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Design of Engineered Cyclodextrin Derivatives for Spontaneous Coating of Highly Porous Metal-Organic Framework Nanoparticles in Aqueous Media

1
Department of Chemistry and Physics, University of Almería, Crta. de Sacramento s/n, E-04120 Almería, Spain
2
Institut des Sciences Moléculaires d’Orsay, UMR CNRS 8214, Université Paris-Sud, Université Paris Saclay, 91400 Orsay, France
3
CycloLab R&D Ltd., Illatos út 7, H-1097 Budapest, Hungary
4
Laboratoire de Physique des Solides, UMR 8502, Université Paris-Sud, 91405 Orsay, France
5
Department of Physical and Analytical Chemistry, University of Oviedo, Julián Clavería 8, 33006 Oviedo, Spain
*
Authors to whom correspondence should be addressed.
Nanomaterials 2019, 9(8), 1103; https://doi.org/10.3390/nano9081103
Received: 23 July 2019 / Revised: 29 July 2019 / Accepted: 30 July 2019 / Published: 1 August 2019
(This article belongs to the Special Issue Nanoconstructs Based on Cyclodextrins)
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Abstract

Nanosized metal-organic frameworks (nanoMOFs) MIL-100(Fe) are highly porous and biodegradable materials that have emerged as promising drug nanocarriers. A challenging issue concerns their surface functionalization in order to evade the immune system and to provide molecular recognition ability, so that they can be used for specific targeting. A convenient method for their coating with tetraethylene glycol, polyethylene glycol, and mannose residues is reported herein. The method consists of the organic solvent-free self-assembly on the nanoMOFs of building blocks based on β-cyclodextrin facially derivatized with the referred functional moieties, and multiple phosphate groups to anchor to the nanoparticles’ surface. The coating of nanoMOFs with cyclodextrin phosphate without further functional groups led to a significant decrease of macrophage uptake, slightly improved by polyethylene glycol or mannose-containing cyclodextrin phosphate coating. More notably, nanoMOFs modified with tetraethylene glycol-containing cyclodextrin phosphate displayed the most efficient “stealth” effect. Mannose-coated nanoMOFs displayed a remarkably enhanced binding affinity towards a specific mannose receptor, such as Concanavalin A, due to the multivalent display of the monosaccharide, as well as reduced macrophage internalization. Coating with tetraethylente glycol of nanoMOFs after loading with doxorubicin is also described. Therefore, phosphorylated cyclodextrins offer a versatile platform to coat nanoMOFs in an organic solvent-free, one step manner, providing them with new biorecognition and/or “stealth” properties. View Full-Text
Keywords: metal-organic frameworks; MIL-100(Fe); β-cyclodextrin; mannose; molecular recognition; “stealth” effect; multivalent effect; isothermal titration calorimetry; macrophage metal-organic frameworks; MIL-100(Fe); β-cyclodextrin; mannose; molecular recognition; “stealth” effect; multivalent effect; isothermal titration calorimetry; macrophage
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Cutrone, G.; Li, X.; Casas-Solvas, J.M.; Menendez-Miranda, M.; Qiu, J.; Benkovics, G.; Constantin, D.; Malanga, M.; Moreira-Alvarez, B.; Costa-Fernandez, J.M.; García-Fuentes, L.; Gref, R.; Vargas-Berenguel, A. Design of Engineered Cyclodextrin Derivatives for Spontaneous Coating of Highly Porous Metal-Organic Framework Nanoparticles in Aqueous Media. Nanomaterials 2019, 9, 1103.

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