Terpenylnaphthoquinones are reductively activated by NADH/NADH dehydrogenase

Alegrı́a, Antonio E.; Sanchez, Sheila; Sanchez-Cruz, Pedro; Nieves, Ileana; Cruz, Nadya; Gordaliza, Marina; Martín-Martín, María Luz

doi:10.1080/02772240400026872

Cited by 2 publications

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“…Semiquinone derivatives of these quinones are generated under anaerobic conditions and in the presence of NADH/NAD + dehydrogenase. Since this enzymatic system is found in mitochondria, a possible pathway in the cytotoxic activity of these terpenylnaphthoquinones could be by interference with or the inhibition of mitochondrial respiration, as reported for other naphthoquinone derivatives, in addition to free radical degradation [ 162 , 163 ]. The results obtained with avarol 1 and avarone 2 supported the mechanism of antitumor action via the reactive oxygen radicals [ 164 , 165 ] but there were also indications of the relevance of arylation of biomolecules, such as proteins [ 144 , 166 , 167 ].…”

Section: Introductionmentioning

confidence: 99%

Synthetic Strategies to Terpene Quinones/Hydroquinones

Gordaliza

2012

Marine Drugs

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The cytotoxic and antiproliferative properties of many natural sesquiterpene-quinones and -hydroquinones from sponges offer promising opportunities for the development of new drugs. A review dealing with different strategies for obtaining bioactive terpenyl quinones/hydroquinones is presented. The different synthetic approches for the preparation of the most relevant quinones/hydroquinones are described.

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Section: Introductionmentioning

confidence: 99%

Synthetic Strategies to Terpene Quinones/Hydroquinones

Gordaliza

2012

Marine Drugs

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“…Semiquinone derivatives of these quinones are generated under anaerobic conditions and in the presence of NADH/NADH dehydrogenase. Since this enzymatic system is found in mitochondria, a possible pathway in the cytotoxic activity of these terpenylnaphthoquinones could be interference with or the inhibition of mitochondrial respiration, as reported for other naphthoquinone derivatives, in addition to free radical degradation [ 29 , 30 ]. The results obtained with avarone and avarol supported the mechanism of antitumor action via the reactive oxygen radicals [ 112 , 113 ], but there were also indications of the relevance of arylation of biomolecules, such as proteins [ 31 , 114 , 115 ].…”

Section: Sar Studies and Mechanism Of Actionmentioning

confidence: 99%

Cytotoxic Terpene Quinones from Marine Sponges

Gordaliza

2010

Marine Drugs

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The 1,4-benzoquinone moiety is a common structural feature in a large number of compounds that have received considerable attention owing to their broad spectrum of biological activities. The cytotoxic and antiproliferative properties of many natural sesquiterpene quinones and hydroquinones from sponges of the order Dictyoceratida, such as avarol, avarone, illimaquinone, nakijiquinone and bolinaquinone, offer promising opportunities for the development of new antitumor agents. The present review summarizes the structure and cytotoxicity of natural terpenequinones/hydroquinones and their bioactive analogues and derivatives.

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Terpenylnaphthoquinones are reductively activated by NADH/NADH dehydrogenase

Cited by 2 publications

References 24 publications

Synthetic Strategies to Terpene Quinones/Hydroquinones

Synthetic Strategies to Terpene Quinones/Hydroquinones

Cytotoxic Terpene Quinones from Marine Sponges

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