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Enhanced diuretic action of furosemide by complexation with β-cyclodextrin in the presence of sodium lauryl sulfate

  • Ramadan I. Al-Shdefat EMAIL logo
Published/Copyright: December 15, 2020
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Green Processing and Synthesis
From the journal Green Processing and Synthesis Volume 9 Issue 1

Abstract

Preparation of inclusion complex using cyclodextrins is a well-known formulation strategy to elevate the solubility of drugs. However, often cyclodextrins alone may not bring a considerable improvement in the solubility of low solubility drugs. In this study, the inclusion complexation of furosemide (FSM) was tried with β-cyclodextrin (β-CD) either with the use or without the use of sodium lauryl sulfate (SLS), which is a surfactant. By using the kneading method, the binary complex of FSM/β-CD in the equal molar ratio was used. FSM and β-CD were kneaded continuously until a thick past was achieved, which was evaporated for a period of about 24 h. The solid complexed product was then crushed and stored in airtight container until use. Phase solubility studies confirmed a stoichiometric ratio of 1:1 (FSM/β-CD and FSM/β-CD with SLS). The apparent stability constant and complexation efficiencies of significantly enhanced in the presence of SLS. The prepared complexes were evaluated for DSC, PXRD, 1H NMR, and in vitro release studies. The results exhibited a significant enhancement in diuresis in rats. It is evident that the addition of SLS with β-CD significantly enhances the solubilizing efficiencies and hence bioavailability of FSM.

Keywords: furosemide; cyclodextrin; complex; solubility; diuretic activity

1 Introduction

Furosemide (FSM) is one of the potent sulfonamide diuretics; it belongs to a loop diuretic group. FSM is frequently used in the management of edema, renal diseases, and hypertension [1,2,3,4,5,6]. It blocks reabsorption of specific ions, including sodium, potassium, and chloride in the loop and ascending limb of Henle, resulting in the loss of these ions and water into the urine, hence the diuretic effect [7,8,9].

FSM, 4-chloro-N-furfuryl-5-sulphamoylanthranillic acid (Figure 1), is a weak acid with three functional groups capable of forming H-bonding, and the free acid portion has been found to appear in seven different polymorphic forms (four polymorphs [I, II, III, IV], two solvates [IV-DMS and V-dioxane], and one amorphous form) [10,11]. According to the BCS (Biopharmaceutics Classification System), FSM is labeled in Class IV drug because of both its limited aqueous solubility (5–20 µg/mL) and low permeability; therefore, it has limited bioavailability (60–65%) and an erratic pharmacokinetic profile [12,13,14].

Figure 1 Chemical structure of FSM.
Figure 1

Chemical structure of FSM.

β-Cyclodextrin (β-CD) belongs to a group of natural cyclic oligosaccharides. Many studies reported the ability of CD complexation to improve water solubility, especially for hydrophobic drugs [15]. Cyclodextrins consists of either 6, 7, or 8 glucopyranose subunits (α,β,γ-cyclodextrin, respectively) connected in a 1,4-configuration with several diameters [16]. The exterior of the CD ring is hydrophilic, and the interior appears to be a lipophilic core in which suitable sized organic molecules can establish a noncovalent binding with the CD (i.e., inclusion complexes) [17]. Inclusion complexation with β-CD is a well-known method to improve the water solubility of water-limited solubility drugs and, therefore, its stability, the kinetics of dissolution, and bioavailability [18].

Surfactants are amphiphilic molecules that depress the surface tension between a gas and a liquid or interfacial tension happening between two liquids or between a liquid and a solid, allowing for easy spreading of a droplet on the surface. With the increase in surfactant concentration in the aqueous phase, the surfactant that will be undergoing adsorption at the surface is increased, resulting in a decrease in surface or interfacial tension [19]. One crucial characteristic of surfactants is the ability to aggregate, forming micelle in solution, which have particular significance in medicine because of their ability to elevate the aqueous solubility of limited aqueous-soluble drugs [20].

