High photodynamic activities of water-soluble inclusion complexes of 5,15-diazaporphyrins in cyclodextrin

• Published in: Organic & biomolecular chemistry Vol. 17; no. 12; pp. 3141 - 3149
• Main Authors: Satake, Shuhei, Shinmori, Hideyuki, Kawabata, Shigeki, Sugikawa, Kouta, Funabashi, Hisakage, Kuroda, Akio, Ikeda, Atsushi
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 20.03.2019; Royal Society of Chemistry
• Subjects: Absorption; Aromatic compounds; Chemistry; Chemistry, Organic; Cyclodextrin; Cyclodextrins; Fluorescence; Inclusion complexes; NMR; Nuclear magnetic resonance; Physical Sciences; Science & Technology; Singlet oxygen; Water chemistry; Wavelengths; OXYGEN; ACID; STABILITY; FULLERENE; PHOTOSENSITIZERS; GAMMA-CYCLODEXTRIN; PORPHYRIN; DERIVATIVES; FREE-BASE
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/c9ob00101h

Water-soluble inclusion complexes of 5,15-diazaporphyrin derivatives in the cavities of two trimethyl--cyclodextrins (TMe--CDxs) were synthesised. In the 2:1 complexes, two aryl groups of the diazaporphyrins protruded from the upper rims of two TMe--CDxs. The complexes displayed high photodynamic activity under photoirradiation at wavelengths longer than 620 nm. Although the substituents on the two aryl groups protruding from TMe--CDx barely affected intracellular uptake by HeLa cells, the cellular uptake of these complexes was as high as that of a TMe--CDx-tetra(4-hydroxyphenyl)porphyrin complex. Furthermore, the diazaporphyrins in the complexes with TMe--CDxs were able to generate high levels of singlet oxygen because of their strong absorption of light with wavelengths greater than 620 nm.