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Water Solubilization of Phthalocyanine Derivatives via Interactions of Long Alkyl Chains and Cyclodextrins: Potential Complexes for Photodynamic Therapy
Author(s) -
Goto Yuya,
Hino Shodai,
Sugikawa Kouta,
Kawasaki Riku,
Ikeda Atsushi
Publication year - 2020
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202000076
Subject(s) - chemistry , photosensitizer , phthalocyanine , alkyl , cyclodextrin , aqueous solution , solubility , fluorescence , free base , photochemistry , hydrophobic effect , organic chemistry , combinatorial chemistry , physics , salt (chemistry) , quantum mechanics
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.