Synthesis of chiral carbosilane dendrimers with L-cysteine and N-acetyl-L-cysteine on their surface and their application as chiral selectors for enantiomer separation by capillary electrophoresis

被引:11
作者
Quintana, Sara [1 ]
Angeles Garcia, Maria [3 ]
Luisa Marina, Maria [3 ]
Gomez, Rafael [1 ,2 ]
Javier de la Mata, F. [1 ,2 ]
Ortega, Paula [1 ,2 ]
机构
[1] Univ Alcala, Dept Quim Organ & Quim Inorgan, Campus Univ, E-28871 Alcala De Henares, Spain
[2] Networking Res Ctr Bioengn Biomat & Nanomed CIBER, Madrid, Spain
[3] Univ Alcala, Dept Quim Analit Quim Fis & Ingn Quim, Campus Univ, E-28871 Alcala De Henares, Spain
关键词
ENANTIOSEPARATION; DRUGS; AGENTS;
D O I
10.1016/j.tetasy.2017.10.028
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The synthesis of chiral carbosilane dendrimers functionalized with cysteine and N-acetylcysteine groups is presented. These dendrimers were obtained through thiol-ene addition reactions and their application as chiral selectors in capillary electrophoresis was investigated. Four drugs used as model compounds were analyzed under different experimental conditions observing that the use of a first generation dendrimer containing 4 terminal N-acetyl-L-cysteine groups enabled the enantiomeric discrimination of razoxane with a discrimination power similar to that obtained with other powerful chiral selectors such as cyclodextrins. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1797 / 1802
页数:6
相关论文
共 31 条
[1]   Chiral Drugs: Chemistry and Biological Action [J].
Anthonsen, Thorleif .
CHEMMEDCHEM, 2012, 7 (03) :534-534
[2]   Synthesis of carbosilane dendrimers containing peripheral (cyclopentadienyl)(aryloxy)titanium(IV) units [J].
Arévalo, S ;
de Jesús, E ;
de la Mata, FJ ;
Flores, JC ;
Gómez, R .
ORGANOMETALLICS, 2001, 20 (12) :2583-2592
[3]   Achiral and chiral separation and analysis of antifungal drugs by HPLC and CE: A comparative study: Mini review [J].
Bounoua, Nadia ;
Sekkoum, Khaled ;
Belboukhari, Nasser ;
Cheriti, Abdelkrim ;
Aboul-Enein, Hassan Y. .
JOURNAL OF LIQUID CHROMATOGRAPHY & RELATED TECHNOLOGIES, 2016, 39 (11) :513-519
[4]  
Du YX, 2010, CHIM OGGI, V28, P37
[5]   Carbosilane cationic dendrimers synthesized by thiol-ene click chemistry and their use as antibacterial agents [J].
Fuentes-Paniagua, Elena ;
Manuel Hernandez-Ros, Jose ;
Sanchez-Milla, Maria ;
Alejandra Camero, M. ;
Maly, Marek ;
Perez-Serrano, Jorge ;
Luis Copa-Patino, Jose ;
Sanchez-Nieves, Javier ;
Soliveri, Juan ;
Gomez, Rafael ;
Javier de la Mata, F. .
RSC ADVANCES, 2014, 4 (03) :1256-1265
[6]   Thiol-Ene Synthesis of Cationic Carbosilane Dendrons: a New Family of Synthons [J].
Fuentes-Paniagua, Elena ;
Pena-Gonzalez, Cornelia E. ;
Galan, Marta ;
Gomez, Rafael ;
Javier de la Mata, F. ;
Sanchez-Nieves, Javier .
ORGANOMETALLICS, 2013, 32 (06) :1789-1796
[7]   Separation of aromatic acids, DOPA, and Methyl-DOPA by capillary electrophoresis with dendrimers as buffer additives [J].
Gao, HY ;
Carlson, J ;
Stalcup, AM ;
Heineman, WR .
JOURNAL OF CHROMATOGRAPHIC SCIENCE, 1998, 36 (03) :146-154
[8]   Novel sulfonic acid-modified Starburst dendrimer used as a pseudostationary phase in electrokinetic chromatography [J].
Gray, AL ;
Hsu, JT .
JOURNAL OF CHROMATOGRAPHY A, 1998, 824 (01) :119-124
[9]  
Hardikar Madan S, 2008, J Indian Med Assoc, V106, P615
[10]   Synthesis of Dendrimer-Type Chiral Stationary Phases Based on the Selector of (1S,2R)-(+)-2-Amino-1,2-diphenylethanol Derivate and Their Enantioseparation Evaluation by HPLC [J].
He, Bao-Jiang ;
Yin, Chuan-Qi ;
Li, Shi-Rong ;
Bai, Zheng-Wu .
CHIRALITY, 2010, 22 (01) :69-76