Encapsulation of monoamine neurotransmitters and trace amines by amphiphilic anionic calix[5]arene micelles

被引:30
作者
Gattuso, Giuseppe [1 ]
Notti, Anna [1 ]
Pappalardo, Sebastiano [2 ]
Parisi, Melchiorre F. [1 ]
Pisagatti, Ilenia [1 ]
Patane, Salvatore [3 ]
机构
[1] Univ Messina, Dipartimento Sci Chim, I-98166 Messina, Italy
[2] Univ Catania, Dipartimento Sci Chim, I-95125 Catania, Italy
[3] Univ Messina, Dipartimento Fis & Sci Terra, I-98166 Messina, Italy
关键词
SODIUM DODECYL-SULFATE; SUPRAMOLECULAR AMPHIPHILE; MOLECULAR RECOGNITION; TRITON X-100; DOPAMINE; SURFACTANT; RECEPTORS; PHENOL; HOST; SEROTONIN;
D O I
10.1039/c4nj01184h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The interactions between hydrochloride salts of biologically relevant amines and micelles formed by a water-soluble p-tert-butylcalix[5]arene were investigated by means of H-1 NMR spectroscopy, using a combination of NOESY and DOSY techniques. DOSY measurements were conveniently employed to assess the micelle affinity towards the target guests (phenylethylamine approximate to histamine approximate to serotonin > tyramine > dopamine > norepinephrine), whereas NOESY studies revealed the approximate position of these cationic guests within the different micellar regions. In general, all the guests were located in the palisade region of the micelle, with the exception of phenethylamine and histamine, the former being bound to the micellar core as well as the palisade, the tatter preferring the outer shell of the micelle.
引用
收藏
页码:5983 / 5990
页数:8
相关论文
共 57 条
[1]   Calixarene-Based Surfactants: Conformational-Dependent Solvation Shells for the Alkyl Chains [J].
Basilio, Nuno ;
Garcia-Rio, Luis .
CHEMPHYSCHEM, 2012, 13 (09) :2368-2376
[2]   Insights into the Structure of the Supramolecular Amphiphile Formed by a Sulfonated Calix[6]arene and Alkyltrimethylammonium Surfactants [J].
Basilio, Nuno ;
Martin-Pastor, M. ;
Garcia-Rio, Luis .
LANGMUIR, 2012, 28 (16) :6561-6568
[3]   Calixarene-Based Surfactants: Evidence of Structural Reorganization upon Micellization [J].
Basilio, Nuno ;
Garcia-Rio, Luis ;
Martin-Pastor, Manuel .
LANGMUIR, 2012, 28 (05) :2404-2414
[4]   Mini-review: Artificial catecholamine receptors in aqueous media [J].
Chui, Jonathan K. W. ;
Fyles, Tom M. .
SUPRAMOLECULAR CHEMISTRY, 2008, 20 (04) :397-405
[5]   Diffusion NMR spectroscopy in supramolecular and combinatorial chemistry: An old parameter - New insights [J].
Cohen, Y ;
Avram, L ;
Frish, L .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (04) :520-554
[6]   Elevated urinary dopamine in adults and children [J].
Davidson, DF .
ANNALS OF CLINICAL BIOCHEMISTRY, 2005, 42 :200-207
[7]   Shape recognition of alkylammonium ions by 1,3-bridged calix[5]arene crown-6 ethers:: Endo- vs exo-cavity complexation [J].
De Salvo, G ;
Gattuso, G ;
Notti, A ;
Parisi, MF ;
Pappalardo, S .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (03) :684-692
[8]   Interaction of dopamine and acetylcholine with an amphiphilic resorcinarene receptor in aqueous micelle system [J].
Demura, M ;
Yoshida, T ;
Hirokawa, T ;
Kumaki, Y ;
Aizawa, T ;
Nitta, K ;
Bitter, I ;
Tóth, K .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (05) :1367-1370
[9]   Self-aggregation and supramolecular structure investigations of triton X-100 and SDP2S by NOESY and diffusion ordered NMR spectroscopy [J].
Denkova, Pavletta S. ;
Van Lokeren, Luk ;
Verbruggen, Ingrid ;
Willem, Rudolph .
JOURNAL OF PHYSICAL CHEMISTRY B, 2008, 112 (35) :10935-10941
[10]   Phenol induced growth in Triton X-100 micelles: Effect of pH and phenols' hydrophobicity [J].
Dharaiya, N. ;
Bahadur, P. .
COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS, 2012, 410 :81-90