Metal-free imidazolium salts inhibit the growth of hepatocellular carcinoma in a mouse model

Gopalan, Began; Zhao, Ke; Kng, Yinling; Suhaimi, Nur-Afidah Mohamed; Riduan, Siti Nurhanna; Zhang, Yugen; Zhuo, Lang

doi:10.1038/labinvest.2011.4

Cited by 13 publications

(10 citation statements)

References 31 publications

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“…More recently, the first animal model to study the antitumor properties of selected imidazolium salts was reported by Zhuo's group. 22 Three imidazolium salts 15-17 were selected in their study, Scheme 8. The antitumor properties of these three IMSs were investigated in hepatocellular carcinoma (HCC) cell lines, and in a xenograft mouse model.…”

Section: Antitumor Activity Of Imidazolium Saltsmentioning

confidence: 99%

Imidazolium salts and their polymeric materials for biological applications

2013

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Imidazolium salts, distinct from their parent imidazoles, are made up of a discrete cation and anion pair, and have found widespread utility as ionic liquids. A lesser known function of such imidazolium salts includes the application of these salts in biological systems, and several areas of bio-applications, including antitumour, antimicrobial, antioxidant and bioengineering applications, will be presented and discussed in this review. The wide-ranging applications and versatility of these imidazolium salts stem from the ease of their structural variation, in which properties such as amphiphilicity, lipophilicity and solubility can be tuned.

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Section: Antitumor Activity Of Imidazolium Saltsmentioning

confidence: 99%

Imidazolium salts and their polymeric materials for biological applications

2013

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“…2,2=-Bipyridine 3 was obtained from Joachim W. Heinicke, Ernst Moritz Arndt University of Greifswald, Greifswald, Germany. The cytotoxic lipophilic imidazolium salt 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride 3 was synthesized as described previously (54)(55)(56). The arylimidamide DB745 2 (23) was kindly provided by David Boykin, Georgia State University, Atlanta, GA.…”

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confidence: 99%

In VitroEffects of Novel Ruthenium Complexes in Neospora caninum and Toxoplasma gondii Tachyzoites

Barna

Debache

Vock

et al. 2013

Antimicrob Agents Chemother

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bUpon the screening of 16 antiproliferative compounds against Toxoplasma gondii and Neospora caninum, two hydrolytically stable ruthenium complexes (compounds 16 and 18) exhibited 50% inhibitory concentrations of 18.7 and 41.1 nM (T. gondii) and 6.7 and 11.3 nM (N. caninum). To achieve parasiticidal activity with compound 16, long-term treatment (22 to 27 days at 80 to 160 nM) was required. Transmission electron microscopy demonstrated the rapid impact on and ultrastructural alterations in both parasites. These preliminary findings suggest that the potential of ruthenium-based compounds should thus be further exploited.T oxoplasma gondii and Neospora caninum are cyst-forming apicomplexan parasites that infect a wide range of hosts. In an immunocompetent host, infection with either parasite does not cause disease (1-3). N. caninum has emerged as one of the most important infectious causes of bovine abortion (4-6). In contrast, T. gondii causes toxoplasmosis in humans and many animal species, either in chronically infected individuals during a decrease in immunoreactivity or if a seronegative mother acquires a primary infection during pregnancy, leading to abortion or serious fetal abnormalities (7-9). Toxoplasmosis treatment is based on only a few chemotherapeutics with considerable adverse effects (10, 11). In Neospora-seropositive cattle, pregnancy and the associated immunomodulation are already sufficient to cause recrudescence, fetal damage, and abortion (2-6). Chemotherapy has been considered a promising option if effective drugs can be identified (12, 13). Several compounds were investigated in vitro (14-16), but only a few were evaluated in small-animal models (14,(17)(18)(19)(20)(21)(22)(23)(24).We have evaluated compounds originally synthesized as anticancer drugs. Currently used metal complexes (25-31) exhibit considerable toxicity. This has stimulated the interest in other compounds with more acceptable toxicity, such as ruthenium complexes (32-36). Effects of ruthenium compounds on some bacteria and parasites have been studied (37-46). "Classical ruthenium complexes" contain heteroatom ligands (e.g., azole derivatives), and NAMI-A and KP-1019 have been evaluated in phase I clinical trials for cancer treatment (47-49). Organometallic complexes are defined by at least one metal-carbon bond. The 6 -arene ruthenium(II) phosphite complexes 5, 6, 12, and 15 to 18 were characterized earlier (50), while [Ru( 6 -p-cymene)(bipyridine)Cl][Cl] 11 was synthesized as shown previously (51). Based on our experiences in the design of selective inhibitors of CYP11B2 (53) and CYP11B1 (54), the pyridine-based compounds 4, 7 to 10, and 14 were from a small in-house library of CYP enzyme inhibitors. 2,2=-Bipyridine 3 was obtained from Joachim W. Heinicke, Ernst Moritz Arndt University of Greifswald, Greifswald, Germany. The cytotoxic lipophilic imidazolium salt 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride 3 was synthesized as described previously (54-56). The arylimidamide DB745 2 (23) was kindly provided by David Bo...

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“…Several reports have shown that imidazolium salts possess promising anticancer activities [13,16,[32][33][34][35][36][37][38][39][40][41]. We evaluated the anticancer activities of lithocholic acid-based imidazolium salts (S1-S10) against three different colorectal cancer cell lines (DLD-1, HT-29, and Caco-2).…”

Section: Imidazolium Salts Decrease Colon Cancer Viability and Metabo...mentioning

confidence: 99%

Establishment of In Vitro and In Vivo Anticolorectal Cancer Efficacy of Lithocholic Acid-Based Imidazolium Salts

Sawicka

Hryniewicka

Gohal

et al. 2022

IJMS

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Imidazolium salts (IMSs) are the subject of many studies showing their anticancer activities. In this research, a series of novel imidazolium salts substituted with lithocholic acid (LCA) and alkyl chains of various lengths (S1–S10) were evaluated against colon cancer cells. A significant reduction in the viability and metabolic activity was obtained in vitro for DLD-1 and HT-29 cell lines when treated with tested salts. The results showed that the activities of tested agents are directly related to the alkyl chain length, where S6–S8 compounds were the most cytotoxic against the DLD-1 line and S4–S10 against HT-29. The research performed on the xenograft model of mice demonstrated a lower tendency of tumor growth in the group receiving compound S6, compared with the group receiving 5-fluorouracil (5-FU). Obtained results indicate the activity of S6 in the induction of apoptosis and necrosis in induced colorectal cancer. LCA-based imidazolium salts may be candidates for chemotherapeutic agents against colorectal cancer.

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Metal-free imidazolium salts inhibit the growth of hepatocellular carcinoma in a mouse model

Cited by 13 publications

References 31 publications

Imidazolium salts and their polymeric materials for biological applications

Imidazolium salts and their polymeric materials for biological applications

In VitroEffects of Novel Ruthenium Complexes in Neospora caninum and Toxoplasma gondii Tachyzoites

Establishment of In Vitro and In Vivo Anticolorectal Cancer Efficacy of Lithocholic Acid-Based Imidazolium Salts

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