Selective recognition of biogenic amine hydrochlorides by heteroditopic dihomooxacalix[4]arenes

被引:20
作者
Gattuso, Giuseppe [1 ]
Notti, Anna [1 ]
Parisi, Melchiorre F. [1 ]
Pisagatti, Ilenia [1 ]
Marcos, Paula Maria [2 ,3 ]
Ascenso, Jose Rosario [4 ]
Brancatelli, Giovanna [5 ]
Geremia, Silvano [5 ]
机构
[1] Univ Messina, Dipartimento Sci Chim, I-98166 Messina, Italy
[2] Univ Lisbon, Ctr Ciencias Mol & Mat, Fac Ciencias, P-1749016 Lisbon, Portugal
[3] Univ Lisbon, Fac Farm, P-1649003 Lisbon, Portugal
[4] Inst Super Tecn, Ctr Quim Estrutural, P-1049001 Lisbon, Portugal
[5] Univ Trieste, Ctr Eccellenza Biocristallog, Dipartimento Sci Chim & Farmaceut, I-34127 Trieste, Italy
关键词
BINDING-PROPERTIES; MOLECULAR RECOGNITION; ALKALINE-EARTH; HEAVY-METAL; RECEPTORS; DOPAMINE; DERIVATIVES; SEROTONIN; TRANSITION; IONOPHORES;
D O I
10.1039/c4nj01423e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Ion-pair recognition-complexation of monoamine neurotransmitters and trace amine hydrochlorides takes place - with outstanding efficiency and selectivity - within the pi-rich cavity and the pocket formed at the lower rim by the two ureido moieties of the tailor-made dihomooxacalixarene receptors 1 and 2. The solid-state structure of 1 is also reported.
引用
收藏
页码:817 / 821
页数:5
相关论文
共 43 条
[11]   Self-assembly dynamics of modular homoditopic bis-calix[5]arenes and long-chain α,ω-alkanediyldiammonium components [J].
Gattuso, Giuseppe ;
Notti, Anna ;
Pappalardo, Andrea ;
Parisi, Melchlorre F. ;
Pisagatti, Ilenia ;
Pappalardo, Sebastiano ;
Garozzo, Domenico ;
Messina, Angela ;
Cohen, Yoram ;
Slovak, Sarit .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (18) :7280-7289
[12]   Recognition in water of bioactive substrates by a sulphonato p-tert-butylcalix[5]arene [J].
Gattuso, Giuseppe ;
Notti, Anna ;
Pappalardo, Sebastiano ;
Parisi, Melchiorre F. ;
Pisagatti, Ilenia .
SUPRAMOLECULAR CHEMISTRY, 2014, 26 (7-8) :597-600
[13]   Picturing the induced fit of calix[5]arenes upon n-alkylammonium cation binding [J].
Gattuso, Giuseppe ;
Notti, Anna ;
Pappalardo, Sebastiano ;
Parisi, Melchiorre F. ;
Pilati, Tullio ;
Terraneo, Giancarlo .
CRYSTENGCOMM, 2012, 14 (08) :2621-2625
[14]   Ion-pair separation via selective inclusion/segregation processes [J].
Gattuso, Giuseppe ;
Notti, Anna ;
Pappalardo, Sebastiano ;
Parisi, Melchiorre F. ;
Pilati, Tullio ;
Resnati, Giuseppe ;
Terraneo, Giancarlo .
CRYSTENGCOMM, 2009, 11 (07) :1204-1206
[15]   A simple ionic triphenylene receptor for catecholamines, serotonin and D-glucosamine in buffered water [J].
Givelet, Cecile ;
Bibal, Brigitte .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (21) :7457-7460
[16]   Clinical utility of monoamine neurotransmitter metabolite analysis in cerebrospinal fluid [J].
Hyland, Keith .
CLINICAL CHEMISTRY, 2008, 54 (04) :633-641
[17]   XDS [J].
Kabsch, Wolfgang .
ACTA CRYSTALLOGRAPHICA SECTION D-BIOLOGICAL CRYSTALLOGRAPHY, 2010, 66 :125-132
[18]   Homooxacalix[3]arene derivatives as ionophores for serotonin-selective membrane electrodes [J].
Katsu, T ;
Ido, K ;
Sagara, S ;
Tsubaki, K ;
Fuji, K .
ELECTROANALYSIS, 2003, 15 (04) :287-293
[19]   Artificial receptors that provides a preorganized hydrophobic environment: A biomimetic approach to dopamine recognition in water [J].
Kim, J ;
Raman, B ;
Ahn, KH .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01) :38-45
[20]   Ion pair receptors [J].
Kim, Sung Kuk ;
Sessler, Jonathan L. .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (10) :3784-3809