Characterization of thymoquinone/hydroxypropyl-β-cyclodextrin inclusion complex: Application to anti-allergy properties

Al‐Qubaisi, Mothanna Sadiq; Abdullah, Rasedee; Flaifel, Moayad Husein; Eid, Eltayeb E M; Hussein‐Al‐Ali, Samer Hasan; Alhassan, Fatah H.; Salih, Ashraf M.; Hussein, Mohd Zobir; Zainal, Zulkarnain; Sani, Dahiru; Al-Jumaily, Abdulmajeed; Saeed, Mohammed Ibrahim

doi:10.1016/j.ejps.2019.03.015

Cited by 48 publications

(39 citation statements)

References 37 publications

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“…For example, Al-Qubaisi et al developed an inclusion complex of thymoquinone and HP-b-CD in order to improve solubility and bioactivity of thymoquinone. In their work, they proved that the entire thymoquinone molecule was entrapped in the HP-b-CD cavity and that the molecule was not degraded by the complexation (Al-Qubaisi et al, 2019). As a result, we demonstrated that the cyclodextrin complexation did not degrade the molecular structure.…”

Section: Discussionmentioning

confidence: 50%

Hydroxypropyl-β-Cyclodextrin Complexes of Styryllactones Enhance the Anti-Tumor Effect in SW1116 Cell Line

Chen

et al. 2020

Front. Pharmacol.

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Styryllactones, a class of compounds obtained from the genus Goniothalamus (Annonaceae), have demonstrated in vitro antitumor activity. However, the aqueous solubility of these compounds is poor. In this study, we identified the absolute configurations of the previously isolated compounds, which were first isolated in our laboratory, by single-crystal X-ray diffraction analysis using Cu Ka radiation. Subsequently, the antitumor activities of the compounds were evaluated by 3-(4,5dimethylthiazol-2-yl)-2,5-diphenyl-tetrazolium bromide staining in four tumor cell lines. The induced apoptosis activity of leiocarpin E-7ʹ-Monoacetate was studied by an annexin V fluorescein isothiocyanate/propidium iodide double-staining experiment, and the caspase activity was tested in the SW1116 cell line. The results demonstrated that the antitumor activities of cheliensisin A and goniodiol-7-monoacetate were limited by their poor water solubility. To address this issue, hydroxypropyl-b-cyclodextrin (HP-b-CD) complexes of the compounds were synthesized by the saturated aqueous method. The complexes were then analyzed using a differential scanning calorimeter. The IC 50 of cheliensisin A was reduced by 45% and 58% against SW1116 and SMMC-7721 cell lines, respectively. Similarly, the IC 50 of goniodiol-7-monoacetate was reduced by 55% and 34% against the two tumor cell lines, respectively. To further evaluate whether the styryllactones and complexes possessed selectivity against cancer cell lines and normal cell lines, toxicity against human normal cell line (HEK293T) was evaluated. The results demonstrated that the HP-b-CD complexes displayed more cytotoxicity than the respective pristine compounds against the HEK293T cell line. However, there existed a therapeutic window when the complexes were applied against cancer cell lines. In summary, the synthesis of several styryllactone compounds complexed with HP-b-CD was reported for the first time. These complexes could significantly enhance the cytotoxic effects of styryllactone compounds.

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Section: Discussionmentioning

confidence: 50%

Hydroxypropyl-β-Cyclodextrin Complexes of Styryllactones Enhance the Anti-Tumor Effect in SW1116 Cell Line

Chen

et al. 2020

Front. Pharmacol.

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“…The topical application of TMQ in wound healing is an effective approach as it offers direct access to the affected sites [17]. Despite its multifunction activity and varied promising medical application, the therapeutic effectiveness of TMQ is restricted because of poor water solubility and low skin penetrability that result in low systemic availability [11,18]. The major limiting factor that hindered the wound healing efficacy of TMQ is its poor aqueous solubility, low skin permeability, and photosensitivity [11,18].…”

