A reinvestigation of the synthesis of arsonolipids (2,3-diacyloxypropylarsonic acids)

Tsivgoulis, Gerasimos M.; Ioannou, Panayiotis V.

doi:10.1016/j.chemphyslip.2008.02.001

Cited by 14 publications

(2 citation statements)

References 49 publications

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“…Acylation of the mono‐ and di‐tetrabutylammonium salts of the resulting acids furnishes the arsonolipids in 20–40% yield after neutralization . This yield can be improved by reducing the arsonic acid (As(V)) to a dithioarsonite (As(III)) before diol acylation and oxidation of the As(III) back to As(V) using H 2 O 2 (35‐55%) . Other mono‐arsonolipids have been synthesized in this way from 2,3,4‐trihydroxybutylarsonic acid, the product of ring‐opening of 3,4‐epoxybutane‐1,2‐diol by sodium arsenite .…”

Section: Arsenolipids and Arsenoliposomesmentioning

confidence: 99%

“…[130,131] This yield can be improved by reducing the arsonic acid (As(V)) to a dithioarsonite (As(III)) before diol acylation and oxidation of the As(III) back to As(V) using H 2 O 2 (35-55%). [132] Other mono-arsonolipids have been synthesized in this way from 2,3,4-trihydroxybutylarsonic acid, the product of ring-opening of 3,4-epoxybutane-1,2-diol by sodium arsenite. [133] Pseudo-arsonolipids analogues, containing bis-arsonic acid groups, have also be synthesized from epihalohydrin [134] and 1,4-dibromo-2,3-butanediol, [135] respectively.…”

Section: Arsenolipids and Arsenoliposomesmentioning

confidence: 99%

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Organic Arsenicals as Functional Motifs in Polymer and Biomaterials Science

Tanaka

Davis

Wilson

2018

Macromol. Rapid Commun.

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Arsenic (As) exhibits diverse (bio)chemical reactivity and biological activity depending upon its oxidation state. However, this distinctive reactivity has been largely overlooked across many fields owing to concerns regarding the toxicity of arsenic. Recently, a clinical renaissance in the use of arsenicals, including organic arsenicals that are known to be less toxic than inorganic arsenicals, alludes to the possibility of broader acceptance and application in the field of polymer and biomaterials science. Here, current examples of polymeric/macromolecular arsenicals are reported to stimulate interest and highlight their potential as a novel platform for functional, responsive, and bioactive materials.

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Section: Arsenolipids and Arsenoliposomesmentioning

confidence: 99%

Section: Arsenolipids and Arsenoliposomesmentioning

confidence: 99%

Organic Arsenicals as Functional Motifs in Polymer and Biomaterials Science

Tanaka

Davis

Wilson

2018

Macromol. Rapid Commun.

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Arsonoliposomes: Preparation and Physicochemical Characterization

Antimisiaris

Ioannou

2009

Methods in Molecular Biology

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Arsonoliposomes (ARSL) which are liposomes that contain arsonolipids in their membranes have shown interesting anticancer and antiparasitic activity in vitro. Their lipid composition (the specific arsonolipids and/or phospholipids used for their preparation, and the relative amounts of each lipid type) highly influences their physicochemical properties as well as their in vivo kinetics and antiparasitic activity; however, their cytotoxicity towards cancer cells is minimally--if at all--modified. ARSL are prepared by a modification of the "one step" method followed or not by sonication (for formation of sonicated or non-sonicated ARSL, respectively). Arsonoliposomes may be composed only of arsonolipids (containing or not cholesterol) [plain ARSL], or they may contain mixtures of arsonolipids with phospholipids (with or without Chol) [mixed ARSL]. Herein, we describe in detail the preparation and physicochemical characterization of ARSL.

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Esterification equilibrium constants of arsonic and arsinic acids

Tsivgoulis

Ioannou

2012

Monatsh Chem

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A reinvestigation of the synthesis of arsonolipids (2,3-diacyloxypropylarsonic acids)

Cited by 14 publications

References 49 publications

Organic Arsenicals as Functional Motifs in Polymer and Biomaterials Science

Organic Arsenicals as Functional Motifs in Polymer and Biomaterials Science

Arsonoliposomes: Preparation and Physicochemical Characterization

Esterification equilibrium constants of arsonic and arsinic acids

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