Enhanced Solubility, Stability, and Herbicidal Activity of the Herbicide Diuron by Complex Formation with β-Cyclodextrin

Shuang Gao; Jing-Yu Jiang; Yan-Yan Liu; Ying Fu; Li-Xia Zhao; Chun-Yan Li; Fei Ye

doi:10.3390/polym11091396

Enhanced Solubility, Stability, and Herbicidal Activity of the Herbicide Diuron by Complex Formation with β-Cyclodextrin

Polymers ◽

10.3390/polym11091396 ◽

2019 ◽

Vol 11 (9) ◽

pp. 1396 ◽

Cited By ~ 9

Author(s):

Shuang Gao ◽

Jing-Yu Jiang ◽

Yan-Yan Liu ◽

Ying Fu ◽

Li-Xia Zhao ◽

...

Keyword(s):

Inclusion Complex ◽

1H Nmr ◽

Water Solubility ◽

Herbicidal Activity ◽

Environmental Damage ◽

Phase Solubility ◽

Scanning Calorimetry ◽

Enhanced Solubility ◽

Phase Solubility Study ◽

Herbicide Diuron

The herbicide diuron is hardly soluble in water and most organic solvents and is usually made into a wettable powder or mixed with soil when used, which causes environmental risk and a reduction in herbicidal efficacy. In this study, the physicochemical properties were changed by using β-cyclodextrin (β-CD) to encapsulate diuron to form an inclusion complex. Some key technologies, including X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), differential scanning calorimetry (DSC), and nuclear magnetic resonance (1H NMR), were used to characterize the inclusion complex. The stoichiometry of the inclusion complex was determined by recording the 1H NMR spectrum or by using a diagram of inclusion ratios. A phase solubility study proved that the formed inclusion complex exhibited higher water solubility. Thermogravimetric analysis (TGA) demonstrated that the formed inclusion complex exhibited better thermal stability. Biological activity studies indicated that the herbicidal activity, in terms of herbicide removal, of the formed inclusion complex was higher than that of the original diuron. In general, the formation of the inclusion complex could reduce the environmental damage caused by diuron and enhance its herbicidal activity, providing an environmentally friendly method for using diuron.

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Preparation, Characterization, and Bioavailability of Host-Guest Inclusion Complex of Ginsenoside Re with Gamma-Cyclodextrin

Molecules ◽

10.3390/molecules26237227 ◽

2021 ◽

Vol 26 (23) ◽

pp. 7227

Author(s):

Hui Li ◽

Guolei Zhang ◽

Wei Wang ◽

Changbao Chen ◽

Lili Jiao ◽

...

Keyword(s):

Inclusion Complex ◽

Water Solubility ◽

Area Under The Curve ◽

Relative Bioavailability ◽

Docking Studies ◽

Solubility Parameters ◽

Phase Solubility ◽

Scanning Calorimetry ◽

Ginsenoside Re

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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Functional Supramolecular of Inclusion Complex of Herbicide Fluroxypyr with HPβCD

Polymers ◽

10.3390/polym10121294 ◽

2018 ◽

Vol 10 (12) ◽

pp. 1294 ◽

Cited By ~ 6

Author(s):

Shuang Gao ◽

Chao Bie ◽

Yanyan Liu ◽

Tianyu Zhang ◽

Ying Fu ◽

...

Keyword(s):

Thermal Stability ◽

Inclusion Complex ◽

Solution Method ◽

Water Solubility ◽

Herbicidal Activity ◽

Saturated Solution ◽

Phase Solubility ◽

Bioactivity Assay ◽

Ft Ir ◽

Tga Analysis

In this study, hydroxypropyl-β-cyclodextrin (HPβCD) was used to form an inclusion complex with fluroxypyr to enhance water solubility and thermal stability. The inclusion complex was prepared by a saturated solution method and characterized by FT-IR, SEM, TGA, and XRD. All results indicated that fluroxypyr successfully entered the HPβCD cavity. In addition, the study of phase solubility identifies that the water solubility of fluroxypyr was greatly improved after the formation of the inclusion complex, and TGA analysis suggested that the formation of the inclusion complex improved the thermal stability. Bioactivity assay tests showed that the inclusion complex still had strong herbicidal activity. Our research showed that HPβCD was a promising carrier for improving the properties of fluroxypyr and, thus, expanding its use in agrochemical formulations.

