Partitioning of drugs in micelles and effect on micellization: Physicochemical insights with tryptophan and diclofenac sodium

Mukhija, Achal; Kishore, Nand

doi:10.1016/j.colsurfa.2016.10.044

Cited by 19 publications

(14 citation statements)

References 34 publications

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“…Indeed, the binding of chloramphenicol to the calixarene-based micelles is enthalpically favored and driven (|Δ H | > | T Δ S |) but entropically unfavored (Sgarlata et al, 2009b ; Bonaccorso et al, 2012 , 2017 ). The favorable enthalpic contribution may be due to the insertion of chloramphenicol within the micelle palisade layer by establishing CH–π, ion–π, and van der Waals interactions between the calixarenes and the aromatic ring and/or the nitro group of chloramphenicol (Choudhary et al, 2015 ; Mukhija and Kishore, 2017 ). This favorable enthalpic contribution could also be attributed to “frustrated” water molecules that leave the micelle core and create a new hydrogen bonding network with the bulk water molecules and the micelle surface.…”

Section: Resultsmentioning

confidence: 99%

“…The less unfavorable Δ H value observed for tetracycline, which eventually leads to a larger affinity for the micelles in solution, is probably due to cation–π interactions between the calixarene hydrophilic head and the aromatic rings of the tetracycline backbone, which advantageously balance the enthalpic cost for desolvation. As in the case of ofloxacin, the large and favorable entropic contribution is due to the release of water molecules from both the guest and the calixarene micellar aggregates (Choudhary et al, 2015 ; Mukhija and Kishore, 2017 ).…”

Section: Resultsmentioning

confidence: 99%

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Binding Affinity and Driving Forces for the Interaction of Calixarene-Based Micellar Aggregates With Model Antibiotics in Neutral Aqueous Solution

et al. 2021

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The search for novel surfactants or drug delivery systems able to improve the performance of old-generation antibiotics is a topic of great interest. Self-assembling amphiphilic calix[4]arene derivatives provide well-defined nanostructured systems that exhibit promising features for antibiotics delivery. In this work, we investigated the capability of two micellar polycationic calix[4]arene derivatives to recognize and host ofloxacin, chloramphenicol, or tetracycline in neutral aqueous solution. The formation of the nanoaggregates and the host–guest equilibria were examined by nano-isothermal titration calorimetry, dynamic light scattering, and mono- and bi-dimensional NMR. The thermodynamic characterization revealed that the calix[4]arene-based micellar aggregates are able to effectively entrap the model antibiotics and enabled the determination of both the species and the driving forces for the molecular recognition process. Indeed, the formation of the chloramphenicol–micelle adduct was found to be enthalpy driven, whereas entropy drives the formation of the adducts with both ofloxacin and tetracycline. NMR spectra corroborated ITC data about the positioning of the antibiotics in the calixarene nanoaggregates.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Binding Affinity and Driving Forces for the Interaction of Calixarene-Based Micellar Aggregates With Model Antibiotics in Neutral Aqueous Solution

et al. 2021

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“…In this context, the binding constants of drugs to micelles can be quantitatively determined using the simple mathematical model known as the Benesi–Hildebrand equation based on the Beer–Lambert law valid in the high micelle concentration region (Benesi and Hildebrand, ). In spite of many reports on the interactions between drugs and conventional surfactants in the literature (Azum et al, , ; Cai et al, ; Chauhan et al, ; Enache and Volanschi, ; Hanif et al, ; Hossain and Hoque, ; Kabir‐ud‐Din et al, ; Kaushal et al, ; Khan et al, ; Khan and Shah, ; Lazaro et al, ; Mukhija and Kishore, ; Naqvi et al, ; Noori et al, ; Rub et al, , , ; Sharma and Jani, ; Ullah et al, ), there is limited number of studies that combine spectroscopy with surface tension measurements or conductometry for the understanding of the mechanism of these types of interactions (Ali et al, ; Ansari et al, ; Gokturk et al, ; Kabir‐ud‐Din et al, , ; Maswal et al, ; Rub et al, ). Previously, we reported a study on the binding characteristics of poorly soluble drugs sulfamethoxazole (SMX) and trimethoprim (TMP) in the presence of sodium dodecyl sulfate (SDS) and Triton X‐100 (TX‐100) micelles employing spectroscopy and surface tension measurements.…”

