Synthesis, characterization and biological activity of gallium(III) complexes with non-symmetrical NO-donor Schiff bases

Padilha, Diego S.; Santos, Yan F.; Giacomin, Letícia Carlos; Castro, Frederico Augusto Vieira de; Pereira, Marcos D.; Rocha, Alexandre B.; Resende, Jackson A. L. C.; Scarpellini, Marciela

doi:10.1016/j.poly.2016.12.020

Cited by 6 publications

(5 citation statements)

References 33 publications

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“…In our calculations, we observed average distances of 1.95 Å for the Ga−O bond in the O−Ga−O, 2.06 Å for the Ga−N bond in the O−Ga−N, and 2.04 Å for the Ga−N bond in the N−Ga−N dispositions in 32a−d and 2-Ga 3+ , values which are in good agreement with similar gallium complexes reported in the literature. 46,47 We would expect the sum of the transverse angles of the ideal octahedral structure to be around Σ angles = 540°(three times 180°), and a deviation from this value could provide an indication of the stability of the complex. Additionally, the difference between the sum of the B3LYP6-31 G(d,p) geometries of 32a−d (see Figure 2) and (9R,10R,12R,13R)-41 were calculated and then compared with the DFT-calculated structure of the gallium(III) piscibactin complex (2-Ga 3+ ) 19 and the X-ray data of the Fe(III)yersiniabactin complex (4-Fe 3+ ), 45 which have adequate values to form the gallium/iron complexes.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Based on our previous studies on 2-Ga 3+ and the X-ray structure of 4-Fe 3+ , just the meridional ( mer ) isomers were considered. In our calculations, we observed average distances of 1.95 Å for the Ga–O bond in the O–Ga–O, 2.06 Å for the Ga–N bond in the O–Ga–N, and 2.04 Å for the Ga–N bond in the N–Ga–N dispositions in 32a–d and 2-Ga 3+ , values which are in good agreement with similar gallium complexes reported in the literature. , We would expect the sum of the transverse angles of the ideal octahedral structure to be around Σ angles = 540° (three times 180°), and a deviation from this value could provide an indication of the stability of the complex. Additionally, the difference between the sum of the Ga-heteroatom bond lengths for N–Ga–N, O–Ga–N, and O–Ga–O dispositions and the transverse distance between heteroatoms N···N, O···N, and O···O, respectively, would give us a degree of distortion of the octahedral structure.…”

Section: Resultsmentioning

confidence: 99%

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Structural Requirements for Ga³⁺ Coordination in Synthetic Analogues of the Siderophore Piscibactin Deduced by Chemical Synthesis and Density Functional Theory Calculations

et al. 2023

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Stereoselective total synthesis of several analogues of piscibactin (Pcb), the siderophore produced by different pathogenic Gram-negative bacteria, was performed. The acid-sensitive α-methylthiazoline moiety was replaced by a more stable thiazole ring, differing in the configuration of the OH group at the C-13 position. The ability of these Pcb analogues to form complexes with Ga3+ as a mimic of Fe3+ showed that the configuration of the hydroxyl group at C-13 as 13S is crucial for the chelation of Ga3+ to preserve the metal coordination, while the presence of a thiazole ring instead of the α-methylthiazoline moiety does not affect such coordination. A complete 1H and 13C NMR chemical shift assignment of the diastereoisomer mixtures around C9/C10 was done for diagnostic stereochemical disposition. Additionally, density functional theory calculations were performed not only for confirming the stereochemistry of the Ga3+ complex among the six possible diastereoisomers but also for deducing the ability of these to form octahedral coordination spheres with gallium. Finally, the lack of antimicrobial activity of Pcb and Pcb thiazole analogue Ga3+ complexes against Vibrio anguillarum agrees with one of the roles of siderophores in protecting pathogens from metal ion toxicity. The efficient metal coordination shown by this scaffold suggests its possible use as a starting point for the design of new chelating agents or vectors for the development of new antibacterials that exploit the “Trojan horse” strategy using the microbial iron uptake mechanisms. The results obtained will be of great help in the development of biotechnological applications for these types of compounds.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Structural Requirements for Ga³⁺ Coordination in Synthetic Analogues of the Siderophore Piscibactin Deduced by Chemical Synthesis and Density Functional Theory Calculations

et al. 2023

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“…It was revealed that the 4-nitrophenol-derived imidazole complex II89 displayed selectivity and anticancer activity against A549. The IC 50 of complex II89 (94.12 ± 4.62) was lower than that of cisplatin (135.10 ± 6.50), which was used as a reference metal drug under the same experimental conditions [ 197 ].…”