Sodium lauryl sulfate (SLS) is one of the anionic surfactants that has the chemical formula of CH3(CH2)11SO4Na. SLS is widely used as an emulsifier, wetting agent, and detergent in cosmetics and pharmaceutical products. SLS is one of the synthetic surfactants of an amphiphilic identity, which consists of an anionic organosulfate (tail – chain consists of 12-atoms of carbons) coupled to a sulfate group since it has a negative charge [21].

This study is developed to evaluate the complexation of FSM with β-CD and confirm the presence of complex formation, increase solubility, and enhance diuretic action of FSM. The prepared complexes were evaluated by phase solubility studies and characterized for various physicochemical investigations such as differential scanning calorimetry (DSC), powder X-ray diffraction (PXRD), 1H NMR, and in vitro release studies. Besides, the in vivo diuretic activity of FSM β-CD in rats is to be evaluated in this study.

2 Materials and methods

2.1 Materials

FSM β-CD and SLS were obtained from Sigma, Aldrich, USA. All chemicals and solvents used in the study were of A.R. grade. Milli Q water (Millipore, Germany) is the water we used for all the studies.

2.2 Phase solubility studies for FSM in binary and ternary systems

Phase solubility studies of FSM/β-CD and FSM/β-CD with 0.5% SLS were used to evaluate complexation [22]. In this study, extra quantities of FSM were added to 10 mL of distilled water containing increment amounts of β-CD and β-CD with 0.5% SLS (5–30 mm). The mixed suspensions were shaken at 100 rpm and 37°C for 72 h in a water bath. The resultant solutions were filtered using a 0.45 µm membrane filter and then analyzed by UV at 272 nm [23]. The binding strength of FSM/β-CD and FSM/β-CD with 0.5% SLS was calculated in terms of apparent stability constant (Ks) using the following equation:

(1)Ks=slopeSo×(1−slope),

where So is the intrinsic solubility of FSM in water and slope is the slope of phase solubility diagram.

The complexation efficiency (CE) is the ratio of complex formed to free β-CD concentration, which is an excellent method to calculate the solubilizing effect of β-CD. The CE was estimated using the following equation:

(2)CE=Slope1−Slope.

2.3 Preparation of complexes in binary and ternary systems

Inclusion complexes containing FSM/β-CD (1:1) were established in preliminary phase solubility studies. The inclusion complexes of FSM/β-CD and FSM/β-CD with 1% (w/v) SLS in 1:1 molar ratio were prepared by utilizing kneading, which is considered as a simple, universal, and cheap technique for preparing complexes. The binary complex of FSM/β-CD in an equal molar ratio was prepared by mixing one mole of FSM and β-CD each in a mortar followed by the addition of about 4 mL of water–ethanol solution (50% v/v). The mixture was continuously kneaded for 15 min until a thick paste was achieved, which was evaporated at 50°C for 24 h. The solid product was then crushed, passed through a No. 80 sieve, and stored in airtight container until use. The ternary complex of FSM/β-CD with SLS was prepared by the same aforementioned procedure, and only 1% SLS was kneaded with FSM/β-CD complex.

2.4 Differential scanning calorimetric studies

DSC studies of pure drug FSM, β-CD, SLS, FSM/β-CD, and FSM/β-CD with SLS were performed using a DSC instrument “(Scinco, DSC N-650, Seoul, Korea).” Precisely weighted samples (5 mg) were pressed in an aluminum pan by pressing with a hand press; the pressed pan was kept on the DSC sample holder and heated to a range of 50–350°C at a warming rate of 20°C/min. The samples were continuously supplied with nitrogen gas with a flow rate of 20 mL/min.

2.5 PXRD studies

PXRD style of pure drug FSM, β-CD, SLS, FSM/β-CD, and FSM/β-CD with SLS were analyzed using “Ultima IV diffractometer” (Rigaku Inc. Tokyo, Japan) at college of Pharmacy, Prince Sattam Bin Abdulaziz University)” in the range of 2–60° (2θ) at a scan speed 0.5 deg min−1. The diffraction pattern of each sample was scanned at voltage/current (40 kV/40 mA) using Cu tube anode. The recorded diffraction patterns were evaluated for crystallinity and amorphic of powder.

