New ferromagnetic dinuclear triply-bridged copper(II) compounds containing carboxylato bridges: Synthesis, X-ray structure and magnetic properties

Youngme, Sujittra; Phatchimkun, Jaturong; Wannarit, Nanthawat; Chaichit, Narongsak; Meejoo, Siwaporn; Albada, Gerard A. van; Reedijk, Jan

doi:10.1016/j.poly.2007.09.009

Cited by 44 publications

(56 citation statements)

References 30 publications

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“…The EPR spectrum of 1 exhibited a broad band having 'g' isotropic values 2.09 which are characteristic for square pyramidal enviroment. Similar spectra having 'g' isotropic values were reported earlier 34,35) for metal saccharide complexes composed of different metal ions. Such isotropic lines usually result due to intermolecular spin exchange, which broadens the spectral lines.…”

supporting

confidence: 85%

Synthesis and Characterization of Glucose-Bis(pyrazole)-Cu(II)/Ni(II) Complexes and Their in Vitro DNA Binding Studies

Tabassum

Bhat

2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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In the forefront is the recent area of glycobiology a "sweet and safe" approach for the development of new drugs in medicinal inorganic chemistry.1) The use of glycosyl substituents for enhanced tissue target, improved solubility and reduced toxicity has attracted many researchers to explore the possibility of carbohydrate-based drug strategies. [2][3][4][5] Chen et al. have synthesized a novel carbohydrate linked to cisplatin analogue, cis-dichloro [(2-b-D-glucopyranosidyl)propane-1,3-diamine]platinum and examined selective cytotoxicity towards cancer cells.6) This complex exhibits specific in vitro antitumour activity against human ovarian cancer cell A2780S and human melanoma cancer cell MeWo. Some of the cancer cell antigens are carbohydrates and several trials are being carried out to develop carbohydrate derived cancer vaccines.7) Globo H is a prominent epitope on cancer cells; therefore a potential vaccine was prepared consisting of the synthetic hexasaccharide chain of Globo H linked to KLH. 8)Recently, Nakase et al. have demonstrated artemisinin tagged to transferrin via carbohydrate chain exhibits high potency and specificity against cancer cells. 9) Carbohydrate linked to biologically relevant molecules like pyrazole and imidazole act as an attractive scaffold for transition metal ions. [10][11][12] The interaction of transition metal-saccharide complexes with DNA is significantly important (DNA is one of the main molecular targets in the action of anticancer drugs), as many naturally occurring antitumour agents are capable of modifying nucleic acids only in presence of metal ions and oxygen. [13][14][15][16] Of these antitumour agents, a vast majority usually contains sugar derivatives as their back bone. Thus, there has been profound interest in the design, study of DNA binding and cleavage properties of glucose-derived transition metal complexes and development of these complexes as metallo-drugs. 17,18) Since there are many alterations in the genes that code for the protein in tumor, the focus of such studies is also on proteins which drive and control cell cycle progression. 19,20) Herein, we describe the synthesis, characterization of Dglucose-bis pyrazolyl metal complexes of Cu(II) 1 and Ni(II) 2 and their binding properties with CT DNA. Furthermore, DNA cleavage of pBR322 DNA by complex 1 was carried out by employing agarose gel electrophoresis. The "binding study" of complex 1 towards human serum albumin (HSA), L-tryptophan and their mixtures with DNA was studied to recognize the most favoured biomolecule, for which it shows highest binding affinity. ExperimentalMaterials and Methods D-Glucose, CuCl 2 · 2H 2 O, NiCl 2 · 6H 2 O (Qualigens), pyrazole (Fluka). Tris (TrisϭTris(hydroxymethyl)aminomethane) base (Merck), 6ϫ loading dye (Fermental Life Science) and super coiled plasmid DNA pBR322 (Genei) were utilized as received. Disodium salt of calf thymus DNA, human serum albumin and L-tryptophan were purchased from Sigma Chemical Company and stored at 4°C. All reagent grade compounds were used w...

