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
    BARET, P
    BEGUIN, CG
    BOUKHALFA, H
    CARIS, C
    LAULHERE, JP
    PIERRE, JL
    SERRATRICE, G
    [J]. 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
    Caris, C
    Baret, P
    Beguin, C
    Serratrice, G
    Pierre, JL
    Laulhere, JP
    [J]. BIOCHEMICAL JOURNAL, 1995, 312 : 879 - 885
  • [4] CHIRAL SIDEROPHORE ANALOGS - FERRICHROME
    DAYAN, I
    LIBMAN, J
    AGI, Y
    SHANZER, A
    [J]. INORGANIC CHEMISTRY, 1993, 32 (08) : 1467 - 1475
  • [5] COORDINATION CHEMISTRY OF MICROBIAL IRON TRANSPORT COMPOUNDS .45. HYDROGEN-BONDING IN CATECHOYLAMIDES
    GARRETT, TM
    CASS, ME
    RAYMOND, KN
    [J]. 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
    NG, CY
    RODGERS, SJ
    RAYMOND, KN
    [J]. 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
    PECORARO, VL
    HARRIS, WR
    WONG, GB
    CARRANO, CJ
    RAYMOND, KN
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (14) : 4623 - 4633
  • [9] STRUCTURE AND BEHAVIOR OF SPERMIDINE SIDEROPHORES
    PETERSON, T
    FALK, KE
    LEONG, SA
    KLEIN, MP
    NEILANDS, JB
    [J]. 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
    RODGERS, SJ
    LEE, CW
    NG, CY
    RAYMOND, KN
    [J]. INORGANIC CHEMISTRY, 1987, 26 (10) : 1622 - 1625