Complexation of biologically active amines by a water-soluble calix[5]arene A nanocalorimetric investigation

被引:26
作者
Arena, Giuseppe [1 ]
Pappalardo, Andrea [1 ]
Pappalardo, Sebastiano [1 ]
Gattuso, Giuseppe [2 ]
Notti, Anna [2 ]
Parisi, Melchiorre F. [2 ]
Pisagatti, Ilenia [2 ]
Sgarlata, Carmelo [1 ]
机构
[1] Univ Catania, Dipartimento Sci Chim, I-95125 Catania, Italy
[2] Univ Messina, Dipartimento Sci Chim, I-98166 Messina, Italy
关键词
Water-soluble calixarenes; Neurotransmitters; Trace amines; Host-guest complexes; Nano-ITC; Driving forces; ISOTHERMAL TITRATION CALORIMETRY; VANT-HOFF; SIGNIFICANT DISCREPANCIES; THERMODYNAMICS; ENTHALPIES; RECOGNITION; SULFONATOCALIXARENES; NEUROTRANSMITTERS; ASSOCIATION; RECEPTORS;
D O I
10.1007/s10973-015-4522-3
中图分类号
O414.1 [热力学];
学科分类号
摘要
Host-guest complexes of an amphiphilic water-soluble p-tert-butylcalix[5]arene bearing 4-sulphonatobutoxy groups at the narrow rim with trace amines (2-phenylethylamine and tyramine) and a neurotransmitter (dopamine), originally investigated via H-1 NMR, have been re-examined via ITC in order to double check the reliability of the values obtained through a van't Hoff analysis of the NMR data. The calorimetrically determined data confirm the existence of a 1:1 host-guest species; however, there are inconsistencies between the van't Hoff derived values and the values determined via direct calorimetry. These discrepancies do not result from proton displacement due to inclusion, but rather result from the temperature dependence of the van't Hoff enthalpies.
引用
收藏
页码:1073 / 1079
页数:7
相关论文
共 44 条
[11]   Calix[5]arene-Based Heteroditopic Receptor for 2-Phenylethylamine Hydrochloride [J].
Gargiulli, Claudia ;
Gattuso, Giuseppe ;
Liotta, Claudia ;
Notti, Anna ;
Parisi, Melchiorre F. ;
Pisagatti, Ilenia ;
Pappalardo, Sebastiano .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (11) :4350-4353
[12]   Encapsulation of monoamine neurotransmitters and trace amines by amphiphilic anionic calix[5]arene micelles [J].
Gattuso, Giuseppe ;
Notti, Anna ;
Pappalardo, Sebastiano ;
Parisi, Melchiorre F. ;
Pisagatti, Ilenia ;
Patane, Salvatore .
NEW JOURNAL OF CHEMISTRY, 2014, 38 (12) :5983-5990
[13]   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
[14]   A supramolecular amphiphile from a new water-soluble calix[5]arene and n-dodecylammonium chloride [J].
Gattuso, Giuseppe ;
Notti, Anna ;
Pappalardo, Andrea ;
Pappalardo, Sebastiano ;
Parisi, Melchiorre F. ;
Puntoriero, Fausto .
TETRAHEDRON LETTERS, 2013, 54 (02) :188-191
[15]   RECENT ADVANCES IN THE MOLECULAR-BIOLOGY OF DOPAMINE-RECEPTORS [J].
GINGRICH, JA ;
CARON, MG .
ANNUAL REVIEW OF NEUROSCIENCE, 1993, 16 :299-321
[16]   Simultaneous determination of equilibrium constants and enthalpy changes by titration calorimetry: Methods, instruments, and uncertainties [J].
Hansen, Lee D. ;
Fellingham, Gilbert W. ;
Russell, Donald J. .
ANALYTICAL BIOCHEMISTRY, 2011, 409 (02) :220-229
[17]   Quantitative NMR Spectroscopy using coaxial inserts containing a reference standard: Purity determinations for military nerve agents [J].
Henderson, TJ .
ANALYTICAL CHEMISTRY, 2002, 74 (01) :191-198
[18]   VANT HOFF REVISITED - ENTHALPY OF ASSOCIATION OF PROTEIN SUBUNITS - COMMENT [J].
HOLTZER, A .
JOURNAL OF PHYSICAL CHEMISTRY, 1995, 99 (34) :13048-13049
[19]   van't Hoff and calorimetric enthalpies from isothermal titration calorimetry: Are there significant discrepancies? [J].
Horn, JR ;
Russell, D ;
Lewis, EA ;
Murphy, KP .
BIOCHEMISTRY, 2001, 40 (06) :1774-1778
[20]   van't Hoff and calorimetric enthalpies II: Effects of linked equilibria [J].
Horn, JR ;
Brandts, JF ;
Murphy, KP .
BIOCHEMISTRY, 2002, 41 (23) :7501-7507