Synthesis and characterization of trans-[Ru(NO)Cl(L)4](PF6)2 (L = isonicotinamide; 4-acetylpyridine) and related species

Calandreli, Ivy; Oliveira, Fernanda Santos de; Liang, Guangchao; Rocha, Zildete; Tfouni, Elia

doi:10.1016/j.inoche.2009.04.024

Cited by 11 publications

(7 citation statements)

References 34 publications

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“…The ratio of the anodic ( E pa ) and cathodic ( E pc ) current peak heights decreases in slow scan rate consistent with a coupled chemical reaction. The results are in line with the loss of NO following reduction process of (Ru-DCBPY) as generally observed for nitrosyl ruthenium complexes [4, 5, 10–16, 22, 58, 65, 66]. A second peak attributed as irreversible process was observed at E 1/2 = − 0.42 V (vs. Ag/AgCl), due to NO 0/− , when the CV was performed in a potential window of + 0.4 to − 0.8 V. In aqueous solution, E 1/2 for (Ru-DCBPY) couples shifts 0.02 V to a higher potential in comparison to cis -[Ru(NO) Cl(bpy) 2 ] 2+ due different σ-donor, π-acceptor character of co-ligands.…”

Section: Resultssupporting

confidence: 88%

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Targeting the mitochondrial VDAC in hepatocellular carcinoma using a polyclonal antibody-conjugated to a nitrosyl ruthenium complex

et al. 2018

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The rational design of anti-cancer agents includes a new approach based on ruthenium complexes that can act as nitric oxide (NO) donor agents against specific cellular targets. One of the most studied classes of those compounds is based on bis(bipyridine) ruthenium fragment and its derivative species. In this work, we present the chemical and cytotoxicity properties against the liver hepatocellular carcinoma cell line HepG2 of cis-[Ru(NO)Cl(dcbpy)] conjugated to a polyclonal antibody IgG (anti-VDAC) recognizing a cell surface marker. UV-visible bands of the ruthenium complex were assigned with the aid of density functional theory, which also allowed estimation of the structures that explain the biological effects of the ruthenium complex-IgG conjugate. The interaction of cis-[Ru(NO)Cl(dcbpy)] with mitochondria was evaluated due to the potential of these organelles as anti-cancer targets, and considering they interact with the anti-VDAC antibody. The cytotoxicity of cis-[Ru(NO)Cl(dcbpy)]-anti-VDAC antibody was up to 80% greater in comparison to the free cis-[Ru(NO)Cl(dcbpy)] complex. We suggest that this effect is due to site-specific interaction of the complex followed by NO release.

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Section: Resultssupporting

confidence: 88%

“…The electrochemistry of nitrosyl ruthenium complexes has been extensively studied in both aqueous and nonaqueous media [37, 39, 65, 66]. In general, these complexes undergo two one-electron processes between − 1.0 and 1.0 V vs. Ag/AgCl centered on the nitrogen oxide derivative ligand [58].…”

Section: Resultsmentioning

confidence: 99%

Targeting the mitochondrial VDAC in hepatocellular carcinoma using a polyclonal antibody-conjugated to a nitrosyl ruthenium complex

et al. 2018

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“…Among the NO donors, ruthenium nitrosyl complexes are particularly attractive because they are stable, can be either water soluble or not, deliver NO at different rates upon activation by reduction at biologically accessible potentials and/or by light irradiation, in either solution or matrices. [14][15][16][17][18]34,[40][41][42][43][44][45][46][47][48][49] These properties can be tuned by the adequate choice of ligands. 14,18 It should be pointed out that interesting biological activities for several of these complexes have already been reported.…”

Section: Introductionmentioning

confidence: 99%

“…; mac = tetraazamacrocycle). 14,18,41,45 The tetraazamacrocyclic Ru II and Ru III complexes exhibit some unusual features compared to alicyclic analogues. 18 One of their fundamental properties is the size of the macrocyclic ring.…”

Section: Introductionmentioning

confidence: 99%

Chemical and photochemical properties of a ruthenium nitrosyl complex with the N-monosubstituted cyclam 1-(3-Propylammonium)-1,4,8,11-tetraazacyclotetradecane

