Monomeric octahedral bismuth(III) benzaldehyde-N1-alkyl thiosemicarbazones: Synthesis, characterization and biological properties

Aygun, Ozlem; Grześkiewicz, Anita M.; Banti, Christina N.; Hadjikakou, Sotiris K.; Kubicki, Maciej; Öztürk, I.I.

doi:10.1016/j.poly.2022.115683

Cited by 16 publications

(13 citation statements)

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“…Following our interest in the biological effects and coordination chemistry of bismuth(III) compounds [25][26][27][28], within the scope of this research, we present a series of bismuth(III) halide compounds containing 5-chloro-2-mercaptobenzothiazole (ClMBZT) (Figure 1). These bismuth(III) compounds were thoroughly analyzed by elemental (C, H, N and S) analysis, Fourier Transform Infrared (FT-IR) spectroscopy, FT-Raman spectroscopy 1H and 13C nuclear magnetic resonance spectroscopy, ultraviolet visible spectroscopy.…”

Section: Synthesis Of [Bibr3(clmbzt)2] (2)mentioning

confidence: 99%

Synthesis, Characterization, Anti-bacterial and Anti-inflammatory Activities of Bismuth(III) Complexes Based on 5-chloro-2-mercaptobenzothiazole

Öztürk

Eser

2022

Hittite Journal of Science and Engineering

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Bismuth, known as a heavy metal, is excluded from this class due to its low toxicity. Due to this feature, bismuth containing compounds have always been interesting compounds in the field of medicinal chemistry. For this reason, the discovery of new bismuth compounds and the investigation of their biological properties are very important for this field. In this study, three new bismuth(III) compounds formulated as [Bi(L)2X3] (L: 5-chloro-2-mercaptobenzothiazole (ClMBZT); X: Cl, Br, and I) were synthesized for the first time and, the molecular structure of them were elucidated by a series of spectroscopic techniques. Thermal stability and degradation steps of the title compounds were analyzed by Thermogravimetric-Differential Thermal Analysis (TG-DTA). The antibacterial study has been conducted against six strains bacteria, and the results indicated that bismuth(III) compounds generally showed more effective antibacterial activity than free ligand. The anti-inflammatory potential of bismuth(III) compounds was investigated through in vitro lipoxygenase enzyme inhibition studies. The results show that bismuth(III) compounds have higher anti-inflammatory potential than free ligand.

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Section: Synthesis Of [Bibr3(clmbzt)2] (2)mentioning

confidence: 99%

Synthesis, Characterization, Anti-bacterial and Anti-inflammatory Activities of Bismuth(III) Complexes Based on 5-chloro-2-mercaptobenzothiazole

Öztürk

Eser

2022

Hittite Journal of Science and Engineering

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“…Thiosemicarbazones coordinate to the metal ion not only as bidentate and tridentate ligands but also as monodentate ligands. 1 , 2 In the case of hybrid donors such as O/N/S species, the tridentate mode generally prevails and TSCs have been shown to form highly kinetically stable complexes in a 1:2 (ML 2 ) fashion when M = Zn(II) or Ga(III), which present optical as well as coordination isomerism. 15 , 19 Of particular interest so far have been the mono(thiosemicarbazonato) complexes of M = Zn(II), Ni(II), Cu(II), and Fe(II) comprising the acenaphthenequinone backbone (denoted AN), and a small number of such MTSCs complexes have been previously reported.…”

Section: Introductionmentioning

confidence: 99%

“…Thiosemicarbazones (TSCs) and corresponding d-block or p-block thiosemicarbazonato metal complexes (MTSCs) have attracted wide research interest due to their antifungal, , antiviral, , or antineoplastic , properties. Their applications in molecular imaging for Positron Emission Tomography have been explored since the observation of hypoxia selectivity in aliphatic derivative 64 Cu-labeled copper(diacetyl-bis( N 4-methylthiosemicarbazone)], [ 64 Cu]Cu(ATSM), and several other Cu-based radiotracers (cyclic, or acyclic) have been investigated preclinically as theranostics. , The occurrence of hypoxia in tumors inversely affects the prognosis and treatment progression in therapy-resistant cases: radiotherapy is generally associated with the production of reactive oxygen species (ROS) and the local pO 2 level .…”

Section: Introductionmentioning

confidence: 99%

“…Thiosemicarbazones exhibit a number of coordination modes in binding to metal ions, acting as either bidentate, or tridentate ligands when their structure includes an additional donor atom. Thiosemicarbazones coordinate to the metal ion not only as bidentate and tridentate ligands but also as monodentate ligands. , In the case of hybrid donors such as O/N/S species, the tridentate mode generally prevails and TSCs have been shown to form highly kinetically stable complexes in a 1:2 (ML 2 ) fashion when M = Zn(II) or Ga(III), which present optical as well as coordination isomerism. , Of particular interest so far have been the mono(thiosemicarbazonato) complexes of M = Zn(II), Ni(II), Cu(II), and Fe(II) comprising the acenaphthenequinone backbone (denoted AN), and a small number of such MTSCs complexes have been previously reported . A relatively small number of mono(thiosemicarbazone) ligands having the phenanthrenequinone (PH) backbone have been shown to form complexes for applications in catalysis: these were the ruthenium, nickel, or palladium complexes, and the ligands involved were used as agents for water analysis − or for precious metals recovery .…”

