Cytotoxicity of electrophilic iron(II)–clathrochelates in human promyelocytic leukemia cell line

Blechinger, Jenny; Varzackii, Oleg A.; Kovalska, Vladyslava; Zelinskii, Genrikh E.; Voloshin, Yan Z.; Kinski, Elisa; Mokhir, Andriy

doi:10.1016/j.bmcl.2015.11.060

Cited by 25 publications

(24 citation statements)

References 14 publications

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“…Moreover, very recently, one of the macrobicyclic iron(II) complexes, the molecule that contains one terminal functionalizing carboxyl group, has been found [11] to possess both high in vitro cytotoxicity and selectivity (as compared with normal cells) against the human promyelocytic leukemia cell line. Earlier, we observed [12] the similar effect of an electrophilic iron(II) hexachloroclathrochelate 6 that easily alkylated glutathione in these cells. It is clear that such a mechanism of cytotoxic activity of cage complexes with an encapsulated metal ion is substantially less probable in the case of metal clathrochelates, the molecules of which do not contain the highly reactive terminal group(s) or atom(s), first of all, the halogen atom(s) as the ribbed substituent(s) in a macrobicyclic framework.…”

Section: Introductionsupporting

confidence: 59%

Synthesis and Structure of the Bis- and Tris-Polyhedral Hybrid Carboranoclathrochelates with Functionalizing Biorelevant Substituents—The Derivatives of Propargylamine Iron(II) Clathrochelates with Terminal Triple C≡C Bond(s)

et al. 2021

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A synthetic strategy for obtaining structurally flexible hybrid iron(II) carboranoclatrochelates functionalized with biorelevant groups, based on a combination of a 1,3-dipolar cycloaddition reaction with nucleophilic substitution of an appropriate chloroclathrochelate precursor, was developed. In its first stage, a stepwise substitution of the dichloroclathrochelate precursor with amine N-nucleophiles of different natures in various solvents was performed. One of its two chlorine atoms with morpholine or diethylamine in dichloromethane gave reactive monohalogenoclathrochelate complexes functionalized with abiorelevant substituents. Further nucleophilic substitution of their remaining chlorine atoms with propargylamine in DMF led to morpholine- and diethylamine-functionalized monopropargylamine cage complexes, the molecules of which contain the single terminal C≡C bond. Their “click” 1,3-cycloaddition reactions in toluene with ortho-carborane-(1)-methylazide catalyzed by copper(II) acetate gave spacer-containing di- and tritopic iron(II) carboranoclatrochelates formed by a covalent linking between their different polyhedral(cage) fragments. The obtained complexes were characterized using elemental analysis, MALDI-TOF mass, UV-Vis, 1H, 1H{11B}, 11B, 11B{1H}, 19F{1H} and 13C{1H}-NMR spectra, and by a single crystal synchrotron X-ray diffraction experiment for the diethylamine-functionalized iron(II) carboranoclathrochelate. Its encapsulated iron(II) ion is situated almost in the center of the FeN6-coordination polyhedron possessing a geometry intermediate between a trigonal prism and a trigonal antiprism with a distortion angle φ of approximately 28º. Conformation of this hybrid molecule is strongly affected by its intramolecular dihydrogen bonding: a flexibility of the carborane-terminated ribbed substituent allowed the formation of numerous C–H…H–B intramolecular interactions. The H(C) atom of this carborane core also forms the intermolecular C–H…F–B interaction with an adjacent carboranoclathrochelate molecule. The N–H…N intermolecular interaction between the diethylamine group of one hybrid molecule and the heterocyclic five-membered 1Н-[1,2,3]-triazolyl fragment of the second molecule of this type caused formation of H-bonded carboranoclathrochelate dimers in the X-rayed crystal.

