Synthesis and NMR study of two lipophilic iron(III) sequestering agents based on 8-hydroxyquinoline; H-bonding and conformational changes

被引:50
作者
Caris, C [1 ]
Baret, P [1 ]
Pierre, JL [1 ]
Serratrice, G [1 ]
机构
[1] UNIV GRENOBLE 1,LEDSS,LAB CHIM BIOMIMET,URA CNRS 332,F-38041 GRENOBLE 9,FRANCE
关键词
D O I
10.1016/0040-4020(96)00166-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of two tripodal iron chelating agents based on 8-hydroxyquinoline is described. The ligands consist of tris(2-aminoethylamine) (spacer) linked in 2- or 7- position to three 8-hydroxyquinoline units (allowing the complexation of iron). NMR study of these ligands in DMSO-d(6) solutions evidence intramolecular H-bond networks inducing conformational changes in relation to the protonation state of the tertiary amine.
引用
收藏
页码:4659 / 4672
页数:14
相关论文
共 22 条
[1]   O-TRENSOX - A PROMISING WATER-SOLUBLE IRON CHELATOR (BOTH FE-III AND FE-II) POTENTIALLY SUITABLE FOR PLANT NUTRITION AND IRON CHELATION-THERAPY [J].
BARET, P ;
BEGUIN, CG ;
BOUKHALFA, H ;
CARIS, C ;
LAULHERE, JP ;
PIERRE, JL ;
SERRATRICE, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (38) :9760-9761
[2]  
BUCHI J, 1956, CHIM ACTA, V39, P1676
[3]   Metabolization of iron by plant cells using O-Trensox, a high-affinity abiotic iron-chelating agent [J].
Caris, C ;
Baret, P ;
Beguin, C ;
Serratrice, G ;
Pierre, JL ;
Laulhere, JP .
BIOCHEMICAL JOURNAL, 1995, 312 :879-885
[4]   CHIRAL SIDEROPHORE ANALOGS - FERRICHROME [J].
DAYAN, I ;
LIBMAN, J ;
AGI, Y ;
SHANZER, A .
INORGANIC CHEMISTRY, 1993, 32 (08) :1467-1475
[5]   COORDINATION CHEMISTRY OF MICROBIAL IRON TRANSPORT COMPOUNDS .45. HYDROGEN-BONDING IN CATECHOYLAMIDES [J].
GARRETT, TM ;
CASS, ME ;
RAYMOND, KN .
JOURNAL OF COORDINATION CHEMISTRY, 1992, 25 (03) :241-253
[6]  
LINAS M, 1973, Biochemistry, V12, P3836
[7]   FERRIC ION SEQUESTERING AGENTS .21. SYNTHESIS AND SPECTROPHOTOMETRIC AND POTENTIOMETRIC EVALUATION OF TRIHYDROXAMATE ANALOGS OF FERRICHROME [J].
NG, CY ;
RODGERS, SJ ;
RAYMOND, KN .
INORGANIC CHEMISTRY, 1989, 28 (11) :2062-2066
[8]   COORDINATION CHEMISTRY OF MICROBIAL IRON TRANSPORT COMPOUNDS .23. FOURIER-TRANSFORM INFRARED-SPECTROSCOPY OF FERRIC CATECHOYLAMIDE ANALOGS OF ENTEROBACTIN [J].
PECORARO, VL ;
HARRIS, WR ;
WONG, GB ;
CARRANO, CJ ;
RAYMOND, KN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (14) :4623-4633
[9]   STRUCTURE AND BEHAVIOR OF SPERMIDINE SIDEROPHORES [J].
PETERSON, T ;
FALK, KE ;
LEONG, SA ;
KLEIN, MP ;
NEILANDS, JB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (26) :7715-7718
[10]   FERRIC ION SEQUESTERING AGENTS .15. SYNTHESIS, SOLUTION CHEMISTRY, AND ELECTROCHEMISTRY OF A NEW CATIONIC ANALOG OF ENTEROBACTIN [J].
RODGERS, SJ ;
LEE, CW ;
NG, CY ;
RAYMOND, KN .
INORGANIC CHEMISTRY, 1987, 26 (10) :1622-1625