Arsenicin A, A Natural Polyarsenical: Synthesis and Crystal Structure

Lü, Di; Rae, A. David; Salem, Geoffrey; Weir, Michelle; Willis, Anthony C.; Wild, S. Bruce

doi:10.1021/om900998q

Cited by 23 publications

(30 citation statements)

References 7 publications

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“…Recently, racemic arsenicin A was synthesized in five steps and 36% overall yield starting from phenylarsinic acid and its crystal structure was described. In a cytotoxicity evaluation on some human carcinoma cell lines 12 , 13 , it proved to be very efficient in inducing cell death in acute promyelocytic leukemia cell lines and in stopping the advancement of pancreatic adenocarcinoma and glioblastoma 13 .…”

Section: Introductionmentioning

confidence: 99%

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: Introductionmentioning

confidence: 99%

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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“…It is then sufficiently clear that arsenicin A is represented by structure 12 , whose vibrational spectra (IR and Raman) have also been thoroughly investigated by Guella 34. The crowning is a very recent report dealing with the total synthesis and XRD of arsenicin A, again fully confirming the structure proposed and establishing its chirality 35. It will be interesting to compare the reported synthetic route with possible biochemical paths.…”

Section: Arsenic From the South Seasmentioning

confidence: 67%

Computing the NMR spectra of the sponge metabolite arsenicin A: when simple becomes difficult

Bagno

2010

J of Physical Organic Chem

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“…In contrast, gentamicin, which is the reference antibiotic, induces inhibition circles of 22, 30 and 22 mm [ 68 ]. Arsenicin A ( 14 , Figure 6 B) has been synthesized and its crystal structure determined [ 101 ]. An improvement in this synthesis has led to (±)-arsenicin A which shows potent antiproliferative activity on acute promyelocytic leukemia cell lines.…”

Section: Natural Products By Taxonmentioning

confidence: 99%

Marine Natural Products from New Caledonia—A Review

et al. 2016

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Marine micro- and macroorganisms are well known to produce metabolites with high biotechnological potential. Nearly 40 years of systematic prospecting all around the New Caledonia archipelago and several successive research programs have uncovered new chemical leads from benthic and planktonic organisms. After species identification, biological and/or pharmaceutical analyses are performed on marine organisms to assess their bioactivities. A total of 3582 genera, 1107 families and 9372 species have been surveyed and more than 350 novel molecular structures have been identified. Along with their bioactivities that hold promise for therapeutic applications, most of these molecules are also potentially useful for cosmetics and food biotechnology. This review highlights the tremendous marine diversity in New Caledonia, and offers an outline of the vast possibilities for natural products, especially in the interest of pursuing collaborative fundamental research programs and developing local biotechnology programs.

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Arsenicin A, A Natural Polyarsenical: Synthesis and Crystal Structure

Cited by 23 publications

References 7 publications

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

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

Computing the NMR spectra of the sponge metabolite arsenicin A: when simple becomes difficult

Marine Natural Products from New Caledonia—A Review

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