Formation of diclofenac molecular ions as the effect of Cu2+-π interaction under electrospray ionization mass spectrometry conditions

被引:4
作者
Ostrowski, Wojciech [1 ]
Linko, Katarzyna [1 ]
Franski, Rafat [1 ]
机构
[1] Adam Mickiewicz Univ, Fac Chem, PL-60780 Poznan, Poland
关键词
diclofenac; copper complexes; cation-pi interactions; electrospray ionisation mass spectrometry; CATION-PI INTERACTIONS; NONSTEROIDAL ANTIINFLAMMATORY DRUGS; TRANSITION-METAL-COMPLEXES; RADICAL CATIONS; GAS-PHASE; COPPER(II); BINDING; ACIDS; DNA;
D O I
10.1255/ejms.1166
中图分类号
O64 [物理化学(理论化学)、化学物理学]; O56 [分子物理学、原子物理学];
学科分类号
070203 ; 070304 ; 081704 ; 1406 ;
摘要
Solutions containing diclofenac (M) and a copper salt (CuCl2, Cu(ClO4)(2), Cu(NO(3)l(2), CuSO4) were analysed by electrospray ionisation mass spectrometry (ESI-MS). Because of the cation-pi interactions in diclofenac-Cu(II) complexes, the diclofenac molecular ion NI++ at m/z 295 was formed. It was found that the solvent composition (methanol versus water/methanol) and counter ion strongly affect the M++ ion formation. Formation pathways of ion M++ are discussed.
引用
收藏
页码:43 / 50
页数:8
相关论文
共 25 条
[11]   Anion-π Interactions-Interactions Between Benzo-Crown Ether Metal Cation Complexes and Counter Ions [J].
Franski, Rafal ;
Gierczyk, Blazej ;
Schroeder, Grzegorz .
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, 2009, 20 (02) :257-262
[12]  
Henderson W., 2005, Mass Spectrometry of Inorganic, Coordination and Organometallic Compounds: Tools-Techniques-Tips
[13]  
Hori A., 2007, CRYSTENGCOMM, V9, P215, DOI [10.1039/b617808a, DOI 10.1039/B617808A]
[14]   Design of a small-molecule catalyst using intramolecular cation-π interactions for enantioselective Diels-Alder and Mukaiyama-Michael reactions:: L-DOPA-derived monopeptide-Cu(II) complex [J].
Ishihara, K ;
Fushimi, M .
ORGANIC LETTERS, 2006, 8 (09) :1921-1924
[15]  
Khan MF, 2009, AM LAB, V41, P44
[16]   Transition metal complexes of diclofenac with potentially interesting anti-inflammatory activity [J].
Kovala-Demertzi, D .
JOURNAL OF INORGANIC BIOCHEMISTRY, 2000, 79 (1-4) :153-157
[17]   Chemistry of the copper(I)-water bond. Some new observations [J].
Naskar, JP ;
Chowdhury, S ;
Drew, MBG ;
Datta, D .
NEW JOURNAL OF CHEMISTRY, 2002, 26 (01) :170-175
[18]   The partitioning of PAHs to egg phospholipids facilitated by copper and proton binding via cation-π interactions [J].
Qu, Xiaolei ;
Wang, Xiaorong ;
Zhu, Dongqiang .
ENVIRONMENTAL SCIENCE & TECHNOLOGY, 2007, 41 (24) :8321-8327
[19]   Cation-π interactions and oxidative effects on Cu+ and Cu2+ binding to Phe, Tyr, Trp, and His amino acids in the gas phase. Insights from first-principles calculations [J].
Departament de Química, Universitat Autònoma de Barcelona, Bellaterra 08193, Spain .
J Phys Chem B, 2006, 47 (24189-24199) :24189-24199
[20]   Radical cations in electrospray mass spectrometry:: Formation of open-shell species, examination of the fragmentation behaviour in ESI-MSn and reaction mechanism studies by detection of transient radical cations [J].
Schaefer, Mathias ;
Drayss, Miriam ;
Springer, Andreas ;
Zacharias, Philipp ;
Meerholz, Klaus .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (31) :5162-5174