Recent Developments in the Chemistry and Biological Applications of Benzoxaboroles

Adamczyk‐Woźniak, Agnieszka; Borys, Krzysztof M.; Sporzyński, Andrzej

doi:10.1021/cr500642d

Cited by 197 publications

(174 citation statements)

References 128 publications

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“…To exploit that attribute, polymers, nanoparticles, and noncovalent assemblies have been decorated with phenylboronic acid and other arylboronic acids. 17,18 …”

mentioning

confidence: 99%

“…As a boronic acid, we chose 2-hydroxymethylphenylboronic acid (benzoxaborole), which has higher affinity than does phenylboronic acid for the glycopyranosides that are abundant in the glycocalyx. 24,19,18 As an immolative linker, we chose the o- hydroxydihydrocinnamic acid derivative known as the trimethyl lock (TML). After being triggered, the TML exhibits extremely high lactonization rates to release a cargo of interest (Scheme 1).…”

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confidence: 99%

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Boronic Acid for the Traceless Delivery of Proteins into Cells

et al. 2015

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The use of exogenous proteins as intracellular probes and chemotherapeutic agents is in its infancy. A major hurdle has been the delivery of native proteins to an intracellular site of action. Herein, we report on a compact delivery vehicle that employs the intrinsic affinity of boronic acids for the carbohydrates that coat the surface of mammalian cells. In the vehicle, benzoxaborole is linked to protein amino groups via a “trimethyl lock”. Immolation of this linker is triggered by cellular esterases, releasing native protein. Efficacy is demonstrated by enhanced delivery of green fluorescent protein and a cytotoxic ribonuclease into mammalian cells. This versatile strategy provides new opportunities in chemical biology and pharmacology.

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“…To exploit that attribute, polymers, nanoparticles, and noncovalent assemblies have been decorated with phenylboronic acid and other arylboronic acids. 17,18 …”

mentioning

confidence: 99%

mentioning

confidence: 99%

Boronic Acid for the Traceless Delivery of Proteins into Cells

et al. 2015

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“…The unique reactivity of the benzoxaborole group [1–3] as well as its lack of toxicity [3–5] have recently attracted much attention for the development of new drugs (Figure 1). Indeed, over the past ten years, a series of therapeutic molecules containing the benzoxaborole function have been synthesized, with antibacterial, antiviral, anticancer, anti-parasitic or anti-inflammatory activities [1,6].…”

Section: Introductionmentioning

confidence: 99%

Adsorption of benzoxaboroles on hydroxyapatite phases

Pizzoccaro¹,

Nikel²,

Sene³

et al. 2016

Acta Biomaterialia

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Benzoxaboroles are a family of molecules that are finding an increasing number of applications in the biomedical field, particularly as a “privileged scaffold” for the design of new drugs. Here, for the first time, we determine the interaction of these molecules with hydroxyapatites, in view of establishing (i) how benzoxaborole drugs may adsorb onto biological apatites, as this could impact on their bioavailability, and (ii) how apatite-based materials can be used for their formulation. Studies on the adsorption of the benzoxaborole motif (C7H7BO2, referred to as BBzx) on two different apatite phases were thus performed, using a ceramic hydroxyapatite (HAceram) and a nanocrystalline hydroxyapatite (HAnano), the latter having a structure and composition more similar to the one found in bone mineral. In both cases, the grafting kinetics and mechanism were studied, and demonstration of the surface attachment of the benzoxaborole under the form of a tetrahedral benzoxaborolate anion was established using 11B solid state NMR (including 11B-31P correlation experiments). Irrespective of the apatite used, the grafting density of the benzoxaborolates was found to be low, and more generally, these anions demonstrated a poor affinity for apatite surfaces, notably in comparison with other anions commonly found in biological media, such as carboxylates and (organo)phosphates. The study was then extended to the adsorption of a molecule with antimicrobial and antifungal properties (3-piperazine-bis(benzoxaborole)), showing, on a more general perspective, how hydroxyapatites can be used for the development of novel formulations of benzoxaborole drugs.

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“…Benzoxaboroles are cyclic derivatives of boronic acids [7]. While the first synthesis of a benzoxaborole dates back to 1957, it is only in 2006 that the research community regained interest in…”

Section: Introductionmentioning

confidence: 99%

“…Finally, in the third part, the importance of boronates/benzoxaborolates for the preparation of new families of materials will be underscored, and emerging applications of (nano)materials involving these anions will be highlighted. In addition to applications in molecular chemistry, boronic acids and benzoxaboroles are also increasingly used in materials chemistry [1,7,10,11]. In most cases, the organoboron function is exposed at the periphery of the material so that its intrinsic reactivity can be exploited to provide a given property to the material (e.g., capacity to bind to diols).…”

Section: Introductionmentioning

confidence: 99%

Coordination Networks Based on Boronate and Benzoxaborolate Ligands

et al. 2016

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Abstract:Despite the extensive range of investigations on boronic acids (R-B(OH) 2 ), some aspects of their reactivity still need to be explored. This is the case for the coordination chemistry of boronate anions (R-B(OH) 3´) , which has only recently been started to be studied. The purpose of this review is to summarize some of the key features of boronate ligands (and of their cyclic derivatives, benzoxaborolates) in materials: (i) coordination properties; (ii) spectroscopic signatures; and (iii) emerging applications.

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Recent Developments in the Chemistry and Biological Applications of Benzoxaboroles

Cited by 197 publications

References 128 publications

Boronic Acid for the Traceless Delivery of Proteins into Cells

Boronic Acid for the Traceless Delivery of Proteins into Cells

Adsorption of benzoxaboroles on hydroxyapatite phases

Coordination Networks Based on Boronate and Benzoxaborolate Ligands

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