its potent antioxidant activity,α-lipoic acid (1,2-dithiolane-3-pentanoic acid) is widely used as a supplement and is recommended for treating a number of conditions including chronic liver disease and diabetes. The poor aqueous solubility of the acid (~0.003 M at 250C) has prompted studies of its interaction with cyclodextrins (CDs) as a possible route to improving its solubility. However, relatively few studies have focused on the isolation of solid CD inclusion complexes of the antioxidant, and in most cases the racemic form of the acid was employed. In the comprehensive study reported here, the bioactive (R)-(+)-enantiomeric form of the molecule was used exclusively, resulting in the isolation and structural characterization of its inclusion complexes with each of the native host CDs (α-, β- and γ-CD) as well as permethylated α-CD (TRIMEA), permethylated β-CD (TRIMEB) and 2,6-dimethylated-β-CD (DIMEB). The α-CD complex crystallizes in the trigonal system, space group R32, with three independent CD molecules in the asymmetric unit and is not isostructural with any known CD complex while the β-CD complex crystallizes in the monoclinic system (C2). With the host γ-CD, an orthorhombic (pseudo-tetragonal) inclusion complex was identified, an unusual result as γ-CD complexes generally crystallize in the tetragonal space group P4212. The complexes with TRIMEA and TRIMEB crystallize in the orthorhombic system (P212121), the modes of inclusion of the (R)-(+)-α-lipoic acid molecule in the respective hosts being reversed: the guest molecule is fully encapsulated by the former host with the dithiolane ring located at the secondary rim, while in the latter host, the dithiolane ring rests on the concave surface of the host cavity at the primary side. A significant level of guest disorder was detected in the inclusion complex with DIMEB (P21). Thermal and phase-solubility analyses complemented the X-ray structural studies.

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26

Russo, Marco, and Paolo Lo Meo. "Binding abilities of a chiral calix[4]resorcinarene: a polarimetric investigation on a complex case of study." Beilstein Journal of Organic Chemistry 13 (December 15, 2017): 2698–709. http://dx.doi.org/10.3762/bjoc.13.268.

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Polarimetry was used to investigate the binding abilities of a chiral calix[4]resorcinarene derivative, bearing L-proline subunits, towards a set of suitably selected organic guests. The simultaneous formation of 1:1 and 2:1 host–guest inclusion complexes was observed in several cases, depending on both the charge status of the host and the structure of the guest. Thus, the use of the polarimetric method was thoroughly revisited, in order to keep into account the occurrence of multiple equilibria. Our data indicate that the stability of the host–guest complexes is affected by an interplay between Coulomb interactions, π–π interactions, desolvation effects and entropy-unfavorable conformational dynamic restraints. Polarimetry is confirmed as a very useful and versatile tool for the investigation of supramolecular interactions with chiral hosts, even in complex systems involving multiple equilibria.

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27

Hunt, Lee E., Susan A. Bourne, and Mino R. Caira. "Inclusion of Hydroxycinnamic Acids in Methylated Cyclodextrins: Host-Guest Interactions and Effects on Guest Thermal Stability." Biomolecules 11, no. 1 (December 31, 2020): 45. http://dx.doi.org/10.3390/biom11010045.

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There is ongoing interest in exploiting the antioxidant activity and other medicinal properties of natural monophenolic/polyphenolic compounds, but their generally low aqueous solubility limits their applications. Numerous studies have been undertaken to solubilize such compounds via supramolecular derivatization with co-crystal formation with biocompatible coformer molecules and cyclodextrin (CD) complexation being two successful approaches. In this study, eight new crystalline products obtained by complexation between methylated cyclodextrins and the bioactive phenolic acids (ferulic, hydroferulic, caffeic, and p-coumaric acids) were investigated using thermal analysis (hot stage microscopy, thermogravimetry, differential scanning calorimetry) and X-ray diffraction. All of the complexes crystallized as ternary systems containing the host CD, a phenolic acid guest, and water. On heating each complex, the primary thermal events were dehydration and liberation of the respective phenolic acid component, the mass loss for the latter step enabling determination of the host-guest stoichiometry. Systematic examination of the X-ray crystal structures of the eight complexes enabled their classification according to the extent of inclusion of each guest molecule within the cavity of its respective CD molecule. This revealed three CD inclusion compounds with full guest encapsulation, three with partial guest inclusion, and two that belong to the rare class of ‘non-inclusion’ compounds.