Ferreira¹,

Tfouni²

2010

J. Braz. Chem. Soc.

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O complexo aminofuncionalizado trans-[Ru(NO)Cl(1-pramcyH)](PF 6 ) 3 (1-pramcyH = 1-(3-propilamônio)-1,4,8,11-tetraazaciclotetradecano) foi sintetizado através da reação do trans-[RuCl(tfms)(1-pramcyH)](tfms) 2 (tfms = trifluorometanossulfonato) com óxido nítrico (NO) em solução aquosa ácida. O complexo foi caracterizado por análise elementar, espectroscópica (UVvis, IV, RMN de 1 H e 13 C) e eletroquímica. Dois valores de pK a (7,0 e 8,2) foram determinados para trans- [Ru(NO) ](PF 6 ) 3 e foram atribuídos a um dos prótons do grupo amina do cyclam e ao propilamônio. A redução do trans- [Ru(NO) ] 3+ leva à saída rápida de cloreto seguida de saída lenta de NO, enquanto a irradiação do complexo em solução aquosa desaerada resulta na labilização fotoquímica do NO. O rendimento quântico para a fotoaquação do NO diminui com o aumento do comprimento de onda de irradiação e com a diminuição do pH, e é observável apenas a l irr < 370 nm. O comportamento do trans- [Ru(NO) ] 3+ é semelhante ao do complexo análogo trans- [Ru(NO) Cl(cyclam)] 2+ , porém difere daquele do complexo com carboxipropil como substituinte.The amine-functionalized trans- [Ru(NO) ](PF 6 ) 3 complex (1-pramcyH = 1-(3-propylammonium)-1,4,8,11-tetraazacyclotetradecane) was synthesized from trans- [RuCl(tfms) (1-pramcyH)](tfms) 2 (tfms = trifluoromethanesulfonate) in acidic aqueous solution in the presence of nitric oxide (NO). The complex was characterized by elemental, spectroscopic (UV-Vis, IR, 1 H and 13 C NMR) and electrochemical analyses. Two pK a values (7.0 and 8.2) were estimated for trans- [Ru(NO) ](PF 6 ) 3 and were assigned to one of the cyclam nitrogen protons and to the protonated aminopropyl group. Reduction of trans- [Ru(NO) ] 3+ results in rapid loss of chloride followed by slower loss of NO, while irradiation of the complex in aqueous deaerated conditions suggests photochemical labilization of NO. The quantum yields for NO photoaquation decrease as the irradiation wavelength increases, being noticeable only at l irr < 370 nm, and increase as pH increases. The behavior of trans- [Ru(NO) ] 3+ , which contains an aminopropyl substituted cyclam, parallels that reported for the analogous complex with the unsubstituted ligand, but differs from that described for the complex in which carboxypropyl is the substituent. Keywords: nitrosyl, ruthenium, nitric oxide donor, substituted cylam, mono-N-functionalized cyclam IntroductionThe discovery of the participation of nitric oxide (NO) in a wide range of physiological processes and pathologies 1 has launched investigations on NO donors, including metal nitrosyl complexes in solution or immobilized in matrices, aiming at the understanding of both fundamental aspects and biological activity for potential applications. Among the NO donors, ruthenium nitrosyl complexes are particularly attractive because they are stable, can be either water soluble or not, deliver NO at different rates upon activation by reduction at biologically accessible Chemical and Photochemical Properties of a Ruthenium Nitrosyl...

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“…The motivation for the use of a quinolinic ligand is based on the biological activity of such a class of organic motifs 41 and on the fact that it has been previously observed that the presence of a second aromatic ring on the N-heterocyclic ligand impacts the electronic properties of the [Ru 3 O] core. 6,39 This study is related to other comparative analyses of the properties of mononuclear ruthenium complexes, [42][43][44][45][46] and the goal of such in-series analysis is to provide useful information about the development of new metal complexes with specific applications, in this case, as metallodrugs.…”

Section: Introductionmentioning

confidence: 99%

A novel triruthenium nitrosyl bearing a quinolinic ligand: a comparison of its spectroscopic behavior with its pyridine analogues

Santos

Silva

et al. 2022

New J. Chem.

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Synthesis and characterization of trans-[Ru(NO)Cl(L)4](PF6)2 (L = isonicotinamide; 4-acetylpyridine) and related species

Cited by 11 publications

References 34 publications

Targeting the mitochondrial VDAC in hepatocellular carcinoma using a polyclonal antibody-conjugated to a nitrosyl ruthenium complex

Targeting the mitochondrial VDAC in hepatocellular carcinoma using a polyclonal antibody-conjugated to a nitrosyl ruthenium complex

Chemical and photochemical properties of a ruthenium nitrosyl complex with the N-monosubstituted cyclam 1-(3-Propylammonium)-1,4,8,11-tetraazacyclotetradecane

A novel triruthenium nitrosyl bearing a quinolinic ligand: a comparison of its spectroscopic behavior with its pyridine analogues

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