Selective recognition of specific G-quadruplex vs. duplex DNA by a phenanthroline derivative

Zhang, Hong; Xiang, Junfeng; Hu, Hanjun; Liu, Yan; Yang, Fengmin; Shen, Gang; Tang, Yalin; Chen, Chuan‐Feng

doi:10.1016/j.ijbiomac.2015.03.034

Cited by 8 publications

(3 citation statements)

References 57 publications

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“…A large number of small heterocyclic molecules have been synthesized and evaluated for their ability to interact with G‐quadruplexes . Among them are the 1,10‐phenanthroline derivatives, such as PhenDC3 and its structural analogues I , tetraaminophenanthroline II , K35, and phenanthroline‐2,9‐bistriazole III (Figure ) . These compounds have been investigated for their capacity to bind and stabilize various G4 topologies and for their selectivity for G‐quadruplex versus duplex structures.…”

Section: Introductionmentioning

confidence: 99%

“…[16] Among them are the 1,10-phenanthroline derivatives, such as PhenDC3 and its structurala nalogues I,t etraaminophenanthroline II,K 35, and phenanthroline-2,9-bistriazole III (Figure 1). [17][18][19][20][21][22][23][24][25][26][27][28] These compounds have been investigated for their capacity to bind and stabilize various G4 topologies and for their selectivity for G-quadruplex versus duplexs tructures.…”

Section: Introductionmentioning

confidence: 99%

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Design, Synthesis, and Evaluation of 2,9‐Bis[(substituted‐aminomethyl)phenyl]‐1,10‐phenanthroline Derivatives as G‐Quadruplex Ligands

et al. 2017

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Genomic sequences able to form guanine quadruplexes (G4) are found in oncogene promoters, in telomeres, and in 5'- and 3'-untranslated regions as well as introns of messenger RNAs. These regions are potential targets for drugs designed to treat cancer. Herein, we present the design and syntheses of ten new phenanthroline derivatives and characterization of their interactions with G4-forming oligonucleotides. We evaluated ligand-induced stabilization and specificity and selectivity of ligands for various G4 conformations using FRET-melting experiments. We investigated the interaction of compound 1 a (2,9-bis{4-[(3-dimethylaminopropyl)aminomethyl]phenyl}-1,10-phenanthroline), which combined the greatest stabilizing effect and specificity for G4, with human telomeric sequences using FRET, circular dichroism, and ESI-MS. In addition, we showed that compound 1 a interferes with the G4 helicase activity of Saccharomyces cerevisiae Pif1. Interestingly, compound 1 a was significantly more cytotoxic toward two human leukemic cell lines than to normal human blood mononuclear cells. These novel phenanthroline derivatives will be a starting point for further development and optimization of potent G4 ligands that have potential as anticancer agents.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Evaluation of 2,9‐Bis[(substituted‐aminomethyl)phenyl]‐1,10‐phenanthroline Derivatives as G‐Quadruplex Ligands

et al. 2017

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“…A gold complex with 6,6-dimethyl-1,10-phenanthroline was synthesized and characterized, and DNA binding and cytotoxic activities were determined [46]. Recently, a phenanthrolin-dicarbocylate ester has been found to show promising anticancer activity with selective DNA-binding activity against several human cancer cell lines [47]. The chemotherapeutic potential of 1,10-phenanthroline and three of its transition metal complexes was determined on two different cancer cells by Deegan et al [48] and they suggested that phen and three metal-phen complexes may have been successful therapeutics.…”

Section: Discussionmentioning

confidence: 99%

Gold(III) compounds-mediated inhibition of lung cancer cell proliferation

Bostancıoğlu

Kaya²,

Koparal³

et al. 2016

Anti-Cancer Drugs

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Research on chemotherapeutics for lung cancer is crucial for designing a new therapeutic strategy against malignant lung tumors. Although radiotherapy and chemotherapy, which are not selective for cancer cells and exert toxic effects on healthy cells, have a limited advantage, they are the primary treatment modalities for non-small lung cancer. In addition to cytotoxicity, resistance of chemotherapeutics results in failure of treatment. This is why it is of utmost importance to focus on the creation of new chemotherapeutics without toxicity for the successful treatment and improved survival of cancer patients. New gold(III) and Pt(II) compounds were synthesized with a heterocyclic ligand using 2-phenylimidazo[4,5-f][1,10]phenanthroline as a ligand and bis-1,4-di[([1,10] phenanthroline-5-il)amino]-2-buten as a bridge molecule. The characterization of the compounds was carried out using a variety of spectroscopic methods (H NMR, IR, MS, and elemental analysis). Their antiproliferative, antitumoral, and apoptotic activities were determined. IR spectra and NMR results confirmed the formation of dinuclear heterocyclic complexes for two metal complexes. Cytotoxicity studies on lung cancer cells (A549) and healthy cells (CHL) showed a marked increase in cytotoxicity with the use of gold(III) complexes, and especially [Au(L)B](PF6)2 showed higher cytotoxic and apoptotic features than cisplatin at lower concentrations in cancer cells. These findings have been supported by results from DAPI staining and colorimetric measurement of the caspase-3 enzyme in both cell lines. Compounds showed selective toxicity on the cancer cells. In the light of the high efficacy of our newly synthesized gold complexes, they might be good and promising anticancer agents compared with cisplatin.

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Green Synthesis of Benzo or Cyclopenta[j][1,7]phenanthroline Derivatives in EtOH under Catalyst‐free Conditions

Wang

Zhang

et al. 2015

Journal of Heterocyclic Chem

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Selective recognition of specific G-quadruplex vs. duplex DNA by a phenanthroline derivative

Cited by 8 publications

References 57 publications

Design, Synthesis, and Evaluation of 2,9‐Bis[(substituted‐aminomethyl)phenyl]‐1,10‐phenanthroline Derivatives as G‐Quadruplex Ligands

Design, Synthesis, and Evaluation of 2,9‐Bis[(substituted‐aminomethyl)phenyl]‐1,10‐phenanthroline Derivatives as G‐Quadruplex Ligands

Gold(III) compounds-mediated inhibition of lung cancer cell proliferation

Green Synthesis of Benzo or Cyclopenta[j][1,7]phenanthroline Derivatives in EtOH under Catalyst‐free Conditions

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