Section: Introductionmentioning

confidence: 99%

Thymoquinone Loaded Topical Nanoemulgel for Wound Healing: Formulation Design and In-Vivo Evaluation

et al. 2021

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Thymoquinone is a natural bioactive with significant therapeutic activity against multiple ailments including wound healing. The poor aqueous solubility and low skin permeability limit its therapeutic efficacy. The present investigation aimed to improve the biopharmaceutical attributes of thymoquinone to enhance its topical efficacy in wound healing. A nanoemulsion-based hydrogel system was designed and characterized as a nanotechnology-mediated drug delivery approach to improve the therapeutic efficacy of thymoquinone, utilizing a high-energy emulsification technique. The black seed oil, as a natural home of thymoquinone, was utilized to improve the drug loading capacity of the developed nanoemulsion system and reduced the oil droplet size to <100 nm through ultrasonication. The influence of formulation composition, and the ultrasonication process conditions, were investigated on the mean globule size and polydispersity index of the generated nanoemulsion. Irrespective of surfactant/co-surfactant ratio and % concentration of surfactant/co-surfactant mixture, the ultrasonication time had a significant (p < 0.05) influence on the mean droplet size and polydispersity index of the generated nanoemulsion. The developed nanoemulgel system of thymoquinone demonstrated the pseudoplastic behavior with thixotropic properties, and this behavior is desirable for topical application. The nanoemulgel system of thymoquinone exhibited significant enhancement (p < 0.05) in skin penetrability and deposition characteristics after topical administration compared to the conventional hydrogel system. The developed nanoemulgel system of thymoquinone exhibited quicker and early healing in wounded Wistar rats compared to the conventional hydrogel of thymoquinone, while showing comparable healing efficacy with respect to marketed silver sulfadiazine (1%) cream. Furthermore, histopathology analysis of animals treated with a developed formulation system demonstrated the formation of the thick epidermal layer, papillary dermis along with the presence of extensive and organized collagen fibers in newly healed tissues. The outcome of this investigation signifies that topical delivery of thymoquinone through nanoemulgel system is a promising candidate which accelerates the process of wound healing in preclinical study.

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“…The inclusion complexes which cyclodextrins form with drug compounds have been shown to enhance not just solubility but also the physical and chemical stabilities of the drug 25,26 . As a result, cyclodextrins may confer beneficial potentiating properties when complexed with various drugs 27,28 . However, to the best of our knowledge, there has been no study to date investigating the effect, if any, on the antimicrobial properties of RES when dissolved in HPβCD.…”

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confidence: 99%

Pterostilbene complexed with cyclodextrin exerts antimicrobial and anti-inflammatory effects

Lim

Preshaw

Lim

et al. 2020

Sci Rep

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tan 1 ✉ Resveratrol (RES) is a natural polyphenol with potential as an adjunctive therapeutic modality for periodontitis. However, its inferior pharmacokinetics and toxicity concerns about its commonly used solvent dimethyl sulfoxide (DMSO) hinder translation to clinical applicability. Our study aimed to investigate the comparative antimicrobial properties of RES and its analogues (pterostilbene [PTS], oxyresveratrol [OXY] and piceatannol [PIC]), utilizing 2-hydroxypropyl-β-cyclodextrin (HpβCD) as a solubiliser, which has a well-documented safety profile and FDA approval. These properties were investigated against Fusobacterium nucleatum, a key periodontal pathogen. PTS demonstrated the most potent antibacterial effects in HPβCD, with MIC > 60-fold lower than that of RES, OXY and PIC. In addition, PTS inhibited F. nucleatum biofilm formation. PTS exerted antimicrobial effects by eliciting leakage of cellular contents, leading to loss of bacterial cell viability. PTS also conferred immunomodulatory effects on F. nucleatum-challenged macrophages via upregulation of antioxidant pathways and inhibition of NF-κB activation. Given the superior antimicrobial potency of PTS against F. nucleatum compared to RES and other analogues, and coupled with its immunomodulatory properties, ptS complexed with HpβCD holds promise as a candidate nutraceutical for the adjunctive treatment of periodontitis.

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Characterization of thymoquinone/hydroxypropyl-β-cyclodextrin inclusion complex: Application to anti-allergy properties

Cited by 48 publications

References 37 publications

Hydroxypropyl-β-Cyclodextrin Complexes of Styryllactones Enhance the Anti-Tumor Effect in SW1116 Cell Line

Hydroxypropyl-β-Cyclodextrin Complexes of Styryllactones Enhance the Anti-Tumor Effect in SW1116 Cell Line

Thymoquinone Loaded Topical Nanoemulgel for Wound Healing: Formulation Design and In-Vivo Evaluation

Pterostilbene complexed with cyclodextrin exerts antimicrobial and anti-inflammatory effects

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