Glycoluril-Derived Molecular Clips are Potent and Selective
Receptors for Cationic Dyes in Water

J 2016

Glycoluril-Derived Molecular Clips are Potent and Selective Receptors for Cationic Dyes in Water

SHE, Nengfang; Damien MONCELET; Laura GILBERG; Xiaoyong LU; Vladimír ŠINDELÁŘ et al.

Základní údaje

Originální název

Glycoluril-Derived Molecular Clips are Potent and Selective Receptors for Cationic Dyes in Water

Autoři

SHE, Nengfang; Damien MONCELET; Laura GILBERG; Xiaoyong LU; Vladimír ŠINDELÁŘ; Volker BRIKEN a Lyle ISAACS

Vydání

Chemistry - A European Journal, WEINHEIM, Wiley, 2016, 0947-6539

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Německo

Utajení

není předmětem státního či obchodního tajemství

Impakt faktor

Impact factor: 5.317

Označené pro přenos do RIV

Ano

Kód RIV

RIV/00216224:14310/16:00088612

Organizační jednotka

Přírodovědecká fakulta

Klíčová slova anglicky

cation-pi interactions; dyes; glycoluril; hydrophobic effects; molecular clip

Štítky

AKR, rivok

Změněno: 26. 4. 2017 22:55, Ing. Andrea Mikešková

Anotace

V originále

Molecular clip 1 remains monomeric in water and engages in host-guest recognition processes with suitable guests. We report the K-a values for 32 1.guest complexes measured by H-1 NMR, UV/Vis, and fluorescence titrations. The cavity of 1 is shaped by aromatic surfaces of negative electrostatic potential and therefore displays high affinity and selectivity for planar and cationic aromatic guests that distinguishes it from CB[n] receptors that prefer aliphatic over aromatic guests. Electrostatic effects play a dominant role in the recognition process whereby ion-dipole interactions may occur between ammonium ions and the C=O groups of 1, between the SO3- groups of 1 and pendant cationic groups on the guest, and within the cavity of 1 by cation-pi interactions. Host 1 displays a high affinity toward dicationic guests with large planar aromatic surfaces (e.g. naphthalene diimide NDI + and perylene diimide PDI +) and cationic dyes derived from acridine (e.g. methylene blue and azure A). The critical importance of cation-pi interactions was ascertained by a comparison of analogous neutral and cationic guests (e.g. methylene violet vs. methylene blue; quinoline vs. N-methylquinolinium; acridine vs. N-methylacridinium; neutral red vs. neutral red H+) the affinities of which differ by up to 380-fold. We demonstrate that the high affinity of 1 toward methylene blue (K-a = 3.92 x 10(7) M-1; K-d = 25 nm) allows for the selective sequestration and destaining of U87 cells stained with methylene blue.

Návaznosti

EE2.3.30.0009, projekt VaV

Název: Zaměstnáním čerstvých absolventů doktorského studia k vědecké excelenci

GA13-15576S, projekt VaV

Název: Syntéza a supramolekulární vlastnosti bambusurilů

Investor: Grantová agentura ČR, Syntéza a supramolekulární vlastnosti bambusurilů

LM2015051, projekt VaV

Název: Centrum pro výzkum toxických látek v prostředí (Akronym: RECETOX RI)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Výzkumná infrastruktura RECETOX

LO1214, projekt VaV

Název: Centrum pro výzkum toxických látek v prostředí (Akronym: RECETOX)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Centrum pro výzkum toxických látek v prostředí

Citovat

SHE, Nengfang; Damien MONCELET; Laura GILBERG; Xiaoyong LU; Vladimír ŠINDELÁŘ; Volker BRIKEN a Lyle ISAACS. Glycoluril-Derived Molecular Clips are Potent and Selective Receptors for Cationic Dyes in Water. Chemistry - A European Journal. WEINHEIM: Wiley, 2016, roč. 22, č. 43, s. 15270-15279. ISSN 0947-6539. Dostupné z: https://doi.org/10.1002/chem.201601796.

@article{1369947,
   author = {She, Nengfang and Moncelet, Damien and Gilberg, Laura and Lu, Xiaoyong and Šindelář, Vladimír and Briken, Volker and Isaacs, Lyle},
   article_location = {WEINHEIM},
   article_number = {43},
   doi = {https://doi.org/10.1002/chem.201601796},
   keywords = {cation-pi interactions; dyes; glycoluril; hydrophobic effects; molecular clip},
   language = {eng},
   issn = {0947-6539},
   journal = {Chemistry - A European Journal},
   title = {Glycoluril-Derived Molecular Clips are Potent and Selective Receptors for Cationic Dyes in Water},
   volume = {22},
   year = {2016}
}

TY  - JOUR
ID  - 1369947
AU  - She, Nengfang - Moncelet, Damien - Gilberg, Laura - Lu, Xiaoyong - Šindelář, Vladimír - Briken, Volker - Isaacs, Lyle
PY  - 2016
TI  - Glycoluril-Derived Molecular Clips are Potent and Selective Receptors for Cationic Dyes in Water
JF  - Chemistry - A European Journal
VL  - 22
IS  - 43
SP  - 15270-15279
EP  - 15270-15279
PB  - Wiley
SN  - 09476539
KW  - cation-pi interactions
KW  - dyes
KW  - glycoluril
KW  - hydrophobic effects
KW  - molecular clip
N2  - Molecular clip 1 remains monomeric in water and engages in host-guest recognition processes with suitable guests. We report the K-a values for 32 1.guest complexes measured by H-1 NMR, UV/Vis, and fluorescence titrations. The cavity of 1 is shaped by aromatic surfaces of negative electrostatic potential and therefore displays high affinity and selectivity for planar and cationic aromatic guests that distinguishes it from CB[n] receptors that prefer aliphatic over aromatic guests. Electrostatic effects play a dominant role in the recognition process whereby ion-dipole interactions may occur between ammonium ions and the C=O groups of 1, between the SO3- groups of 1 and pendant cationic groups on the guest, and within the cavity of 1 by cation-pi interactions. Host 1 displays a high affinity toward dicationic guests with large planar aromatic surfaces (e.g. naphthalene diimide NDI + and perylene diimide PDI +) and cationic dyes derived from acridine (e.g. methylene blue and azure A). The critical importance of cation-pi interactions was ascertained by a comparison of analogous neutral and cationic guests (e.g. methylene violet vs. methylene blue; quinoline vs. N-methylquinolinium; acridine vs. N-methylacridinium; neutral red vs. neutral red H+) the affinities of which differ by up to 380-fold. We demonstrate that the high affinity of 1 toward methylene blue (K-a = 3.92 x 10(7) M-1; K-d = 25 nm) allows for the selective sequestration and destaining of U87 cells stained with methylene blue.
ER  -

SHE, Nengfang; Damien MONCELET; Laura GILBERG; Xiaoyong LU; Vladimír ŠINDELÁŘ; Volker BRIKEN a Lyle ISAACS. Glycoluril-Derived Molecular Clips are Potent and Selective Receptors for Cationic Dyes in Water. \textit{Chemistry - A European Journal}. WEINHEIM: Wiley, 2016, roč.~22, č.~43, s.~15270-15279. ISSN~0947-6539. Dostupné z: https://doi.org/10.1002/chem.201601796.

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