Synthesis of copper(II) complexes of isatin thiosemicarbazone derivatives: In vitro anti-cancer, DNA binding, and cleavage activities

Ali, Amna Qasem; Teoh, Siang Guan; Eltayeb, Naser Eltaher; Ahamed, Mohamed B. Khadeer; Majid, Amin Malik Shah Abdul

doi:10.1016/j.poly.2014.02.025

Cited by 47 publications

(12 citation statements)

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“…Thiosemicarbazone derivatives exhibit important biological activities [ 11 ], such as antibacterial [ 12 ], antimalarial, [ 13 ] and antitumor activities [ 14 ]. The antiproliferative properties of thiosemicarbazones have been attributed to their ability to chelate metal ions because of the presence of an NNS (Nitrogen–Nitrogen–Sulfur) tridentate set of donor atoms that bind not only iron, but also copper [ 15 , 16 , 17 ], molybdenum [ 18 ], nickel [ 16 , 19 ], zinc [ 17 , 19 ], and ruthenium [ 20 ]. The thiosemicarbazone-metal complexes are lipophilic and pass through the cell membrane to release the metal intracellularly.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, DNA Binding, and Antiproliferative Activity of Novel Acridine-Thiosemicarbazone Derivatives

Almeida

Lafayette

Silva

et al. 2015

IJMS

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In this work, the acridine nucleus was used as a lead-compound for structural modification by adding different substituted thiosemicarbazide moieties. Eight new (Z)-2-(acridin-9-ylmethylene)-N-phenylhydrazinecarbothioamide derivatives (3a–h) were synthesized, their antiproliferative activities were evaluated, and DNA binding properties were performed with calf thymus DNA (ctDNA) by electronic absorption and fluorescence spectroscopies. Both hyperchromic and hypochromic effects, as well as red or blue shifts were demonstrated by addition of ctDNA to the derivatives. The calculated binding constants ranged from 1.74 × 104 to 1.0 × 106 M−1 and quenching constants from −0.2 × 104 to 2.18 × 104 M−1 indicating high affinity to ctDNA base pairs. The most efficient compound in binding to ctDNA in vitro was (Z)-2-(acridin-9-ylmethylene)-N-(4-chlorophenyl) hydrazinecarbothioamide (3f), while the most active compound in antiproliferative assay was (Z)-2-(acridin-9-ylmethylene)-N-phenylhydrazinecarbothioamide (3a). There was no correlation between DNA-binding and in vitro antiproliferative activity, but the results suggest that DNA binding can be involved in the biological activity mechanism. This study may guide the choice of the size and shape of the intercalating part of the ligand and the strategic selection of substituents that increase DNA-binding or antiproliferative properties.

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Section: Introductionmentioning

confidence: 99%

Synthesis, DNA Binding, and Antiproliferative Activity of Novel Acridine-Thiosemicarbazone Derivatives

Almeida

Lafayette

Silva

et al. 2015

IJMS

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“…For instance, they can accumulate in cancerous cells due to the selective permeability of their membranes to copper compounds [15,16]. Also, copper(II) complexes have been widely utilized in metal-mediated DNA cleavage for generating activated oxygen species [17][18][19].…”

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confidence: 99%

A novel cationic copper(II) Schiff base complex: Synthesis, characterization, crystal structure, electrochemical evaluation, anti-cancer activity, and preparation of its metal oxide nanoparticles

Ebrahimipour

Sheikhshoaie

Castro

et al. 2015

Inorganica Chimica Acta

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“…On the other hand, the Cu(II) complexes can be used to cleave the DNA via oxidative pathway. In this case, in the work of Teoh and contributors, Cu(II) complexes of isatin thiosemicarbazone derivatives demonstrated this capacity [46]. Each Cu(II) metal center is bonded by one tridentate k 3 These binuclear Cu(II) complexes demonstrate the biological importance of indole moiety for activity, highlighted in green squares (Figure 9).…”

Section: Isatin Derived Ligandsmentioning

confidence: 90%

“…The compound 18 can interact with the hydrophobic center of DNA more effectivelly. 46 On the other hand, the complex 20 showed promising potency as antimicrobial drug against B. subtilis (MIC: 10.35 µg/mL), S. aureus (MIC: 8.56 µg/mL), P. aeruginosa (MIC: 21.36 µg/mL), S. epidermidis (MIC: 6.50 µg/mL), and P. vulgaris (MIC: 17.64 µg/mL) in comparison with ciprofloxacin. The presence of H atom at N4-position makes the complex less lipophilic.…”

Section: Isatin Derived Ligandsmentioning

confidence: 99%

Phosphine- and Isatin-Copper Complexes: Anticancer Activity, Mechanisms of Action and Structure-Activity Relationship Examples from the Last Ten Years

Nascimento-Júnior¹

2019

MACIJ

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Platinum-based metallodrugs candidates are extensively evaluated as antineoplastic agents against several tumoral cell lines, representing a considerable advance in cancer treatment. On the other hand, the hostile off-site toxicity has been limited their potential uses in clinical step. Thus, the search for novel active and selective antitumor drugs is a leading issue in the medicinal inorganic chemistry. As follow, the research focused on less toxic metals has strategic importance and several copper complexes have revealed promising activity. In addition, copper is an essential metal, which can increase the chances of reduced side effects. This review brings some copper complexes that showed highlighted anticancer activity as drug prototypes from the last ten years (2010-2019), involving phosphine and isatin ligands, different redox states, modes of action and the study of structure-activity relationship (SAR).

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Synthesis of copper(II) complexes of isatin thiosemicarbazone derivatives: In vitro anti-cancer, DNA binding, and cleavage activities

Cited by 47 publications

References 56 publications

Synthesis, DNA Binding, and Antiproliferative Activity of Novel Acridine-Thiosemicarbazone Derivatives

Synthesis, DNA Binding, and Antiproliferative Activity of Novel Acridine-Thiosemicarbazone Derivatives

A novel cationic copper(II) Schiff base complex: Synthesis, characterization, crystal structure, electrochemical evaluation, anti-cancer activity, and preparation of its metal oxide nanoparticles

Phosphine- and Isatin-Copper Complexes: Anticancer Activity, Mechanisms of Action and Structure-Activity Relationship Examples from the Last Ten Years

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