Monomerization of Phthalocyanines in Water via Their
Supramolecular Interactions with Cucurbiturils

J 2023

Monomerization of Phthalocyanines in Water via Their Supramolecular Interactions with Cucurbiturils

KOCISCAKOVA, Lucia, Carola RANDO, Magdalena KOZLIKOVA, Miloslav MACHACEK, Veronika NOVAKOVA et. al.

Základní údaje

Originální název

Monomerization of Phthalocyanines in Water via Their Supramolecular Interactions with Cucurbiturils

Autoři

KOCISCAKOVA, Lucia, Carola RANDO (380 Itálie, domácí), Magdalena KOZLIKOVA, Miloslav MACHACEK, Veronika NOVAKOVA, Vladimír ŠINDELÁŘ (203 Česká republika, garant, domácí) a Petr ZIMČÍK

Vydání

Journal of Organic Chemistry, WASHINGTON, AMER CHEMICAL SOC, 2023, 0022-3263

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 3.600 v roce 2022

Kód RIV

RIV/00216224:14310/23:00133131

Organizační jednotka

Přírodovědecká fakulta

DOI

http://dx.doi.org/10.1021/acs.joc.2c02413

UT WoS

000911953800001

Klíčová slova anglicky

IN-VITRO; PHOTODYNAMIC THERAPY; ZINC PHTHALOCYANINE; PHOTOSENSITIZERS; COMPLEXES; FAMILY

Štítky

rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 30. 1. 2024 21:10, Mgr. Pavla Foltynová, Ph.D.

Anotace

V originále

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.

Návaznosti

EF17_043/0009632, projekt VaV

Název: CETOCOEN Excellence

GA20-09212S, projekt VaV

Název: Využití supramolekulárních interakcí ke zlepšení fotodynamických vlastností fotosensitizérů

Investor: Grantová agentura ČR, Využití supramolekulárních interakcí ke zlepšení fotodynamických vlastností fotosensitizérů

LM2018121, projekt VaV

Název: Výzkumná infrastruktura RECETOX (Akronym: RECETOX RI)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, RECETOX RI

MUNI/A/1209/2022, interní kód MU

Název: Molekuly, komplexy, makrocykly a xerogely

Investor: Masarykova univerzita, Molekuly, komplexy, makrocykly a xerogely

857560, interní kód MU
(Kód CEP: EF17_043/0009632)

Název: CETOCOEN Excellence (Akronym: CETOCOEN Excellence)

Investor: Evropská unie, CETOCOEN Excellence, Spreading excellence and widening participation

Citovat

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.

@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.

Podrobný výpis o publikaci