N-hydroxymethylation of ethylene-bridged glycine metal(II) complexes by formaldehyde

Ng, Chew-Hee; Teo, Soon-Beng; Teoh, Siang Guan; Fun, Hoong‐Kun; Declercq, Jean‐Paul

doi:10.1016/s0020-1693(02)01092-7

Cited by 11 publications

(8 citation statements)

References 24 publications

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“…The corresponding glycinate rings of the octahedral diaqua[N,N -ethylenedi(N-hydroxymethylglycinato)]copper(II), derived from the N-hydroxymethylation of Cu(edda), have a bigger bite angle (79.5(1) • ). 20 These, together with other angles about the copper atom, show severe distortion of the octahedral geometry.…”

Section: Crystal Structure Of 1amentioning

confidence: 98%

Synthesis, characterization, DNA-binding study and anticancer properties of ternary metal(ii) complexes of edda and an intercalating ligand

et al. 2008

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A series of ternary metal(ii) complexes {M(phen)(edda); 1a (Cu), 1b (Co), 1c (Zn), 1d (Ni); H(2)edda = N,N(')-ethylenediaminediacetic acid} of N,N'-ethylene-bridged diglycine and 1,10-phenanthroline were synthesized and characterized by elemental analysis, FTIR, UV-visible spectroscopy and magnetic susceptibility measurement. The interaction of these complexes with DNA was investigated using CD and EPR spectroscopy. MTT assay results of 1a-1c , screened on MCF-7 cancer cell lines, show that synergy between the metal and ligands results in significant enhancement of their antiproliferative properties. Preliminary results from apoptosis and cell cycle analyses with flow cytometry are reported. seems to be able to induce cell cycle arrest at G(0)/G(1). The crystal structure of 1a is also included.

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Section: Crystal Structure Of 1amentioning

confidence: 98%

Synthesis, characterization, DNA-binding study and anticancer properties of ternary metal(ii) complexes of edda and an intercalating ligand

et al. 2008

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“…Complex 10a 3+ contains one prim–sec-oxidimethaneamine bridge and an additional prim–sec-methylene bridge, forming a four-membered chelate ring . Furthermore, one of the endocyclic nitrogen donor carries a pendant CH 2 –OH substituent . The Medaza complex 1b 3+ yielded the singly bridged, monomethylideneimine species 8b 3+ and the nonbridged, bis-methylideneimine species 11b 3+ as byproducts. In all bridged complexes ( 6a 3+ , 7 3+ , 8b 3+ , 9 3+ , and 10a 3+ ), the two 1,4-diazepan-6-amine frames exclusively exhibited a cis configuration (Figure ) regardless of whether a cis- ( 1 3+ ) or trans- ( 2 3+ ) configured template was used as starting material!…”

Section: Resultsmentioning

confidence: 99%

“…Additional byproducts were not isolated. However, in the slow reaction of the trans -Medaza derivative 2b 3+ (method iii) a series of hemiaminals ( 3b 3+ – 5b 3+ ) with one or two pending carbinolamino groups were formed and could be isolated and characterized. Notably, in these hemiaminals, the trans orientation of the two Medaza frames is retained. The fractions with the singly bridged species 6a 3+ and 7 3+ contained a considerable amount of protonated free ligand H 3 L 3+ or H 3 MeL 3+ .…”

Section: Resultsmentioning

confidence: 99%

Formation and Base Hydrolysis of Oxidimethaneamine Bridges in Co^III–Amine Complexes

et al. 2013

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cis-[CoL2](3+) (1a(3+)), trans-[CoL2](3+) (2a(3+)), cis-[Co(MeL)2](3+) (1b(3+)), and trans-[Co(MeL)2](3+) (2b(3+)), L = 1,4-diazepan-6-amine (daza) and MeL = 6-methyl-1,4-diazepan-6-amine (Medaza), were allowed to react as templates in acetonitrile with paraformaldehyde and triethylamine. Several Co(III) complexes, where two adjacent amino groups of two ligand moieties are interlinked by an oxidimethaneamine bridge, were obtained. Connection of a primary with a secondary amino group (prim-sec bridging) was found to be predominant. The singly and doubly bridged daza- and Medaza-derivatives 7a(3+), 9a(3+) and 7b(3+), 9b(3+) were characterized by crystal-structure analysis. The bridging process resulted in a slight lengthening of the mean Co-N distance, a red shift of the A1g-T1g transition, and an increase of the Co(III)/Co(II) reduction potential. Several minor components, which could be only partially separated by chromatographic methods, were also formed. The daza-derivatives 6a(3+) (prim-prim bridged) and 10a(3+) (bidentate coordination of one daza frame) formed in small quantities. The Medaza derivatives 3b(3+) and 4b(3+) (trans configuration of the Medaza frames, with additional pending carbinolamino groups), and 8b(3+) (with a methylideneimino group) represent intermediates of the condensation process. Their structure was again corroborated by X-ray diffraction. All bridged species (6a(3+), 7a(3+), 7b(3+), 8b(3+), 9a(3+), 9b(3+), and 10a(3+)) exhibited exclusively a cis orientation of the two diazepane frames, even if the trans configured 2a(3+) or 2b(3+) were used as starting materials. Molecular mechanics calculations indicate that in the bridged species with a trans configuration steric strain is substantially more pronounced. In alkaline aqueous media, 9a(3+) and 9b(3+) revealed a complete degradation of the bridges whereby the original 1a(3+) and 1b(3+) reformed. The pseudo-first-order rate constant k(obs) of the degradation reaction was found to depend linearly on OH(-) concentration. The degradation of the first bridge is about 100 times faster than the degradation of the second. The mechanism of formation and degradation of such oxidimethaneamine bridges is discussed.