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28

Chao, Shuang, Ziyan Shen, Yuxin Pei, Yinghua Lv, Xiaolin Chen, Jiaming Ren, Ke Yang, and Zhichao Pei. "Pillar[5]arene-based supramolecular photosensitizer for enhanced hypoxic-tumor therapeutic effectiveness." Chemical Communications 57, no. 62 (2021): 7625–28. http://dx.doi.org/10.1039/d1cc02959b.

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A galactose-targeting supramolecular photosensitizer system DOX@GP5⊃NBSPD was constructed based on a host–guest inclusion complex, which could achieve the enhanced hypoxic-tumor therapeutic effectiveness by chemo-photodynamic combination.

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29

Giastas, Petros, Konstantina Yannakopoulou, and Irene M. Mavridis. "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." Acta Crystallographica Section B Structural Science 59, no. 2 (March 26, 2003): 287–99. http://dx.doi.org/10.1107/s010876810300257x.

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The present investigation is part of an ongoing study on the influence of the long end-functonalized guest molecules DBA and BNZ in the crystal packing of β-cyclodextrin (βCD) dimeric complexes. The title compounds are 2:2 host:guest complexes showing limited host–guest hydrogen bonding at the primary faces of the βCD dimers. Within the βCD cavity the guests exhibit mutual π...π interactions and between βCD dimers perpendicular NH...π interactions. The DBA guest molecule exhibits one extended and two bent conformations in the complex. The BNZ guest molecule is not planar inside βCD, in contrast to the structure of BNZ itself, which indicates that the cavity isolates the molecules and forbids the π...π stacking of the aromatic rings. NMR spectroscopy studies show that in aqueous solution both DBA and BNZ form strong complexes that have 1:1 stoichiometry and structures similar to the solid state ones. The relative packing of the dimers is the same in both complexes. The axes of two adjacent dimers form an angle close to 20° and have a lateral displacement ≃2.45 Å, both of which characterize the screw-channel mode of packing. Although the βCD/BNZ complex indeed crystallizes in a space group characterizing the latter mode, the βCD/DBA complex crystallizes in a space group with novel dimensions not resembling any of the packing modes reported so far. The new lattice is attributed to the three conformations exhibited by the guest in the crystals. However, this lattice can be transformed into another, which is isostructural to that of the βCD/BNZ inclusion complex, if the conformation of the guest is not taken into account.

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30

Joshi, Hrishikesh, Sivaramapanicker Sreejith, Ranjan Dey, and Mihaiela C. Stuparu. "Host–guest interaction between corannulene and γ-cyclodextrin: mass spectrometric evidence of a 1 : 1 inclusion complex formation." RSC Advances 6, no. 111 (2016): 110001–3. http://dx.doi.org/10.1039/c6ra24549h.

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31

Guzei, Ilia A., and Kelsey C. Miles. "Ab initioX-ray structural characterization of an inclusion compound with a compositionally disordered chiral guest: no prior knowledge of the crystal composition." Acta Crystallographica Section C Structural Chemistry 72, no. 3 (February 10, 2016): 179–83. http://dx.doi.org/10.1107/s2053229616001972.

