Functional, Aromatic, and Fluorinated Monothiosemicarbazones: Investigations into Their Structures and Activity toward the Gallium-68 Incorporation by Microwave Irradiation

Sarpaki, Sophia; Cortezon‐Tamarit, Fernando; Exner, Rüdiger M.; Song, Kexin; Aguiar, Sara R. M. M. de; Ge, Haobo; Pourzand, Charareh; Paisey, Stephen J.; Kociok‐Köhn, Gabriele; Dilworth, Jonathan R.; Carroll, Laurence; Pascu, Sofia I.

doi:10.1021/acsomega.1c07396

Cited by 3 publications

(2 citation statements)

References 66 publications

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“…The ligand (L1) was synthesized taking reference from literature. [25] Thiosemicarbazide (0.91 gm, 0.01 M) was weighed and dissolved in approximately 20 mL of ethanol. Upon dissolution, the ethanolic solution of acenaphthenequinone (1.82 g, 0.01 M) was added with constant stirring.…”

Section: Synthesis Of Acenaphthenequinone Thiosemicarbazone (L1)mentioning

confidence: 99%

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Synthesis, Characterization,Computational Studies and Antimicrobial activity evaluation of Mixed ligand‐Metal complexes of selected thiosemicarbazones

Khan,

Zehra,

Alvi

et al. 2024

ChemistrySelect

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The current work reports the synthesis of mixed ligand‐metal complexes of (2‐(2‐oxoacenaphthylen‐1 ylidene)hydrazinecarbothioamide) (L1) and carbamothioyl‐2‐chloronicotinohydrazonic acid (L2) and imidazole (im), triphenylphosphine (PPh3) and pyridine (py) ligands with Cu (II), Zn (II), Fe (II) and Co (II) salts.The chacterization was done through FT‐IR, NMR, UV‐visible, and elemental analysis. The X‐ray diffraction (XRD) patterns of [Cu(L1)(im)2(SO4)] demonstrated the crystalline morphology. In the FT‐IR spectra of the ligands, the characteristic frequencies corresponding to ν(C=N) (imine) and ν(C=S) (thiocarbonyl) were observed around 1650 and 1130 cm−1 respectively, which shifted upon complexation. In the 1H NMR spectra, the peak due to the NH proton was observed downfield, whereas that of ‐NH2 was observed comparatively upfield owing to its secondary amine nature. The molecular docking was performed against transforming growth beta (tgf‐β), protease of SARS‐CoV‐2 (Mpro) and aspartate kinase (Asp) kinase.The molecular simulation with the docked complex of [Zn(L2)(py)2(SO4)] and [Zn(L1)(PPh3)2(SO4)] with Asp kinase showed significant stability during the simulation time of 100 ns. The relative free energies of the simulated complexes were calculated with the molecular mechanics Poison‐Boltmann surface area (MM‐PBSA). The complexes were tested against ten bacterial strains and showed enhanced antibacterial activity than the ligands. [Cu(L1)(im)2(SO4)], [Zn(L1)(im)2(SO4)], [Fe(L1)(im)2(SO4)] and [Co(L1)(im)2(Cl2)] were found to be active against E.coli.

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Section: Synthesis Of Acenaphthenequinone Thiosemicarbazone (L1)mentioning

confidence: 99%

“…The ligand (L1) was synthesized taking reference from literature [25] . Thiosemicarbazide (0.91 gm, 0.01 M) was weighed and dissolved in approximately 20 mL of ethanol.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis, Characterization,Computational Studies and Antimicrobial activity evaluation of Mixed ligand‐Metal complexes of selected thiosemicarbazones

Khan,

Zehra,

Alvi

et al. 2024

ChemistrySelect

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Chalcogen-based fluorescent probes for metal ion detection: Principles, applications, and design strategies

Liu,

Zhang,

Jiang

et al. 2024

Coordination Chemistry Reviews

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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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Functional, Aromatic, and Fluorinated Monothiosemicarbazones: Investigations into Their Structures and Activity toward the Gallium-68 Incorporation by Microwave Irradiation

Cited by 3 publications

References 66 publications

Synthesis, Characterization,Computational Studies and Antimicrobial activity evaluation of Mixed ligand‐Metal complexes of selected thiosemicarbazones

Synthesis, Characterization,Computational Studies and Antimicrobial activity evaluation of Mixed ligand‐Metal complexes of selected thiosemicarbazones

Chalcogen-based fluorescent probes for metal ion detection: Principles, applications, and design strategies

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

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