Enhancement of iodinin solubility by encapsulation into cyclodextrin nanoparticles

Anthony Prandina; Lars Herfindal; Sylvie Radix; Pål Rongved; Stein O Døskeland; Marc Le Borgne; Florent Perret

doi:10.1080/14756366.2017.1421638

Enhancement of iodinin solubility by encapsulation into cyclodextrin nanoparticles

J Enzyme Inhib Med Chem. 2018 Dec;33(1):370-375. doi: 10.1080/14756366.2017.1421638.

Authors

Anthony Prandina^{1

2}, Lars Herfindal³, Sylvie Radix¹, Pål Rongved², Stein O Døskeland⁴, Marc Le Borgne¹, Florent Perret⁵

Affiliations

¹ a Université de Lyon, Université Claude Bernard Lyon 1, Faculté de Pharmacie - ISPB, EA 4446 Bioactive Molecules and Medicinal Chemistry, SFR Santé Lyon-Est CNRS UMS3453 - INSERM US7 , Lyon Cedex , France.
² b Department of Pharmaceutical Chemistry, School of Pharmacy , University of Oslo , Oslo , Norway.
³ c Centre for Pharmacy, Department of Clinical Science , University of Bergen , Bergen , Norway.
⁴ d Department of Biomedicine , University of Bergen , Bergen , Norway.
⁵ e Université de Lyon, Université Claude Bernard Lyon 1, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, UMR 5246 CNRS - CPE Lyon - INSA , Villeurbanne Cedex , France.

Abstract

Phenazine is known to regroup planar nitrogen-containing heterocyclic compounds. It was used here to enhance the bioavailability of the biologically important compound iodinin, which is near insoluble in aqueous solutions. Its water solubility has led to the development of new formulations using diverse amphiphilic α-cyclodextrins (CDs). With the per-[6-desoxy-6-(3-perfluorohexylpropanethio)-2,3-di-O-methyl]-α-CD, we succeeded to get iodinin-loaded nanoformulations with good parameters such as a size of 97.9 nm, 62% encapsulation efficiency and efficient control release. The study presents an interesting alternative to optimizing the water solubility of iodinin by chemical modifications of iodinin.

Keywords: Iodinin; amphiphilic α-cyclodextrin; encapsulation; nanoparticles; solubility.

MeSH terms

Animals
Apoptosis / drug effects
Cell Line, Tumor
Dose-Response Relationship, Drug
Molecular Structure
Nanoparticles / chemistry*
Particle Size
Phenazines / chemistry*
Phenazines / pharmacology
Rats
Solubility
Structure-Activity Relationship
Surface Properties
alpha-Cyclodextrins / chemistry*
alpha-Cyclodextrins / pharmacology

Substances

Phenazines
alpha-Cyclodextrins
phenazine
iodinin

Grants and funding

The present work was supported by the “Partenariats Hubert Curien” (PHC) (Campus France, Programme Aurora, Grant Agreement No. 27460VC), by the Norwegian Research Council [Grant Agreement No. 213191/F11] and the Norwegian Cancer Society (Project no.: 4529447). Pr. Marc Le Borgne also thanks the “Institut français d’Oslo” for their support via the Åsgard Programme 2010. This scientific work was also supported by financial support from Rhône-Alpes region through an Explo’ra Sup scholarship (academic year 2012–2013).