Bis-(hydroxyamino)triazines: highly stable hydroxylamine-based ligands for iron(iii) cations

Gun, Jenny; Ekeltchik, Irina; Lev, Ovadia; Shelkov, Rimma; Melman, Artem

doi:10.1039/b508138f

Cited by 22 publications

(14 citation statements)

References 23 publications

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“…The arrangement of N - and O -atoms in molecule 1 is reminiscent of metal binding molecules derived from triazine cores reported by Melman. 4,13–15 Therefore, metalations of 1 with the biologically relevant metals copper(II), nickel(II), and zinc(II) were evaluated to define the coordination sphere accessible with this new ligand construct. A copper(II) complex of 1 was achieved by the addition of one equivalent of anhydrous copper chloride (CuCl 2 ) in absolute EtOH to a solution of 1 and stirred overnight.…”

Section: Resultsmentioning

confidence: 99%

“…Inspired by the work of Melman and others, 4, 13–15 wherein triazine rings were N -substituted with hydroxylamine and employed for chelation to form an Fe(III) 5,5,5 ring complex; here, we explore copper(II), nickel(II) and zinc(II) complexes of 1 , in which the triazine has been functionalized to include a hydrazine and a pyrazolone moiety, leading to a unique 6,5,5 oxygen to metal binding ring system. The preference for this specific binding may lead to a more prominent chelating agent compared to triazine derivatives that have been explored in the past.…”

Section: Introductionmentioning

confidence: 99%

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A new triazine bearing a pyrazolone group capable of copper, nickel, and zinc chelation

et al. 2018

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Interests in inorganic applications of triazines is growing. In this report, metal complexes of copper(II), nickel(II), and zinc(II) and a novel class of chelates comprising a triazine ring substituted with a hydrazine group and pyralozone are evaluated using spectrophotometric methods, single crystal X-ray diffractometry, and electrochemistry. Complexes with copper(II) include a single chelate and two chloride atoms to satisfy a trigonal bipryamidal coordination sphere. The nickel(II) and zinc(II) complexes are comprised of two chelating groups that adopt an octahedral geometry around the metal ion. Irreversible redox activity was observed with the copper(II) complex but no redox activity was observed with the ligand alone or zinc(II) and nickel(II) complexes. Use of the coumarin carboxylic acid assay shows that the ligand motif is capable of preventing redox cycling of copper in biological conditions and could thus serve as an antioxidant preventative agent. Cellular toxicity studies show that the new triazine molecule could have therapeutic applications in the µM concentration range based on the measured EC=1.183±2 mM. Altogether this work shows that by merging triazine chemistry into inorganic compounds, there is potential to explore a range applications thanks to the new architecture.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A new triazine bearing a pyrazolone group capable of copper, nickel, and zinc chelation

et al. 2018

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“…Synthesis of the bis(hydroxyamino)triazine ligands was based on facile nucleophilic substitution at the 1,3,5-triazine rings (Scheme 1). Sequential substitution of three chlorine atoms in 2,4,6-trichloro-1,3,5-triazine proceeded with high selectivity in all stages thus providing ligands with general formula 2a-c. 27,28 This method allows an easy adjustment of the structural properties of the ligands by introducing different substituents at position 4. More complex structures can be introduced using tethered carboxylic groups in compounds of type 2b.…”

Section: Resultsmentioning

confidence: 99%

Distinctive structural features of hydroxyamino-1,3,5-triazine ligands leading to enhanced hydrolytic stability of their titanium complexes

et al. 2006

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Three bis(homoleptic) titanium complexes of hydroxyamino-1,3,5-triazine ligands were synthesized and characterized, and their kinetic behavior in THF-water solutions was studied at various pH conditions using UV-vis, based on the characteristic Ti-O band at 380 nm. One of these complexes, , was analyzed by X-ray crystallography. Due to the characteristic electronic structure of the triazine rings, high electron density on the nitrogen atoms leads to strong N-Ti bonds, as indicative by the 2.0 A coordinative bond lengths in the X-ray structure. Consequently, these complexes exhibit high hydrolytic stability over a wide pH range, where hydrolysis was observed to be promoted by basic conditions. At neutral pH, t(1/2) was estimated to be >200 h, whereas at pH = 5.5, no hydrolysis was observed for a period of at least three days.

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“…[43,44] However, the resulting iron complexes are stable in a wide pH range and cannot be used to release active iron species on demand by varying pH mildly by the enzymatic logic systems. Recently reported new 2,6-bis-[hydroxyA C H T U N G T R E N N U N G (methyl)amino]-1,3,5-triazine (BHT) iron ligands [45] have been shown to possess a special set of properties. Fe III complexes of BHT ligands have both very low Fe II /Fe III redox potential at neutral pH and strong pH dependency of the dissociation constant.…”

Section: Introductionmentioning

confidence: 99%

Biomolecular Oxidative Damage Activated by Enzymatic Logic Systems: Biologically Inspired Approach

et al. 2009

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Systems that perform oxidative damage to biomolecules through catalytic cascades in the presence of iron-redox labile species were activated by enzymatic logic gates that process chemical input signals according to built-in logic operations. AND/OR enzymatic logic gates were composed of glucose oxidase (GOx) and GOx/esterase, respectively. The AND/OR logic functions of the enzyme gates were activated by application of glucose-oxygen and glucose-ethyl acetate input signals, respectively. The enzymatic logic gates, upon activation by specific patterns of the chemical input signals, produced acidic solutions and triggered release of redox labile iron species from a complex that is unstable under acidic conditions. This resulted in the activation of a catalytic cascade, which produced reactive oxygen species (ROS) and subsequently yielded oxidative damage in biomolecules. Functional integration of the enzyme-based logic systems with the catalytic redox cascade that performs damage in biomolecules on demand is a first step towards "smart" systems capable of programmed detection, identification, and neutralization of potential biohazards.

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Bis-(hydroxyamino)triazines: highly stable hydroxylamine-based ligands for iron(iii) cations

Cited by 22 publications

References 23 publications

A new triazine bearing a pyrazolone group capable of copper, nickel, and zinc chelation

A new triazine bearing a pyrazolone group capable of copper, nickel, and zinc chelation

Distinctive structural features of hydroxyamino-1,3,5-triazine ligands leading to enhanced hydrolytic stability of their titanium complexes

Biomolecular Oxidative Damage Activated by Enzymatic Logic Systems: Biologically Inspired Approach

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