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The crystal structure and absolute configuration of a molecular host/guest/impurity inclusion complex were established unequivocally in spite of our having no prior knowledge of its chemical composition. The host (4R,5R)-4,5-bis(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolane, (I), displays expected conformational features. The crystal-disordered chiral guest 4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one, (II), is present in the crystal 85.1 (4)% of the time. It shares a common site with 4a-hydroperoxymethyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one, (III), present 14.9 (4)% of the time, which is the product of autoxidation of (II). This minor peroxide impurity was isolated, and the results of nuclear magnetic resonance, mass spectrometry, and X-ray fluorescence studies are consistent with the proposed structure of (III). The complete structure was therefore determined to be (4R,5R)-4,5-bis(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolane–4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one–4a-hydroperoxymethyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one (1/0.85/0.15), C31H30O4·0.85C10H14O·0.15C10H14O3, (IV). There are host–host, host–guest, and host–impurity hydrogen-bonding interactions of typesSandDin the solid state. We believe that the crystals of (IV) were originally prepared to establish the chirality of the guest (II) by means of X-ray diffraction analysis of host/guest crystals obtained in the course of chiral resolution during cocrystallization of (II) with (I). In spite of the absence of `heavy' elements, the absolute configurations of all anomeric centres in the structure are assigned asRbased on resonant scattering effects.

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32

Roy, Mahendra Nath, Milan Chandra Roy, and Kanak Roy. "Investigation of an inclusion complex formed by ionic liquid and β-cyclodextrin through hydrophilic and hydrophobic interactions." RSC Advances 5, no. 70 (2015): 56717–23. http://dx.doi.org/10.1039/c5ra09823h.

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An investigation of the inclusion behavior of a guest ionic liquid (IL) 1-methyl-3-octylimidazolium tetrafluoroborate into the host cavity of β-cyclodextrin in aqueous solution has been carried out towards modern research to gain a far reaching effect.

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33

Caira, Mino R., Susan A. Bourne, Halima Samsodien, and Vincent J. Smith. "Inclusion complexes of 2-methoxyestradiol with dimethylated and permethylated β-cyclodextrins: models for cyclodextrin–steroid interaction." Beilstein Journal of Organic Chemistry 11 (December 16, 2015): 2616–30. http://dx.doi.org/10.3762/bjoc.11.281.

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The interaction between the potent anticancer agent 2-methoxyestradiol (2ME) and a series of cyclodextrins (CDs) was investigated in the solid state using thermal analysis and X-ray diffraction, while the possibility of enhancing its poor aqueous solubility with CDs was probed by means of equilibrium solubility and dissolution rate measurements. Single crystal X-ray diffraction studies of the inclusion complexes between 2ME and the derivatised cyclodextrins heptakis(2,6-di-O-methyl)-β-CD (DIMEB) and heptakis(2,3,6-tri-O-methyl)-β-CD (TRIMEB) revealed for the first time the nature of the encapsulation of a bioactive steroid by representative CD host molecules. Inclusion complexation invariably involves insertion of the D-ring of 2ME from the secondary side of each CD molecule, with the 17-OH group generally hydrogen bonding to a host glycosidic oxygen atom within the CD cavity, while the A-ring and part of the B-ring of 2ME protrude from the secondary side. In the case of the TRIMEB·2ME complex, there is evidence that complexation proceeds with mutual conformational adaptation of host and guest molecules. The aqueous solubility of 2ME was significantly enhanced by CDs, with DIMEB, TRIMEB, randomly methylated β-CD and hydroxypropyl-β-CD being the most effective hosts. The 2:1 host–guest β-CD inclusion complex, prepared by two methods, yielded very rapid dissolution in water at 37 °C relative to untreated 2ME, attaining complete dissolution within 15 minutes (co-precipitated complex) and 45 minutes (complex from kneading).

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34

Sun, Yun-Xia, Jing-Yi Zhu, Wen-Xiu Qiu, Qi Lei, Si Chen, and Xian-Zheng Zhang. "Versatile Supermolecular Inclusion Complex Based on Host–Guest Interaction for Targeted Gene Delivery." ACS Applied Materials & Interfaces 9, no. 49 (December 2017): 42622–32. http://dx.doi.org/10.1021/acsami.7b14963.

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35

Cruz, Jennifer R., Bridget A. Becker, Kevin F. Morris, and Cynthia K. Larive. "NMR characterization of the host-guest inclusion complex between β-cyclodextrin and doxepin." Magnetic Resonance in Chemistry 46, no. 9 (September 2008): 838–45. http://dx.doi.org/10.1002/mrc.2267.