2.6 1H NMR spectral analysis

1H NMR spectra of FSM, β-CD, SLS, FSM/β-CD, and FSM/β-CD with SLS were recorded in the DMSO solvent using “Bruker program on UltraShield Plus 500 MHz (Bruker)” instrument that works at 500 MHz. The values of chemical shifts of β-CD in the inclusion complexes were calculated that confirmed the inclusion of FSM in the β-CD cavity.

2.7 In vitro drug release

The release studies of FSM, β-CD, SLS, FSM/β-CD, and FSM/β-CD with SLS were performed using the USP II paddle-type method. The apparatus was set with a paddle speed of 75 rpm at 37 ± 0.5°C, and 0.1 N HCl (pH 1.2) used as a dissolution medium. The aliquot of 5 mL of the sample was withdrawn at each time point (0, 10, 20, 30, 40, 50, and 60 min) and compensated with new media. The samples were filtered, suitably diluted, and analyzed by UV at 272 nm [23].

2.8 Diuretic activity

The diuretic activity of the complexes was evaluated in male Wistar rats by dividing the animals into four groups of four rats each. Group I composed of vehicle-treated rats of 2 mL/100 g of body weight as the control. Group II composed of rats treated with standard FSM (10 mg/kg) orally. Binary (FSM/β-CD) and ternary (FSM/β-CD with 0.5% SLS) complexes were given orally (10 mg/kg equivalent to FSM) in group III and IV, respectively. Each animal was kept isolated in a metabolic cage 24 h before the start of the experiment and then fasted overnight with free access to water. The total urine output (mL) of each rat was measured after 24 h. The pH, conductivity, and total dissolved solids (TDS) were measured for every treated group. The diuretic activity of the prepared complexes was calculated from the ratio of the mean urine output in the test group and in the reference group (FSM treated group). The diuretic activity is considered nil, little, moderate, and good for values <7.2, 0.72–1.00, 1.00–1.5, and >1.5, respectively [24]. The experimental procedure was approved by the Animal Ethics Committee of Pharmacy Faculty, Jadara University, Jordan.

3 Results and discussion

3.1 Phase solubility studies of FSM in binary and in ternary systems

The phase solubility diagrams of binary (FSM/β-CD) and ternary (FSM/β-CD with 0.5% SLS) systems showed a linear A.L. type solubility curves of FSM against increasing concentration of β-CD and β-CD with 0.5% SLS (Figure 2). According to Higuchi Connors [22], A.L. type curve with slope values less than 1 was suggested for the formation of 1:1 stoichiometric complex. The data of apparent stability constants (Ks) and complexation efficiencies of the prepared complexes were presented in Table 1. The apparent stability constants (Ks) of 280 M−1 and 326 M−1 were obtained for FSM/β-CD and FSM/β-CD with 0.5% SLS systems, respectively. CE was considered as more reliable data for complexation. CE of FSM/β-CD and FSM/β-CD with 0.5% SLS systems was obtained as 0.0266 and 0.0301, respectively. It was revealed from the data that the addition of 0.5% SLS to the β-CD did not change the phase solubility curve, but enhanced the interaction of FSM with β-CD by increasing the stability constant.

Figure 2 Phase solubility curves of FSM/β-CD and FSM/β-CD with SLS.
Figure 2

Phase solubility curves of FSM/β-CD and FSM/β-CD with SLS.

Table 1

Complexation parameters of FSM/β-CD and FSM/β-CD with SLS

ComplexesSlopeStability constant (Ks)Complexation efficiency (CE)
FSM/β-CD0.0256276 M−10.0262
FSM/β-CD with 0.5% SLS0.0343373 M−10.0355

3.2 DSC studies

The scanned DSC curves FSM, β-CD, SLS, FSM/β-CD, and FSM/β-CD with SLS are shown in Figure 3. A sharp endothermic peak of FSM at 216°C was shown, which evidenced drug purity. An endothermic peak of β-CD was observed around 143°C due to the loss of water. The DSC curve of FSM/β-CD was evidenced with a diminished endothermic peak of FSM. However, FSM/β-CD with SLS showed complete disappearance of the endothermic peak of FSM, suggesting complex formation.

