The First Polyarsenic Organic Compound from Nature: Arsenicin A from the New Caledonian Marine Sponge Echinochalina bargibanti.

Mancini, Ines; Guella, Graziano; Frostin, Maryvonne; Hnawia, Edouard; Laurent, Dominique; Debitus, Cécile; Pietra, Francesco

doi:10.1002/chin.200714214

Cited by 8 publications

(17 citation statements)

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“…The synthesis of an analogue was crucial for the challenging structural determination of the natural metabolite Arsenicin A 10 . The model compound 9,10-dimethyl-2,4,6,8-tetraoxa-1,3,5,7,-tetraarsa-tricyclo[3.3.1.13,7]decane ( 2 , Fig.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and in-vitro anticancer evaluation of polyarsenicals related to the marine sponge derived Arsenicin A

Mancini

Planchestainer

Defant

2017

Sci Rep

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In the light of the promising bioactivity of the tetraarsenic marine metabolite arsenicin A, the dimethyl analogue 2 and four isomeric methylene homologues (including the natural product itself) were obtained using a one-pot microwave-assisted synthesis, starting from arsenic (III) oxide. Due to the poor diagnostic value of the NMR technique in the structural elucidation of these molecules, they were fully characterized by mass spectrometry and infrared (IR)-spectroscopy, comparing density functional theory (DFT) simulated and experimental spectra. This synthetic procedure provided a fast and efficient access to the cytotoxicity evaluation of organoarsenical leads of the natural hit molecule. From in vitro screening, each tested compound resulted in being more active than the FDA-approved arsenic trioxide, with the most lipophilic molecule in the series showing the best growth inhibition of both leukemia and solid tumor cell lines. These results may open promising perspectives in the development of new more potent and selective arsenical drugs against solid tumors.

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Section: Resultsmentioning

confidence: 99%

“…Reported as the first organic polyarsenic compound ever found naturally, its adamantane cage resembles arsenolite structure (Fig. 1 ) 10 . It is unusual, because natural organoarsenicals isolated so far included monoarsenic metabolites, mostly as apolar methylated forms, or water soluble betaine and arsenosugars 11 .…”

Section: Introductionmentioning

confidence: 98%

Synthesis and in-vitro anticancer evaluation of polyarsenicals related to the marine sponge derived Arsenicin A

Mancini

Planchestainer

Defant

2017

Sci Rep

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“…Sloth et al (2005a) detected DMAA, DMAP, and DMAE in the liver of hooded seal and DMAE in the kidney of harp seal. Mancini et al (2006) identified a novel polyarsenic compound (arsenicin A; C 3 H 6 As 4 O 3 ) in the marine sponge Echinochalina bargibanti from the coast of New Caledonia. Recently, various thio-arsenicals were also identified in the urine of sheep feeding on marine algae and humans exposed to arsenic from groundwater.…”

Section: Newly Identified Arsenicalsmentioning

confidence: 99%

Arsenic in Marine Mammals, Seabirds, and Sea Turtles

Kunito

Kubota

Fujihara

et al. 2008

Reviews of Environmental Contamination and Toxicology

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“…The first adamantine-type polyarsenic compound ever found in nature, arsenicin A, it was isolated from the organic extract of the poecilosclerid sponge Echinochalina bargibanti collected from the northeastern coast of New Caledonia by Mancini et al (2006). Arsenicin A is a bactericide and fungicide effective against human pathogens.…”

Section: Arsenic In Aquatic Organismsmentioning

confidence: 99%