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36

Rasouli, Sajad, and Seyed Majid Hashemianzadeh. "Thermal behavior of cyclodextrin/adamantane host/guest inclusion complex in an aqueous media." Journal of Molecular Liquids 390 (November 2023): 123096. http://dx.doi.org/10.1016/j.molliq.2023.123096.

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37

Lee, Jae-ung, Sung-Sik Lee, Sungyul Lee, and Han Bin Oh. "Noncovalent Complexes of Cyclodextrin with Small Organic Molecules: Applications and Insights into Host–Guest Interactions in the Gas Phase and Condensed Phase." Molecules 25, no. 18 (September 4, 2020): 4048. http://dx.doi.org/10.3390/molecules25184048.

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Cyclodextrins (CDs) have drawn a lot of attention from the scientific communities as a model system for host–guest chemistry and also due to its variety of applications in the pharmaceutical, cosmetic, food, textile, separation science, and essential oil industries. The formation of the inclusion complexes enables these applications in the condensed phases, which have been confirmed by nuclear magnetic resonance (NMR) spectroscopy, X-ray crystallography, and other methodologies. The advent of soft ionization techniques that can transfer the solution-phase noncovalent complexes to the gas phase has allowed for extensive examination of these complexes and provides valuable insight into the principles governing the formation of gaseous noncovalent complexes. As for the CDs’ host–guest chemistry in the gas phase, there has been a controversial issue as to whether noncovalent complexes are inclusion conformers reflecting the solution-phase structure of the complex or not. In this review, the basic principles governing CD’s host–guest complex formation will be described. Applications and structures of CDs in the condensed phases will also be presented. More importantly, the experimental and theoretical evidence supporting the two opposing views for the CD–guest structures in the gas phase will be intensively reviewed. These include data obtained via mass spectrometry, ion mobility measurements, infrared multiphoton dissociation (IRMPD) spectroscopy, and density functional theory (DFT) calculations.

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38

Rácz, Csaba-Pal, Gheorghe Borodi, Mihaela Maria Pop, Irina Kacso, Szabolcs Sánta, and Maria Tomoaia-Cotisel. "Structure of the inclusion complex of β-cyclodextrin with lipoic acid from laboratory powder diffraction data." Acta Crystallographica Section B Structural Science 68, no. 2 (February 25, 2012): 164–70. http://dx.doi.org/10.1107/s0108768112004284.

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The crystal structure of the inclusion complex of β-cyclodextrin with lipoic acid was determined from laboratory powder diffraction data. Thermogravimetric data was used to estimate the number of water molecules in the crystal structure. Lipoic acid is included in β-cyclodextrin through its primary face with the five-membered ring reaching the center plane of the cyclodextrin cavity and its fatty acid chain adopting a bent conformation. Lipoic acid and β-cyclodextrin form a channel-like packing which is stabilized by guest–host hydrogen bonding and close contacts, host–host intermolecular interactions and hydrogen bonding involving the water molecules.

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39

Roy, Kanak, Subhadeep Saha, Biswajit Datta, Lovely Sarkar, and Mahendra Nath Roy. "Study on Host-Guest Inclusion Complexation of a Drug in Cucurbit [6]uril." Zeitschrift für Physikalische Chemie 232, no. 2 (February 23, 2018): 281–93. http://dx.doi.org/10.1515/zpch-2017-0003.

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AbstractAssembly of pyridine-2-aldoxime drug with cucurbit [6]uril (CB[6]) has been investigated by1H-NMR and 2D-ROESY NMR, UV-Vis spectroscopy, FT-IR spectroscopy, surface tension and conductivity measurements in aqueous saline environment. The distinct cationic receptor feature and the cavity dimension of the CB[6] emphasize that the macro-cyclic host molecule remain as complex with the nerve stimulus drug molecule. The results obtained from surface tension and specific conductivity measurements suggest 1:1 inclusion complex formation between drug and CB[6]. The stability constant evaluated by UV-Vis spectroscopic approach is 2.21×105M−1at 298.15 K, which indicates that the complex is sufficiently stable at physiological temperature.

