The crystal structure of first copper(II) complex of a pyridine-2-carboxamidrazone – a potential antitumor agent

Gokhale, Nikhil H.; Padhyé, Subhash; Rathbone, Daniel L.; Billington, David C.; Lowe, Phillip R.; Schwalbe, Carl H.; Newton, C. J.

doi:10.1016/s1387-7003(00)00185-4

Cited by 42 publications

(16 citation statements)

References 20 publications

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“…In addition, the shift of the amide ν(C_O) to lower frequencies (by 4 cm − 1 ) and the azomethine ν(C_N) to higher frequencies (by 9 cm − 1 ) confirms the involvement of these groups in the copper complexation. The shift of azomethine C_N stretching vibrations on metal complexation towards higher frequencies has been previously observed for the other amidrazone derivatives [25,30]. What is more, the very intense band observed at 1525 cm − 1 in the IR spectrum of the free ligand and attributed to the ν(C_N) vibrations of 2-pyridyl rings in the spectrum of 3 transforms into a broad absorption peak with the maximum at 1531 cm − 1 .…”

Section: Spectroscopic Studiessupporting

confidence: 71%

“…These properties made them useful in design and synthesis of novel functional materials [23,24]. Furthermore, amidrazone derivatives are of interest as ligands in medicinal chemistry following the reports on antitumor properties of their Cu(II), Au(III) and Pt(II) complexes [25][26][27] or antibacterial [28,29], antimalarial [30] and insulinmimetic activities [22] of many other 3d transition metal complexes.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, crystal structure and biological activities of a novel amidrazone derivative and its copper(II) complex — A potential antitumor drug

Mazur

Modzelewska-Banachiewicz

Paprocka

et al. 2012

Journal of Inorganic Biochemistry

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Section: Spectroscopic Studiessupporting

confidence: 71%

Section: Introductionmentioning

confidence: 99%

Synthesis, crystal structure and biological activities of a novel amidrazone derivative and its copper(II) complex — A potential antitumor drug

Mazur

Modzelewska-Banachiewicz

Paprocka

et al. 2012

Journal of Inorganic Biochemistry

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“…Amidrazones can be used as versatile ligands and their complexes were shown antibacterial [13], antitumor [14], and insulin-mimetic activities [15]. The importance of amidrazones revealed more when their anticancer [16,17] and enzymatic inhibitory [18,19] properties were observed. Furthermore, they were used in synthesis of heterocycles [20], acrylonitrile polymers [21][22][23], and pyridines [24].…”

Section: Introductionmentioning

confidence: 99%

DFT and MP2 study of simple and water-assisted tautomerism in amidrazones

Tavakol

2011

Struct Chem

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DFT and MP2 methods were used to calculate structural parameters, vibrational modes, solvent effect, and energetic properties of amidrazones. Amidrazones can be presented by three tautomeric forms and six isomers. All tautomers and transition states were optimized at the B3LYP/6-311??g** and MP2/6-311??G** levels of theory. The relative stabilities of amidrazone isomers in the gas phase were found to be as 1Z. The calculated energy differences between E and Z isomers are very low and between different tautomers are nearly low, but the energy barriers for tautomerism interconversions at the gas phase are high. The kinetic and thermodynamic data in solvents (chloroform, tetrahydrofuran, acetone, and water) are nearly similar to those in the gas phase but their rate constants are slightly less than those in the gas phase. Moreover, equilibrium and rate constants of intermolecular tautomerism in presence of 1-3 molecules of water were calculated. Computed energy barriers show that the barrier energy of water-assisted tautomerism is very lower than that in simple tautomerism and also calculated binding energies show that water can stabilize transition states more than tautomers. Therefore, this water-assisted tautomerism can be performed fast, especially with the assistance of two molecules of water.

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“…For example, cis-[dichloro(N 1 -(2-benzyloxybenzylidene) pyridine-2-carboxamidrazone)copper(II)] ([Cu(BBPC)], 37), in which the copper is coordinated in a distorted square planer geometry (Fig. (17)) [140], has an IC 50 value of 3 µM against MCF-7 tumor cells, which is four times more potent than the ligand alone. The authors suggested that the generation of copper(I) species through intracellular enzymatic reduction may count for the antitumor activity [141][142][143] [137], was shown to have potent antitumor activity.…”

Section: Ligands Based On Analogs Of Thiosemicarbazonementioning

confidence: 99%

Copper in Medicine: Homeostasis, Chelation Therapy and Antitumor Drug Design

Wang¹,

Guo

2006

CMC

187

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As one of the most important essential transition metals, copper is involved in a variety of biological processes such as embryo development, connective tissue formation, temperature control and nerve cell function. It is also related to severe diseases such as Wilson's and Menkes diseases and some neurological disorders. Novel components of copper homeostasis include copper-transporting P-type ATPases, Menkes and Wilson proteins, and copper chaperones in humans have been identified and characterized at the molecular level. These findings have paved the way towards better understanding of the role of copper deficiency or copper toxicity in physiological and pathological conditions. Therefore, organic compounds that can interfere with copper homeostasis may find therapeutic application in copper-dependent diseases. The antitumor activity of copper complexes was reported several decades ago, and many new complexes have demonstrated great antitumor potential. Copper complexes may have relatively lower side effects than platinum-based drugs, and are suggested to be able to overcome inherited or acquired resistance of cisplatin. In this overview, the most recent advances in copper homeostasis, copper-related chelation therapy and design of copper-based antitumor complexes will be summarized.

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The crystal structure of first copper(II) complex of a pyridine-2-carboxamidrazone – a potential antitumor agent

Cited by 42 publications

References 20 publications

Synthesis, crystal structure and biological activities of a novel amidrazone derivative and its copper(II) complex — A potential antitumor drug

Synthesis, crystal structure and biological activities of a novel amidrazone derivative and its copper(II) complex — A potential antitumor drug

DFT and MP2 study of simple and water-assisted tautomerism in amidrazones

Copper in Medicine: Homeostasis, Chelation Therapy and Antitumor Drug Design

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