Evaluation of the antiulcerogenic activity of violacein and its modulation by the inclusion complexation with β-cyclodextrin

Nelson Durán; Giselle Z Justo; Patrícia S Melo; Mariângela B.M De Azevedo; Alba R.M Souza Brito; Ana B.A Almeida; Marcela Haun

doi:10.1139/y03-033

Evaluation of the antiulcerogenic activity of violacein and its modulation by the inclusion complexation with β-cyclodextrin

Canadian Journal of Physiology and Pharmacology ◽

10.1139/y03-033 ◽

2003 ◽

Vol 81 (4) ◽

pp. 387-396 ◽

Cited By ~ 28

Author(s):

Nelson Durán ◽

Giselle Z Justo ◽

Patrícia S Melo ◽

Mariângela B.M De Azevedo ◽

Alba R.M Souza Brito ◽

...

Keyword(s):

Gastric Ulcer ◽

Inclusion Complex ◽

Protective Action ◽

Inclusion Complexation ◽

Positive Control ◽

Gastric Injury ◽

Antiulcer Activity ◽

Scanning Calorimetry ◽

Molar Ratios ◽

Rat Liver Cells

The effects of β-cyclodextrin (βCD) inclusion complexation on the ability of violacein to prevent gastric ulceration in mice were studied. ViolaceinβCD inclusion complexes were prepared in 1:1 and 1:2 molar ratios and analysed by differential scanning calorimetry and powder X-ray diffractometry. Violacein previously administered orally at 10 mg/kg significantly reduced indomethacin-induced gastric lesions, as well as 100 mg/kg of cimetidine (positive control). However, βCD complexation in both molar ratios significantly potentiated the protective action of violacein. In the HClethanol-induced gastric ulcer model, violacein and the 1:2 inclusion complex (10 mg/kg, p.o.) inhibited gastric damage by almost 85%, whereas a 63% reduction was observed for the positive control, lansoprazole, at 30 mg/kg. In contrast, treatment with the 1:1 inclusion complex resulted in almost total disappearance of the antiulcer activity in this model. No significant changes in stress-induced gastric injury were found. In addition, the 1:2 inclusion complex improved the antilipoperoxidant activity of violacein in rat liver cells exposed to t-butyl hydroperoxide, whereas the 1:1 complex was less active than violacein. In summary, the 1:2 βCD inclusion complex has gastroprotective properties similar to or higher than that of violacein. An increase in mucosal defensive mechanisms and protection against peroxidative damage might be involved.Key words: violacein, β-cyclodextrin, gastric ulcer, lipid peroxidation, hepatocyte.

Polypseudorotaxane Hydrogels Based on F127 Block-Selected Inclusion Complexation with α-Cyclodextrin

Advanced Materials Research ◽

10.4028/www.scientific.net/amr.482-484.1898 ◽

2012 ◽

Vol 482-484 ◽

pp. 1898-1903

Author(s):

Ying Xue Zhou ◽

Xiao Dong Fan ◽

Dan Xue

Keyword(s):

Thermal Stability ◽

Inclusion Complex ◽

Inclusion Complexation ◽

Wide Angle ◽

Acryloyl Chloride ◽

X Ray Diffraction ◽

Scanning Calorimetry ◽

X Ray ◽

Thermal Stability Of ◽

Channel Type

Supramolecular hydrogels were formed through F127, acryloyl chloride modified F127 inclusion complex with α-cyclodextrin, respectively. The structure of modified copolymers and inclusion complex was characterized by Fourier transform infrared spectroscopy (FTIR) and hydrogen nuclear magnetic resonance (1H-NMR). Hydrogels formed from supramolecular inclusion are imparted channel-type structure investigated by wide angle x-ray diffraction (WAXRD). Differential scanning calorimetry (DSC) and TG experiments showed that thermal stability of hydrogels depend on the nature of axis polymer. The relative model was proposed to elucidate the inclusion complexes and hydrogels formation.

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.

Gastroprotective Effect of Myricetin on Ethanol-Induced Acute Gastric Injury in Rats

Evidence-based Complementary and Alternative Medicine ◽

10.1155/2021/9968112 ◽

2021 ◽

Vol 2021 ◽

pp. 1-9

Author(s):

Hee-seon Park ◽

Chang-Seob Seo ◽

Eun Bok Baek ◽

Jin-hyung Rho ◽

Young-Suk Won ◽

...

