Formation of lipid membrane‐incorporated small π‐molecules bearing hydrophilic groups

Ikeda Atsushi

Ashizawa Kengo

Tsuchiya Yuki

Ueda Masafumi

Sugikawa Kouta

RSC Advances

Nineteen poorly water‐soluble π‐conjugated molecules were evaluated in terms of their ability to be stably incorporated into lipid membranes. The resulting lipid membrane-incorporated π‐conjugated guest molecules (LMIGs) were classified into four categories, including (i) those that formed stable LMIGs; (ii) those where some of guest molecules precipitated; (iii) those that formed small self‐aggregates consisting of lipids and/or guest molecules; and (iv) those that leaked some of the guest molecules into the bulk water. Compounds belonging to category (ii) were confirmed by UV‐vis absorption analysis. In contrast, compounds belonging to categories (i), (iii) and (iv) were discriminated based on their 1H NMR spectra and the broadening or disappearance of the peaks of the guest molecules and the lipids in LMIGs and large liposomes. Several LMIGs could be converted from one category to another using other lipids. Furthermore, the guest molecules belonging to category (iv) were successfully predicted using the octanol‐water partition coefficient, which was calculated by simulation.

Chemistry [ 430 ]

eng

Royal Society of Chemistry

This journal is © The Royal Society of Chemistry 2016

This is the accepted manuscript of an article is available at http://dx.doi.org/10.1039/C6RA18635A.

This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。

[ISSN] 2046-2069

[DOI] 10.1039/C6RA18635A