Synthesis of new calix[4]arene derivatives and evaluation of their cytotoxic activity

Oğuz, Mehmet; Yildirim, Ayse; Durmus, Irem Mukaddes; Karakurt, Serdar

doi:10.1007/s00044-021-02813-7

Cited by 4 publications

(2 citation statements)

References 33 publications

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“…Among the wide variety of macrocycles, calixarenes stand out for their ease of functionalization, which allows the introduction of different groups along the upper and/or lower rims [ 1 ]. This has led to calixarenes being used in biomedical fields as biocatalysts [ 2 ] and anti-tumor agents [ 3 , 4 ], and they have shown excellent antibacterial [ 5 , 6 , 7 ], antifungal [ 8 , 9 ] and anticancer properties [ 10 , 11 , 12 , 13 ]. Calixarenes can exhibit amphiphilic properties when phenolic rings are functionalized with ionic groups and alkyl substituents.…”

Section: Introductionmentioning

confidence: 99%

Aggregation, Cytotoxicity and DNA Binding in a Series of Calix[4]arene Amphiphile Containing Aminotriazole Groups

et al. 2023

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The present work focuses on the study of the aggregation and complexing properties of calixarenes as potential DNA condensation agents for gene delivery. In the current study, 1,4-triazole derivatives of calix[4]arenes 7 and 8 containing monoammonium fragments were synthesized. The synthesized compound’s structure was characterized by using various spectroscopic techniques (FTIR, HRESI MS, ¹H NMR and ¹³C NMR). The interactions between a series of calix[4]arene-containing aminotriazole groups (triazole-containing macrocycles with diethylenetriammonium fragments (3 and 4) and triazole-containing macrocycles with monoammonium fragments (7 and 8)) and calf thymus DNA were carried out via UV absorption, fluorescence spectroscopy, dynamic light scattering and zeta potential measurements. The role of the binding forces of calixarene–DNA complexes was analyzed. Photophysical and morphological studies revealed the interaction of the calixarenes 3, 4 and 8 with ct-DNA, which transformed the fibrous structure of ct-DNA to completely condensed compact structures that are 50 nm in diameter. The cytotoxic properties of calixarenes 3, 4, 7 and 8 against cancerous cells (MCF7, PC-3) as well as a healthy cell line (HSF) were investigated. Compound 4 was found to have the highest toxic effect on MCF7 breast adenocarcinoma (IC50 3.3 μM).

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Section: Introductionmentioning

confidence: 99%

Aggregation, Cytotoxicity and DNA Binding in a Series of Calix[4]arene Amphiphile Containing Aminotriazole Groups

et al. 2023

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“…In addition, a similar preparation based on the thiacalix [4]arene platform PTX014 was obtained (Figure 1), and its antitumor activity was shown [22]. Modern macrocyclic systems have demonstrated unprecedented advantages in the diagnosis and therapy of neoplastic diseases in recent years, using the advantages of supramolecular chemistry [25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42][43]. Highly specific detection and topical therapy are still the main targets for theranostic anticancer agents.…”

Section: Introductionmentioning

confidence: 99%

Fluorescein-Labeled Thiacalix[4]arenes as Potential Theranostic Molecules: Synthesis, Self-Association, and Antitumor Activity

et al. 2022

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In this paper, a series of thiacalix[4]arenes were synthesized as potential theranostic molecules for antitumor therapy. We propose an original strategy for the regioselective functionalization of thiacalix[4]arene with a fluorescent label to obtain antiangiogenic agent mimetics. The aggregation properties of the synthesized compounds were determined using the dynamic light scattering. The average hydrodynamic diameter of self-associates formed by the macrocycles in 1,3-alternate conformation is larger (277–323 nm) than that of the similar macrocycle in cone conformation (185–262 nm). The cytotoxic action mechanism of the obtained compounds and their ability to penetrate into of human lung adenocarcinoma and human duodenal adenocarcinoma cells were established using the MTT-test and flow cytometry. Thiacalix[4]arenes in 1,3-alternate conformation did not have a strong toxic effect. The toxicity of macrocycles in cone conformations on HuTu-80 and A549 cells (IC50 = 21.83–49.11 µg/mL) is shown. The resulting macrocycles are potential theranostic molecules that combine both the pharmacophore fragment for neoplasmas treatment and the fluorescent fragment for monitoring the delivery and biodistribution of nanomedicines.

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Novel mitochondrial and DNA damaging fluorescent Calix[4]arenes bearing isatin groups as aromatase inhibitors: Design, synthesis and anticancer activity

Oguz,

Saglik,

Oguz

et al. 2024

Bioorganic & Medicinal Chemistry

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Synthesis of new calix[4]arene derivatives and evaluation of their cytotoxic activity

Cited by 4 publications

References 33 publications

Aggregation, Cytotoxicity and DNA Binding in a Series of Calix[4]arene Amphiphile Containing Aminotriazole Groups

Aggregation, Cytotoxicity and DNA Binding in a Series of Calix[4]arene Amphiphile Containing Aminotriazole Groups

Fluorescein-Labeled Thiacalix[4]arenes as Potential Theranostic Molecules: Synthesis, Self-Association, and Antitumor Activity

Novel mitochondrial and DNA damaging fluorescent Calix[4]arenes bearing isatin groups as aromatase inhibitors: Design, synthesis and anticancer activity

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