Cucurbiturils: from synthesis to high-affinity binding and catalysis

被引:1256
作者
Assaf, Khaleel I. [1 ]
Nau, Werner M. [1 ]
机构
[1] Jacobs Univ Bremen, D-28759 Bremen, Germany
关键词
HOST-GUEST COMPLEXES; EARTH METAL-IONS; ENANTIODIFFERENTIATING 4+4 PHOTOCYCLODIMERIZATION; SUPRAMOLECULAR SELF-ASSEMBLIES; FLUORESCENT DYE DISPLACEMENT; HIGH-ENERGY WATER; MOLECULAR RECOGNITION; GAMMA-CYCLODEXTRIN; PK(A) SHIFTS; ELECTROCHEMICAL PROPERTIES;
D O I
10.1039/c4cs00273c
中图分类号
O6 [化学];
学科分类号
070301 [无机化学];
摘要
In the wide area of supramolecular chemistry, cucurbit[n]urils (CBn) present themselves as a young family of molecular containers, able to form stable complexes with various guests, including drug molecules, amino acids and peptides, saccharides, dyes, hydrocarbons, perfluorinated hydrocarbons, and even high molecular weight guests such as proteins (e.g., human insulin). Since the discovery of the first CBn, CB6, the field has seen tremendous growth with respect to the synthesis of new homologues and derivatives, the discovery of record binding affinities of guest molecules in their hydrophobic cavity, and associated applications ranging from sensing to drug delivery. In this review, we discuss in detail the fundamental properties of CBn homologues and their cyclic derivatives with a focus on their synthesis and their applications in catalysis.
引用
收藏
页码:394 / 418
页数:25
相关论文
共 248 条
[1]
New Chiral Cyclohexylhemicucurbit[6]uril [J].
Aav, Riina ;
Shmatova, Elena ;
Reile, Indrek ;
Borissova, Maria ;
Topic, Filip ;
Rissanen, Kari .
ORGANIC LETTERS, 2013, 15 (14) :3786-3789
[2]
Abraham R. J., 1973, J CHEM SOC PERK T, V2, P1521
[3]
Cucurbiturils as fluorophilic receptors [J].
Assaf, Khaleel I. ;
Nau, Werner M. .
SUPRAMOLECULAR CHEMISTRY, 2014, 26 (09) :657-669
[4]
Manipulating photochemical reactivity of coumarins within cucurbituril nanocavities [J].
Barooah, Nilotpal ;
Pemberton, Barry C. ;
Sivaguru, J. .
ORGANIC LETTERS, 2008, 10 (15) :3339-3342
[5]
Non-covalent interactions of coumarin dyes with cucurbit[7]uril macrocycle: modulation of ICT to TICT state conversion [J].
Barooah, Nilotpal ;
Mohanty, Jyotirmayee ;
Pal, Haridas ;
Bhasikuttan, Achikanath C. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (26) :5055-5062
[6]
Photodimerization and complexation dynamics of coumarins in the presence of cucurbit[8]urils [J].
Barooah, Nilotpal ;
Pemberton, Barry C. ;
Johnson, Alexander C. ;
Sivaguru, J. .
PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2008, 7 (12) :1473-1479
[7]
Supramolecular Catalysis by Cucurbit[7]uril and Cyclodextrins: Similarity and Differences [J].
Basilio, Nuno ;
Garcia-Rio, L. ;
Moreira, J. A. ;
Pessego, M. .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (03) :848-855
[8]
Behrend R, 1905, LIEBIGS ANN CHEM, V339, P1
[9]
Toward theranostic nanoparticles: CB[7]-functionalized iron oxide for drug delivery and MRI [J].
Benyettou, Farah ;
Milosevic, Irena ;
Lalatonne, Yoann ;
Warmont, Fabienne ;
Assah, Rana ;
Olsen, John-Carl ;
Jouaid, Mustapha ;
Motte, Laurence ;
Platas-Iglesias, Carlos ;
Trabolsi, Ali .
JOURNAL OF MATERIALS CHEMISTRY B, 2013, 1 (38) :5076-5082
[10]
Drastically decreased reactivity of thiols and disulfides complexed by cucurbit[6]uril [J].
Berbeci, Lidia Strimbu ;
Wang, Wei ;
Kaifer, Angel E. .
ORGANIC LETTERS, 2008, 10 (17) :3721-3724