Figure 3 Comparative DSC spectra of complexes.
Figure 3

Comparative DSC spectra of complexes.

3.3 PXRD studies

The PXRD is a valuable technique to identify the crystallinity/amorphocity of compounds. The PXRD patterns of FSM, β-CD, SLS, FSM/β-CD, and FSM/β-CD with SLS are shown in Figure 4. The FSM pure drug showed many sharp peaks confirming its crystalline nature. The FSM/β-CD and FSM/β-CD with SLS exhibited broad and diffused peaks evidenced its amorphocity of FSM after complexation.

Figure 4 Comparative PXRD pattern of complexes.
Figure 4

Comparative PXRD pattern of complexes.

3.4 1H NMR spectral analysis

The 1H NMR spectra of FSM showed a characteristic peak in the range of 7.0–8.4 ppm. The hydrogen atoms (H3 and H5) are present in the inner portion of β-CD molecules, which are responsible for interaction with drug molecules. The 1H NMR spectra of FSM/β-CD and FSM/β-CD with SLS complexes evidenced with the change in chemical shift of H3 and H5 atoms β-CD cavity, which confirms the inclusion of FSM inside the β-CD cavity (Figure 5).

Figure 5 Comparative 1H NMR spectra of complexes.
Figure 5

Comparative 1H NMR spectra of complexes.

3.5 In vitro drug release studies

Dissolution of FSM alone was found to be very slow (22.6% in 1 h), which was due to insolubility of FSM in water. A release of 59.3% and 77.2% was noted after 1 h from complex FSM/β-CD and FSM/β-CD with SLS, respectively. The maximum release of FSM from FSM/β-CD with SLS was probably due to the presence of SLS surfactant (Figure 6). This study demonstrates that when FSM is complexed with β-CD with SLS, there is a significant elevation of the rate of dissolution of the drug.

Figure 6 Comparative release profile of complexes.
Figure 6

Comparative release profile of complexes.

3.6 Diuretic activity

The urine output and its measured parameters are presented in Table 2. It was observed that the measured urine volume was found significantly higher in FSM/β-CD-treated (**p < 0.01) and FSM/β-CD + SLS-treated (**p < 0.001) groups in comparison to the FSM-treated group. The pH and conductivity of the complex treated group also increased in comparison to the control group. The diuretic activity of the FSM/β-CD complex was found moderate with a value of 1.25. However, a good diuretic activity was shown by FSM/β-CD + SLS with a value of 1.57. This enhancement in the diuretic activity was probably because of the presence of SLS. In conclusion, the bioavailability of FSM was increased when complexed with β-CD and SLS.

Table 2

Diuretic activity parameters of complexes in rats

GroupUrine volume (mL)pHConductivity (ms)TDS (g/L)Diuretic activity (Vt/Vr)
Control8.23 ± 0.797.028.473.11—
FSM29.75 ± 4.57*6.675.182.20—
FSM/β-CD37.42 ± 6.43**6.817.664.551.25
FSM/β-CD + SLS46.83 ± 3.88***6.729.755.841.57

Values represent the mean ± SEM (n = 6). Data were analyzed using one-way analysis of variance (ANOVA) followed by Tukey’s test.

*p < 0.05, **p < 0.01, ***p < 0.001.

4 Conclusion

The inclusion complexes of FSM in binary (FSM/β-CD) and ternary (FSM/β-CD with SLS) were successfully developed. Phase solubility studies confirmed the inclusion complexation of FSM with β-CD in the absence or presence of SLS. The release of the FSM by β-CD complexation in the presence of SLS showed a synergistic action in the solubility of FSM due to the surfactant properties of SLS. In conclusion, the SLS blend with β-CD offers a unique formulation approach to enhance the solubility and diuretic action of FSM.