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Zhang, Xiaodong, Jun Xie, Zhiling Xu, Zhu Tao, and Qianjun Zhang. "The interaction between cucurbit[8]uril and baicalein and the effect on baicalein properties." Beilstein Journal of Organic Chemistry 16 (January 10, 2020): 71–77. http://dx.doi.org/10.3762/bjoc.16.9.

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The host–guest interactions between baicalein (BALE) and cucurbit[8]uril (Q[8]) and the corresponding properties of the inclusion complex were studied using 1H NMR, IR and UV–vis spectroscopy and DTA. The results showed that BALE forms an inclusion compound (1:1) with Q[8], and the properties of baicalein are changed by cucurbit[8]uril.

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41

Lupu, Andrei Cristian, Mihaela Bombos, Gabriel Vasilievici, and Liviu-Dan Miron. "Synthesis and Characterization of Inclusion Complex of Diminazene Aceturate with b-Ciclodextrin." Revista de Chimie 70, no. 6 (July 15, 2019): 2136–40. http://dx.doi.org/10.37358/rc.19.6.7291.

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Cyclodextrins (CD) are macrocyclic biopolymers with potential applications in the delivery of small and macro-molecular therapeutic agents. Despite the potent host-guest inclusion property, their inherent lack of cellular binding ability has limited applications in drug delivery. Herein, we functionalized b-cyclodextrin (b-CD) with diminazene aceturate(DIMA), which are bioactive molecules, widely distributed some cells, and responsible for antiprotozoal activity. The inclusion complex of DIMA with b-CD was confirmed with textural, thermogravimetric, calorimetric, spectroscopic, and microscopic techniques. Thus, the proposed inclusion complex b-CD-DIMA system could be used as a site-specific drug delivery carrier.

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42

Ramešová, Šárka, Romana Sokolová, Ilaria Degano, Magdaléna Hromadová, Miroslav Gál, Viliam Kolivoška, and Maria Perla Colombini. "The influence of the host–guest interaction on the oxidation of natural flavonoid dyes." Collection of Czechoslovak Chemical Communications 76, no. 12 (2011): 1651–67. http://dx.doi.org/10.1135/cccc2011106.

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The influence of the molecular cavity protection on degradation processes of bioorganic compounds quercetin and luteolin used as the original dyes in old tapestries was studied. The degradation processes were studied by electrochemical methods in aqueous media. The products of the exhaustive electrolysis were separated and identified by GC-MS analysis. Cyclic voltammetry characteristics indicate that the inclusion complex is formed. The inclusion affects the redox potentials of both oxidation waves related to the different dissociation forms of the flavonoid molecule. It was shown that decomposition products formed by the oxidation of quercetin are stabilized in the cavity of β-cyclodextrin, including the main oxidation product 2(3′,4′-dihydroxybenzoyl)-2,4,6-trihydroxybenzofuran-3(2H)-one. The formation of the 1:1 inclusion complex of luteolin with β-cyclodextrin is supported by the enhancement of fluorescence intensity. In the case of quercetin, a decrease of fluorescence intensity occurs when 1:1 inclusion complex with β-cyclodextrin is formed.

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43

Mohammed-Saeid, Waleed, Abdalla H. Karoyo, Ronald E. Verrall, Lee D. Wilson, and Ildiko Badea. "Inclusion Complexes of Melphalan with Gemini-Conjugated β-Cyclodextrin: Physicochemical Properties and Chemotherapeutic Efficacy in In-Vitro Tumor Models." Pharmaceutics 11, no. 9 (August 22, 2019): 427. http://dx.doi.org/10.3390/pharmaceutics11090427.

