Water Solubilization of Phthalocyanine Derivatives via Interactions of Long Alkyl Chains and Cyclodextrins: Potential Complexes for Photodynamic Therapy. Issue 10 (21st July 2020)

• Record Type: Journal Article
• Authors: Goto, Yuya; Hino, Shodai; Sugikawa, Kouta; Kawasaki, Riku; Ikeda, Atsushi
• Is Part Of: Asian journal of organic chemistry. Volume 9:Issue 10(2020)
• Page Start: 1589
• Page End: 1596
• Publication Date: 2020-07-21
• Subjects: phthalocyanines -- cyclodextrins -- host-guest systems -- drug delivery -- supramolecular chemistry; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202000076
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: Five types of cyclodextrins, based on α‐cyclodextrin (α‐CDx) and β‐cyclodextrin (β‐CDx), were used to make hydrophobic phthalocyanine (Pc) derivatives with long alkyl chains soluble in water via a high‐speed vibration milling method. Aqueous solutions of DMe‐β‐CDx‐based complexes were found to be the most stable, for at least 1 week over those containing α‐CDx. Although DMe‐β‐CDx complexes containing a free‐base Pc and Zn−Pc with eight dodecyl chains showed greater solubility than their α‐CDx‐base counterparts, α‐CDx complexes containing a free‐base Pc and Zn−Pc with eight dodecyl chains show no self‐aggregation of the Pcs and, as a result, exhibit fluorescence signals. Overall, it was found that the α‐CDx−Zn−Pc complex exhibits higher photodynamic activity than that of the commercially available and widely used photosensitizer Photofrin. Abstract : A phthalocyanine derivative with eight long alkyl chains was soluble in water through interactions with α‐cyclodextrins. The complex exhibited high photodynamic activity toward the HeLa cells.