New copper(I) complexes bearing lomefloxacin motif: Spectroscopic properties, in vitro cytotoxicity and interactions with DNA and human serum albumin

Komarnicka, Urszula K.; Starosta, Radosław; Kyzioł, Agnieszka; Płotek, Michał; Puchalska, M.; Jeżowska‐Bojczuk, Małgorzata

doi:10.1016/j.jinorgbio.2016.09.015

Cited by 40 publications

(23 citation statements)

References 69 publications

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“…The majority of ruthenium(II) aminomethylphosphanes' coordination compounds exhibited cytotoxicity in vitro against cancer cells close to cisplatin [10]. Moreover, the synthesized copper(I) and copper(II) complexes with phosphanes modified with quinolones (i.e., ciprofloxacin PCp, sparfloxacin PSf, lomefloxacin PLm, norfloxacin PNr) turned out to be more active than the parent antibiotics, and noteworthy possessed cytotoxicity in vitro towards selected cancer cell lines higher than cisplatin [11][12][13][14]. These findings encouraged us to implement quinolones' phosphanes as well to half-sandwich ruthenium(II) complexes and investigate their prospective anticancer activity.…”

Section: Introductionmentioning

confidence: 99%

Polymeric micelle-mediated delivery of half-sandwich ruthenium(II) complexes with phosphanes derived from fluoroloquinolones for lung adenocarcinoma treatment

Kołoczek

Skórska-Stania

Cierniak

et al. 2018

European Journal of Pharmaceutics and Biopharmaceutics

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Novel half-sandwich ruthenium(II) complexes with aminomethyl(diphenyl)phosphine derived from fluoroloquinolones (RuPCp, RuPSf, RuPLm, RuPNr) were being investigated as alternatives to well-established metal-based chemotherapeutics. All compounds were characterized by elemental analysis, selected spectroscopic methods (i.e., absorption and fluorescence spectroscopies, ESI-MS, NMR, circular dichroizm), X-ray diffractometry, ICP-MS, and electrochemical techniques. To overcome low solubility, serious side effects connected with systemic cytotoxicity of ruthenium complexes, and acquiring the resistance of cancer cells, polymeric nanoformulations based on Pluronic P-123 micelles loaded with selected Ru(II) complexes were prepared and characterized. Resulting micelles (RuPCp_M, RuPNr_M) enabled efficient drug accumulation inside human lung adenocarcinoma (A549 tumor cell line), proved by confocal microscopy and ICP-MS analysis, allowing cytotoxic action. Studied complexes exhibited promising cytotoxicity in vitro with IC50 values significantly lower than the reference drug - cisplatin. The fluorescence spectroscopic data (CT-DNA titration, in vitro cell staining) together with analysis of DNA fragmentation (pBR322 plasmid, comet assay) provided clear evidence for the interaction with DNA inducing apoptotic cell death.

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Section: Introductionmentioning

confidence: 99%

Polymeric micelle-mediated delivery of half-sandwich ruthenium(II) complexes with phosphanes derived from fluoroloquinolones for lung adenocarcinoma treatment

Kołoczek

Skórska-Stania

Cierniak

et al. 2018

European Journal of Pharmaceutics and Biopharmaceutics

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“…Copper, as the active centre of many enzymes, plays an important role in development and function of human organs and tissues [20][21][22]. To date, copper-based complexes have been extensively synthesised and investigated as anticancer agents because of their high antitumor activity and advantages relative to other metal anticancer complexes [23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38]. Thiosemicarbazones are formed by a condensation reaction of thiosemicarbazide and aldehydes or ketones.…”

Section: Introductionmentioning

confidence: 99%

Designing anticancer copper(II) complexes by optimizing 2-pyridine-thiosemicarbazone ligands

Deng

Zhang

et al. 2018

European Journal of Medicinal Chemistry

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To develop potential next-generation metal anticancer agents, we designed and synthesised five Cu(II) 2-pyridine-thiosemicarbazone complexes by modifying the hydrogen atom at the N-4 position of ligands, and then investigated their structure-activity relationships and anticancer mechanisms. Modification of the N-4 position with different groups caused significant differences in cellular uptake and produced superior antitumor activity. Cu complexes arrested the cell cycle at S phase, leading to down-regulation of levels of cyclin and cyclin-dependent kinases and up-regulation of expression of cyclin-dependent kinase inhibitors. Cu complexes exerted chemotherapeutic effects via activating p53 and inducing production of reactive oxygen species to regulate expression of the B-cell lymphoma-2 family of proteins, causing a change in the mitochondrial membrane potential and release of cytochrome c to form a dimer with apoptosis protease activating factor-1, resulting in activation of caspase-9/3 to induce apoptosis. In addition, Cu complexes inhibited telomerase by down-regulating the c-myc regulator gene and expression of the human telomerase reverse transcriptase.

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“…They showed the potential to induce a programmed cell death by apoptosis with the ability to induce reactive oxygen species and single strand breaks formation in addition to DNA intercalation. Ciprofloxacin 54 and norfloxacin 55 complexes were the most potent ones with IC 50 ranges 2.5–5.9 and 2.4–5.0 µM, respectively, when screened using human A549 and murine colon carcinoma CT26 cell lines . Lomefloxacin was also coordinated with different metal ions Mn(II), Co(II), Ni(II), Cu(II), and Zn(II)) and investigated for the biological activity along with the parent free drug.…”

Section: Fluoroquinolone Metal Ion Complexes With Anticancer Activitymentioning

confidence: 99%

Towards anticancer fluoroquinolones: A review article

Abdel-AAl

Abdel‐Aziz

Shaykoon

et al. 2019

Archiv der Pharmazie

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Different studies about the anticancer potential of several medically used antibacterial fluoroquinolones have been established. Fluoroquinolone derivatives, like some anticancer drugs, such as doxorubicin, can achieve antitumor activity via poisoning of type II human DNA topoisomerases. Interestingly, structural features required for the anticancer activity of quinolones have been determined. Most of the chemical modifications required to convert antibacterially acting fluoroquinolones into their anticancer analogs were at position 7 and the carboxylic group at position 3. This review highlights the antitumor potential of fluoroquinolones in general and summarizes the chemical modifications carried out on fluoroquinolones to become anticancer agents. Moreover, the review gives a quick recap on metal ion chelates with fluoroquinolones and their substantial role in topoisomerase poisoning and antitumor potential improvement. Hence, it should be highly interesting for researchers attempting to design and synthesize novel anticancer fluoroquinolone candidates. K E Y W O R D S anticancer, DNA topoisomerase, metal ion complexes, quinolones Arch Pharm Chem Life Sci. 2019;352:1800376.wileyonlinelibrary.com/journal/ardp

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New copper(I) complexes bearing lomefloxacin motif: Spectroscopic properties, in vitro cytotoxicity and interactions with DNA and human serum albumin

Cited by 40 publications

References 69 publications

Polymeric micelle-mediated delivery of half-sandwich ruthenium(II) complexes with phosphanes derived from fluoroloquinolones for lung adenocarcinoma treatment

Polymeric micelle-mediated delivery of half-sandwich ruthenium(II) complexes with phosphanes derived from fluoroloquinolones for lung adenocarcinoma treatment

Designing anticancer copper(II) complexes by optimizing 2-pyridine-thiosemicarbazone ligands

Towards anticancer fluoroquinolones: A review article

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