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“…It is evident from Fig. 4 that in case of nickel(II)-edda-type complexes, the s-cis configuration keeps its form whether we change carboxylate shape (even large enough to prevent additional coordination of the second water molecule as was the case for [Ni(baboc)(H 2 O)] complex) or introduce substituents on the CH 2 of carboxylate or nitrogens of diamine (with +I or −I effects: 19 ). However, extending the diamine (1,3-pdda) or carboxylate (asymmetric "edap") length for the -CH 2group usually makes a change in the starting configuration i.e.…”

Section: Papermentioning

confidence: 99%

“…[14][15][16] While s-cis geometry of the pure [Cu(edda)(H 2 O) 2 ] complex is not yet crystallographically confirmed, the X-ray structure of the s-cis-[Ni(edda)(H 2 O) 2 ] complex was reported by several authors. 18,19 Furthermore, nickel(II) ion surrounded by bis N-hydroxymethyl-edda ligand (abbreviated as OHMeedda) also adopts s-cis geometry 19 while for the Ni-1,3-pdda complex (1,3-pdda stands for 1,3-propanediamine-N,N′-diacetate anion) the uns-cis geometry was found to be dominant one 20 by X-ray analysis. In the case of Ni-eddp (eddp stands for ethylenediamine-N,N′-di-3-propionate ion) the proposed uns-cis geometry accounts for the larger six-membered carboxylate arms being able to encircle nickel(II) in equatorial plane.…”

Section: Introductionmentioning

confidence: 99%

Nickel(ii) in chelate N2O2 environment. DFT approach and in-depth molecular orbital and configurational analysis

et al. 2013

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The O-N-N-O-type tetradentate ligands H2S,S-eddp (H2S,S-eddp stands for S,S-ethylenediamine-N,N'-di-2-propionic acid) and H2edap (H2edap stands for ethylenediamine-N-acetic-N'-3-propionic acid) and the corresponding novel octahedral nickel(II) complexes have been prepared and characterized. N2O2 ligands coordinate to the nickel(II) ion via four donor atoms (two deprotonated carboxylate atoms and two amine nitrogens) affording octahedral geometry in the case of all investigated Ni(II) complexes. A six coordinate, octahedral geometry has been verified crystallographically for the s-cis-[Ni(S,S-eddp)(H2O)2] complex. Structural data correlating similarly chelated Ni(II) complexes have been used to carry out an extensive configuration analysis. Molecular mechanics and Density Functional Theory (DFT) have been used to model the most stable geometric isomer, yielding, at the same time, significant structural and spectroscopic (TDDFT) data. The results from density functional studies have been compared to X-ray data. Natural Bond Orbital (NBO) and Natural Energetic Decomposition Analysis (NEDA) have been done for the [Ni(edda-type)(H2O)(2-n)] and nH2O fragments. Molecular orbital analysis (MPA) is given as well. The infra-red and electronic absorption spectra of the complexes are discussed in comparison to the related complexes of known geometries.

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N-hydroxymethylation of ethylene-bridged glycine metal(II) complexes by formaldehyde

Cited by 11 publications

References 24 publications

Synthesis, characterization, DNA-binding study and anticancer properties of ternary metal(ii) complexes of edda and an intercalating ligand

Synthesis, characterization, DNA-binding study and anticancer properties of ternary metal(ii) complexes of edda and an intercalating ligand

Formation and Base Hydrolysis of Oxidimethaneamine Bridges in Co^III–Amine Complexes

Nickel(ii) in chelate N2O2 environment. DFT approach and in-depth molecular orbital and configurational analysis

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N-hydroxymethylation of ethylene-bridged glycine metal(II) complexes by formaldehyde

Cited by 11 publications

References 24 publications

Synthesis, characterization, DNA-binding study and anticancer properties of ternary metal(ii) complexes of edda and an intercalating ligand

Synthesis, characterization, DNA-binding study and anticancer properties of ternary metal(ii) complexes of edda and an intercalating ligand

Formation and Base Hydrolysis of Oxidimethaneamine Bridges in CoIII–Amine Complexes

Nickel(ii) in chelate N2O2 environment. DFT approach and in-depth molecular orbital and configurational analysis

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Formation and Base Hydrolysis of Oxidimethaneamine Bridges in Co^III–Amine Complexes