Metal–N-saccharide chemistry: synthesis and structure determination of two Cu(II) complexes containing glycosylamines

Zhang, Wei; Jiang, Tao; Sumei, Ren; Zhang, Zhongwei; Guan, Hongzai; Yu, Jun

doi:10.1016/j.carres.2004.05.030

Cited by 9 publications

(3 citation statements)

References 12 publications

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“…Few methods have been used for tailoring the sugar-modified ligand, and generally, most of the hydroxyl groups have been blocked through acetal formation, leaving either only one alkoxy group or vicinal diols free for metal complexation reactions. In the second category the C1 position has been modified via glycosylamine formation where metal ion binding is mainly governed by the amine portion of the ligand . Formation of Schiff's bases by condensing the amino sugar with aromatic aldehydes has been known since 1922, but the first report on its metal complexation appeared after about 60 years .…”

Section: Introductionmentioning

confidence: 99%

Tri- and Tetranuclear Copper(II) Complexes Consisting of Mononuclear Cu(II) Chiral Building Blocks with a Sugar-Derived Schiff's Base Ligand

2006

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A new sugar-derived Schiff's base ligand N-(3-tert-butyl-2-hydroxybenzylidene)-4,6-O-ethylidene-beta-D-glucopyranosylamine (H3L1) has been developed which afforded the coordinatively labile, alcoholophilic trinuclear Cu(II) complex [Cu3(L1)2(CH3OH)(H2O)] (1). Complex 1 has been further used in the synthesis of a series of alcohol-bound complexes with a common formula of [Cu3(L1)2(ROH)2] (R = Me (2), Et (3), nPr (4), nBu (5), nOct (6)). X-ray structural analyses of complexes 2-6 revealed the collinearity of trinuclear copper(II) centers with Cu-Cu-Cu angles in the range of 166-172 degrees . The terminal and central coppers are bound with NO3 and O4 atoms, respectively, and exhibit square-planar geometry. The trinuclear structures of 2-6 can be viewed as the two {Cu(L1)}- fragments capture a copper(II) ion in the central position, which is further stabilized by a hydrogen-bonding interaction between the alcohol ligands and the sugar C-3 alkoxo group. Complex 2 exhibits a strong antiferromagnetic interaction between the Cu(II) ions (J = -238 cm(-1)). Diffusion of methanol into a solution of complex 1 in a chloroform/THF mixed solvent afforded the linear trinuclear complex [Cu(3)(L1)2(CH3OH)2(THF)2] (7). The basic structure of 7 is identical to complex 2; however, THF binding about the terminal coppers (Cu-O(THF) = 2.394(7) and 2.466(7) A) has introduced the square-pyramidal geometry, indicating that the planar trinuclear complexes 2-6 are coordinatively unsaturated and the terminal metal sites are responsible for further ligations. In the venture of proton-transfer reactions, a successful proton transfer onto the saccharide C-3 alkoxo group has been achieved using 4,6-O-ethylidene-d-glucopyranose, resulting in the self-assembled tetranuclear complex, [Cu4(HL1)4] (8), consisting of the mononuclear Cu(II) chiral building blocks, {Cu(HL1)}.

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Section: Introductionmentioning

confidence: 99%

Tri- and Tetranuclear Copper(II) Complexes Consisting of Mononuclear Cu(II) Chiral Building Blocks with a Sugar-Derived Schiff's Base Ligand

2006

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“…À1 was assigned to a d(NÀH) vibration of the glycosidic ligand [25]. Additionally, a single band at ca.…”

Section: CMmentioning

confidence: 99%

Synthesis and Characterization of a New Macrocyclic Copper(II) Complex with an N‐Glycosidic Pendant Arm: in vitro Cytotoxicity and Binding Studies with Calf‐Thymus DNA

Mathur

Tabassum

2006

Chemistry & Biodiversity

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The new macrocyclic complex 2-amino-2-deoxy-N-[2-(1,3,5,8,11-pentaazacyclotridecan-3-yl)ethyl]-beta-D-glucopyranosylamine copper(II) dichloride (1a) was prepared and thoroughly characterized by various techniques. Molar-conductance measurements showed that 1a (and its Ni analogue 1b) are ionic in nature. On the basis of spectroscopic data, both complexes were assigned a square-planar geometry, and found to be highly stabile and hydrolytically robust in H2O over a wide range of pH, as confirmed by cyclic voltammetry (CV). The Cu(II) complex 1a was found to bind to CT-DNA, with a binding constant Kb of 2.4x10(3) M(-1), as derived by UV/VIS titration, and confirmed by CV, circular dichroism (CD), and viscosity measurements. DNA binding seems to occur mostly via H-bonding. In an in vitro antitumor MTT assay, 1a exhibited significant anticancer activity against the SY5Y and PC-12 cell lines, with an estimated IC50 value in the micromolar range for SYSY, similar to the standard drug 5-fluorouracil.

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“…5 However the complexity and diversity of carbohydrates found in nature makes the synthesis of carbohydrates a challenging task despite the numerous efforts documented. 6 One reason is that different carbohydrate scaffolds often manifest moderate to drastic different reactivity in various reactions. 7 Several glycosylamines are known, but as far as the glycosylamine derived Schiff base molecules are concerned, the literature is scarce.…”

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confidence: 99%

Synthesis of Novel Schiff Bases from the Reaction of 3-O-methyl-4, 6-O-benzylidene-β-D-glucopyranosylamine with substituted aldehydes

Shen

Zhao

Zheng

et al. 2009

Journal of Chemical Research

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Metal–N-saccharide chemistry: synthesis and structure determination of two Cu(II) complexes containing glycosylamines

Cited by 9 publications

References 12 publications

Tri- and Tetranuclear Copper(II) Complexes Consisting of Mononuclear Cu(II) Chiral Building Blocks with a Sugar-Derived Schiff's Base Ligand

Tri- and Tetranuclear Copper(II) Complexes Consisting of Mononuclear Cu(II) Chiral Building Blocks with a Sugar-Derived Schiff's Base Ligand

Synthesis and Characterization of a New Macrocyclic Copper(II) Complex with an N‐Glycosidic Pendant Arm: in vitro Cytotoxicity and Binding Studies with Calf‐Thymus DNA

Synthesis of Novel Schiff Bases from the Reaction of 3-O-methyl-4, 6-O-benzylidene-β-D-glucopyranosylamine with substituted aldehydes

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