Unexpected DNA binding properties with correlated downstream biological applications in mono vs. bis-1,8-naphthalimide Ru(<scp>ii</scp>)-polypyridyl conjugates

Ryan, Gary J.; Poynton, Fergus E.; Elmes, Robert B. P.; Erby, Marialuisa; Williams, D.C.; Quinn, Susan J.; Gunnlaugsson, Thorfinnur

doi:10.1039/c5dt00360a

Cited by 38 publications

(48 citation statements)

References 93 publications

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“…Here, T m of CT‐DNA is found to be 85.97 °C in the buffer; after addition of the Pd(II) complexes, T m of the DNA increases to 88 and 88.5 °C for complexes 1 and 2 , respectively. The results show the possibility of partial intercalation between the CT‐DNA and the two complexes …”

Section: Resultsmentioning

confidence: 94%

“…An increase in absorbance at 260 nm is attributed to intercalation of small molecules to ds‐DNA. Nevertheless, the slight shift in the T m value of CT‐DNA in the presence of complexes suggests non‐classical modes such as partial intercalation, groove binding and/or surface binding modes . The melting curves of CT‐DNA in the absence and presence of the complexes are presented in Figure .…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, characterization and biological activities of two novel orthopalladated complexes: Interactions with DNA and bovine serum albumin, antitumour activity and molecular docking studies

Karami

Hashemi

Lipkowski

et al. 2017

Applied Organom Chemis

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[Pd(L 1 )(C,N)]CF 3 SO 3 and [Pd(L 2 )(C,N)]CF 3 SO 3 (L 1 = 2,2′-bipyridine, L 2 = 1,10-phenanthroline and C,N = benzylamine) novel orthopalladated complexes have been synthesized and characterized using various techniques. The binding of the complexes with native calf thymus DNA (CT-DNA) was monitored using UVvisible absorption spectrophotometry, fluorescence spectroscopy and thermal denaturation studies. Our results indicate that these complexes can strongly bind to CT-DNA via partial intercalative mode. In addition, fluorescence spectrometry of bovine serum albumin (BSA) with the complexes shows that the fluorescence quenching mechanism of BSA is a static process. The results of site-competitive replacement experiments with specific site markers clearly indicate that the complexes bind to site I of BSA. Notably, the complexes exhibit significant in vitro cytotoxicity against two human cancer cell lines (Jurkat and MCF-7) with IC 50 values varying from 37 to 53 μM. Finally, a molecular docking experiment effectively proves the binding of the Pd(II) complexes to DNA and BSA.

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Section: Resultsmentioning

confidence: 94%

Section: Resultsmentioning

confidence: 99%

Synthesis, characterization and biological activities of two novel orthopalladated complexes: Interactions with DNA and bovine serum albumin, antitumour activity and molecular docking studies

Karami

Hashemi

Lipkowski

et al. 2017

Applied Organom Chemis

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“…Ryan and coworkers have reported DNA binding behavior of mono and bis‐1,8‐naphthalimide Ru(II)‐polypyridyl conjugates ( 122 and 123 ; Figure ) by monitoring the absorption bands of naphthalimide and Ru(II) center . The observed 37 % hypochromism of the 1,8‐naphthalimide band of compound 122 in the presence increased concentration of st‐DNA suggested the possibility of intercalation with DNA (Table ).…”

Section: Metal Complexesmentioning

confidence: 97%

1,8‐Naphthalimide: A Potent DNA Intercalator and Target for Cancer Therapy

Tandon

Luxami

Kaur

et al. 2017

The Chemical Record

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The poor pharmacokinetics, side effects and particularly the rapid emergence of drug resistance compromise the efficiency of clinically used anticancer drugs. Therefore, the discovery of novel and effective drugs is still an extremely primary mission. Naphthalimide family is one of the highly active anticancer drug based upon effective intercalator with DNA. In this article, we review the discovery and development of 1,8-naphthalimide moiety, and, especially, pay much attention to the structural modifications and structure activity relationships. The review demonstrates how modulation of the moiety affecting naphthalimide compound for DNA binding that is achieved to afford a profile of antitumor activity. The DNA binding of imide and ring substitution at naphthalimide, bisnaphthalimide, naphthalimide-metal complexes is achieved by molecular recognition through intercalation mode. Thus, this synthetic/natural small molecule can act as a drug when activation or inhibition of DNA function, is required to cure or control the cancer disease. The present study is a review of the advances in 1,8-naphthalimide-related research, with a focus on how such derivatives are intercalated into DNA for their anticancer activities.

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“…Accordingly, eliminating a specific biological target, DNA, found predominantly in cancer cells, is the approach in use. Though various mechanisms can be found for damaging DNA, tailoring a metal complex that fits all the above and possesses the ability to interact and manipulate vital aspects in cell proliferation is an added advantage, in fact the best strategy to date . Then again, the hydrophobic nature of synthetic complexes in the normal biological medium, water, is one of the major experimental drawbacks in bioinorganic studies and can be remedied with the introduction of new functional groups.…”

Section: Introductionmentioning

confidence: 99%

Water‐soluble Schiff base Cu(II) and Zn(II) complexes: Synthesis, DNA targeting ability and chemotherapeutic potential of Cu(II) complex for hepatocellular carcinoma –in vitroandin vivoapproach

Pravin¹,

Kumaravel²,

Senthilkumar

et al. 2017

Applied Organom Chemis

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Reliable compounds with low toxicity are tempting potential chemotherapeutics. With an aim of achieving less toxic but more potent metallodrugs, four new-generation hydrophilic Cu(II) and Zn(II) complexes with DNA-targeting properties were synthesized and characterized using various physicochemical data. The excellent DNA binding and cleavage results confirmed the mode of binding of DNA with the complexes and their ability to denature it. The profound in vitro cytotoxicity exhibited by complex 3 against a panel of cell lines (HeLa, MCF-7 and HepG-2) along with NHDF (normal human dermal fibroblasts) with distinct activity towards HepG-2 and low toxicity to NHDF prompted in vivo studies of induced hepatocellular carcinoma-affected Swiss albino rats. On evaluating various serum hepatic, biological and histopathological parameters, complex 3 showed excellent activity in restoring the damaged liver to normal. As a means of identifying the pathway of DNA damage, flow cytometric evaluation of cell cycle analysis was performed, which revealed S phase arrest-induced apoptosis in HepG-2 cells by complex 3, making it a cell cycle-specific drug.

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Unexpected DNA binding properties with correlated downstream biological applications in mono vs. bis-1,8-naphthalimide Ru(ii)-polypyridyl conjugates

Cited by 38 publications

References 93 publications

Synthesis, characterization and biological activities of two novel orthopalladated complexes: Interactions with DNA and bovine serum albumin, antitumour activity and molecular docking studies

Synthesis, characterization and biological activities of two novel orthopalladated complexes: Interactions with DNA and bovine serum albumin, antitumour activity and molecular docking studies

1,8‐Naphthalimide: A Potent DNA Intercalator and Target for Cancer Therapy

Water‐soluble Schiff base Cu(II) and Zn(II) complexes: Synthesis, DNA targeting ability and chemotherapeutic potential of Cu(II) complex for hepatocellular carcinoma –in vitroandin vivoapproach

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