Transition Metal Bis(2-Bromophenyl)disulfide Complexes

Anacona, J.R.; Gómez, Jofre

doi:10.4067/s0717-97072008000400012

Cited by 4 publications

(4 citation statements)

References 24 publications

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“…The modest effect of the C56S mutation on inhibition in the Mg 2+ compared to the Mn 2+ context also suggests a differential chelation effect in the active site. Although we did not find significant complexation between DIBA-1 and Mn 2+ prior to IN binding under our experimental conditions, it is not excluded that such a complexation may occur with Mn 2+ , but not with Mg 2+ , in the active site context for proximity reasons, based on a recent study on complexes involving bis(2-bromophenyl)disulfide and transition metals ( 39 ). However, DIBA-1 was clearly and reproducibly a better inhibitor in the context of Mg 2+ than Mn 2+ , suggesting that the differential effect originates mainly in the zinc ejection which can be considered as the most potent inhibition mechanism.…”

Section: Discussioncontrasting

confidence: 60%

“…Indeed, adding DTT or β-mercaptoethanol to the reaction mixture blocked the DIBA-1 inhibitory effect ( Figure 2 E). Recently, it has been reported that complexation reactions between bis(2-bromophenyl)disulfide and transition metal ions, including manganese, may occur ( 39 ). To address the question of the possible complexation between DIBA-1 and Mn 2+ —which could explain the higher IC 50 values obtained in the presence of Mn 2+ compared to Mg 2+ —we tested the influence of the order of addition of the reagents on the IC 50 value.…”

Section: Resultsmentioning

confidence: 99%

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A cooperative and specific DNA-binding mode of HIV-1 integrase depends on the nature of the metallic cofactor and involves the zinc-containing N-terminal domain

Carayon¹,

Leh²,

Henry³

et al. 2010

Nucleic Acids Research

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HIV-1 integrase catalyzes the insertion of the viral genome into chromosomal DNA. We characterized the structural determinants of the 3′-processing reaction specificity—the first reaction of the integration process—at the DNA-binding level. We found that the integrase N-terminal domain, containing a pseudo zinc-finger motif, plays a key role, at least indirectly, in the formation of specific integrase–DNA contacts. This motif mediates a cooperative DNA binding of integrase that occurs only with the cognate/viral DNA sequence and the physiologically relevant Mg2+ cofactor. The DNA-binding was essentially non-cooperative with Mn2+ or using non-specific/random sequences, regardless of the metallic cofactor. 2,2′-Dithiobisbenzamide-1 induced zinc ejection from integrase by covalently targeting the zinc-finger motif, and significantly decreased the Hill coefficient of the Mg2+-mediated integrase–DNA interaction, without affecting the overall affinity. Concomitantly, 2,2′-dithiobisbenzamide-1 severely impaired 3′-processing (IC50 = 11–15 nM), suggesting that zinc ejection primarily perturbs the nature of the active integrase oligomer. A less specific and weaker catalytic effect of 2,2′-dithiobisbenzamide-1 is mediated by Cys 56 in the catalytic core and, notably, accounts for the weaker inhibition of the non-cooperative Mn2+-dependent 3′-processing. Our data show that the cooperative DNA-binding mode is strongly related to the sequence-specific DNA-binding, and depends on the simultaneous presence of the Mg2+ cofactor and the zinc effector.

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Section: Discussioncontrasting

confidence: 60%

Section: Resultsmentioning

confidence: 99%

A cooperative and specific DNA-binding mode of HIV-1 integrase depends on the nature of the metallic cofactor and involves the zinc-containing N-terminal domain

Carayon¹,

Leh²,

Henry³

et al. 2010

Nucleic Acids Research

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“…Changes observed in the weak absorption bands at 400-600 cm À1 in the spectra of the complexes were assigned to the M-O stretching vibrations [42,43]. The IR spectra of the phen-containing complexes 4d, 4f and 4g were similar to each other and showed new absorption bands characteristic of chelating phenanthroline [44], these occurring at ca.…”

Section: Ir Spectramentioning

confidence: 88%

Isolation and characterisation of silver(I) complexes of substituted coumarin-4-carboxylates which are effective against Pseudomonas aeruginosa biofilms

et al. 2014

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a b s t r a c tA novel series of coumarin-4-carboxylate ligands (2a-2l), their Ag(I) complexes (3a-3l) together with a number of their phenanthroline adducts (4d, 4f and 4g) have been synthesised and characterised. The ligands were prepared by either acid or base hydrolysis of their corresponding esters or by demethylation of a methylated acid derivative. The esters (1a-1i) were synthesised by an aromatic electrophilic substitution reaction between the conjugate base of substituted phenols and a vinyltriphenylphosphonium salt. The novel series of Ag(I) carboxylate complexes were prepared by reaction of silver nitrate with the coumarin ligands in aqueous/alcohol solution. The Ag(I) phenanthroline adducts were prepared by reaction of the Ag(I) complex with 1,10-phenanthroline in aqueous/alcohol solution. A selection of complexes were screened for their in vitro antibacterial activity against Pseudomonas aeruginosa grown planktonically or as a biofilm as well as a number of other clinically important strains, Escherichia coli, MRSA and Staphylococcus aureus. The activity against the P. aeruginosa biofilm was found to be significantly greater than against the planktonic bacteria.

