Potential Eye Drop Based on a Calix[4]arene Nanoassembly for Curcumin Delivery: Enhanced Drug Solubility, Stability, and Anti-Inflammatory Effect

Mol Pharm. 2017 May 1;14(5):1610-1622. doi: 10.1021/acs.molpharmaceut.6b01066. Epub 2017 Apr 10.

Abstract

Curcumin is an Indian spice with a wide spectrum of biological and pharmacological activities but poor aqueous solubility, rapid degradation, and low bioavailability that affect medical benefits. To overcome these limits in ophthalmic application, curcumin was entrapped in a polycationic calix[4]arene-based nanoaggregate by a simple and reproducible method. The calix[4]arene-curcumin supramolecular assembly (Calix-Cur) appeared as a clear colloidal solution consisting in micellar nanoaggregates with size, polydispersity index, surface potential, and drug loading percentage meeting the requirements for an ocular drug delivery system. The encapsulation in the calix[4]arene nanoassembly markedly enhanced the solubility, reduced the degradation, and improved the anti-inflammatory effects of curcumin compared to free curcumin in both in vitro and in vivo experiments. Calix-Cur did not compromise the viability of J774A.1 macrophages and suppressed pro-inflammatory marker expression in J774A.1 macrophages subjected to LPS-induced oxidative stress. Histological and immunohistochemical analyses showed that Calix-Cur reduced signs of inflammation in a rat model of LPS-induced uveitis when topically administrated in the eyes. Overall, the results supported the calix[4]arene nanoassembly as a promising nanocarrier for delivering curcumin to anterior ocular tissues.

Keywords: calix[4]arene; curcumin; drug delivery; inflammation; uveitis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Calixarenes / chemistry*
  • Cell Line
  • Curcumin / administration & dosage*
  • Curcumin / chemistry*
  • Curcumin / therapeutic use
  • Drug Carriers / chemistry
  • Inflammation / drug therapy
  • Macrophages / drug effects
  • Macrophages / metabolism
  • Ophthalmic Solutions / chemistry*
  • Phenols / chemistry*
  • Uveitis / drug therapy

Substances

  • Drug Carriers
  • Ophthalmic Solutions
  • Phenols
  • calix(4)arene
  • Calixarenes
  • Curcumin