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β-cyclodextrin (βCD) has been widely explored as an excipient for pharmaceuticals and nutraceuticals as it forms stable host–guest inclusion complexes and enhances the solubility of poorly soluble active agents. To enhance intracellular drug delivery, βCD was chemically conjugated to an 18-carbon chain cationic gemini surfactant which undergoes self-assembly to form nanoscale complexes. The novel gemini surfactant-modified βCD carrier host (hereafter referred to as 18:1βCDg) was designed to combine the solubilization and encapsulation capacity of the βCD macrocycle and the cell-penetrating ability of the gemini surfactant conjugate. Melphalan (Mel), a chemotherapeutic agent for melanoma, was selected as a model for a poorly soluble drug. Characterization of the 18:1βCDg-Mel host–guest complex was carried out using 1D/2D 1H NMR spectroscopy and dynamic light scattering (DLS). The 1D/2D NMR spectral results indicated the formation of stable and well-defined 18:1βCDg-Mel inclusion complexes at the 2:1 host–guest mole ratio; whereas, host–drug interaction was attenuated at greater 18:1βCDg mole ratio due to hydrophobic aggregation that accounts for the reduced Mel solubility. The in vitro evaluations were performed using monolayer, 3D spheroid, and Mel-resistant melanoma cell lines. The 18:1βCDg-Mel complex showed significant enhancement in the chemotherapeutic efficacy of Mel with 2–3-fold decrease in Mel half maximal inhibitory concentration (IC50) values. The findings demonstrate the potential applicability of the 18:1βCDg delivery system as a safe and efficient carrier for a poorly soluble chemotherapeutic in melanoma therapy.

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44

Hichri, S., N. Matoussi, and R. Abderrahim. "Synthesis and characterization of inclusion complex of -cyclodextrin and triazole picrate." Bulletin of the Chemical Society of Ethiopia 37, no. 4 (May 12, 2023): 973–82. http://dx.doi.org/10.4314/bcse.v37i4.13.

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ABSTRACT. Inclusion complex between 3-amino-1,2,4-triazole picrate and β-cyclodextrin was synthesized in order to increase the picrate solubility. The complex was obtained by co-precipitation method and its stoichiometry is 1:1 (guest–host). The structure of picrate and complex has been established by UV, X-ray diffractometry powder spectra, TGA, DSC, IR, 1H NMR, and 13C NMR. The influence of the effect of pH on the complexation has been discussed. The value of apparent formation constant is 1.2 x 104. KEY WORDS: Amino triazole, Picrate, Inclusion complex, pH Bull. Chem. Soc. Ethiop. 2023, 37(4), 973-982. DOI: https://dx.doi.org/10.4314/bcse.v37i4.13

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45

Li, Hui, Guolei Zhang, Wei Wang, Changbao Chen, Lili Jiao, and Wei Wu. "Preparation, Characterization, and Bioavailability of Host-Guest Inclusion Complex of Ginsenoside Re with Gamma-Cyclodextrin." Molecules 26, no. 23 (November 29, 2021): 7227. http://dx.doi.org/10.3390/molecules26237227.

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This work aimed at improving the water solubility of Ginsenoside (G)-Re by forming an inclusion complex. The solubility parameters of G-Re in alpha (α), beta (β), and gamma (γ) cyclodextrin (CD) were investigated. The phase solubility profiles were all classified as AL-type that indicated the 1:1 stoichiometric relationship with the stability constants Ks which were 22 M−1 (α-CD), 612 M−1 (β-CD), and 14,410 M−1 (γ-CD), respectively. Molecular docking studies confirmed the results of phase solubility with the binding energy of −4.7 (α-CD), −5.10 (β-CD), and −6.70 (γ-CD) kcal/mol, respectively. The inclusion complex (IC) of G-Re was prepared with γ-CD via the water-stirring method followed by freeze-drying. The successful preparation of IC was confirmed by powder X-ray diffraction (XRD), Fourier transform-infrared spectroscopy (FT-IR), differential scanning calorimetry (DSC), and scanning electron microscopy (SEM). In-vivo absorption studies were carried out by LC-MS/MS. Dissolution rate of G-Re was increased 9.27 times after inclusion, and the peak blood concentration was 2.7-fold higher than that of pure G-Re powder. The relative bioavailability calculated from the ratio of Area under the curve AUC0–∞ of the inclusion to pure G-Re powder was 171%. This study offers the first report that describes G-Re’s inclusion into γ-CD, and explored the inclusion complex’s mechanism at the molecular level. The results indicated that the solubility could be significantly improved as well as the bioavailability, implying γ-CD was a very suitable inclusion host for complex preparation of G-Re.