  1. Conflict of interest: The author reports no conflict of interest associated with this manuscript.

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Received: 2020-09-02
Revised: 2020-10-21
Accepted: 2020-11-08
Published Online: 2020-12-15

© 2020 Ramadan I. Al-Shdefat, published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

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https://doi.org/10.1515/gps-2020-0069
Keywords for this article
furosemide; cyclodextrin; complex; solubility; diuretic activity
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Articles in the same Issue

  1. Obituary for Prof. Dr. Jun-ichi Yoshida
  2. Regular Articles
  3. Optimization of microwave-assisted manganese leaching from electrolyte manganese residue
  4. Crustacean shell bio-refining to chitin by natural deep eutectic solvents
  5. The kinetics of the extraction of caffeine from guarana seed under the action of ultrasonic field with simultaneous cooling
  6. Biocomposite scaffold preparation from hydroxyapatite extracted from waste bovine bone
  7. A simple room temperature-static bioreactor for effective synthesis of hexyl acetate
  8. Biofabrication of zinc oxide nanoparticles, characterization and cytotoxicity against pediatric leukemia cell lines
  9. Efficient synthesis of palladium nanoparticles using guar gum as stabilizer and their applications as catalyst in reduction reactions and degradation of azo dyes
  10. Isolation of biosurfactant producing bacteria from Potwar oil fields: Effect of non-fossil fuel based carbon sources
  11. Green synthesis, characterization and photocatalytic applications of silver nanoparticles using Diospyros lotus
  12. Dielectric properties and microwave heating behavior of neutral leaching residues from zinc metallurgy in the microwave field
  13. Green synthesis and stabilization of silver nanoparticles using Lysimachia foenum-graecum Hance extract and their antibacterial activity
  14. Microwave-induced heating behavior of Y-TZP ceramics under multiphysics system
  15. Synthesis and catalytic properties of nickel salts of Keggin-type heteropolyacids embedded metal-organic framework hybrid nanocatalyst
  16. Preparation and properties of hydrogel based on sawdust cellulose for environmentally friendly slow release fertilizers
  17. Structural characterization, antioxidant and cytotoxic effects of iron nanoparticles synthesized using Asphodelus aestivus Brot. aqueous extract
  18. Phase transformation involved in the reduction process of magnesium oxide in calcined dolomite by ferrosilicon with additive of aluminum
  19. Green synthesis of TiO2 nanoparticles from Syzygium cumini extract for photo-catalytic removal of lead (Pb) in explosive industrial wastewater
  20. The study on the influence of oxidation degree and temperature on the viscosity of biodiesel
  21. Prepare a catalyst consist of rare earth minerals to denitrate via NH3-SCR
  22. Bacterial nanobiotic potential
  23. Green synthesis and characterization of carboxymethyl guar gum: Application in textile printing technology
  24. Potential of adsorbents from agricultural wastes as alternative fillers in mixed matrix membrane for gas separation: A review
  25. Bactericidal and cytotoxic properties of green synthesized nanosilver using Rosmarinus officinalis leaves
  26. Synthesis of biomass-supported CuNi zero-valent nanoparticles through wetness co-impregnation method for the removal of carcinogenic dyes and nitroarene
  27. Synthesis of 2,2′-dibenzoylaminodiphenyl disulfide based on Aspen Plus simulation and the development of green synthesis processes
  28. Catalytic performance of the biosynthesized AgNps from Bistorta amplexicaule: antifungal, bactericidal, and reduction of carcinogenic 4-nitrophenol
  29. Optical and antimicrobial properties of silver nanoparticles synthesized via green route using honey
  30. Adsorption of l-α-glycerophosphocholine on ion-exchange resin: Equilibrium, kinetic, and thermodynamic studies
  31. Microwave-assisted green synthesis of silver nanoparticles using dried extracts of Chlorella vulgaris and antibacterial activity studies
  32. Preparation of graphene oxide/chitosan complex and its adsorption properties for heavy metal ions
  33. Green synthesis of metal and metal oxide nanoparticles from plant leaf extracts and their applications: A review
  34. Synthesis, characterization, and electrochemical properties of carbon nanotubes used as cathode materials for Al–air batteries from a renewable source of water hyacinth
  35. Optimization of medium–low-grade phosphorus rock carbothermal reduction process by response surface methodology