Section: Imidazole-based Supermolecules As Medicinal Agentsmentioning

confidence: 99%

Comprehensive Insights into Medicinal Research on Imidazole-Based Supramolecular Complexes

Tan

Zhang

et al. 2023

Pharmaceutics

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The electron-rich five-membered aromatic aza-heterocyclic imidazole, which contains two nitrogen atoms, is an important functional fragment widely present in a large number of biomolecules and medicinal drugs; its unique structure is beneficial to easily bind with various inorganic or organic ions and molecules through noncovalent interactions to form a variety of supramolecular complexes with broad medicinal potential, which is being paid an increasing amount of attention regarding more and more contributions to imidazole-based supramolecular complexes for possible medicinal application. This work gives systematical and comprehensive insights into medicinal research on imidazole-based supramolecular complexes, including anticancer, antibacterial, antifungal, antiparasitic, antidiabetic, antihypertensive, and anti-inflammatory aspects as well as ion receptors, imaging agents, and pathologic probes. The new trend of the foreseeable research in the near future toward imidazole-based supramolecular medicinal chemistry is also prospected. It is hoped that this work provides beneficial help for the rational design of imidazole-based drug molecules and supramolecular medicinal agents and more effective diagnostic agents and pathological probes.

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“…These compounds may show excellent properties, such as antitumor and antibacterial activity [5,6], catalytic property [7,8], as fluorescent sensor [9] and so on. As part of our interest in synthesis, structure and property of Schiff base compounds, in this paper, a new Schiff base compound is reported.…”

Section: Commentmentioning

confidence: 99%

The crystal structure (E)-4-methyl-N′-(2-nitrobenzylidene)benzenesulfonohydrazide, C₁₄H₁₃N₃O₄S

Tai

2017

Zeitschrift Für Kristallographie - New Crystal Structures

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CCDC no.: 1577203The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters. Source of materialsThe title compound was synthesized according to the literature [4]. 0.186 g (1 mmol) 4-toluenesulfonyl hydrazide was dissolved in 15 mL ethanol solution. An amount of 0.151 g (1 mmol) of 2-nitrobenzaldehyde was added to the above mentioned solution. This mixture was refluxed at 80°C for 4 h and filtered. The resulting solution was evaporated at room temperature. Light yellow crystals of the title compound were obtained after a week.

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Synthesis, characterization and biological activity of gallium(III) complexes with non-symmetrical NO-donor Schiff bases

Cited by 6 publications

References 33 publications

Structural Requirements for Ga³⁺ Coordination in Synthetic Analogues of the Siderophore Piscibactin Deduced by Chemical Synthesis and Density Functional Theory Calculations

Structural Requirements for Ga³⁺ Coordination in Synthetic Analogues of the Siderophore Piscibactin Deduced by Chemical Synthesis and Density Functional Theory Calculations

Comprehensive Insights into Medicinal Research on Imidazole-Based Supramolecular Complexes

The crystal structure (E)-4-methyl-N′-(2-nitrobenzylidene)benzenesulfonohydrazide, C₁₄H₁₃N₃O₄S

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Synthesis, characterization and biological activity of gallium(III) complexes with non-symmetrical NO-donor Schiff bases

Cited by 6 publications

References 33 publications

Structural Requirements for Ga3+ Coordination in Synthetic Analogues of the Siderophore Piscibactin Deduced by Chemical Synthesis and Density Functional Theory Calculations

Structural Requirements for Ga3+ Coordination in Synthetic Analogues of the Siderophore Piscibactin Deduced by Chemical Synthesis and Density Functional Theory Calculations

Comprehensive Insights into Medicinal Research on Imidazole-Based Supramolecular Complexes

The crystal structure (E)-4-methyl-N′-(2-nitrobenzylidene)benzenesulfonohydrazide, C14H13N3O4S

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Structural Requirements for Ga³⁺ Coordination in Synthetic Analogues of the Siderophore Piscibactin Deduced by Chemical Synthesis and Density Functional Theory Calculations

Structural Requirements for Ga³⁺ Coordination in Synthetic Analogues of the Siderophore Piscibactin Deduced by Chemical Synthesis and Density Functional Theory Calculations

The crystal structure (E)-4-methyl-N′-(2-nitrobenzylidene)benzenesulfonohydrazide, C₁₄H₁₃N₃O₄S