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46

Dudev, Todor, and Tony Spassov. "Inclusion Complexes between β-Cyclodextrin and Gaseous Substances—N2O, CO2, HCN, NO2, SO2, CH4 and CH3CH2CH3: Role of the Host’s Cavity Hydration." Inorganics 12, no. 4 (April 9, 2024): 110. http://dx.doi.org/10.3390/inorganics12040110.

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The thermodynamic aspects of the process of inclusion complex formation between β-cyclodextrin (acting as a host) and gaseous substances (guests; N2O, CO2, NO2, SO2, HCN, CH4, CH3CH2CH3) are studied by employing well-calibrated and tested density functional theory (DFT) calculations. This study sheds new light on the intimate mechanism of the β-cyclodextrin/gas complex formation and answers several intriguing questions: how the polarity and size of the guest molecule influence the complexation thermodynamics; which process of encapsulation by the host macrocycle is more advantageous—insertion to the central cavity without hydration water displacement or guest binding accompanied by a displacement of water molecule(s); what the major factors governing the formation of the complex between β-cyclodextrin and gaseous substances are. The special role that the cluster of water molecules inside the host’s internal cavity plays in the encapsulation process is emphasized.

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47

Uyar, Tamer, Ahmed El-Shafei, Xingwu Wang, Jale Hacaloglu, and Alan E. Tonelli. "The Solid Channel Structure Inclusion Complex Formed Between Guest Styrene and Host γ-Cyclodextrin." Journal of Inclusion Phenomena and Macrocyclic Chemistry 55, no. 1-2 (December 7, 2005): 109–21. http://dx.doi.org/10.1007/s10847-005-9026-5.

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48

Majhi, Koushik, Rijia Khatun, Sourav Jana, Alakananda Hajra, Aparna Shukla, Pralay Maiti, Arka Dey, Partha Pratim Ray, and Subrata Sinha. "Synthesis and characterization of host–guest inclusion complex of m-cresol with β-cyclodextrin." Journal of Inclusion Phenomena and Macrocyclic Chemistry 90, no. 1-2 (November 17, 2017): 61–73. http://dx.doi.org/10.1007/s10847-017-0765-x.

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49

Elbashir, Abdalla A., Fatima Altayib Alasha Abdalla, and Hassan Y. Aboul-Enein. "Host-guest inclusion complex of mesalazine and β-cyclodextrin and spectrofluorometric determination of mesalazine." Luminescence 30, no. 4 (September 9, 2014): 444–50. http://dx.doi.org/10.1002/bio.2758.

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50

Du, Xin-Zhen, Yong Zhang, Xian-Zhi Huang, Yun-Bao Jiang, Yao-Qun Li, and Guo-Zhen Chen. "Intense Room-Temperature Phosphorescence of 1-Bromonaphthalene in Organized Media of Beta-Cyclodextrin and Triton X-100." Applied Spectroscopy 50, no. 10 (October 1996): 1273–76. http://dx.doi.org/10.1366/0003702963904999.

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In aerated aqueous solution, intense room-temperature phosphorescence (RTP) of 1-bromonaphthalene (1-BrN) is observed with an host–guest inclusion complex composed of Triton X-100, 1-BrN, and beta-cyclodextrin (β-CD). Triton X-100 is incorporated into the hydrophobic cavity of β-CD as the second guest molecule, and a 1:1:1 ternary complex is formed. This complex, with a polar head group, can be well distributed in aqueous solution, and stable RTP is obtained. Ethanol further enhances the RTP of the ternary complex, whereas 1-propanol and 1-butanol greatly attenuate RTP. Spectral analyses indicate that 1-BrN in the β-CD cavity is replaced by 1-propanol and 1-butanol.

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