Keyword(s):

Gastric Ulcer ◽

Alcohol Intake ◽

Cell Loss ◽

Positive Control ◽

Gastric Injury ◽

Total Glutathione ◽

Bioactive Properties ◽

Cyclooxygenase 1 ◽

Oral Doses ◽

Cox 1

The flavonoid myricetin is abundant in vegetables and has various bioactive properties, including anti-inflammatory and antioxidative activities. In the present study, we explored the effects of myricetin on alcohol-induced gastric ulcer in a rat model. To induce gastric ulcer, absolute ethanol (5 mL/kg body weight) was orally administrated to each rat. The positive control and myricetin-treated groups were given oral doses of omeprazole (20 mg/kg) or myricetin (12 mg/kg), respectively, 1 hour prior to the administration of absolute alcohol. We found that pretreatment with myricetin significantly decreased alcohol-induced gastric ulcer, hemorrhage, hyperemia, and epithelial cell loss in the gastric mucosa. Myricetin pretreatment reduced the level of malondialdehyde (MDA) and increased that of total glutathione (GSSG/GSH) and superoxide dismutase (SOD) in gastric tissues. In addition, it elevated the expression levels of cyclooxygenase-1 (COX-1) and prostaglandin E2 (PGE2) and decreased the phosphorylation of nuclear factor kappa B (NF-κB). Together, these results indicate that myricetin effectively inhibits ethanol-induced acute gastric injury by preventing oxidative damage, stimulating PGE2 production, and inhibiting NF-κB activation. We suggest that myricetin may be an alternative treatment for gastric injury caused by alcohol intake.

Nerolidol, an Antiulcer Constituent from the Essential Oil of Baccharis dracunculifolia DC (Asteraceae)

Zeitschrift für Naturforschung C ◽

10.1515/znc-2007-7-812 ◽

2007 ◽

Vol 62 (7-8) ◽

pp. 537-542 ◽

Cited By ~ 68

Author(s):

Fernando Canani Klopell ◽

Marivane Lemos ◽

João Paulo Barreto Sousa ◽

Eros Comunello ◽

Edson Luis Maistro ◽

...

Keyword(s):

Gastric Ulcer ◽

Essential Oil ◽

Positive Control ◽

Control Group ◽

Antiulcer Activity ◽

Gastric Lesions ◽

Ulcerative Lesion ◽

Ulcer Model ◽

Antiulcerogenic Activity ◽

Lesion Index

In this study, the antiulcerogenic effect of essential oil from Baccharis dracunculifolia was evaluated using the model of acute gastric lesions induced by ethanol. The ulcerative lesion index (ULI) was significantly reduced by oral administration of the essential oil of B. dracunculifolia at doses of 50, 250 and 500 mg/kg which reduced the lesions by 42.79, 45.70 and 61.61%, respectively. The analysis of the chemical composition of the essential oil from B. dracunculifolia by GC showed that this was composed mainly of mono- and sesquiterpenes and the majority compound was nerolidol. Therefore, antiulcerogenic activity of nerolidol (50, 250 and 500 mg/kg) was investigated using ethanol-, indomethacin- and stress-induced ulcer models in rat. In the stress-induced ulcer model, a significant reduction of the ULI in animals treated with nerolidol (50, 250 and 500 mg/kg) and cimetidine (100 mg/kg) was observed, compared to the control group (p < 0.05). The percentage of inhibition of ulcer was 41.22, 51.31, 56.57 and 53.50% in groups treated with 50, 250, 500 mg/kg of nerolidol and 100 mg/kg of cimetidine (positive control), respectively. Regarding ethanol- and indomethacin- induced ulcer models, it was observed that the treatment with nerolidol (250 and 500 mg/ kg) significantly reduced the ULI in comparison with the control group (p < 0.05). The dose of 50 mg/kg reduced the parameters analyzed but this was not statistically significant. In the ethanol-induced model percentage of inhibition of ulcer was 34.20, 52.63, 87.63 and 50.87% in groups treated with 50, 250, 500 mg/kg of nerolidol and 30 mg/kg of omeprazol (positive control), respectively. In indomethacin-ulcer the percentage of inhibition of ulcer was 34.69, 40.80, 51.02 and 46.93% in groups treated with 50, 250, 500 mg/kg of nerolidol and 100 mg/ kg of cimetidine (positive control), respectively. The results of this study show that nerolidol displays antiulcer activity, as it significantly inhibited the formation of ulcers induced in different animal models. However, further pharmacological and toxicological investigations, to delineate the mechanism(s) of action and the toxic effects, are required to allow the use of nerolidol for the treatment of gastric ulcer

Co-Amorphous Formulations of Furosemide with Arginine and P-Glycoprotein Inhibitor Drugs

Pharmaceutics ◽

10.3390/pharmaceutics13020171 ◽

2021 ◽

Vol 13 (2) ◽

pp. 171

Author(s):

Marika Ruponen ◽

Konsta Kettunen ◽

Monica Santiago Pires ◽

Riikka Laitinen

Keyword(s):

