Enhancement in Guest Molecule Incorporation into Lipid Membranes in the Presence of Zinc‐Porphyrin Anchor Molecules. Issue 1 (3rd January 2019)

• Record Type: Journal Article
• Authors: Goto, Yuya; Sugikawa, Kouta; Ikeda, Atsushi
• Is Part Of: ChemistrySelect. Volume 4:Issue 1(2019)
• Page Start: 134
• Page End: 137
• Publication Date: 2019-01-03
• Subjects: coordination modes -- cyclodextrins -- drug delivery -- liposomes -- porphyrinoids; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201803462
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: Bipyridines with an octanol–water partition coefficient <1.9 were previously found to leak out of lipid membranes because of their hydrophilicity. However, we herein report that the addition of zinc‐porphyrin anchor molecules to the lipid resulted in reduced leakage percentages for both 3, 3′‐bipyridine and 4, 4′‐bipyridine due to the formation of coordination bonds between the pyridyl nitrogen atoms in the bipyridine molecules and the zinc(II) center in the zinc‐porphyrin moiety. In contrast, due to the general lack of interactions between 2, 2′‐bipyridine and the zinc‐porphyrin, the leakage percentage of 2, 2′‐bipyridine did not change upon the addition of zinc‐porphyrin to the lipid membranes. Abstract : Hydrophilic bipyridines are known to leak from hydrophobic lipid membranes. In this study, 3, 3′‐bipyridine and 4, 4′‐bipyridine were incorporated into lipid‐membranes by the presence of 5, 10, 15, 20‐tetraphenyl‐ 21H, 23H ‐porphine zinc(II) (Zn‐Por), thereby reducing leakage. This effect was barely observed for 2, 2′‐bipyridine due to its weaker interactions with Zn‐Por.