Characterization of the species-specific acid-base equilibria of adrenaline and noradrenaline

被引:4
作者
Mirzahosseini, Arash [1 ,2 ]
Palla, Tamas [1 ,2 ]
Orgovan, Gabor [1 ,2 ]
Toth, Gergo [1 ,2 ]
Noszal, Bela [1 ,2 ]
机构
[1] Semmelweis Univ, Dept Pharmaceut Chem, Hogyes E U 9, H-1092 Budapest, Hungary
[2] Hungarian Acad Sci, Res Grp Drugs Abuse & Doping Agents, Budapest, Hungary
关键词
Catecholamine; Epinephrine; pK(a); Microspeciation; NMR-pH titration; DISSOCIATION-CONSTANTS; METAL-IONS; COMPLEXES; DOPAMINE; IONIZATION; STABILITY; AMINES; PH;
D O I
10.1016/j.jpba.2019.02.035
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
Adrenaline, noradrenaline, the biogenic catecholamines of vital importance, and four closely related compounds were studied by H-1 NMR-pH titrations, and the resulting acid-base properties are quantified in terms of three macroscopic and twelve microscopic protonation constants for both molecules. The species-specific basicities are interpreted by means of inductive and shielding effects by comparing the protonation constants of the catecholamines, including dopamine. The site-specific basicities determined this way could be key parameters for the interpretation of biochemical behavior. (C) 2019 Published by Elsevier B.V.
引用
收藏
页码:215 / 219
页数:5
相关论文
共 25 条
[1]   COPPER(II), COBALT(II), AND NICKEL(II) COMPLEXES OF VARIOUS ANTIHISTAMINIC COMPOUNDS - THEIR STABILITY AND THERMODYNAMIC VALUES [J].
ANDREWS, AC ;
OBRIEN, TD ;
LYONS, TD .
JOURNAL OF THE CHEMICAL SOCIETY, 1962, (MAY) :1776-&
[2]   COMPARATIVE STUDY ON IONIZATION OF CATECHOL AMINES IN AQUEOUS-SOLUTIONS [J].
ANTIKAINEN, PJ ;
WITIKAINEN, U .
ACTA CHEMICA SCANDINAVICA, 1973, 27 (06) :2075-2082
[3]   A two model receptor system of the alpha1D adrenergic receptor to describe interactions with epinephrine and BMY7378 [J].
Bautista, DL ;
Morris, DH ;
Stein, L ;
Asher, W ;
Hammitt, T .
JOURNAL OF CHEMICAL INFORMATION AND MODELING, 2006, 46 (01) :334-344
[4]  
Bjerrum N, 1923, Z PHYS CHEM-STOCH VE, V106, P219
[5]   Activation mechanism of the β2-adrenergic receptor [J].
Dror, Ron O. ;
Arlow, Daniel H. ;
Maragakis, Paul ;
Mildorf, Thomas J. ;
Pan, Albert C. ;
Xu, Huafeng ;
Borhani, David W. ;
Shaw, David E. .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2011, 108 (46) :18684-18689
[6]  
Gerard C, 1997, B SOC CHIM FR, V134, P1069
[7]   COMPLEXES OF 3,4-DIHYDROXYPHENYL DERIVATIVES .4. EQUILIBRIUM STUDIES ON SOME TRANSITION-METAL COMPLEXES FORMED WITH ADRENALINE AND NORADRENALINE [J].
GERGELY, A ;
KISS, T ;
DEAK, G ;
SOVAGO, I .
INORGANICA CHIMICA ACTA-BIOINORGANIC CHEMISTRY, 1981, 56 (01) :35-40
[8]   The effect of pH on β2 adrenoceptor function -: Evidence for protonation-dependent activation [J].
Ghanouni, P ;
Schambye, H ;
Seifert, R ;
Lee, TW ;
Rasmussen, SGF ;
Gether, U ;
Kobilka, BK .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2000, 275 (05) :3121-3127
[9]   NMR-STUDIES OF CATECHOLAMINES ACID DISSOCIATION EQUILIBRIA IN AQUEOUS-SOLUTIONS [J].
GRANOT, J .
FEBS LETTERS, 1976, 67 (03) :271-275
[10]   COMPLEXES OF ADRENALIN AND RELATED COMPOUNDS WITH NI2+, CU2+, ZN2+, CD2+ AND PB2+ [J].
GRGASKUZNAR, B ;
SIMEON, V ;
WEBER, OA .
JOURNAL OF INORGANIC & NUCLEAR CHEMISTRY, 1974, 36 (09) :2151-2154