Storage Conditions ◽

Scanning Calorimetry ◽

Glycoprotein P ◽

Molar Ratios ◽

P Glycoprotein ◽

Permeation Studies ◽

Poorly Soluble ◽

Biopharmaceutics Classification ◽

Permeability Assay ◽

Simultaneous Dissolution

In this study, the amino acid arginine (ARG) and P-glycoprotein (P-gp) inhibitors verapamil hydrochloride (VER), piperine (PIP) and quercetin (QRT) were used as co-formers for co-amorphous mixtures of a Biopharmaceutics classification system (BCS) class IV drug, furosemide (FUR). FUR mixtures with VER, PIP and QRT were prepared by solvent evaporation, and mixtures with ARG were prepared by spray drying in 1:1 and 1:2 molar ratios. The solid-state properties of the mixtures were characterized with X-ray powder diffraction (XRPD), Fourier-transform infrared spectroscopy (FTIR) and differential scanning calorimetry (DSC) in stability studies under different storage conditions. Simultaneous dissolution/permeation studies were conducted in side-by-side diffusion cells with a PAMPA (parallel artificial membrane permeability assay) membrane as a permeation barrier. It was observed with XRPD that ARG, VER and PIP formed co-amorphous mixtures with FUR at both molar ratios. DSC and FTIR revealed single glass transition values for the mixtures (except for FUR:VER 1:2), with the formation of intermolecular interactions between the components, especially salt formation between FUR and ARG. The co-amorphous mixtures were found to be stable for at least two months under an elevated temperature/humidity, except FUR:ARG 1:2, which was sensitive to humidity. The dissolution/permeation studies showed that only the co-amorphous FUR:ARG mixtures were able to enhance both the dissolution and permeation of FUR. Thus, it is concluded that formulating co-amorphous salts with ARG may be a promising option for poorly soluble/permeable FUR.

Novel Chiral Recognition in Host−Guest Inclusion Complexes Depends on Their Molar Ratios: Efficient Resolution of 2,2‘-Dihydroxy-1,1‘-biphenyl Derivatives and CD Spectral Study of Inclusion Complex Crystals

The Journal of Organic Chemistry ◽

10.1021/jo9622800 ◽

1997 ◽

Vol 62 (5) ◽

pp. 1192-1193 ◽

Cited By ~ 5

Author(s):

Koichi Tanaka ◽

Ayao Moriyama ◽

Fumio Toda

Keyword(s):

Inclusion Complex ◽

Inclusion Complexes ◽

Spectral Study ◽

Chiral Recognition ◽

Molar Ratios ◽

Complex Crystals

RESVERATROL INCLUSION COMPLEX WITH β-CYCLODEXTRIN (RCD): CHARACTERIZATION AND EVALUATION OF TOXICITY IN WISTAR RATS

International Journal of Pharmacy and Pharmaceutical Sciences ◽

10.22159/ijpps.2017v9i1.15399 ◽

2016 ◽

Vol 9 (1) ◽

pp. 27 ◽

Cited By ~ 2

Author(s):

V. S. K. Nishihira ◽

N. J. Mezzomo ◽

M. D. Baldissera ◽

R. A. Vaucher ◽

C. G. Pinto ◽

...

Keyword(s):

Inclusion Complex ◽

Oral Administration ◽

Biochemical Parameters ◽

Wistar Rats ◽

Metabolic Diseases ◽

Hematological Parameters ◽

Density Lipoprotein ◽

Blood Parameters ◽

Control Group ◽

Scanning Calorimetry

Objective: The aim of this study was to characterise the resveratrol inclusion complex with β-cyclodextrin (RCD) and evaluate their toxicity in wistar rats.Methods: The RCD were prepared in ultra-turrax. For characterization of the RCD were used: Fourier transform infra-red Spectroscopy, Nuclear Magnetic Resonance (NMR), Differential Scanning Calorimetry (DSC) and X-ray powder diffraction. The RCD and others 4 treatments were performed by the chronic oral administration in 35 rats during 60 ds. After the treatments they were euthanized and the serum blood were collected to analyzed some hemogram and biochemical parameters including aspartyl aminotransferase (AST); alanine aminotransferase (AST); phosphatase alkaline (ALP); total bilirubin (TB); direct bilirubin (DB); total protein (TP); total cholesterol (TC), triacylglycerol (TAG), very low-density lipoprotein (VLDL), high-density lipoprotein (HDL), calcium, iron and phosphate using fully automated biochemistry analyzer.Results: The characterization results indicated a successful formation of the RCD. All hematological parameters analysed were within the normal values in all the groups. Furthermore, the hemogram and biochemical parameters were significantly (P>0.05) similar to the control group.Conclusion: The daily oral administration during 60 d of RCD are not harmful on blood parameters of Wistar rats. Thus, RCD can be used safely for treatment of some metabolic diseases.

