Synthesis, structure and DNA binding studies of 9-phenyldibenzo[a,c] phenazin-9-ium

Kundu, Suman; Biswas, Manas Kumar; Banerjee, Ananya; Bhadra, Kakali; Kumar, Gopinatha Suresh; Drew, Michael G. B.; Bhadra, Rupak K.; Ghosh, Prasanta

doi:10.1039/c2ra22317a

Cited by 9 publications

(3 citation statements)

References 59 publications

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“…33a-d Groove binding shows little or no perturbation on the helicity, while intercalation enhances the intensity of both the bands by stabilizing the right handed B-conformation of DNA. 34 On addition of the complexes to CT DNA, considerable changes in the positive and negative bands were observed which were indicative of intercalative mode of binding (Fig. 11).…”

Section: Dna Interaction Studiesmentioning

confidence: 98%

Half-sandwich RuCl₂(η⁶-p-cymene) core complexes containing sulfur donor aroylthiourea ligands: DNA and protein binding, DNA cleavage and cytotoxic studies

et al. 2016

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A series of Ru(ii)(η(6)-p-cymene) complexes (1-4) bearing the general formula [RuCl2(η(6)-p-cymene)L] (L = monodentate aroylthiourea ligand) has been synthesized and characterized by analytical and various spectroscopic techniques. The neutral monodentate coordination of aroylthiourea with Ru via an S atom was confirmed by single crystal X-ray diffraction study. The complexes were tested for their ability to interact with DNA and protein. The complexes bound with calf thymus DNA (CT DNA) with the intrinsic binding constant value in the order of 10(4) M(-1). The intercalative mode of binding was confirmed by the ethidium bromide (EB) displacement study. The interaction of the complexes with CT DNA was further supported by viscosity measurements and circular dichroic (CD) spectra. The Ru(ii) complexes cleaved the supercoiled DNA without the need of any external agent. The spectroscopic evidence showed good binding efficacy of the complexes with BSA (Bovine Serum Albumin). The alterations in the secondary structure of BSA by the Ru(ii) complexes were confirmed by synchronous fluorescence spectra. Cytotoxicity examination by MTT assay was carried out in two cancer cell lines (MCF7 and A549) and one non-cancerous cell line (L929). Complex 4 showed significant activity [IC50 = 52.3 (MCF7) and 54.6 (A549) μM] which was comparable with that of similar known complexes. The morphological changes assessed by Hoechst staining revealed that the cell death occurred by apoptosis.

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Section: Dna Interaction Studiesmentioning

confidence: 98%

Half-sandwich RuCl₂(η⁶-p-cymene) core complexes containing sulfur donor aroylthiourea ligands: DNA and protein binding, DNA cleavage and cytotoxic studies

et al. 2016

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“…[10][11][12][13] Deoxyribonucleic acid (DNA) has long stood as a unique polymer due to its role in biology and biochemistry, 14 contains the genetic instructions for the development and functioning of living organisms, the target molecule for many drugs, especially antitumor therapies, 15,16 always to be the hot topic of research. [17][18][19] In recent years, promoting a research focus many investigators focus on the interaction between small molecules and DNA, [20][21][22] where characterizing polyphenol-DNA interactions has been integral to understanding the bioactivity of said polyphenol micronutrient DNA ligands and presents opportunities for the design of new and effective drugs against a variety of diseases, 23 but rarely consideration about structure- activity relationship between small molecules was taken. Therefore, comparing the interactions between DNA and different avones, a polyphenol subclass, can shed light on which aspects of avones which are required for DNA binding and which parts are expendable.…”

Section: Introductionmentioning

confidence: 99%

Interaction of flavones with DNA in vitro: structure–activity relationships

Chen

Liu

et al. 2015

RSC Adv.

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Flavones are polyphenolic compounds endowed with diverse pharmacological and biological activities with which have many derivatives with different structures.In this work, UV−vis spectroscopy, fluorescence spectroscopy and molecular docking have been used to investigate the structure-activity relationship of the interaction between different flavones and DNA in vitro. From it we could know the studied flavones are all intercalate into the double helix of DNA, suggest that the same skeleton structure in flavones may the main reason for the interaction mode. At the same time, we could find that different flavones lead to different results in the interaction which results from different structure between them, such as the number of hydroxyl groups, the location of hydroxyl groups, and steric hindrance et al. These findings are important in the research about structure-activity relationships, which may meaningful for drug discovery, drug design, novel medicines design and help us understand the structure-activity relationship between flavones at the molecular level.

