Phenanthroline-2,9-bistriazoles as selective G-quadruplex ligands

Nielsen, Mads C.; Larsen, Anders Foller; Abdikadir, Faisal Hussein; Ulven, Trond

doi:10.1016/j.ejmech.2013.11.027

Cited by 41 publications

(30 citation statements)

References 82 publications

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“…The IC 50 concentration of curcumin against MCF‐7, M19‐MEL and HeLa cell lines are 27.4, 32.9 and 21.7 μg/mL, respectively. The free phendione ligand is very active against cancer as reported earlier (IC 50 = 5 to 7 μg/mL). The chitosan–phendione is showing less activity than the free ligand phendione (IC 50 = 170 to 200 μg/mL).…”

Section: Resultssupporting

confidence: 74%

CuO‐loaded hydrophobically modified chitosan as hybrid carrier for curcumin delivery and anticancer activity

Kamaraj

Maheswari

Ezhilarasu³

et al. 2017

Asia-Pacific J Chem Eng

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The hydrophobic modification of chitosan was performed by the incorporation of aromatic phendione to the amino group of chitosan to improve the hydrophobic drug encapsulation efficiency and anticancer activity. The phendione‐modified chitosan was coated with the copper oxide (CuO) nanoparticles to obtain the hybrid material for the model drug (curcumin) delivery. The synthesized hybrid nanoparticles were characterized by Fourier transform infrared, proton nuclear magnetic resonance, thermogravimetric analysis, X‐ray diffraction, atomic force microscopy, and scanning electron microscopy techniques. The extent of phendione modification on chitosan, presence of CuO nanoparticles, drug encapsulation, and size and morphology of the prepared hybrid materials were observed by using the techniques mentioned. The drug release studies were performed on simulated gastric fluid (pH 1.2) and simulated body fluid (pH 7.4) to analyze the release kinetics of curcumin from the chitosan and chitosan–phendione with CuO. The drug release was also monitored at different initial drug loading conditions. As the initial loading of drug decreased, the rate of drug release was also decreased. Mostly, the drug release followed a non‐Fickian, case II type transport mechanism. The drug‐loaded chitosan–phendione and chitosan with CuO nanoparticles were investigated for anticancer activities toward the cell lines M19‐MEL, MCF‐7, and HeLa. © 2017 Curtin University and John Wiley & Sons, Ltd.

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Section: Resultssupporting

confidence: 74%

CuO‐loaded hydrophobically modified chitosan as hybrid carrier for curcumin delivery and anticancer activity

Kamaraj

Maheswari

Ezhilarasu³

et al. 2017

Asia-Pacific J Chem Eng

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“…As a proof of concept, some ligands were designed to selectively target the G-4 forms of h_kit1 or h_kit2. So far, several small molecules belonging to different scaffolds have been demonstrated to bind one G-4 structure of KIT and to reduce basal levels of c-kit expression in a dose-dependent manner and in different cell lines [9], [21]–[25]. On the contrary, a triarylpyridine derivative was found to reduce the stability of G-4 in KIT and increments KIT gene expression in HGC-27 cells [26].…”

Section: Introductionmentioning

confidence: 99%

Sequencing and G-Quadruplex Folding of the Canine Proto-Oncogene KIT Promoter Region: Might Dog Be Used as a Model for Human Disease?

et al. 2014

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Downregulation of gene expression by induction of non-canonical DNA structures at promotorial level is a novel attractive anticancer strategy. In human, two guanine-rich sequences (h_kit1 and h_kit2) were identified in the promotorial region of oncogene KIT. Their stabilization into G-quadruplex structures can find applications in the treatment of leukemias, mastocytosis, gastrointestinal stromal tumor, and lung carcinomas which are often associated to c-kit mis-regulation. Also the most common skin cancer in domestic dog, mast cell tumor, is linked to a mutation and/or to an over-expression of c-kit, thus supporting dog as an excellent animal model. In order to assess if the G-quadruplex mediated mechanism of regulation of c-kit expression is conserved among the two species, herein we cloned and sequenced the canine KIT promoter region and we compared it with the human one in terms of sequence and conformational equilibria in physiologically relevant conditions. Our results evidenced a general conserved promotorial sequence between the two species. As experimentally confirmed, this grants that the conformational features of the canine kit1 sequence are substantially shared with the human one. Conversely, two isoforms of the kit2 sequences were identified in the analyzed dog population. In comparison with the human counterpart, both of them showed an altered distribution among several folded conformations.

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“…Phenanthroline derivatives attracted attention in the last years especially due to their biological effects [1][2][3] , materials science applications 4 , crystal engineering 5,6 , their unique p-electrons delocalization 7,8 and complexation properties 9 . Phenanthrolines polycyclic skeletons are also present in sterols, sex hormones, cardiac glycosides, bile acids and morphine alkaloids 10 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structure, antimycobacterial and anticancer evaluation of new pyrrolo-phenanthroline derivatives

Matarneh

Mangalagiu

Shova³

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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A study concerning design, synthesis, structure and in vitro antimycobacterial and anticancer evaluation of new fused derivatives with pyrrolo[2,1-c] [4,7]phenanthroline skeleton is described. The strategy adopted for synthesis involves a [3 + 2] dipolar cycloaddition of several in situ generated 4,7-phenanthrolin-4-ium ylides to different substituted alkynes and alkenes. Stereo-and regiochemistry of cycloaddition reactions were discussed. The structure of the new compounds was proven unambiguously, single-crystal X-ray diffraction studies including. The antimycobacterial and anticancer activity of a selection of new synthesized compounds was evaluated against Mycobacterium tuberculosis H37Rv under aerobic conditions and 60 human tumour cell line panel, respectively. Five of the tested compounds possess a moderate antimycobacterial activity, while two of the compounds have a significant antitumor activity against renal cancer and breast cancer.

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Phenanthroline-2,9-bistriazoles as selective G-quadruplex ligands

Cited by 41 publications

References 82 publications

CuO‐loaded hydrophobically modified chitosan as hybrid carrier for curcumin delivery and anticancer activity

CuO‐loaded hydrophobically modified chitosan as hybrid carrier for curcumin delivery and anticancer activity

Sequencing and G-Quadruplex Folding of the Canine Proto-Oncogene KIT Promoter Region: Might Dog Be Used as a Model for Human Disease?

Synthesis, structure, antimycobacterial and anticancer evaluation of new pyrrolo-phenanthroline derivatives

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