Synthesis, characterization and antiproliferative activity of metal complexes with the Schiff base derived from the condensation 1:2 of 2,6-diformyl-4-methylphenol and 5,6-diamino-1,3-dimethyluracil

Illán‐Cabeza, Nuria A.; Hueso-Ureña, Francisco; Moreno‐Carretero, Miguel N.; Martínez-Martos, José Manuel; Ramírez-Expósito, María Jesús

doi:10.1016/j.jinorgbio.2007.10.008

Cited by 47 publications

(13 citation statements)

References 31 publications

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“…5-Aminouracil is a pyrimidine nucleobase analog of thymine and the pyrimidine nucleoside analogs substituted at the 5-position of the heterocycle are known to possess potent biological properties. [15] The fluorescent imaging is one of the nonevasive optical imaging techniques used for monitoring, evaluating prognosis of cancer, and for imaging the metal compounds in various biological environments. [8] Moreover, the azo compounds derived from 5-aminouracil received only sporadic attention and a very few reports of these compounds are known so far.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, fluorescence imaging, and cytotoxicity studies of a uracil‐based azo derivative and its metal complexes

Philip

Thomas

Mohanan

2018

J Chinese Chemical Soc

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A uracil‐based heterocyclic azo derivative was prepared by coupling diazotized 5‐aminouracil with 2‐naphthol. This ligand, viz., 1‐(2,4‐dioxopyrimidine‐5‐yl)‐azo‐naphth‐2‐ol (HNAP), was used as a precursor for the synthesis of a series of complexes with manganese(II), cobalt(II), nickel(II), copper(II), and zinc(II) ions. Various physicochemical measurements UV–Visible, Infrared (IR), 1H NMR, 13C Nuclear Magnetic Resonance (NMR), and electron spin resonance (ESR) spectral studies were employed to characterize the ligand and the metal complexes. The ligand showed good selectivity toward Mn2+ over the other metal ions with a detection limit of 1.36 μM. This probe was used for the confocal fluorescence imaging of Mn2+ ions in Michigan Cancer Foundation‐7 (MCF‐7) cells. The ligand and the metal complexes were tested for their cytotoxicity on the MCF‐7 cell line. It was observed that complexation of HNAP with the metal ions exhibited a promising cytotoxicity.

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Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, fluorescence imaging, and cytotoxicity studies of a uracil‐based azo derivative and its metal complexes

Philip

Thomas

Mohanan

2018

J Chinese Chemical Soc

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“…The structure of the thiosemicarbazide moiety confers a good chelating capacity and this property can be increased in thiosemicarbazone by inserting suitable aldehyde or ketone possessing a further donor atom to render the ligand polydentate. [4] They show biological activities including antibacterial antifungal, [5] antidiabetic, [6] antitumor, [7,8] antiproliferative, [9] anticancer, [10] herbicidal, [11] anticorrosion, and antiinflammatory activities. [6] This type of Schiff bases represent an important class of compounds because they are utilized as starting materials in the synthesis of industrial products.…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic Characterization andIn VitroAntibacterial Activity of Some Novel Metal Complexes With Schiff Base Ligands Derived From Thiosemicarbazide

Sakthilatha

Deepa

Rajavel

2014

Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-

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Six novel mononuclear Schiff base metal complexes of the type [ML 1 L 2 ]X and [ML 1 L 2 X], where M D Cu(II), Ni(II), Co(II), Mn(II), Zn(II), and VO(IV) have been synthesized by condensation of 1-(1-(pyridine-2-yl)ethylidene)thiosemicarbazide (L 1 ) and 1-(1-(2,4-dihydroxyphenyl)ethylidene)thiosemicarbazide (L 2 ) in the presence of divalent metal salts. The synthesized ligands and complexes were structurally characterized on the basis of elemental analysis, IR, UV-visible, 1 H NMR spectroscopy, molar conductance, magnetic susceptibility measurements, and electrochemical studies. The in vitro antibacterial study reveals that the metal complexes inhibit the growth of bacteria more than the free ligands.

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“…Transition metal complexes of Schiff base ligands have proved to be of great interest due to their applications including anti-inflammatory [9], antidiabetic [10], antitumor [11], antiproliferative [12], and anticancer properties [13,14]. In recent years, such Schiff base derivatives and their transition metal complexes have been extensively investigated for their interactions with DNA [15][16][17].…”

Section: Introductionmentioning

confidence: 99%

A Schiff base ligand N-(2-hydroxylacetophenone)-3-oxapentane-1,5-diamine and its nickel(II) complex: synthesis, crystal structure, antioxidation, and DNA-binding properties

Jia

Kou

et al. 2011

Transition Met Chem

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A new Schiff base ligand N-(2-hydroxylacetophenone)-3-oxapentane-1,5-diamine (HL) and its Ni complex, [Ni 2 (L) 2 (NO 3 ) 2 ], have been synthesized and characterized by physicochemical and spectroscopic methods. The X-ray crystal structure of [Ni 2 (L) 2 (NO 3 ) 2 ] shows it to be a dinuclear 2:2 complex, in which each Ni(II) atom is in a distorted octahedral geometry. The two Ni(II) atoms are dibridged by two phenoxo ligands, forming a Ni 2 O 2 parallelogram-type moiety. The interactions between free HL and the complex with calf thymus DNA have been investigated, and the binding constant and linear Stern-Volmer quenching constant suggest that the two compounds bind to DNA via the intercalation mode. The binding affinity of the complex was higher than that of HL. Antioxidant assays in vitro showed that the Ni(II) complex possesses significant antioxidant activity.

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Synthesis, characterization and antiproliferative activity of metal complexes with the Schiff base derived from the condensation 1:2 of 2,6-diformyl-4-methylphenol and 5,6-diamino-1,3-dimethyluracil

Cited by 47 publications

References 31 publications

Synthesis, characterization, fluorescence imaging, and cytotoxicity studies of a uracil‐based azo derivative and its metal complexes

Synthesis, characterization, fluorescence imaging, and cytotoxicity studies of a uracil‐based azo derivative and its metal complexes

Spectroscopic Characterization andIn VitroAntibacterial Activity of Some Novel Metal Complexes With Schiff Base Ligands Derived From Thiosemicarbazide

A Schiff base ligand N-(2-hydroxylacetophenone)-3-oxapentane-1,5-diamine and its nickel(II) complex: synthesis, crystal structure, antioxidation, and DNA-binding properties

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