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“…Previously, we synthesized and reported a novel 9-phenyldibenzo[a[,]c]phenazin-9-ium cation [1 + ] as [1] [CuCl 2 ] and as [1] [I], and the 3D structure was also evaluated by us [10]. The existence of the monovalent Cu(I) in [1] [CuCl 2 ] was also ascertained.…”

Section: Introductionmentioning

confidence: 99%

In vitro and in vivo Anticancer Effects of a Novel 9-Phenyldibenzo[a,c]phenazin-9-ium Cation and Its Ligands

Das

Banerjee²,

Biswas³

et al. 2014

Chemotherapy

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Background: Multidrug resistance (MDR) is a major problem in cancer treatment. Cu complexes possess the ability to overcome MDR in cancer. Therefore, the search for new Cu complexes is of great clinical significance and we address the anticancer effects of a previously synthesized novel 9-phenyldibenzo[a,c]phenazin-9-ium cation [1⁺] as [1] [CuCl₂] and as [1] [I]. Methods: The existence of the monovalent Cu(I) in [1] [CuCl₂] was proven by electron paramagnetic resonance (EPR) studies and in vivo anticancer effects were studied in animals. Results: The monovalent nature of the Cu ion in [1] [CuCl₂] was determined through EPR. The mean survival time of mice bearing doxorubicin-resistant Ehrlich ascites carcinoma cells is longer when [1] [I] is injected intraperitoneally whereas [1] [CuCl₂] does not significantly increase the median survival in tumor-bearing mice. Compounds do not follow the immunomodulatory route and only [1] [I] shows cytotoxic activity in both MDR and drug-sensitive leukemia cell lines. Conclusion: An organic iodide complex rather than a cupric complex possesses direct cytotoxic potential.

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Synthesis, structure and DNA binding studies of 9-phenyldibenzo[a,c] phenazin-9-ium

Abstract: Synthesis, structure and DNA binding studies of 9-phenyldibenzo[a,c] phenazin-9-ium3

Cited by 9 publications

References 59 publications

Half-sandwich RuCl₂(η⁶-p-cymene) core complexes containing sulfur donor aroylthiourea ligands: DNA and protein binding, DNA cleavage and cytotoxic studies

Half-sandwich RuCl₂(η⁶-p-cymene) core complexes containing sulfur donor aroylthiourea ligands: DNA and protein binding, DNA cleavage and cytotoxic studies

Interaction of flavones with DNA in vitro: structure–activity relationships

In vitro and in vivo Anticancer Effects of a Novel 9-Phenyldibenzo[a,c]phenazin-9-ium Cation and Its Ligands

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Synthesis, structure and DNA binding studies of 9-phenyldibenzo[a,c] phenazin-9-ium

Abstract: Synthesis, structure and DNA binding studies of 9-phenyldibenzo[a,c] phenazin-9-ium3

Cited by 9 publications

References 59 publications

Half-sandwich RuCl2(η6-p-cymene) core complexes containing sulfur donor aroylthiourea ligands: DNA and protein binding, DNA cleavage and cytotoxic studies

Half-sandwich RuCl2(η6-p-cymene) core complexes containing sulfur donor aroylthiourea ligands: DNA and protein binding, DNA cleavage and cytotoxic studies

Interaction of flavones with DNA in vitro: structure–activity relationships

In vitro and in vivo Anticancer Effects of a Novel 9-Phenyldibenzo[a,c]phenazin-9-ium Cation and Its Ligands

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Half-sandwich RuCl₂(η⁶-p-cymene) core complexes containing sulfur donor aroylthiourea ligands: DNA and protein binding, DNA cleavage and cytotoxic studies

Half-sandwich RuCl₂(η⁶-p-cymene) core complexes containing sulfur donor aroylthiourea ligands: DNA and protein binding, DNA cleavage and cytotoxic studies