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ISSN 1998-9539

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. Goldshlegera@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:
@2Corresponding author E-mail:
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 ФΔIV 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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