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EVALUATION OF ORALLY DISINTEGRATING TABLET OF IBUPROFEN-β-CYCLODEXTRIN INCLUSION COMPLEX

International Journal of Applied Pharmaceutics ◽

10.22159/ijap.2020v12i2.34848 ◽

2020 ◽

pp. 60-64

Author(s):

NUR AINI DEWI PURNAMASARI ◽

PRATAMA ANGGI SAPUTRA

Keyword(s):

Inclusion Complex ◽

Dissolution Rate ◽

Spray Drying ◽

Water Solubility ◽

The Other ◽

Molar Ratio ◽

Taste Masking ◽

Scanning Calorimetry ◽

Orally Disintegrating Tablet ◽

Dissolution Efficiency

Objective: This study aims to determine the effect of the inclusion complex formation of ibuprofen (IB) with β-cyclodextrin (β-CD) in improving water solubility and taste masking as well as to study the effect of the combined use of super disintegrants in IB-β-CD ODT (Orally disintegrating tablet). Methods: IB-β-CD inclusion complex was prepared by spray drying technique with a 1:1 molar ratio. ODTs were prepared by the direct compression method using various ratios of Ac-Di-Sol® and Kollidon® CL as super disintegrant. The inclusion complex was characterized using spectroscopy FT-IR (Fourier-transform infrared) and DSC (Differential Scanning Calorimetry). The physical properties and dissolution rate of ODTs were evaluated. Dissolved drug concentration at 60 min (Q60) and Dissolution Efficiency (DE60) was calculated using the dissolution test result. Results: The unpleasant taste of IB had been successfully masked by IB-β-CD. Formula 1 was observed having 14.5 sec of disintegration, fastest compared to the other formulas. Moreover DE60 value of formula I was higher than the other formulas (113.45). Conclusion: IB-β-CD Inclusion complex prepared by spray drying method (1: 1) increased the water solubility and masked the unpleasant taste compared to IB moreover combination of Ac-Di-Sol® and Kollidon® CL increased ODT dissolution rate.

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Improvement of Water Solubility of Josamycin by Inclusion Complex with -Cyclodextrin

ISRN Analytical Chemistry ◽

10.5402/2012/673564 ◽

2012 ◽

Vol 2012 ◽

pp. 1-6 ◽

Cited By ~ 1

Author(s):

J. El Harti ◽

Y. Cherrah ◽

A. Bouklouze

Keyword(s):

Inclusion Complex ◽

Water Solubility ◽

Inclusion Complexation ◽

Infrared Spectrometry ◽

Resonance Spectroscopy ◽

Phase Solubility ◽

X Ray Diffraction ◽

The Family ◽

The Stability ◽

Low Solubility

Josamycin propionate (JMP) is an antibiotic belonging to the family of macrolide. According to the Biopharmaceutical Classification System (BCS), this compound can be classed in class II, low solubility and high permeability. In order to increase its apparent water solubility, inclusion complexation between Josamycin propionate and γ-cyclodextrin (γ-CD) was studied. UV spectrophotometric method was employed to investigate the phase-solubility profile and the stability constant of the complexation in aqueous medium. Solid state of the binary system prepared by coevaporation (in 50%-50% ethanol/water) has been characterized using powder X-ray diffraction (XRD) and Fourier transformation-infrared spectrometry (FTIR). These techniques indicate that JMP forms an association complex with γ-CD. The shift in the nuclear magnetic resonance spectroscopy (1H NMR) confirms the existence of the inclusion complex. Also the results obtained showed an enhancement of the solubility in water of Josamycin propionate.

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β-Cyclodextrin as water-solubility enhancer for butylated hydroxytoluene

Chemical Papers ◽

10.1515/chempap-2015-0078 ◽

2015 ◽

Vol 69 (5) ◽

Cited By ~ 1

Author(s):

Marcin Lukasiewicz ◽

Stanislaw Kowalski ◽

Anna Ptaszek ◽

Pawel Ptaszek

Keyword(s):

Water Solubility ◽

Radical Scavenging Activity ◽

Antioxidant Properties ◽

Radical Scavenging ◽

Ternary Systems ◽

Butylated Hydroxytoluene ◽

Phase Solubility ◽

Solubility Study ◽

Phase Solubility Study ◽

Endothermic Process

AbstractThe phenomenon of the increase in solubility of the non-polar phenolic antioxidant - butylated hydroxytoluene (BHT) - in aqueous solutions containing β-cyclodextrin (CD) was studied. The complexation of BHT by CD was investigated using a phase solubility study. This method makes it possible to calculate the apparent formation constant for the host-guest complex. In addition, the thermodynamic properties were evaluated, revealing a spontaneous endothermic process of complex formation. Two solubility models were also used to verify their applicability to predicting the BHT concentration in solution. Those models included the modified Apelblat and Buchowski-Ksiazczak equations. In order to investigate the antioxidant properties of the BHT/CD/water ternary systems, a radical scavenging activity using a DPPH stable radical was performed. The experiments indicated that the antioxidant activity is temperature- and CD concentration-dependent. It was shown that complexation may inhibit the radical scavenging by BHT or change the scavenging stoichiometry.