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Section: Introductionsupporting

confidence: 59%

Synthesis and Structure of the Bis- and Tris-Polyhedral Hybrid Carboranoclathrochelates with Functionalizing Biorelevant Substituents—The Derivatives of Propargylamine Iron(II) Clathrochelates with Terminal Triple C≡C Bond(s)

et al. 2021

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“…2 Owing to this, these cage complexes have found use as electrocatalysts for hydrogen evolution 1b,3 and as prospective materials for biomedical applications, 4 including topological drugs, 5 anti-fibrillogenic agents, 6 and selective cytotoxic compounds. 7 Paramagnetic cobalt(II) clathrochelates have also been recognized as single-molecule magnets (SMMs), 8 i.e. molecules able to retain their magnetization in the absence of an applied magnetic field, 9 and they are expected to revolutionize the field of high-density information storage or quantum computing.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, X-ray structure and electrochemical properties of hybrid binuclear metallophthalocyaninate-capped tris-pyridineoximates

et al. 2017

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“…In vitro cytotoxic studies of the complexes ( 1 , 2 , 3 and 4 ) including cisplatin (which is considered as control) were analysed against three tumour cell lines, HeLa (human cervical adenocarcinoma), MiaPaCa‐2 (human pancreatic carcinoma) and B16F10 (murine melanoma cancer cells), and one normal cell N1H/3T3 (fibroblast cells) using MTT assay, which is used extensively for in vitro cytotoxic studies. [ 67 ] Six concentrations of each complex (5,10,25,50,75 and 100 μg) were treated with the three tumour cell lines (selected) and cisplatin (control) except normal cells (Figure 8). IC 50 and cell viability are given in Table 8 and Figure 9.…”

Section: Resultsmentioning

confidence: 99%

Biological evaluation, molecular docking, DNA interaction and thermal studies of new bioactive metal complexes of 2‐hydroxybenzaldehyde and fluorobenzamine Schiff base ligand

Bengi

Maddikayala

Reddy

2020

Applied Organom Chemis

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Funding information DST-FIST Program of India Schiff base ligand named 2-((E)-(2-fluorophenylimino)methyl)phenol (HL) was prepared by the condensation of 2-hydroxybenzaldehyde and 2-fluorobenzamine in 1:1 molar ratio. The coordination behaviour of a series of transition metal ions with the synthesized HL ligand, [Cr(HL) 2 ] (1), [Fe (HL) 2 ] (2), [Co(HL) 2 ] (3) and [Cu(HL) 2 ] (4) is reported. The structure and bonding of the metal complexes have been deduced by analytical and spectral studies. Based on the above studies, the metal centres were found to be octahedral for all the complexes. The activation thermodynamic properties were calculated using the Coats-Redfern method. Thermal decomposition processes of complexes 1, 2, 3 and 4 are non-spontaneous; that is, the complexes are thermally stable. The positive value of Gibbs free energy of decomposition (ΔG*) for all the complexes is non-spontaneous processes. DNA binding properties of these metal complexes, investigated using UV-visible absorption, fluorescence and viscosity measurement studies, imply that the complexes bind to DNA by intercalation. The intrinsic binding constant K b from the electronic absorption studies are 3.12 × 10 4 M −1 , 1.86 × 10 4 M −1 , 3.96 × 10 4 M −1 and 5.89 × 10 4 M −1 , and the Stern-Volmer quenching constant K sv values from fluorescence studies are 2.29 × 10 4 M −1 , 1.92 × 10 4 M −1 , 5.62 × 10 4 M −1 and 8.91 × 10 4 M −1 , for the complexes 1, 2, 3 and 4, respectively. DNA photo cleavage activities of these complexes were studied with supercoiled pUC19 DNA, in the presence of H 2 O 2. GOLD 3.1 program was used to evaluate binding affinities of complexes with human DNA topoisomerase I protein. in vitro cytotoxic and antimicrobial studies revealed higher activity of metal complexes, compared with the ligand.

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Cytotoxicity of electrophilic iron(II)–clathrochelates in human promyelocytic leukemia cell line

Cited by 25 publications

References 14 publications

Synthesis and Structure of the Bis- and Tris-Polyhedral Hybrid Carboranoclathrochelates with Functionalizing Biorelevant Substituents—The Derivatives of Propargylamine Iron(II) Clathrochelates with Terminal Triple C≡C Bond(s)

Synthesis and Structure of the Bis- and Tris-Polyhedral Hybrid Carboranoclathrochelates with Functionalizing Biorelevant Substituents—The Derivatives of Propargylamine Iron(II) Clathrochelates with Terminal Triple C≡C Bond(s)

Synthesis, X-ray structure and electrochemical properties of hybrid binuclear metallophthalocyaninate-capped tris-pyridineoximates

Biological evaluation, molecular docking, DNA interaction and thermal studies of new bioactive metal complexes of 2‐hydroxybenzaldehyde and fluorobenzamine Schiff base ligand

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