Monomerization of Phthalocyanines in Water via Their Supramolecular Interactions with Cucurbiturils

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Publikace nespadá pod Filozofickou fakultu, ale pod Přírodovědeckou fakultu. Oficiální stránka publikace je na webu muni.cz.
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KOCISCAKOVA Lucia RANDO Carola KOZLIKOVA Magdalena MACHACEK Miloslav NOVAKOVA Veronika ŠINDELÁŘ Vladimír ZIMČÍK Petr

Rok publikování 2023
Druh Článek v odborném periodiku
Časopis / Zdroj Journal of Organic Chemistry
Fakulta / Pracoviště MU

Přírodovědecká fakulta

Citace
www https://pubs.acs.org/doi/10.1021/acs.joc.2c02413
Doi http://dx.doi.org/10.1021/acs.joc.2c02413
Klíčová slova IN-VITRO; PHOTODYNAMIC THERAPY; ZINC PHTHALOCYANINE; PHOTOSENSITIZERS; COMPLEXES; FAMILY
Popis Aggregation of phthalocyanines (Pcs) represents a problematic feature that decreases the potential of these macrocycles in a number of applications. In this work, we present a supramolecular approach based on the interaction of aminoadamantyl-substituted Pcs with bulky and hydrophilic cucurbit[7]uril (CB[7]) to increase the levels of Pc monomers in water. A series of zinc(II) Pcs substituted at positions alpha or beta by an aminoadamantyl substituent (with a different level of alkylation of nitrogen) were prepared from the corresponding phthalonitriles. A H-1 nuclear magnetic resonance study of the interaction of phthalonitriles with CB[7] in water confirmed the formation of an inclusion complex with an aminoadamantyl moiety with Ka values of similar to 1012 M-1. The interaction of CB[7] with Pcs in water substantially weakened H-type aggregation and improved both fluorescence and singlet oxygen production, confirming that this approach is efficient for the monomerization of Pcs. In vitro evaluation of the photodynamic activity of prepared Pcs led to EC50 values in the submicromolar range on HeLa and SK-MEL-28 cells. However, the activity decreased for at least an order of magnitude after host-guest interaction with CB[7] despite better photophysical properties. This was attributed to a much lower uptake by cells due to the very bulky and hydrophilic character of the Pc-CB[7] assembly.
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