Calixarene: A Versatile Material for Drug Design and Applications

Hussain, Muhammad Ajaz; Ashraf, Muhammad; Muhammad, Gulzar; Tahir, Muhammad Nawaz; Bukhari, Syed Nasir Abbas

doi:10.2174/1381612822666160928143328

Cited by 36 publications

(15 citation statements)

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“…It is active against beef and dog tapeworms. In addition, it is useful for treating diseases caused by these parasites, such as cancer, metabolic diseases, artery constriction, endometriosis, and rheumatoid arthritis, among others [68]. In spite of its broad clinical application, the efficacy of niclosamide can be affected by its very low solubility in water (230 ng/mL).…”

Section: Calix[n]arenesmentioning

confidence: 99%

Calixarenes: Generalities and Their Role in Improving the Solubility, Biocompatibility, Stability, Bioavailability, Detection, and Transport of Biomolecules

2019

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The properties and characteristics of calix[n]arenes are described, as well as their capacity to form amphiphilic assemblies by means of the design of synthetic macrocycles with a hydrophilic head and a hydrophobic tail. Their interaction with various substances of interest in pharmacy, engineering, and medicine is also described. In particular, the role of the calix[n]arenes in the detection of dopamine, the design of vesicles and liposomes employed in the manufacture of systems of controlled release drugs used in the treatment of cancer, and their role in improving the solubility of testosterone and anthelmintic drugs and the biocompatibility of biomaterials useful for the manufacture of synthetic organs is emphasized. The versatility of these macrocycles, able to vary in size, shape, functional groups, and hydrophobicity and to recognize various biomolecules and molecules with biological activity without causing cytotoxicity is highlighted.

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Section: Calix[n]arenesmentioning

confidence: 99%

Calixarenes: Generalities and Their Role in Improving the Solubility, Biocompatibility, Stability, Bioavailability, Detection, and Transport of Biomolecules

2019

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“…Each type of CD has a cavity with slightly different sizes that confers on them a selectivity for well-sized molecules. Another synthetic host able to sequester hydrophobic molecules and ions is calixarene [41]. According to the residues' nature, calixarenes host-guest complexes can be obtained in an organic or a water environment.…”

Section: Conceptmentioning

confidence: 99%

Supramolecular Chemistry and Self-Organization: A Veritable Playground for Catalysis

2019

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The directed assembly of molecular building blocks into discrete supermolecules or extended supramolecular networks through noncovalent intermolecular interactions is an ongoing challenge in chemistry. This challenge may be overcome by establishing a hierarchy of intermolecular interactions that, in turn, may facilitate the edification of supramolecular assemblies. As noncovalent interactions can be used to accelerate the reaction rates and/or to increase their selectivity, the development of efficient and practical catalytic systems, using supramolecular chemistry, has been achieved during the last few decades. However, between discrete and extended supramolecular assemblies, the newly developed “colloidal tectonics” concept allows us to link the molecular and macroscopic scales through the structured engineering of colloidal structures that can be applied to the design of predictable, versatile, and switchable catalytic systems. The main cutting-edge strategies involving supramolecular chemistry and self-organization in catalysis will be discussed and compared in this review.

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“…In addition, calixarenes have many other structural characteristics including the easy modification of their basic core and rim via covalent attachment to various chemical scaffolds, the limited toxicity and immune responses (Geraci et al, 2008). The above advantages make these cyclic oligomers ideal for the design of new drugs and building blocks for drug carriers in biomedical fields (Da Silva et al, 2004;Hussain et al, 2017). In this regard, calixarenes and their derivatives are currently being studied and used in a variety of medicinal applications beyond their traditional place in chemistry.…”

Section: Introductionmentioning

confidence: 99%

Structural Design, Synthesis, and Preliminary Biological Evaluation of Novel Dihomooxacalix[4]arene-Based Anti-tumor Agents

Wang

Han

et al. 2019

Front. Chem.

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Calixarene and its derivatives have extensively served as promising anti-tumor agents. Previously, we have synthesized a series of calix[n]arene polyhydroxyamine derivatives (n = 4, 6, 8) and found that 5,11,17,23-tetra-tert-butyl-25,27-bis [N-(2-hydroxyethyl)aminocarbonylmethoxyl] calix[4]arene (CLX-4) displayed significant effect toward SKOV3, A549, SW1990, HeLa, Raji, and MDA-MB-231 cancer cells. In the present work, we find a replacement of calix[4]arene bone and synthesized 19 novel structurally related dihomooxacalix[4]arene amide derivatives 4A−4S to optimize its efficacy. Their abilities to induce cytotoxicity in human lung carcinoma (A549) cells, breast cancer (MCF-7) cells, cervical cancer (HeLa) cells, hepatocellular carcinoma (HepG2) cells, as well as human umbilical vein endothelial (HUVEC) cells are evaluated in vitro. Encouraging results show that the majority of dihomooxacalix[4]arene amide derivatives are effective at inhibiting A549 cell proliferation with the corresponding IC 50 ranging from 0.6 to 20.1 µM. In particular, compounds 4A, 4D, and 4L explore markedly increased potency (IC 50 value is 2.0 ± 0.5 µM, 0.7 ± 0.1 µM, and 1.7 ± 0.4 µM) over the cytotoxicity profiles of control CLX-4, whose IC 50 value is 2.8 ± 0.3 µM. More interestingly, 4A also demonstrates the perfect cytotoxic effect against MCF-7, HeLa, and HepG2 cells with IC 50 values of 1.0 ± 0.1 µM, 0.8 ± 0.2 µM, and 2.7 ± 0.4 µM. In addition, the results proved that our synthesized 4A has much lower toxicity (41%) to normal cells at a concentration of 10 µM than that of 4D (90%). To reveal the mechanisms, the key indicators including the cell cycle and apoptosis are observed by the flow cytometry analysis in MCF-7 cells. The results demonstrate that both 4A and 4D can induce the MCF-7 cell cycle arrest in G0/G1 phase and cell apoptosis. Therefore, our finding proves that the dihomooxacalix[4]arene amide derivatives are convenient platforms for potential supramolecular anticancer agents.

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Calixarene: A Versatile Material for Drug Design and Applications

Cited by 36 publications

References 0 publications

Calixarenes: Generalities and Their Role in Improving the Solubility, Biocompatibility, Stability, Bioavailability, Detection, and Transport of Biomolecules

Calixarenes: Generalities and Their Role in Improving the Solubility, Biocompatibility, Stability, Bioavailability, Detection, and Transport of Biomolecules

Supramolecular Chemistry and Self-Organization: A Veritable Playground for Catalysis

Structural Design, Synthesis, and Preliminary Biological Evaluation of Novel Dihomooxacalix[4]arene-Based Anti-tumor Agents

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