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Two Novel Palbociclib-Resorcinol and Palbociclib-Orcinol Cocrystals with Enhanced Solubility and Dissolution Rate

Pharmaceutics ◽

10.3390/pharmaceutics14010023 ◽

2021 ◽

Vol 14 (1) ◽

pp. 23

Author(s):

Chenxin Duan ◽

Wenwen Liu ◽

Yunwen Tao ◽

Feifei Liang ◽

Yanming Chen ◽

...

Keyword(s):

Water Solubility ◽

Cancer Drug ◽

X Ray Diffraction ◽

Scanning Calorimetry ◽

Dissolution Rates ◽

Intrinsic Dissolution ◽

X Ray ◽

Enhanced Solubility

Palbociclib (PAL) is an effective anti-breast cancer drug, but its use has been partly restricted due to poor bioavailability (resulting from extremely low water solubility) and serious adverse reactions. In this study, two cocrystals of PAL with resorcinol (RES) or orcinol (ORC) were prepared by evaporation crystallization to enhance their solubility. The cocrystals were characterized by single crystal X-ray diffraction, Hirshfeld surface analysis, powder X-ray diffraction, differential scanning calorimetry, thermogravimetric analysis, Fourier transform infrared and scanning electron microscopy. The intrinsic dissolution rates of the PAL cocrystals were determined in three different dissolution media (pH 1.0, pH 4.5 and pH 6.8), and both cocrystals showed improved dissolution rates at pH 1.0 and pH 6.8 in comparison to the parent drug. In addition, the cocrystals increased the solubility of PAL at pH 6.8 by 2–3 times and showed good stabilities in both the accelerated stability testing and stress testing. The PAL-RES cocrystal also exhibited an improved relative bioavailability (1.24 times) than PAL in vivo pharmacokinetics in rats. Moreover, the in vitro cytotoxicity assay of PAL-RES showed an increased IC50 value for normal cells, suggesting a better biosafety profile than PAL. Co-crystallization may represent a promising strategy for improving the physicochemical properties of PAL with better pharmacokinetics.

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Preparation and characterization of artemether inclusion complexes with hydroxypropyl-β-cyclodextrin

Tropical Journal of Pharmaceutical Research ◽

10.4314/tjpr.v16i10.7 ◽

2017 ◽

Vol 16 (10) ◽

pp. 2359-2364

Author(s):

Zwanden Sule Yahaya ◽

Kenneth C. Ofokansi ◽

Suzane T. Allagh ◽

Pat G. Bhatia

Keyword(s):

Complex Formation ◽

Inclusion Complex ◽

Dissolution Rate ◽

Inclusion Complexes ◽

In Vitro Dissolution ◽

Phase Solubility ◽

Inclusion Complex Formation ◽

Scanning Calorimetry ◽

Ft Ir

Purpose: To investigate experimentally the inclusion of artemether into the cavity of hydroxypropyl-β-cyclodextrin and examine its effect on the solubility and dissolution rate of the drug.Methods: Inclusion complexes of artemether with hydroxypropyl-β-cyclodextrin of molar ratios 1:1, 1:2 and 1:3 were prepared using the kneading method. Phase solubility analysis and in vitro dissolution studies were utilized in evaluating the influence of inclusion complex formation on the solubility and dissolution rate of the drug. The complexes were characterized using differential scanning calorimetry (DSC) and Fourier transform infrared spectroscopy (FT-IR). The inclusion complex containing equimolar concentrations of artemether and hydroxypropyl-β-cyclodextrin was then formulated into tablets via direct compression and evaluated for various pharmaceutical characteristics including hardness, friability, absolute drug content and comparative in vitro dissolution profiles with some commercially available brands of artemether.Results: The phase solubility diagram for the formed complexes in water at 37 oC indicated a linear curve soluble complex system (referred to as the AL system), and a stability constant (KC) value of 143 M-1. Evidence consistent with inclusion complex formation was obtained using FT-IR and DSC. The formulated inclusion complex tablets exhibited a higher rate of dissolution than the pure drug and commercial brands, showing 3.9-, 1.8- and 1.6-fold increases, respectively, over a period of 15 min.Conclusion: Inclusion complexation of artemether with hydroxypropyl-β-cyclodextrin is a promising approach to enhance the solubility and dissolution rate of the drug.Keywords: Artemether, 2-Hydroxypropyl-β-cyclodextrin, Dissolution, Solubility enhancement, Inclusion complex

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Design of Experiment Approach to Assess The Effect Of Formulation Variables On Extrusion And Spheronization Of Telmisartan And Cilostazol Loaded Pellets And Its Pharmacokinetic Study

Current Drug Therapy ◽

10.2174/1566523221666210301103849 ◽

2021 ◽

Vol 16 ◽

Author(s):

Kalpana Patel ◽

Prutha Godhani ◽

Hemangini Patel ◽

Vaishali Thakkar ◽

Tejal Gandhi ◽

...

