| KOCISCAKOVA, Lucia, Carola RANDO, Magdalena KOZLIKOVA, Miloslav MACHACEK, Veronika NOVAKOVA, Vladimír ŠINDELÁŘ a Petr ZIMČÍK. Monomerization of Phthalocyanines in Water via Their Supramolecular Interactions with Cucurbiturils. Journal of Organic Chemistry. WASHINGTON: AMER CHEMICAL SOC, 2023, roč. 88, č. 2, s. 988-1002. ISSN 0022-3263. Dostupné z: https://dx.doi.org/10.1021/acs.joc.2c02413. |
Další formáty:
BibTeX
LaTeX
RIS
@article{2364221,
author = {Kociscakova, Lucia and Rando, Carola and Kozlikova, Magdalena and Machacek, Miloslav and Novakova, Veronika and Šindelář, Vladimír and Zimčík, Petr},
article_location = {WASHINGTON},
article_number = {2},
doi = {http://dx.doi.org/10.1021/acs.joc.2c02413},
keywords = {IN-VITRO; PHOTODYNAMIC THERAPY; ZINC PHTHALOCYANINE; PHOTOSENSITIZERS; COMPLEXES; FAMILY},
language = {eng},
issn = {0022-3263},
journal = {Journal of Organic Chemistry},
title = {Monomerization of Phthalocyanines in Water via Their Supramolecular Interactions with Cucurbiturils},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.2c02413},
volume = {88},
year = {2023}
}
TY - JOUR
ID - 2364221
AU - Kociscakova, Lucia - Rando, Carola - Kozlikova, Magdalena - Machacek, Miloslav - Novakova, Veronika - Šindelář, Vladimír - Zimčík, Petr
PY - 2023
TI - Monomerization of Phthalocyanines in Water via Their Supramolecular Interactions with Cucurbiturils
JF - Journal of Organic Chemistry
VL - 88
IS - 2
SP - 988-1002
EP - 988-1002
PB - AMER CHEMICAL SOC
SN - 00223263
KW - IN-VITRO
KW - PHOTODYNAMIC THERAPY
KW - ZINC PHTHALOCYANINE
KW - PHOTOSENSITIZERS
KW - COMPLEXES
KW - FAMILY
UR - https://pubs.acs.org/doi/10.1021/acs.joc.2c02413
N2 - 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.
ER -
KOCISCAKOVA, Lucia, Carola RANDO, Magdalena KOZLIKOVA, Miloslav MACHACEK, Veronika NOVAKOVA, Vladimír ŠINDELÁŘ a Petr ZIMČÍK. Monomerization of Phthalocyanines in Water via Their Supramolecular Interactions with Cucurbiturils. \textit{Journal of Organic Chemistry}. WASHINGTON: AMER CHEMICAL SOC, 2023, roč.~88, č.~2, s.~988-1002. ISSN~0022-3263. Dostupné z: https://dx.doi.org/10.1021/acs.joc.2c02413.
|
