Synthesis, spectra and properties of the first protono- and ionogenic tris-dioximate iron(II) clathrochelates

Belaya, Irina; Zelinskii, Genrikh E.; Belov, Alexander S.; Varzatskii, Оleg А.; Novikov, Valentin V.; Dolganov, Alexander V.; Kozłowski, Henryk; Szyrwiel, Łukasz; Bubnov, Yurii N.; Voloshin, Yan Z.

doi:10.1016/j.poly.2012.03.047

Cited by 23 publications

(9 citation statements)

References 25 publications

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“…The clathrochelates were prepared as described elsewhere. 35 BSA and HSA were obtained commercially (fraction V from Sigma-Aldrich s and fraction V protease free from Fisher Bioreagents s , respectively). 0.05 M Tris-HCl aqueous buffer (pH 7.9), 0.05 M aqueous phosphate buffers (pH 5 and pH 6), and 0.05 M aqueous acetate buffer (pH 3.7) were used as solvents.…”

Section: Methodsmentioning

confidence: 99%

Induced CD of iron(ii) clathrochelates: sensing of the structural and conformational alterations of serum albumins

et al. 2019

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Section: Methodsmentioning

confidence: 99%

Induced CD of iron(ii) clathrochelates: sensing of the structural and conformational alterations of serum albumins

et al. 2019

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“…The preparative synthetic protocols and spectral and analytical data for the compounds 1-12 are presented in the ESI section. † The mono-and difunctionalized carboxyphenylsulfide iron(II) clathrochelates 1-6 were synthesized using nucleophilic substitution of the corresponding mono-and dichloroclathrochelate precursors shown in Schemes 2 and 3 as reported; 21 the alkylsulfide clathrochelate 7 was prepared analogously to the arylsulfide clathrochelates 4-6 as shown in Scheme 3. The synthesis of the cage compounds 8 and 9 (the amide derivative of the macrobicyclic complex 5 and its methyl ester, respectively) was performed as shown in Scheme 4 as described elsewhere.…”

Section: Methodsmentioning

confidence: 99%

Induced chirality of cage metal complexes switched by their supramolecular and covalent binding

et al. 2018

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An ability of the ribbed-functionalized iron(ii) clathrochelates to induce a CD output in interactions with a protein, covalent bonding or supramolecular interactions with a low-molecular-weight chiral inductor, was discovered. The interactions of CD inactive, carboxyl-terminated iron(ii) clathrochelates with serum albumin induced their molecular asymmetry, causing an appearance of strong CD signals in the range of 350-600 nm, whereas methyl ester and amide clathrochelate derivatives remained almost CD inactive. The CD spectra of carboxyl-terminated clathrochelates on supramolecular interactions or covalent bonding with (R)-(+)-1-phenylethylamine gave a substantially lower CD output than with albumin, affected by both the solvent polarity and the isomerism of clathrochelate's ribbed substituents. In supramolecular assemblies, the bands were most intensive for ortho-substituted carboxyl-terminated clathrochelates. The ortho- and meta-phenylethylamide cage complexes in tetrachloromethane inverted the signs of their CD bands compared with those in acetonitrile. It was suggested that the tris-dioximate metal clathrochelates possess a Russian doll-like molecular system. Because of the distorted TP-TAP geometry, their coordination polyhedron had no inversion centre and possessed an inherent chirality together with the equiprobability of its left(Λ)- and right(Δ)-handle twists. The selective fixation of one of these C-distorted conformations resulted in the appearance of the CD signal in the range of their visible metal-to-ligand charge transfer bands. Calculations by DFT methods were used to illustrate the possible conformations of the macrobicyclic molecules, as well as the intramolecular interactions between the cage framework and optically active distal substituents responsible for the chirality induction of the metal-centred coordination polyhedra.

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“…The iron(II) mono-and bis-clathrochelates under study were obtained as described previously. [4,32,[37][38][39][40][41][42] ESI-MS were obtained on a Bruker MicrOTOF-Q spectrometer equipped with an Apollo II electrospray ionization source with an ion funnel. The instrumental parameters were .…”

Section: Methodsmentioning

confidence: 99%

“…[29][30][31] We thus aimed on studying cation-receptor properties of halogen-containing iron(II) mono-and bis-clathrochelates (Scheme 1) having from two (FeBd 2 (Cl 2 Gm)(BF) 2 , FeBd 2 (Br 2 Gm)(BF) 2 , FeBd 2 (I 2 Gm) (BF) 2 , {FeBd 2 (BrGm)(BF) 2 } 2 and {FeBd 2 (IGm)(BF) 2 } 2 ) to six (Fe(Cl 2 Gm) 3 (Bn-C 4 H 9 ) 2 ) chlorine atoms in their chelate α-dioximate fragments. Note that these reactive compounds have been earlier recognized as convenient macrobicyclic precursors for their further functionalization with N,O,C,Snucleophiles [3,24,27,[29][30][31][32][33][34][35][36][37][38] (including those with ionophoric, pharmacophoric and fluorophoric groups), and for the design of hybride and multicentered compounds. [24,27,28] Here we also describe the cation-receptor properties of their dimethyl-and diamine-containing clathrochelate analogs FeBd 2 Dm(BF) 2 …”

Section: Introductionmentioning

confidence: 99%

ESI-MS Study of Ionization Pathways and Cation-Receptor Properties of the Iron(II) Mono- and Bis-Clathrochelates

Varzatskii¹,

Shul’ga²,

Kozłowski³

et al. 2014

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Ionization pathways of iron(II) di-and hexachloromonoclathrochelates, bis-clathrochelates and their oximehydrazonate, dimethyl-and diamine-containing macrobicyclic analogs, and the cation-receptor properties of such cage compounds towards alkali metal cations (as individual ions or their mixtures) as well as the competitive complexation in the presence of 18-crown-6 were studied by ESI-MS method. Ionization of iron(II) mono-and bis-clathrochelates under the conditions of ESI-MS experiments was found to proceed via different pathways. The macrobicyclic iron(II

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Synthesis, spectra and properties of the first protono- and ionogenic tris-dioximate iron(II) clathrochelates

Cited by 23 publications

References 25 publications

Induced CD of iron(ii) clathrochelates: sensing of the structural and conformational alterations of serum albumins

Induced CD of iron(ii) clathrochelates: sensing of the structural and conformational alterations of serum albumins

Induced chirality of cage metal complexes switched by their supramolecular and covalent binding

ESI-MS Study of Ionization Pathways and Cation-Receptor Properties of the Iron(II) Mono- and Bis-Clathrochelates

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