Keyword(s):

Inclusion Complex ◽

Solid Dispersion ◽

Pharmacokinetic Study ◽

Class Ii ◽

Phase Solubility ◽

Solubility Study ◽

Drug Content ◽

Bcs Class Ii ◽

Apparent Solubility ◽

Phase Solubility Study

Background: Solubility is an important parameter that affects availability of drug in systemic circulation. Drugs having poor solubility belonging to BCS class II eventually results in lower dissolution and bioavailability. Hence, improvement of solubility is a challenging task. Hence the present work focusses on using solid dispersion and inclusion complex approach for both telmisartan and cilostazol belonging to BCS Class II drugs. Objective: The present study was carried out to improve apparent solubility of telmisartan and cilostazol (BCS-Class II drugs) and optimization as pellets along with its pharmacokinetic study. Methods: Phase solubility study was carried out to screen the excipients such as, PVPK30, PVA, HPMC E5 and β-CD. Solvent evaporation method was adopted to prepare the solid dispersions and inclusion complex of both the drugs. Pellets were optimized by extrusion spheronization method using 32 factorial design and characterized by morphology, drug content, DSC, FTIR, XRD, SEM, in-vitro studies and drug content study Results: Phase solubility study showed improved apparent solubility of telmisartan with HPMC E5 (1:3) by solid dispersion and cilostazol with β-CD (1:3) using inclusion complexation method. Drug characterization did not reveal any incompatibility. Formulation was optimized on the basis of acceptable pellet properties, including acceptable spherical shape and micromeritics properties. The percent friability of all batches was found to be less than 1%. The optimized pellets of both drugs prepared with micro crystalline cellulose provided desirable maximum release with acceptable release profile. Conclusion: The formulated pellets when studied in vivo showed superior pharmacokinetic profile. The drawback associated with apparent solubility and bioavailability of both drugs can thus be alleviated by use of novel pellet formulation.

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Preparation and characterization of cyanazine–hydroxypropyl-beta-cyclodextrin inclusion complex

RSC Advances ◽

10.1039/c9ra04448e ◽

2019 ◽

Vol 9 (45) ◽

pp. 26109-26115 ◽

Cited By ~ 7

Author(s):

Shuang Gao ◽

Chao Bie ◽

Qiuyu Ji ◽

Haiyang Ling ◽

Chunyan Li ◽

...

Keyword(s):

Thermal Stability ◽

Inclusion Complex ◽

Water Solubility ◽

Herbicidal Activity ◽

Beta Cyclodextrin ◽

Cyclodextrin Inclusion ◽

Cyclodextrin Inclusion Complex ◽

Hydroxypropyl Beta Cyclodextrin

Cyanazine/HPβCD inclusion complex was prepared to improve water solubility and thermal stability and herbicidal activity of cyanazine.

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INTESTINAL ABSORPTION OF EPROSARTAN MESYLATE FROM SELF EMULSIFYING SYSTEM AND CYCLODEXTRIN COMPLEX

International Journal of Pharmacy and Pharmaceutical Sciences ◽

10.22159/ijpps.2017v9i2.16215 ◽

2017 ◽

Vol 9 (2) ◽

pp. 302

Author(s):

Mohammed M. Abdol Quader ◽

Mohamed A. Osman ◽

Gamal M. El Maghraby

Keyword(s):

Inclusion Complex ◽

Intestinal Absorption ◽

Inclusion Complexation ◽

Solubility Diagram ◽

Phase Solubility ◽

Font Size ◽

Transport Parameters ◽

Cyclodextrin Complex ◽

Scanning Calorimetry ◽

Intestinal Membrane

Objective: The aim of this work was to determine the intestinal membrane transport parameters of eprosartan mesylate (EM) and to investigate self-nano emulsifying drug delivery systems (SNEDDS) and inclusion complexation with hydroxypropyl b cyclodextrin (HPbCD) for enhanced intestinal absorption of eprosartan mesylate. Methods: The intestinal absorption was monitored using the in situ rabbit intestinal perfusion technique. SNEDDS was developed using labrafil, Lauroglycol with a tween in the presence of ethanol. Inclusion complexation was achieved by construction of phase solubility diagram in the presence of HPbCD. The prepared complex was evaluated using Fourier Transform Infrared Spectroscopy (FTIR) and differential scanning calorimetry (DSC). Results: The drug was found to be poorly absorbed from the jejuno-ileum and the colon with the absorption being mainly through paracellular pathway. An inclusion complex was developed between the drug and HPβCD. Perfusion of the drug in the nanoemulsion formulation or as an inclusion complex resulted in a significant increase in the intestinal absorption of the drug compared with the control.Conclusion: SNEDDS and inclusion complexation are promising strategies for enhanced intestinal absorption of eprosartan mesylate.

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