Section: Introductionmentioning

confidence: 99%

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Structural and Functional Diversity in Rigid Thiosemicarbazones with Extended Aromatic Frameworks: Microwave-Assisted Synthesis and Structural Investigations

et al. 2023

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The long-standing interest in thiosemicarbazones (TSCs) has been largely driven by their potential toward theranostic applications including cellular imaging assays and multimodality imaging. We focus herein on the results of our new investigations into: (a) the structural chemistry of a family of rigid mono(thiosemicarbazone) ligands characterized by extended and aromatic backbones and (b) the formation of their corresponding thiosemicarbazonato Zn(II) and Cu(II) metal complexes. The synthesis of new ligands and their Zn(II) complexes was performed using a rapid, efficient and straightforward microwave-assisted method which superseded their preparation by conventional heating. We describe hereby new microwave irradiation protocols that are suitable for both imine bond formation reactions in the thiosemicabazone ligand synthesis and for Zn(II) metalation reactions. The new thiosemicarbazone ligands, denoted HL, mono(4- R -3-thiosemicarbazone)quinone, and their corresponding Zn(II) complexes, denoted ZnL 2 , mono(4- R -3-thiosemicarbazone)quinone, where R = H, Me, Ethyl, Allyl, and Phenyl, quinone = acenapthnenequinone (AN), aceanthrenequinone (AA), phenanthrenequinone (PH), and pyrene-4,5-dione (PY) were isolated and fully characterized spectroscopically and by mass spectrometry. A plethora of single crystal X-ray diffraction structures were obtained and analyzed and the geometries were also validated by DFT calculations. The Zn(II) complexes presented either distorted octahedral geometry or tetrahedral arrangements of the O/N/S donors around the metal center. The modification of the thiosemicarbazide moiety at the exocyclic N atoms with a range of organic linkers was also explored, opening the way to bioconjugation protocols for these compounds. The radiolabeling of these thiosemicarbazones with 64 Cu was achieved under mild conditions for the first time: this cyclotron-available radioisotope of copper ( t 1/2 = 12.7 h; β+ 17.8%; β– 38.4%) is well-known for its proficiency in positron emission tomography (PET) imaging and for its theranostic potential, on the basis of the preclinical and clinical cancer research of established bis(thiosemicarbazones), such as the hypoxia tracer 64 Cu-labeled copper(diacetyl-bis( N 4-methylthiosemicarbazone)], [ 64 Cu]Cu(ATSM). Our labeling reactions proceeded in high radiochemical incorporation (>80% for the most sterically unencumbered ligands) showing promise of these species as building blocks for theranostics and synthetic scaffolds for multimodality imaging probes. The corresponding “cold” Cu(II) metalations were also performed under the mild conditions mimicking the radiolabeling protocols. Interestingly, room temperature or mild heating led to Cu(II) incorporation in the 1:1, as well as 1:2 metal: ligand ratios in the new complexes, as evident from extensive mass spectr...

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“…The most common one is as N,S bidentate chelate [3,4], coordination mode that affords the formation of a very stable five-membered chelate ring, but many others are described in the literature, for example S monodentante [5,6], N,S bidentate chelate and S bridge [7,8] Crystals 2022, 12, 310 2 of 12 or N,S bidentate chelate and N bridge [9]. This, together with the control of protonation/deprotonation and the nature of auxiliary anions, lead to the formation of different structures such as monomers [10][11][12], dimers [13][14][15] or coordination polymers [16][17][18]. In addition to their fascinating structural properties, TSCs have a wide range of applications in different fields as catalysis [19][20][21], metal detoxification [22][23][24], metal sensing [25][26][27] or medicine [28][29][30][31].…”

Section: Introductionmentioning

confidence: 99%

Influence of the Reaction Conditions in the Crystal Structures of Zn(II) and Ni(II) Coordination Compounds with a Dissymmetric Bis(Thiosemicarbazone) Ligand

et al. 2022

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The new ligand HMeATSM, derived from condensation of 2-3-butanedione with 4-methyl-3-thiosemicarbazide and 2,4-dimethyl-3-thiosemicarbazide, has been synthesized. Its reactivity with nickel(II) and zinc(II) nitrates was explored and the resulting complexes were thoroughly characterized by elemental analysis, conductivity, mass spectrometry, IR, 1H and 13C NMR spectroscopies and their structures were confirmed by single-crystal X-ray diffraction. The results showed that the complex [Ni(MeATSM)]NO3 1 is formed under every reaction condition. In contrast, the reaction with zinc(II) nitrate depends on the temperature and the presence of LiOH.H2O, leading to the obtaining of complexes [Zn(MeATSM)(OH2)](NO3) 2 and [Zn(Me2TS)2(OH2)](NO3)2 3. The crystal structures of complexes 1 and 2 show that the dissymmetric ligand acts as a N2S2 tetradentate monoanionic ligand. The structural preferences of the metals also determine the structure of the complexes: whereas nickel(II) is in a square-planar environment, the zinc atom prefers a distorted square-base pyramid geometry imposed by the coordination mode and the planarity of the bis(thiosemicarbazone) ligand. In contrast, in complex 3, containing two bidentate Me2TS ligands, the Zn(II) is in a trigonal bipyramid arrangement. In all the complexes, the nitrate ion is not coordinated to the metal and acts as a counterion.

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Monomeric octahedral bismuth(III) benzaldehyde-N1-alkyl thiosemicarbazones: Synthesis, characterization and biological properties

Cited by 16 publications

References 46 publications

Synthesis, Characterization, Anti-bacterial and Anti-inflammatory Activities of Bismuth(III) Complexes Based on 5-chloro-2-mercaptobenzothiazole

Synthesis, Characterization, Anti-bacterial and Anti-inflammatory Activities of Bismuth(III) Complexes Based on 5-chloro-2-mercaptobenzothiazole

Structural and Functional Diversity in Rigid Thiosemicarbazones with Extended Aromatic Frameworks: Microwave-Assisted Synthesis and Structural Investigations

Influence of the Reaction Conditions in the Crystal Structures of Zn(II) and Ni(II) Coordination Compounds with a Dissymmetric Bis(Thiosemicarbazone) Ligand

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