A systematic evaluation of molecular recognition phenomena. 2. Interaction between phosphates and nucleotides with hexaazamacrocyclic ligands containing diethylic ether spacers

被引:34
作者
Anda, C
Llobet, A
Salvado, V
Martell, AE
Motekaitis, RJ
机构
[1] Univ Girona, Dept Quim, Girona, Spain
[2] Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA
关键词
D O I
10.1021/ic9908468
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The host-guest interactions between ortho- (Ph), pyro- (Pp), and tripolyphosphate (Tr) anions together with ATP (At), ADP (Ad), and AMP (Am) nucleotides and the two hexaazamacrocyclic ligands 1,15-dioxa-4,8,12, 18,22,26-hexaazacyclooctacosane (Pn) and 1,13-dioxa-4,7,10,16,20,24-hexaazacyclohexacosane (Op) have been investigated by potentiometric equilibrium methods. Ternary complexes an formed in aqueous solution as a result of hydrogen bond formation and Coulombic attraction between the host and the guest. Formation constants for all the species obtained are reported. The selectivity of the Pn and Op ligands with regard to the different phosphate and nucleotide substrates is discussed and illustrated with total species distribution diagrams. A comparison is also carried out, with the results obtained in this work and those obtained previously with three other closely related hexaazamacrocyclic Ligands. This comparison manifests the importance of ligand basicity, rigidity, and pi-stacking capability in order to understand their binding and selectivity.
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页码:3000 / 3008
页数:9
相关论文
共 47 条
  • [1] MULTIFUNCTIONAL MOLECULAR RECOGNITION OF ATP, ADP AND AMP NUCLEOTIDES BY THE NOVEL RECEPTOR 2,6,10,13,17,21-HEXAAZA[22]METACYCLOPHANE
    AGUILAR, JA
    GARCIAESPANA, E
    GUERRERO, JA
    LUIS, SV
    LLINARES, JM
    MIRAVET, JF
    RAMIREZ, JA
    SORIANO, C
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (21) : 2237 - 2239
  • [2] A systematic evaluation of molecular recognition phenomena.: 1.: Interaction between phosphates and nucleotides with hexaazamacrocyclic ligands containing m-xylylic spacers
    Anda, C
    Llobet, A
    Salvado, V
    Reibenspies, J
    Motekaitis, RJ
    Martell, AE
    [J]. INORGANIC CHEMISTRY, 2000, 39 (14) : 2986 - 2999
  • [3] INTERACTION OF HEXAAZAALKANES WITH PHOSPHATE TYPE ANIONS - THERMODYNAMIC, KINETIC, AND ELECTROCHEMICAL CONSIDERATIONS
    ANDRES, A
    ARAGO, J
    BENCINI, A
    BIANCHI, A
    DOMENECH, A
    FUSI, V
    GARCIAESPANA, E
    PAOLETTI, P
    RAMIREZ, JA
    [J]. INORGANIC CHEMISTRY, 1993, 32 (16) : 3418 - 3424
  • [4] [Anonymous], 1992, DETERMINATION USE ST
  • [5] [Anonymous], 1997, SUPRAMOLECULAR CHEM
  • [6] Neutral anion receptors: design and application
    Antonisse, MMG
    Reinhoudt, DN
    [J]. CHEMICAL COMMUNICATIONS, 1998, (04) : 443 - 448
  • [7] Basicity properties of two paracyclophane receptors. Their ability in ATP and ADP recognition in aqueous solution
    Bazzicalupi, C
    Bencini, A
    Bianchi, A
    Fusi, V
    Giorgi, C
    Granchi, A
    Paoletti, P
    Valtancoli, B
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1997, (04): : 775 - 781
  • [8] Thermodynamics of phosphate and pyrophosphate anions binding by polyammonium receptors
    Bazzicalupi, C
    Bencini, A
    Bianchi, A
    Cecchi, M
    Escuder, B
    Fusi, V
    Garcia-España, E
    Giorgi, C
    Luis, SV
    Maccagni, G
    Marcelino, V
    Paoletti, P
    Valtancoli, B
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (29) : 6807 - 6815
  • [9] BEER PD, 1992, NATO ADV SCI I C-MAT, V371, P105
  • [10] POTENTIAL ATPASE MIMICS BY POLYAMMONIUM MACROCYCLES - CRITERIA FOR CATALYTIC ACTIVITY
    BENCINI, A
    BIANCHI, A
    GARCIAESPANA, E
    SCOTT, EC
    MORALES, L
    WANG, BG
    DEFFO, T
    TAKUSAGAWA, F
    MERTES, MP
    MERTES, KB
    PAOLETTI, P
    [J]. BIOORGANIC CHEMISTRY, 1992, 20 (01) : 8 - 29