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“…In contrast to the reactions of Pd(OAc) 2 with the dichalcogenides {HL Y } 2 , the corresponding reactions of nickel(II) acetate with the dichalcogenides did not result in cleavage of the Se–Se or Te–Te bonds. This is not completely surprising because the analogous disulfide {HL S } 2 forms monomeric complexes of the type [Ni{κ 5 -L S } 2 (solvent)] or dimeric complexes of the type [(Ni{κ 5 -L S } 2 ) 2 ], where the disulfide moiety coordinates but remains intact. , Similarly, other disulfides have been observed to coordinate through one of the disulfide sulfur atoms to nickel. − Only one example of a ditelluride coordinating to nickel has been claimed but was not proven unambiguously, e.g., by X-ray diffraction…”

Section: Resultsmentioning

confidence: 99%

Solvents and Ligands Matter: Structurally Variable Palladium and Nickel Clusters Assembled by Tridentate Selenium- and Tellurium-Containing Schiff Bases

2022

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Structurally variable organochalcogen clusters containing palladium(II) and nickel(II) ions were assembled starting from the salicylidene-substituted dichalcogenides (Y–C6H4–NCH–C6H4–OH)2 ({HLY}2, where Y = Se or Te), and palladium or nickel acetate. The tetrameric palladium clusters contain reduced chalcogenolato ligands {Y–C6H4–NCH–C6H4–O)}2– ({L′Y}2–, where Y = Se or Te), while the initially formed trimeric nickel clusters contain the intact, coordinated dichalcogenides. The palladium clusters have a general formula of [Pd4(L′Y)4] and represent the first examples of palladium complexes where both a gyrobifastigial and a pseudocubane arrangement of the central Pd4Y4 unit could be established with the same ligand, only depending on the solvents used for crystallization. Reduced density gradient (RDG) considerations based on density functional theory calculations suggest that the commonly referred to stabilizing chalcogen–palladium or palladium–palladium interactions for the two geometric arrangements are weak van der Waals contacts resulting from the contact of two nonbinding lone pairs. In the case of the pseudocubane arrangement, a repulsive steric effect, which is indicated by RDG analysis, is clearly supported by the cuplike distortions detected in the solid-state structure of the compound. In contrast to the reactions with palladium acetate, where the dichalcogenides were cleaved, during similar reactions with nickel acetate, the dichalcogenides remained intact and trimeric clusters of the composition [Ni-μ2-κ2-(Ni{κ5-LY}2)2-μ2-(OAc)2] (Y = Se, Te) were formed. Air oxidation and hydrolysis of [Ni-μ2-κ2-(Ni{κ5-LTe}2)2-μ2-(OAc)2] gave a rare example of a hexanuclear nickel cluster of the composition [Ni2-κ5-(Ni4-κ6-μ6-{(L′Te 2O3)(L′TeO2)2}2)-μ2-(H2O)2], which is composed of a well-defined framework consisting of tellurinic anhydride and tellurinate units, which proves the comparably higher oxidation sensitivity of the trinickel dichalcogenide complexes. Electron spray ionization mass spectrometry spectra of both the palladium and nickel clusters indicate that they show fluctional behavior with varying nuclearity in solution and can adopt multiple charge states especially because of the noninnocence of the chalcogen-based ligands. The complexes were fully characterized by spectroscopic methods, elemental analyses, and X-ray diffraction.

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Transition Metal Bis(2-Bromophenyl)disulfide Complexes

Cited by 4 publications

References 24 publications

A cooperative and specific DNA-binding mode of HIV-1 integrase depends on the nature of the metallic cofactor and involves the zinc-containing N-terminal domain

A cooperative and specific DNA-binding mode of HIV-1 integrase depends on the nature of the metallic cofactor and involves the zinc-containing N-terminal domain

Isolation and characterisation of silver(I) complexes of substituted coumarin-4-carboxylates which are effective against Pseudomonas aeruginosa biofilms

Solvents and Ligands Matter: Structurally Variable Palladium and Nickel Clusters Assembled by Tridentate Selenium- and Tellurium-Containing Schiff Bases

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