Anionic cyclodextrins as versatile hosts for pharmaceutical nanotechnology: Synthesis, drug delivery, enantioselectivity, contrast agents for MRI

Int J Pharm. 2015 Aug 15;492(1-2):275-90. doi: 10.1016/j.ijpharm.2015.06.004. Epub 2015 Jul 10.

Abstract

The review presents a full library of single-isomer primary rim per-carboxylate- and per-sulfate-α-, -β- and -γ-cyclodextrin (CD) derivatives and their potential for pharmaceutical nanotechnology. Recent advances in cyclodextrin chemistry have enabled robust methods for the synthesis of single-isomer anionic CDs. Numerous nanobio-applications have been already reported for these negatively charged derivatives, which alone or in combination with other biodegradable molecular platforms can become important carriers for targeted drug delivery and release. Specialized applications are also discussed, such as chiral separations, as well as the ability of per-6-carboxylated-cyclodextrins to coordinate with metal cations and especially with lanthanide cations that makes them candidates as contrast agents for Magnetic Resonance Imaging.

Keywords: Anionic cyclodextrins; Carboxylate-; Cation binding; Drug carriers; Hydroxypropyl-beta-cyclodextrin (PubChem CID: 90479739); Negatively charged; Sugammadex (PubChem CID: 6918584); Sulfate-; alpha-Cyclodextrin (PubChem CID: 444913); beta-Cyclodextrin (PubChem CID: 444041); gamma-Cyclodextrin (PubChem CID: 86575).

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Animals
  • Contrast Media / chemistry
  • Cyclodextrins / chemistry*
  • Drug Delivery Systems
  • Humans
  • Magnetic Resonance Imaging
  • Nanotechnology
  • Stereoisomerism
  • Technology, Pharmaceutical

Substances

  • Contrast Media
  • Cyclodextrins