The Supramolecular Organogel Formed by Self-Assembly of Ursolic Acid Appended with Aromatic Rings

Lu, Jinrong; Hu, Jiang; Liang, Yinghua; Cui, Wenquan

doi:10.3390/ma12040614

Cited by 16 publications

(13 citation statements)

References 35 publications

(36 reference statements)

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“…Some triterpenes, including oleanolic acid, are known as materials forming gels in organic solutions. Such organogels can be useful as matrixes in the synthesis of gold nanoparticles or as potential drug carriers, and interest in other possible applications of these systems is still growing. , Here, we demonstrated that the rheological properties of oleanolic acid can be modulated by human serum albumin, and this finding may be useful for designing drug formulations based on oleanolic acid as the API. Interfacial shear rheology is also linked to the long-term stability of thin films at interfaces, thus the results of our study can be helpful in predicting the stability and shelf life of pharmaceutical dispersions containing oleanolic acid and albumin.…”

Section: Resultsmentioning

confidence: 79%

Physicochemical Characterization of Oleanolic Acid–Human Serum Albumin Complexes for Pharmaceutical and Biosensing Applications

2020

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Among numerous compounds found in marine organisms, triterpenes have attracted considerable research interest due to a beneficial impact on health including anti-inflammatory, antitumor, antiviral, and antioxidation effects. Specifically, new functionalities of oleanolic acid (OLA) have been revealed recently, indicating possible applications in nutrition and pharmaceuticals. However, this bioactive material has limited value due to low water solubility and stability. Therefore, oleanolic acid needs a carrier that protects it and enables controlled release in the human body. Innovative drug delivery systems provide a promising strategy for overcoming these problems. However, the development of those systems requires a comprehensive understanding of the physicochemical properties of triterpenes and their carriers as well as the interactions between them. Among numerous substances, human serum albumin (HSA) has been widely studied as a drug carrier. In addition, human serum albumin is the main blood plasma protein responsible for the transport of drugs and metabolites; therefore, the interactions between that protein and other substances are of physiological and pharmaceutical importance. Moreover, sensing the HSA level in blood plasma is an important challenge that requires binding studies on a molecular scale. The aim of this study was to investigate the properties of oleanolic acid in the presence of human serum albumin in terms of thermodynamics, morphology, and viscoelasticity at the air/water interface. Moreover, the wettability, surface free energy, and topography of the films after deposition on the solid substrate were determined. The results have been discussed in terms of providing physicochemical insight into the interfacial behavior of the OLA–HSA complex, which is crucial for pharmaceutical and bioanalytical applications.

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Section: Resultsmentioning

confidence: 79%

Physicochemical Characterization of Oleanolic Acid–Human Serum Albumin Complexes for Pharmaceutical and Biosensing Applications

2020

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“…Furthermore, UA is a natural molecule with self-assembly properties, which can combine with other chemical molecules to form supramolecular compounds with specific structures and properties ( Lu et al, 2019 ; Grosu et al, 2020 ). Paclitaxel (PTX) is one of the chemotherapeutic drugs widely used in clinic.…”

Section: Review Of Ua Nanoformulationsmentioning

confidence: 99%

Nanoformulations of Ursolic Acid: A Modern Natural Anticancer Molecule

et al. 2021

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Background: Ursolic acid (UA) is a natural pentacyclic triterpene derived from fruit, herb, and other plants. UA can act on molecular targets of various signaling pathways, inhibit the growth of cancer cells, promote cycle stagnation, and induce apoptosis, thereby exerting anticancer activity. However, its poor water-solubility, low intestinal mucosal absorption, and low bioavailability restrict its clinical application. In order to overcome these deficiencies, nanotechnology, has been applied to the pharmacological study of UA.Objective: In this review, we focused on the absorption, distribution, and elimination pharmacokinetics of UA in vivo, as well as on the research progress in various UA nanoformulations, in the hope of providing reference information for the research on the anticancer activity of UA.Methods: Relevant research articles on Pubmed and Web of Science in recent years were searched selectively by using the keywords and subheadings, and were summarized systematically.Key finding: The improvement of the antitumor ability of the UA nanoformulations is mainly due to the improvement of the bioavailability and the enhancement of the targeting ability of the UA molecules. UA nanoformulations can even be combined with computational imaging technology for monitoring or diagnosis.Conclusion: Currently, a variety of UA nanoformulations, such as micelles, liposomes, and nanoparticles, which can increase the solubility and bioactivity of UA, while promoting the accumulation of UA in tumor tissues, have been prepared. Although the research of UA in the nanofield has made great progress, there is still a long way to go before the clinical application of UA nanoformulations.

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“…Furthermore, the author introduced the aromatic ring into the molecular structure of ursolic acid through the connection of the amide bond. Using the π-π stacking effect of the aromatic ring and the hydrogen bonding effect of the amide bond, ursolic acid can also self-assemble into a transparent nanofiber organogel in other aromatic solvents, such as chlorobenzene, which provided a new idea for the design of supramolecular gels [86].…”

Section: Other Natural-drugs-based Low-molecular-weight Supramolecular Gelsmentioning

confidence: 99%

Development of Natural-Drugs-Based Low-Molecular-Weight Supramolecular Gels

Luo

Jian

et al. 2021

Gels

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Natural small molecular drugs with excellent biocompatibility, diverse pharmacological activities, and wide sources play an increasingly important role in the development of new drug and disease treatment. In recent years, the utilization of paclitaxel, camptothecin, rhein, curcumin, and other natural small molecular drugs with unique rigid backbone structures and modifiable multiple sites as building blocks to form gels by self-assembly has attracted widespread attention. The obtained low-molecular-weight supramolecular gel not only retains the general characteristics of the gel but also overcomes the shortcomings of natural drugs, such as poor water solubility and low bioavailability. It has the advantages of high drug loading, low toxicity, and outstanding stimulus responsiveness, which is widely used in biomedical fields. Here, we provided a comprehensive review of natural-drugs-based low-molecular-weight supramolecular gels reported in recent years and summarized their assembly mechanism, gel structure, gel properties, and potential applications. It is expected to provide a reference for further research of natural-drugs-based supramolecular gels.

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The Supramolecular Organogel Formed by Self-Assembly of Ursolic Acid Appended with Aromatic Rings

Cited by 16 publications

References 35 publications

Physicochemical Characterization of Oleanolic Acid–Human Serum Albumin Complexes for Pharmaceutical and Biosensing Applications

Physicochemical Characterization of Oleanolic Acid–Human Serum Albumin Complexes for Pharmaceutical and Biosensing Applications

Nanoformulations of Ursolic Acid: A Modern Natural Anticancer Molecule

Development of Natural-Drugs-Based Low-Molecular-Weight Supramolecular Gels

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