Lawsone Dimerization in Cobalt(III) Complexes toward the Design of New Prototypes of Bioreductive Prodrugs

Bustamante, Francisco L. S.; Metello, Julia M.; Castro, Frederico Augusto Vieira de; Pinheiro, Carlos B.; Pereira, Marcos D.; Lanznaster, Maurício

doi:10.1021/ic302175t

Cited by 46 publications

(26 citation statements)

References 22 publications

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“…[6][7][8][9][10][11][12] Thus, the naphthoquinone acylhydrazones 6a-m were assessed for their anticancer effects against MCF-7 and HCT116 cell lines using MTT viability assay. The results of the compounds after 24 h of treatment are summarized in Figure 6.…”

Section: Biological Assaymentioning

confidence: 99%

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Synthesis and biological assessment of novel acylhydrazone derivatives of 2-methyl-1,4-naphthoquinone

Elaridi¹,

Bouhadi²,

Atallah³

et al. 2017

Org.Commun.

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Naphthoquinones are medicinally important molecules with a diverse array of biological properties such as antimicrobial, antifungal, antiviral, anti-inflammatory, anti-artherosclerotic and anticarcinogenic activities. In this study, we report the simple and direct preparation of a new group of novel menadione-hydrazone conjugates by reaction of 2-methyl-1,4-naphthoquinones with several aliphatic, aromatic and nucleobase hydrazides. The menadione-hydrazone conjugates were produced in excellent yields and characterized by IR, NMR and HRMS. The menadione derivatives were tested for their anticancer effects against human colon cancer HCT116 and human breast cancer MCF-7 cell lines. Interestingly, the molecules displayed disparate activities against both cell lines; the menadione hydrazones derived from the lipophilic myristic hydrazide and stearic hydrazide exhibited the most potent activity against HCT116 cell lines with IC50 of 89 and 64 μM. The most effective compounds against MCF-7 cells were the lauric hydrazide and benzoic hydrazide-derived menadione hydrazones with IC50 of 56 µM.

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Section: Biological Assaymentioning

confidence: 99%

“…1 A multitude of naturally occurring naphthoquinones reportedly exhibit a diverse array of biological activities including fungicidal, 2 antibacterial, 3 antiviral, 4 antimalarial, 5 anticancer, 1,[6][7][8][9][10][11][12] in addition to effects that counter inflammation 13 and artherosclerosis.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological assessment of novel acylhydrazone derivatives of 2-methyl-1,4-naphthoquinone

Elaridi¹,

Bouhadi²,

Atallah³

et al. 2017

Org.Commun.

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“…Além de platina e rutênio, complexos de cobalto também têm sido estudados como PDAHs por possuírem dois estados de oxidação acessíveis, +3 inerte e +2 lábil. 10,13,49,[54][55][56] Os complexos de Co 3+ são inativos e agem como carreadores da droga, desativando-a. No ambiente hipóxico de um tumor, o complexo de Co 3+ é reduzido ao respectivo complexo de Co 2+ , liberando a droga citotóxica coordenada.…”

Section: Figura 12 Complexo De Rutênio Investigado Por Brindell E Counclassified

“…Essa condição específica dos tumores sólidos vem sendo explorada para o desenvolvimento de novos fármacos seletivos -substâncias capazes de circularem intactas pelo organismo que sejam seletivamente reduzidas no ambiente tumoral hipóxico, tornando-se citotóxicas. 4,9,10 Para que ocorra a biorredução dessas substâncias, com sua consequente ativação, é necessário que além da condição de hipóxia, exista uma ou mais biomoléculas capazes de ativar essas substâncias, reduzindo-as às espécies citotóxicas. [7][8][9][10] Essa ativação pode ocorrer através das oxirredutases -enzimas que catalisam reações de oxidação-redução.…”

Section: Introductionunclassified

“…4,9,10 Para que ocorra a biorredução dessas substâncias, com sua consequente ativação, é necessário que além da condição de hipóxia, exista uma ou mais biomoléculas capazes de ativar essas substâncias, reduzindo-as às espécies citotóxicas. [7][8][9][10] Essa ativação pode ocorrer através das oxirredutases -enzimas que catalisam reações de oxidação-redução. 8-11 Oxirredutases monoeletrônicas geram um intermediário radicalar, o qual é sensível ao oxigênio e pode ser facilmente reoxidado.…”

Section: Introductionunclassified

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Redox Activation as Strategy for the Development of New Drugs Applied to the Cancer Treatment

Palmeira-Mello¹,

Lanznaster²

2015

Revista Virtual De Química

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Redox activation has been exploited in the development of drugs for treatment of several diseases, including cancer. Some cancers generate solid tumors that have a poor vascularization, which leads to the generation of hypoxic environments, which in turn, limit the effectiveness of both radio and chemotherapies. These regions have a higher reducing capability when compared to normoxic tissues. Thus, substances capable of circulating intact through the body can be reduced and activated selectively in the hypoxic region of the tumor, becoming cytotoxic. Based on this strategy, five classes of Prodrugs Activated by Hypoxia (PDAHs) are described and include nitro(hetero)cycles (p. eg. nitrogen mustards and nitroimidazoles), aromatic N-oxides, aliphatic Noxides, quinones and transition metal complexes. In this review, some advances in the development of PDAHs are discussed, focusing on the relationship between the redox properties and biological activity.

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Two two‐dimensional supramolecular copper(II) and cobalt(III) complexes derived from a new quinazoline‐type ligand: Syntheses, structures, and spectral, thermal, electrochemical and antimicrobial activity studies

Chai

Tang

Zhang

et al. 2017

Applied Organom Chemis

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Two two‐dimensional supramolecular copper(II) and cobalt(III) complexes, Cu(L1)2 (1; HL1 = 2‐hydroxy‐3‐methoxybenzaldehyde oxime) and [Co(L2)2]2⋅2CH3COOCH2CH3 (2; HL2 = 1‐(2‐{[(E)‐3‐methoxy‐2‐hydroxybenzylidene]amino}phenyl)ethanone oxime), have been synthesized via complexation of Cu(II) nitrate trihydrate and Co(II) acetate tetrahydrate with HL. A plausible reaction mechanism for the formation of HL1 is proposed. HL was synthesized and characterized using infrared, 1H NMR and 13C NMR spectra, as well as elemental analysis. Complexes 1 and 2 were investigated using single‐crystal X‐ray diffraction and have a 2:1 ligand‐to‐metal ratio. Different geometric features of both complexes are observed. In their crystal structures, 1 and 2 form infinite two‐dimensional structures and 2 forms a three‐dimensional supramolecular framework. Electron paramagnetic resonance spectra of 1 and 2 were also investigated. Moreover, thermal and electrochemical properties and antimicrobial activity of 2 were also studied. In addition, the calculated HOMO and LUMO energies show the character of complex 1.

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Lawsone Dimerization in Cobalt(III) Complexes toward the Design of New Prototypes of Bioreductive Prodrugs

Cited by 46 publications

References 22 publications

Synthesis and biological assessment of novel acylhydrazone derivatives of 2-methyl-1,4-naphthoquinone

Synthesis and biological assessment of novel acylhydrazone derivatives of 2-methyl-1,4-naphthoquinone

Redox Activation as Strategy for the Development of New Drugs Applied to the Cancer Treatment

Two two‐dimensional supramolecular copper(II) and cobalt(III) complexes derived from a new quinazoline‐type ligand: Syntheses, structures, and spectral, thermal, electrochemical and antimicrobial activity studies

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