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Intercalation of benzoxaborolate anions in layered double hydroxides: toward hybrid formulations for benzoxaborole drugs

Intercalation of benzoxaborolate anions in layered double hydroxides: toward hybrid formulations for benzoxaborole drugs
Intercalation of benzoxaborolate anions in layered double hydroxides: toward hybrid formulations for benzoxaborole drugs
Benzoxaboroles are a family of cyclic derivatives of boronic acids, whose reactivity makes them interesting candidates for the development of novel drugs. In this study, we describe the preparation of the first hybrid organic–inorganic materials involving benzoxaboroles, as a first step toward their use as new formulations for such drugs. The materials were prepared by intercalation of the simplest benzoxaborole (C7H6BO(OH), BBzx) or of its fluorinated analogue (C7H5FBO(OH), AN2690, a recently developed antifungal drug), both taken under their anionic form (benzoxaborolate), into a biodegradable inorganic matrix (a Mg–Al layered double hydroxide). Extensive characterization was carried out on the materials, notably by powder X-ray diffraction and multinuclear (11B, 27Al, 13C, 19F, 25Mg, and 1H) solid state NMR, in order to describe their structure, particularly in the vicinity of the organoboron species. Three crystalline phases involving benzoxaborolate anions in association with Ca2+ or Mg2+ cations were also prepared as part of this work (Mg(C7H6BO(OH)2)2·10H2O, Mg(C7H6BO(OH)2)2·7H2O and Ca3(C7H6BO(OH)2)5(C7H6BO2)·3H2O), in order to assist in the interpretation of the spectroscopic data. A DFT computational model of the interlayer space was proposed, which is consistent with the experimental observations. Several properties of the materials were then determined with a view of using them as part of novel formulations, namely the maximum loading capacity toward benzoxaborol(at)es, the optimal storage conditions, and the release kinetics in simulated physiological media. All in all, this study serves as a benchmark not only for the development of novel formulations for benzoxaborole drugs, but more generally for the preparation of a novel class of organic–inorganic materials involving benzoxaborol(at)es.
0897-4756
1242-1254
Sene, Saad
c494d51d-cb87-4871-b171-b4be6e48621a
Bégu, Sylvie
95840cd7-80f6-4ff2-9c95-4b85226af325
Gervais, Christel
78fc21b7-6fca-45b7-be26-8c859d9bf44f
Renaudin, Guillaume
7d1e6a84-41ad-48a9-8c65-e904eeb00e8d
Mesbah, Adel
45db1a76-b5f6-45eb-8aad-722ad9fba02f
Smith, Mark E.
abd04fbf-5f56-459d-89ec-e51ab2598c09
Mutin, P. Hubert
ceefdb7b-926c-4901-be0a-3169b2985e82
Van Der Lee, Arie
e8f5fc0e-85d0-43f9-8207-3760489233c3
Nedelec, Jean-marie
a326da09-4237-4906-bd0b-b7d84ced66ee
Bonhomme, Christian
546cdb7b-d2a5-4428-9a51-1d060703d50b
Laurencin, Danielle
5f5fceb8-0be6-4a68-abf6-7dc66068db63
Sene, Saad
c494d51d-cb87-4871-b171-b4be6e48621a
Bégu, Sylvie
95840cd7-80f6-4ff2-9c95-4b85226af325
Gervais, Christel
78fc21b7-6fca-45b7-be26-8c859d9bf44f
Renaudin, Guillaume
7d1e6a84-41ad-48a9-8c65-e904eeb00e8d
Mesbah, Adel
45db1a76-b5f6-45eb-8aad-722ad9fba02f
Smith, Mark E.
abd04fbf-5f56-459d-89ec-e51ab2598c09
Mutin, P. Hubert
ceefdb7b-926c-4901-be0a-3169b2985e82
Van Der Lee, Arie
e8f5fc0e-85d0-43f9-8207-3760489233c3
Nedelec, Jean-marie
a326da09-4237-4906-bd0b-b7d84ced66ee
Bonhomme, Christian
546cdb7b-d2a5-4428-9a51-1d060703d50b
Laurencin, Danielle
5f5fceb8-0be6-4a68-abf6-7dc66068db63

Sene, Saad, Bégu, Sylvie, Gervais, Christel, Renaudin, Guillaume, Mesbah, Adel, Smith, Mark E., Mutin, P. Hubert, Van Der Lee, Arie, Nedelec, Jean-marie, Bonhomme, Christian and Laurencin, Danielle (2015) Intercalation of benzoxaborolate anions in layered double hydroxides: toward hybrid formulations for benzoxaborole drugs. Chemistry of Materials, 27 (4), 1242-1254. (doi:10.1021/cm504181w).

Record type: Article

Abstract

Benzoxaboroles are a family of cyclic derivatives of boronic acids, whose reactivity makes them interesting candidates for the development of novel drugs. In this study, we describe the preparation of the first hybrid organic–inorganic materials involving benzoxaboroles, as a first step toward their use as new formulations for such drugs. The materials were prepared by intercalation of the simplest benzoxaborole (C7H6BO(OH), BBzx) or of its fluorinated analogue (C7H5FBO(OH), AN2690, a recently developed antifungal drug), both taken under their anionic form (benzoxaborolate), into a biodegradable inorganic matrix (a Mg–Al layered double hydroxide). Extensive characterization was carried out on the materials, notably by powder X-ray diffraction and multinuclear (11B, 27Al, 13C, 19F, 25Mg, and 1H) solid state NMR, in order to describe their structure, particularly in the vicinity of the organoboron species. Three crystalline phases involving benzoxaborolate anions in association with Ca2+ or Mg2+ cations were also prepared as part of this work (Mg(C7H6BO(OH)2)2·10H2O, Mg(C7H6BO(OH)2)2·7H2O and Ca3(C7H6BO(OH)2)5(C7H6BO2)·3H2O), in order to assist in the interpretation of the spectroscopic data. A DFT computational model of the interlayer space was proposed, which is consistent with the experimental observations. Several properties of the materials were then determined with a view of using them as part of novel formulations, namely the maximum loading capacity toward benzoxaborol(at)es, the optimal storage conditions, and the release kinetics in simulated physiological media. All in all, this study serves as a benchmark not only for the development of novel formulations for benzoxaborole drugs, but more generally for the preparation of a novel class of organic–inorganic materials involving benzoxaborol(at)es.

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e-pub ahead of print date: 19 January 2015
Published date: 24 February 2015

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Local EPrints ID: 440902
URI: http://eprints.soton.ac.uk/id/eprint/440902
ISSN: 0897-4756
PURE UUID: f455a1d4-c53e-4d25-a0eb-33b7c2c345a7

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Date deposited: 22 May 2020 16:37
Last modified: 22 May 2020 16:37

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Contributors

Author: Saad Sene
Author: Sylvie Bégu
Author: Christel Gervais
Author: Guillaume Renaudin
Author: Adel Mesbah
Author: Mark E. Smith
Author: P. Hubert Mutin
Author: Arie Van Der Lee
Author: Jean-marie Nedelec
Author: Christian Bonhomme
Author: Danielle Laurencin

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