Maleimide-bearing nanogels as novel mucoadhesive materials for drug delivery

Abstract

Novel class of mucoadhesive polymers has been developed via polymerisation of 2,5-dimethylfuran-protected 3-maleimidoethyl butylacrylate in the presence of presynthesised poly(N-vinylpyrrolidone) nanogel scaffolds. The resulting maleimide-bearing nanogels were capable of forming covalent linkages with mucosal membranes.

Mucoadhesive maleimide-functionalised liposomes for drug delivery to urinary bladder

“…Recently we have demonstrated for the first time that polymers functionalised with maleimide 82 groups exhibit excellent mucoadhesive properties to conjunctival tissues ex vivo and the ability of these 83 materials to retain on mucosal tissues was comparable to well-known mucoadhesive chitosan 84 (Tonglairoum et al, 2016). This excellent mucoadhesive performance of maleimide-functionalised 85 polymers is due to their ability to form covalent linkages with thiol-groups present in mucins.…”

“…They were then placed on dry ice, before being 218 completely embedded in OCT to conserve the liposome-loaded mucus membrane. Samples were then 219 left on dry ice for 3 h. 220 The in vitro release of NaFI from liposomes was studied using a dialysis method adopted from 241 our previous publication (Tonglairoum et al, 2016). In brief, 2 mL of NaFI-loaded liposomes in AU 242 solution was transferred in a Pur-A-Lyzer™ Maxi 3500 dialysis membrane and immersed in 30 mL of 243 AU (pH 6.4) that was then shaken at 80 spm for 24 h at 37 °C.…”

Acrylated Eudragit® E PO as a novel polymeric excipient with enhanced mucoadhesive properties for application in nasal drug delivery

“…Examples of cationic polymers with proven mucoadhesive properties include chitosan (Sogias et al, 2008) and some synthetic polymers of methacrylate nature with tertiary-amino-and quaternary ammonium-functional groups (Keely et al, 2005;Fefelova et al, 2007). Some attempts were reported to improve mucoadhesive properties of chitosan and other polymers through their chemical functionalisation, for example, attachment of thiol- (Bernkop-Schnurch, 2004;Bernkop-Schnurch, 2005), acrylate- (Davidovich-Pinhas et al, 2011;Shitrit et al, 2017), methacrylate- (Kolawole et al, 2018), catechol- (Kim et al, 2015), maleimide- (Tonglairoum et al, 2016;Shtenberg et al, 2017;Sahatsapan et al, 2018) and other groups .…”

Synthesis and evaluation of mucoadhesive acryloyl-quaternized PDMAEMA nanogels for ocular drug delivery

“…thiols, maleimides, catechols, etc. [8][9][10][11] In the past decade, there has been some interest in the utilization of acrylated polymers as covalent bond forming mucoadhesive functionalities. 12 First reported in 2010, acrylated polymers exhibit mucoadhesive properties as a consequence of their ability to undergo a Michael-type reaction with thiol/sulfide groups present in the cysteine-rich termini of the mucin glycoproteins at the mucosal surface.…”