  36. The study of rod-shaped TiO2 composite material in the protection of stone cultural relics
  37. Eco-friendly synthesis of AuNPs for cutaneous wound-healing applications in nursing care after surgery
  38. Green approach in fabrication of photocatalytic, antimicrobial, and antioxidant zinc oxide nanoparticles – hydrothermal synthesis using clove hydroalcoholic extract and optimization of the process
  39. Green synthesis: Proposed mechanism and factors influencing the synthesis of platinum nanoparticles
  40. Green synthesis of 3-(1-naphthyl), 4-methyl-3-(1-naphthyl) coumarins and 3-phenylcoumarins using dual-frequency ultrasonication
  41. Optimization for removal efficiency of fluoride using La(iii)–Al(iii)-activated carbon modified by chemical route
  42. In vitro biological activity of Hydroclathrus clathratus and its use as an extracellular bioreductant for silver nanoparticle formation
  43. Evaluation of saponin-rich/poor leaf extract-mediated silver nanoparticles and their antifungal capacity
  44. Propylene carbonate synthesis from propylene oxide and CO2 over Ga-Silicate-1 catalyst
  45. Environmentally benevolent synthesis and characterization of silver nanoparticles using Olea ferruginea Royle for antibacterial and antioxidant activities
  46. Eco-synthesis and characterization of titanium nanoparticles: Testing its cytotoxicity and antibacterial effects
  47. A novel biofabrication of gold nanoparticles using Erythrina senegalensis leaf extract and their ameliorative effect on mycoplasmal pneumonia for treating lung infection in nursing care
  48. Phytosynthesis of selenium nanoparticles using the costus extract for bactericidal application against foodborne pathogens
  49. Temperature effects on electrospun chitosan nanofibers
  50. An electrochemical method to investigate the effects of compound composition on gold dissolution in thiosulfate solution
  51. Trillium govanianum Wall. Ex. Royle rhizomes extract-medicated silver nanoparticles and their antimicrobial activity
  52. In vitro bactericidal, antidiabetic, cytotoxic, anticoagulant, and hemolytic effect of green-synthesized silver nanoparticles using Allium sativum clove extract incubated at various temperatures
  53. The green synthesis of N-hydroxyethyl-substituted 1,2,3,4-tetrahydroquinolines with acidic ionic liquid as catalyst
  54. Effect of KMnO4 on catalytic combustion performance of semi-coke
  55. Removal of Congo red and malachite green from aqueous solution using heterogeneous Ag/ZnCo-ZIF catalyst in the presence of hydrogen peroxide
  56. Nucleotide-based green synthesis of lanthanide coordination polymers for tunable white-light emission
  57. Determination of life cycle GHG emission factor for paper products of Vietnam
  58. Parabolic trough solar collectors: A general overview of technology, industrial applications, energy market, modeling, and standards
  59. Structural characteristics of plant cell wall elucidated by solution-state 2D NMR spectroscopy with an optimized procedure
  60. Sustainable utilization of a converter slagging agent prepared by converter precipitator dust and oxide scale
  61. Efficacy of chitosan silver nanoparticles from shrimp-shell wastes against major mosquito vectors of public health importance
  62. Effectiveness of six different methods in green synthesis of selenium nanoparticles using propolis extract: Screening and characterization
  63. Characterizations and analysis of the antioxidant, antimicrobial, and dye reduction ability of green synthesized silver nanoparticles
  64. Foliar applications of bio-fabricated selenium nanoparticles to improve the growth of wheat plants under drought stress
  65. Green synthesis of silver nanoparticles from Valeriana jatamansi shoots extract and its antimicrobial activity
  66. Characterization and biological activities of synthesized zinc oxide nanoparticles using the extract of Acantholimon serotinum
  67. Effect of calcination temperature on rare earth tailing catalysts for catalytic methane combustion
  68. Enhanced diuretic action of furosemide by complexation with β-cyclodextrin in the presence of sodium lauryl sulfate
  69. Development of chitosan/agar-silver nanoparticles-coated paper for antibacterial application
  70. Preparation, characterization, and catalytic performance of Pd–Ni/AC bimetallic nano-catalysts
  71. Acid red G dye removal from aqueous solutions by porous ceramsite produced from solid wastes: Batch and fixed-bed studies
  72. Review Articles
  73. Recent advances in the catalytic applications of GO/rGO for green organic synthesis
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