Carbohydrate Multivalent Systems: Synthesis and Therapeutic Opportunities

Reina, José J.; Rojo, Javier

doi:10.1142/9781783267200_0017

Cited by 1 publication

(1 citation statement)

References 83 publications

(111 reference statements)

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“…Nature uses a well-known strategy, named multivalent effect, to increase this low affinity by gathering multiple copies of sugars to achieve a global binding potency toward their receptors higher than that for the sum of the monovalent interactions [27]. Inspired by this natural approach, a vast number of structures decorated with multiple carbohydrate moieties have been tested as potential theranostic agents in biosensing and biomedicine [22,28,29].…”

Section: Introductionmentioning

confidence: 99%

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

Cutrone

Casas-Solvas

et al. 2019

Nanomaterials

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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.

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