ANTIOXIDANT AND GASTRIC ULCER HEALING EFFECT OF ORTHOSIPHONSTAMINEUS (BENTH.) LEAVES EXTRACT IN ASPIRIN-INDUCED RATS

Asian Journal of Pharmaceutical and Clinical Research ◽

10.22159/ajpcr.2017.v10i2.15873 ◽

2017 ◽

Vol 10 (2) ◽

pp. 397 ◽

Cited By ~ 2

Author(s):

Ari - Yuniarto

Keyword(s):

Gastric Ulcer ◽

Ulcer Healing ◽

Control Group ◽

Histopathological Analysis ◽

Antiulcer Activity ◽

Gastric Ulcer Healing ◽

Orthosiphon Stamineus ◽

Mucosal Integrity ◽

Healing Effect ◽

Dpph Method

Objective: In the gastrointestinal system, gastric ulcer is one of the common serious problems in human life and gives contribution against morbidity and mortality incidence. The pathophysiology of gastric ulcer is an imbalance between aggressive factor and mucosal integrity factor. Increase of aggressive factors and decrease of mucosal integrity factors have potential against developed of gastric ulcer disease. The objective of the research was to evaluate antioxidant and gastric ulcer healing effect of Orthosiphon stamineus (Benth.) leaves extract in aspirin-induced rats.Methods: In vivo antiulcer activity of Orthosiphon leaves extract was evaluated through several parameters involves gastric acidity, number of ulcers, diameters of ulcers, ulcer index (UI), and healing ratio. Dose level of Orthosiphon leaves extract which used in this study such as 250 and500 mg/kg, respectively. Antioxidant activity of Orthosiphon leaves extract was evaluated by 1,1-diphenyl-2-picrylhydrazyl hydrate (DPPH) method. Histopathological of the stomach was performed using hematoxylin-eosin stained.Results: The results of the study showed that groups which given Orthosiphon leaves extract have significantly different for gastric ulcer healing compared to the control group and were supported by histopathological analysis. The Orthosiphon leaves extract also showed maximum scavengingactivity at a concentration of 100 µg/ml (58.86% inhibition) and minimum at 50 μg/ml (29.60% inhibition) with inhibitory concentration 50% (IC )50 84.54 µg/ml when compared to ascorbic acid as the standard with IC5.08 µg/ml by DPPH method.Conclusion: It can be concluded that from the experimental study of O. stamineus (Benth.) leaves extract has potential antiulcer activity in aspirin- induced rats model and antioxidant effect using DPPH method. Stomach tissues regeneration in gastric ulcer model might be affected by the improvement of antioxidant status.Keywords: Orthosiphon stamineus (Benth.), Extract, Ulcer, Aspirin, 1,1-diphenyl-2-picrylhydrazyl hydrate.

Guest-Host Inclusion Complex Formation of 2-, 3-, and 4-Aminobenzoic Acids with Native and Modified Cyclodextrins

International Letters of Chemistry Physics and Astronomy ◽

10.18052/www.scipress.com/ilcpa.69.10 ◽

2016 ◽

Vol 69 ◽

pp. 10-21 ◽

Cited By ~ 1

Author(s):

Narayanasamy Rajendiran ◽

J. Thulasidhasan ◽

M. Jude Jenita

Keyword(s):

Inclusion Complex ◽

Inclusion Complexation ◽

Aminobenzoic Acid ◽

Time Resolved ◽

H Nmr ◽

Buffer Solutions ◽

Aminobenzoic Acids ◽

Modified Cyclodextrins ◽

Ft Ir ◽

Uv Visible

The inclusion complexation of 2-aminobenzoic acid (2ABA), 3-aminobenzoic acid (3ABA), and 4-aminobenzoic acid (4ABA) with α-cyclodextrin (α-CD), β-cyclodextrin (β-CD), hydroxypropyl-α-cyclodextrin (HP-α-CD) and hydroxypropyl-β-cyclodextrin (HP-β-CD) were studied in buffer solutions of differentpHs (pH~1 andpH~7) and it was carried out using UV-Visible, steady-state and time-resolved fluorescence. Dual fluorescence was observed for all the compounds in aqueous and CD medium. All the ABAs forms 1:1 inclusion complex at pH ~ 1 solution and mixture of 1:1 and 1:2 inclusion complex at pH ~7. With CDs, dual luminescence appeared at pH ~ 1 indicates, both NH3+and COOH groups are present in the interior of the CDs cavities. FT-IR,1H NMR, results suggest ABAs formed a stable inclusion complex with the CDs.

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.