Demonstration of In Vitro Host-Guest Complex Formation and Safety of para-Sulfonatocalix[8]arene as a Delivery Vehicle for Two Antibiotic Drugs

Moussa, Yvonne E.; Ong, Yu Qing Elysia; Perry, John D.; Cheng, Zhengqi; Kayser, Veysel; Cruz, Esteban; Kim, Ryung Rae; Sciortino, Natasha F.; Wheate, Nial J.

doi:10.1016/j.xphs.2018.08.016

Cited by 20 publications

(6 citation statements)

References 35 publications

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“…The binding energy of all three host-guest complexes is shown in Table 3. The binding energy is calculated according to the 1:1 binding stoichiometric for calix[4]arene and calix[6]arene (Fahmy et al, 2020) and 1:2 for calix[8]arene to drug ratio (Moussa et al, 2018). For smaller calix[n]arene, n=4,6 can only accommodate one drug molecule in the cavity, whereas n>6 can hold two drug molecules within a single macrocycle (Moussa et al, 2018).…”

Section: Computational Studiesmentioning

confidence: 99%

“…The binding energy is calculated according to the 1:1 binding stoichiometric for calix[4]arene and calix[6]arene (Fahmy et al, 2020) and 1:2 for calix[8]arene to drug ratio (Moussa et al, 2018). For smaller calix[n]arene, n=4,6 can only accommodate one drug molecule in the cavity, whereas n>6 can hold two drug molecules within a single macrocycle (Moussa et al, 2018). The calix[8]-PABA inclusion has the highest binding energy, -0.06189492 Ry, compared with the other two host-guest complexes; reveals PABA can generate optimal complexes with calix[8]arene (Kandeel et al, 2021).…”

Section: Computational Studiesmentioning

confidence: 99%

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Energy Band Gap Investigation using First Principle Simulation and Tauc Plot Method of Calixarene and Calixarene-Drug Inclusion Complexes

Abd Karim,

Supian,

Wong

et al. 2023

JSML

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Calixarene has attract attention especially in drug delivery and drug sensor systems due to its peculiar properties, such as functional diversity of the upper and lower rims, hydrophobic cavity, chemical stability, zero toxicity, and controlled release profile. These properties make this supramolecule an ideal candidate for drug encapsulation and sensors. P-aminobenzoic acid (PABA) is a drug in sunscreen which is widely used as a ultraviolet (UV) filter and sunburn protector to protect against solar rays. The calix[n]arene (n=4,6,8) and the host-guest interaction of calix[n]-PABA were characterized using UV–visible spectroscopy and the first-principles pseudopotential method, based on the density functional theory (DFT) and the plane-wave method as implemented into Quantum Espresso code. The DFT calculation is performed to find the estimated calix[n]arene and calix[n]arene-drug band gap. The band gap calculated using DFT has usually underestimated the insulating materials for about 30 – 50% of the experimental gap values, depending on the selected type of exchange-correlation chosen. The optical band gap value of calix[n]arene and calix[n]-PABA obtained from the UV-Visible absorption spectrum estimated using the Tauc plot are then compared with the band gap computed by DFT. The band gap narrowing shown by the complexes indicates that calix[n]arene and PABA reacted. Besides, calix[8]arene is the most promising host in this study since the calix[8]-PABA complex has the most significant binding energy. The band gaps and binding energy results will become a reference for future research in calixarene and calixarene-drug material.

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Section: Computational Studiesmentioning

confidence: 99%

Section: Computational Studiesmentioning

confidence: 99%

Energy Band Gap Investigation using First Principle Simulation and Tauc Plot Method of Calixarene and Calixarene-Drug Inclusion Complexes

Abd Karim,

Supian,

Wong

et al. 2023

JSML

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“…Wheate and colleagues investigated the potential for 4-sufonatocalix [8]arene, 41 (Figure 9), to act as a vehicle for the antibiotics isoniazid and ciprofloxacin [33]. In human kidney cells (HEK-293), the isoniazid complex was shown to increase uptake owing to the solubilizing effects of the macrocycle by 35%, although the ciprofloxacin complex showed no effects up to its solubility limit of 185 μg mL −1 .…”

Section: Drug-delivering Calixarenesmentioning

confidence: 99%

Antimicrobial Activity of Calixarenes and Related Macrocycles

et al. 2020

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Calixarenes and related macrocycles have been shown to have antimicrobial effects since the 1950s. This review highlights the antimicrobial properties of almost 200 calixarenes, resorcinarenes, and pillararenes acting as prodrugs, drug delivery agents, and inhibitors of biofilm formation. A particularly important development in recent years has been the use of macrocycles with substituents terminating in sugars as biofilm inhibitors through their interactions with lectins. Although many examples exist where calixarenes encapsulate, or incorporate, antimicrobial drugs, one of the main factors to emerge is the ability of functionalized macrocycles to engage in multivalent interactions with proteins, and thus inhibit cellular aggregation.

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“…[19][20][21][22][23] Moreover, macrocycles that are able to adjust their conformation 24,25 and thereby guest binding properties in different biological environments, have the potential to be used as selective and targeted drug delivery and discovery systems. [26][27][28][29] Within the field of responsive molecules, azobenzene-containing macrocycles in particular have attracted attention in supramolecular chemistry due to their compliance to the aforementioned criteria. 30 Binding of the guest to these macrocycles can be influenced by changing the physical or chemical environment of the complex, for example, by irradiation with UV-Vis light, as well as by variations in pH, temperature or redox potential.…”

Section: Introductionmentioning

confidence: 99%

Large Stimuli-Responsive Azobenzene Macrocycles as Functional Cavitands: Synthesis and Detection by NMR and MS Methods

Roithmeyer

Uudsemaa

Trummal

et al. 2023

Preprint

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Azobenzene macrocycles are widely investigated as potential drug delivery systems and as part of molecular machines due to their photo-responsive properties. Herein, we synthesize a series of new azobenzene macrocycles, featuring up to eight switchable repeating units. We study the influence of different reaction conditions, base equivalents, concentration, reactant addition time and stirring time, on the formation of the macrocycles of different sizes, ranging from 10 to 40 aromatic rings in the macrocyclic architectures. High-resolution mass spectrometry and ion mobility (IM) mass spectrometry experiments and 1H and diffusion-ordered spectroscopy (DOSY) NMR are used to detect the presence of the macrocycles in gas phase and solution, respectively. While MS methods lead to the identification of the macrocycles, the differentiation between the different sizes of these macrocycles with DOSY NMR is limited. The responsiveness of the Z-to-E photo-switching of the smallest of the macrocycles, exhibiting 2 azobenzene units and in total 10 aromatic rings, separated with column chromatography, is studied with irradiation experiments, using both UV-Vis light and thermal excitation, and monitoring the sample with UV-Vis absorption and 1H NMR spectroscopy after the excitation. DFT calculations help shed light on the conformation of this isolated species.

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Demonstration of In Vitro Host-Guest Complex Formation and Safety of para-Sulfonatocalix[8]arene as a Delivery Vehicle for Two Antibiotic Drugs

Cited by 20 publications

References 35 publications

Energy Band Gap Investigation using First Principle Simulation and Tauc Plot Method of Calixarene and Calixarene-Drug Inclusion Complexes

Energy Band Gap Investigation using First Principle Simulation and Tauc Plot Method of Calixarene and Calixarene-Drug Inclusion Complexes

Antimicrobial Activity of Calixarenes and Related Macrocycles

Large Stimuli-Responsive Azobenzene Macrocycles as Functional Cavitands: Synthesis and Detection by NMR and MS Methods

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