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 (156 Čína), Damien MONCELET (250 Francie), Laura GILBERG (276 Německo, domácí), Xiaoyong LU (156 Čína), Vladimír ŠINDELÁŘ (203 Česká republika, garant, domácí), Volker BRIKEN (840 Spojené státy) a Lyle ISAACS (840 Spojené státy)

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

Kód RIV

RIV/00216224:14310/16:00088612

Organizační jednotka

Přírodovědecká fakulta

DOI

http://dx.doi.org/10.1002/chem.201601796

UT WoS

000384807600005

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://dx.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 = {http://dx.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://dx.doi.org/10.1002/chem.201601796.

Podrobný výpis o publikaci