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confidence: 85%

Synthesis and Characterization of Glucose-Bis(pyrazole)-Cu(II)/Ni(II) Complexes and Their in Vitro DNA Binding Studies

Tabassum

Bhat

2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…S1-S6 (ESI †). For comparison purposes, the structural data of compounds 1-7 and of some other relevant hetero triply-bridged dinuclear Cu(II) compounds previously studied 10,12 are summarized in Table 1.…”

Section: Description Of the Crystal Structuresmentioning

confidence: 99%

Hetero triply-bridged dinuclear copper(ii) compounds with ferromagnetic coupling: a challenge for current density functionals

Wannarit

Pakawatchai

Mutikainen

et al. 2013

Phys. Chem. Chem. Phys.

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“…These parameters were in good agreement to the values reported for other related square pyramidal Cu (II) systems39 and are typical of axially symmetrical d 9 Cu (II) complexes. The trend g || > g ⟂ > 2 revealed that the unpaired electron is present in the d

x^{2} − y^{2}

orbital 40. For a Cu (II) complex, g || is a parameter sensitive enough to indicate covalence.…”

Section: Resultsmentioning

confidence: 98%

Synthesis and enantiopreferential DNA‐binding profile of late 3d transition metal R‐ and S‐enantiomeric complexes derived from N,N‐bis‐(1‐benzyl‐2‐ethoxyethane): Validation of R‐enantiomer of copper(II) complex as a human topoisomerase II inhibitor

et al. 2011

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To evaluate the biological preference of chiral drug candidates for molecular target DNA, new potential metal-based chemotherapeutic agents 1-3 (a and b) of late 3d transition metals Ni(II), Cu(II), and Zn(II), respectively, derived from (R)- and (S)-2-amino-2-phenylethanol with CH(2) CH(2)  linker were synthesized and thoroughly characterized. Interaction studies of 1-3 (a and b) with calf thymus DNA in Tris buffer were studied by electronic absorption titrations, luminescence titrations, cyclic voltammetry, and circular dichroism. The results reveal that the extent of DNA binding of R-enantiomer of copper 1a was highest in comparison to rest of the complexes via electrostatic interaction mode. The nuclease activity of 1(a and b) with supercoiled pBR322 DNA was further examined by gel electrophoresis, which reveals that complex 1a exhibits a remarkable DNA cleavage activity (concentration dependent) with pBR322DNA, and the cleavage activity of both enantiomers of complex 1 was significantly enhanced in the presence of activators. The activating efficiency follows the order Asc > H(2) O(2) > MPA for 1a, and reverse order was observed for 1b, because of the differences in enantioselectivity and conformation. Further, it was observed that cleavage reaction involves singlet oxygen species and superoxide radicals via oxidative cleavage mechanism. In addition, complex 1a exhibits significant inhibitory effects on the topoisomerase II (topo II) activity at a very low concentration ∼24 μM, which suggest that complex 1a is indeed catalytic inhibitor or (poison) of human topo II.

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New ferromagnetic dinuclear triply-bridged copper(II) compounds containing carboxylato bridges: Synthesis, X-ray structure and magnetic properties

Cited by 44 publications

References 30 publications

Synthesis and Characterization of Glucose-Bis(pyrazole)-Cu(II)/Ni(II) Complexes and Their in Vitro DNA Binding Studies

Synthesis and Characterization of Glucose-Bis(pyrazole)-Cu(II)/Ni(II) Complexes and Their in Vitro DNA Binding Studies

Hetero triply-bridged dinuclear copper(ii) compounds with ferromagnetic coupling: a challenge for current density functionals

Synthesis and enantiopreferential DNA‐binding profile of late 3d transition metal R‐ and S‐enantiomeric complexes derived from N,N‐bis‐(1‐benzyl‐2‐ethoxyethane): Validation of R‐enantiomer of copper(II) complex as a human topoisomerase II inhibitor

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