Phthalocyanines and Metal Phthalocyanines with Phosphoryl Groups: Supramolecular Ensembles, Photochemical and Photobiological Properties

Polina A. Mikhina,^a,b Denis V. Mishchenko,^a,c Mariya A. Lapshina,^a Pavel A. Tarakanov,^a,d@1 Vladimir E. Baulin,^d and Nataliya F. Goldshleger^a@2

^aInstitute of Problems of Chemical Physics RAS, 142432 Chernogolovka, Russia

^bLomonosov Moscow State University, 119991 Moscow, Russia

^cScientific and Educational Center of Moscow State Regional University in Chernogolovka, 141014 Mytishchi, Russia

^dInstitute of Physiologically Active Compounds RAS, 1142432 Chernogolovka, Russia

^@¹Corresponding author E-mail: pavel369@inbox.ru

^@²Corresponding author E-mail: nfgold@icp.ac.ru

DOI: 10.6060/mhc200391g

Macroheterocycles 2020 13(2) 113-125

Based on the supramolecular approach, the conditions for the solubilization and disaggregation of phosphoryl-containing phthalocyanines and their metal complexes (I-IV) in the aqueous environment due to the formation of supramolecular ensembles are found. For the first time, zinc phthalocyaninate with phosphoryl-containing groups in the macrocycle (IV) was studied as a potential photosensitizer in various media. The supramolecular organization of Ps in solution, the singlet oxygen quantum yield Ф_Δ^IV in DMSO (0.48 ± 0.05) and an organized microheterogeneous medium based on cationic cetyltriphenylphosphonium bromide (0.54 ± 0,05) in combination with low cytotoxicity, sufficiently high phototoxicity (IC₅₀ dose) and the formation of intracellular reactive oxygen species in vitro upon irradiation allow one to consider phosphoryl-containing phthalo- and metallophthalocyanines as deserving of attention and further research as compounds useful for PDT.

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Phthalocyanines and Metal Phthalocyanines with Phosphoryl Groups: Supramolecular Ensembles, Photochemical and Photobiological Properties

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