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.

Basic information

Original name

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

Authors

SHE, Nengfang (156 China), Damien MONCELET (250 France), Laura GILBERG (276 Germany, belonging to the institution), Xiaoyong LU (156 China), Vladimír ŠINDELÁŘ (203 Czech Republic, guarantor, belonging to the institution), Volker BRIKEN (840 United States of America) and Lyle ISAACS (840 United States of America)

Edition

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

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

Germany

Confidentiality degree

není předmětem státního či obchodního tajemství

Impact factor

Impact factor: 5.317

RIV identification code

RIV/00216224:14310/16:00088612

Organization unit

Faculty of Science

DOI

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

UT WoS

000384807600005

Keywords in English

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

Abstract

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.

Links

EE2.3.30.0009, research and development project

Name: Zaměstnáním čerstvých absolventů doktorského studia k vědecké excelenci

GA13-15576S, research and development project

Name: Syntéza a supramolekulární vlastnosti bambusurilů

Investor: Czech Science Foundation

LM2015051, research and development project

Name: Centrum pro výzkum toxických látek v prostředí (Acronym: RECETOX RI)

Investor: Ministry of Education, Youth and Sports of the CR

LO1214, research and development project

Name: Centrum pro výzkum toxických látek v prostředí (Acronym: RECETOX)

Investor: Ministry of Education, Youth and Sports of the CR

Citovat

SHE, Nengfang, Damien MONCELET, Laura GILBERG, Xiaoyong LU, Vladimír ŠINDELÁŘ, Volker BRIKEN and Lyle ISAACS. Glycoluril-Derived Molecular Clips are Potent and Selective Receptors for Cationic Dyes in Water. Chemistry - A European Journal. WEINHEIM: Wiley, 2016, vol. 22, No 43, p. 15270-15279. ISSN 0947-6539. Available from: 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 and Lyle ISAACS. Glycoluril-Derived Molecular Clips are Potent and Selective Receptors for Cationic Dyes in Water. \textit{Chemistry - A European Journal}. WEINHEIM: Wiley, 2016, vol.~22, No~43, p.~15270-15279. ISSN~0947-6539. Available from: https://dx.doi.org/10.1002/chem.201601796.

Detailed Information on Publication Record