Section: Introductionmentioning

confidence: 99%

Interactions and Solubilization of Poorly Soluble Drugs in Aerosol‐OT Micelles

Göktürk

TAMER

2018

J Surfact & Detergents

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Absorption spectroscopy, conductivity, and surface tension measurements were carried out at 298 K to study the solubilization of poorly soluble drugs sulfamethoxazole (SMX) and trimethoprim (TMP) in Aerosol‐OT (AOT) micellar media. The binding constants of SMX and TMP to AOT micelles were determined by applying the Benesi–Hildebrand equation. A comparison of the binding constants indicates that the binding tendency of TMP with AOT micelles is higher than that of SMX. To better analyze the incorporation of drugs into anionic AOT micellar media, surface tension measurements were performed in the presence of SMX and TMP in aqueous media. The influence of TMP and SMX on the surface properties of AOT was determined using the Gibbs Adsorption Isotherm. Changes in the surface properties of AOT determined by surface tension measurements in the presence of drugs are in good agreement with the binding constants determined spectrophotometrically. Calculated surface parameters indicate higher incorporation of TMP with AOT than that of SMX. Comparison of the aqueous solubility of TMP and SMX with micellar media indicated solubility enhancements for both poorly soluble drugs. A special attempt was made to highlight simultaneous interactions of TMP and SMX with AOT using both surface tension and conductometric measurements that can be used to determine counterion‐binding parameters.

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“…A drug molecule has to pass through the cellular and nuclear membranes before to reach their target inside the cancer cells. Because the biological membranes represent complex multicomponent structures, the surfactant micelles with much less complexity have been used as model systems for biomembranes aiming to investigate the interactions of different drug molecules with biological membranes [ 28 , 29 , 30 , 31 , 32 , 33 , 34 ]. The surfactant micelles are also useful in drug delivery as they ensure the transport to specific sites of action, minimize drug degradation and loss, prevent harmful side effects and increase drug bioavailability [ 35 , 36 ].…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic Investigation of the Interaction of the Anticancer Drug Mitoxantrone with Sodium Taurodeoxycholate (NaTDC) and Sodium Taurocholate (NaTC) Bile Salts

et al. 2017

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The focus of the present work was to investigate the interaction of the anticancer drug mitoxantrone with two bile salts, sodium taurodeoxycholate (NaTDC) and sodium taurocholate (NaTC). Ultraviolet-visible (UV-Vis) absorption and electron paramagnetic resonance (EPR) spectroscopy were used to quantify the interaction and to obtain information on the location of mitoxantrone in bile salt micelles. The presence of submicellar concentrations of both bile salts induces mitoxantrone aggregation and the extent of drug aggregation in NaTDC is higher than in NaTC. For micellar bile salts concentrations, mitoxantrone monomers are entrapped in the micellar core. Binding constants, micelle/water partition coefficients and the corresponding thermodynamic parameters for binding and partitioning processes were estimated using the changes in monomer absorbance in the presence of bile salts. Binding interaction of mitoxantrone is stronger for NaTDC than NaTC micelles, whereas partitioning efficiency is higher for NaTC micelles for all investigated temperatures. Thermodynamic parameters indicate that both binding and partitioning processes are spontaneous and entropy controlled. The spectral behavior and thermodynamic parameters indicate distinct types of mitoxantrone interaction with NaTDC and NaTC micelles supported by the differences in nature and structure of bile salts micelles.

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Partitioning of drugs in micelles and effect on micellization: Physicochemical insights with tryptophan and diclofenac sodium

Cited by 19 publications

References 34 publications

Binding Affinity and Driving Forces for the Interaction of Calixarene-Based Micellar Aggregates With Model Antibiotics in Neutral Aqueous Solution

Binding Affinity and Driving Forces for the Interaction of Calixarene-Based Micellar Aggregates With Model Antibiotics in Neutral Aqueous Solution

Interactions and Solubilization of Poorly Soluble Drugs in Aerosol‐OT Micelles

Spectroscopic Investigation of the Interaction of the Anticancer Drug Mitoxantrone with Sodium Taurodeoxycholate (NaTDC) and Sodium Taurocholate (NaTC) Bile Salts

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